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If you spend a significant amount of time in any town, one of the food searches you’re bound to go on is the search for the best pizza in that area.

We started our search for the best pizza in Annapolis, Maryland when we used to travel weekly to Annapolis by boat. Now that we’re officially residents of the area, we’ve been able to put even more effort into sampling local pizzas. Over the years, we’ve had a chance to try the pizza offerings from several different restaurants in Annapolis and, now that we live here, we find we’re looking even more regularly for the places that consistently offer the best pizza.

Dining and drink specials, pricing, available menu items, and hours can change frequently at these establishments, and may not be fully up-to-date after our initial publication date. Please confirm any important details before you order or go to these restaurants by calling or checking their website, or social media pages.  All images and opinions are our own. 

Where to Find A Great Pizza in Annapolis, Maryland

Whether you’re touring the area for a weekend, visiting a family member at the Naval Academy, or living here full-time, you might find yourself searching for the best pizza in Annapolis.

While the term “best” can be a bit subjective, because it is largely dictated by your own favorite style of pizza, here’s our list of our favorite spots we’ve enjoyed so far. As you’ll see, we favor brick oven or wood-fired crust, tangy tomato sauce, unique pairings, and fresh toppings.

While we’re sharing all of our favorite pizza shops to visit, we’ve decided to present these in a slightly unorthodox order; the top listings are what we’d call a special occasion pizza that in some way provides a unique pizza experience that is worth a special visit out of your way,  all the way to down to great spots for very good pizza to please many palates and feed a group.

Without further ado, here are our favorite pizza spots in Annapolis.

Vin 909

909 Bay Ridge Ave, Annapolis, MD 21403  vin909wine.com

 

Vin 909 gets our vote as one of our all-time favorite pizza spots in Annapolis. Vin 909 pizza is so good, that it qualifies as a pretty special and memorable event when we go.

Not only is Vin 909 a welcoming little bistro just at the edge of Eastport, it’s also a spot for delicious farm-to-table offerings, salads, and a wine bar that also happens to make a fantastic wood-fired crust with the perfect savory sauce and topping options. Any of the fresh salads make a perfect side. We also often start things off with their famous House-Pulled Warm Mozzarella small plate.

While we think of any Vin 909 meal as a special event, it’s really not the sort of place needs to be reserved for special occasions, although its smaller dining areas do mean that seating can be limited. The pizza and other offerings are reasonably priced and the restaurant itself is upscale casual, intimate, and extremely welcoming.

Vin 909 also has limited parking in a small restaurant lot, but any restaurant with parking in the Annapolis/Eastport area is already a bit of a gem! While Vin 909 can accommodate small groups and families, the warm and inviting atmosphere and the excellent selection of wine and dessert mean it’s the ideal spot for a fun and fancy date night.

The Fox’s Den

179B Main St, Annapolis, MD 21401 foxsden.com

The Fox’s Den is located on Main Street, marked by a very low-profile sign above the doorway.  You’ll go down a long flight of stairs into this cozy bar and pizza spot, that serves gourmet wood-fired pizza, and delicious sides and offers a notable selection of local beers, IPAs, craft cocktails, and whiskies.

The Fox’s Den specializes in gourmet toppings and inventive pairings. We love the Sausage Party pizza, which gets extra points for its inclusion of pesto sauce in the mix, as well as the Fig & Pig pizza which provides a wonderful combination of fig, brie, and mint.

We also appreciate the $5 off pizzas on Mondays for a discounted way to sample these pies. Pair that deal with their Monday through Thursday happy hour deals from 5 -6  where you can save $2 on their always impressive draft list, as well as $3 off the house cocktails — the Sneaky Neighbor being an all-time favorite. The sides like the Brussels sprouts, duck fat fries, and locally sourced seasonal salads are another great way to round out your order.

Timber Pizza Co.

192 West St, Annapolis, MD 21401  timberpizza.com

Timber Pizza Co. is a new addition to the Annapolis pizza scene. From what we’ve heard and seen so far it has received a warm welcome, with many folks flocking to this West Street location.

We first enjoyed Timber Pizza when their mobile wood-fired oven on wheels made a few appearances at Tides + Tunes, the local Thursday Night concert series in Eastport. From what we learned chatting with their team members, Timber has several other DMV locations including one in DC, and two locations in Virginia, making the move to Annapolis a natural extension of the business.

Their wood-fired approach and bright and sunny space on their new storefront on West Street had people lining up to get their 12-inch pies when they opened. We particularly enjoy their Green Monster and their Margarita options. The menu is nicely rounded out by fresh salad options and desserts as well as empanadas as apps.

The Italian Market

126 Defense Hwy, Annapolis, MD 21401  theitalianmarket.com

The Italian Market is something to behold for any Italian treat, not just pizza. We were there during Christmastime when the center shop area was full of Italian Christmas cookies, nougat, and Italian specialty candies, as well as Panettone.

The market always features an impressive wine selection, delicious gelato, entrees, salads, and pizza.  The in the round dining area that flanks the shop, is meant to bring the feel of an Italian piazza dining experience right here to Annapolis.

The eat-in and take-out options include many authentic Italian entrees that we’d love to try, but on that day, we were there just for the pizza. We heard that it was true New York Style Pizza with that thin foldable crust, tangy tomato sauce, and perfect cheese mix, and we were happy to learn that was an accurate description. We were there after lunch and just took a warmed-up slice to go, but true to its reputation, the pizza at The Italian Market was an excellent slice of  New York pizza.

We’ll be returning again to have a whole pie, as well as to sample some of the deli sandwiches, entrees, and a bit of that gelato too. Employees were friendly, welcoming, and speedy with the service. On Mondays, the Italian Market offers a deal on this great pizza: If you buy 1 New York Style Large you can get 1 Medium Cheese for $7.00. They also offer a gluten-free option.

Sammy’s Pizza Kitchen

1007 Bay Ridge Ave A, Annapolis, MD 21403 sammyspizzakitchen.com

Sammy’s was a favorite stop of ours when we kept our boat in Eastport. Everything here is delicious, especially the pasta entrees and salads. The pizzas are a classic variety, just your basic great slice made to be special with their homemade tomato sauce which can be jazzed up with their variety of toppings. Sammy’s pizzas were something we order frequently – especially while moving or on those nights when cooking doesn’t seem appealing. It’s another great place for affordable pizza with high-quality ingredients that will please a crowd.

The service at Sammy’s is also excellent with welcoming staff who are clearly working hard to make sure every pasta and pizza dish comes out hot. Sammy’s Pizza Kitchen is a full-service Italian restaurant offering salads and pasta dishes like the Fusilli Primavera and the Springach Stuffed Eggplant which are just a few of the other menu items that we love. The balsamic salad dressing that accompanies their house salad is also excellent.

The dining room offers a welcoming space to enjoy your pizza inside, or to make it a night out with a glass of wine, salad, or entree. But if you feel like just having a pizza night at home, the pick up for takeout is speedy, and we’ve had fast service from delivery as well.

Little Italy

1411 Forest Dr, Annapolis, MD 21403 littleitalyannapolis.com

We aren’t 100% sure of this, so we’ll try to confirm this with the owners, but given the nearly identical menu offerings and weekly specials, we think Little Italy and Sammy’s  Italian Pizza Kitchen may be run by the same folks.  We apologize if we have that wrong! Either way, the pizza at Little Italy is also excellent, and the Forest Drive location is more convenient for pizza lovers who are further away from the Eastport area where Sammy’s is located. The Monday special on cheese pizza – a large pizza for $9.99 is an excellent value and is something we look forward to getting either from Little Italy or Sammy’s. While Little Italy can be a takeout pizza spot, it is also a casual restaurant that offers a dining area for family dining. The parking area is a little tight since it shares space with a number of businesses, but you can usually find a spot to pick up or place your order.

Ledo Pizza

505 S Cherry Grove Ave, Annapolis, MD 21401, many other locations in the area  ledopizza.com

Ledo Pizza is a Maryland institution. Since we both grew up in New England, we had not heard of this state-wide chain until we moved to the area. If you’re from out of state, and you’ve never tried a Ledo’s Pizza you certainly owe it to yourself to give it a try. However, if you’ve lived in Maryland your whole life, then maybe Ledo’s isn’t a special event, and there’s a good chance it is more like your regular weekly pizza spot.

The unique square shape of Ledo’s pizza cut into even small squares that can be eaten in 2-4 bites, and the excellent heavy application of hearty sauce and toppings, make Ledo’s fully its own thing.

This is a great style of pizza if you’re feeding a crowd, especially because of the way Ledo slices small squares — makes it perfect for kids or any time someone just wants a bite. Ledo’s of course offers all the classic toppings, but we love the original cheese. There’s a Ledo’s in nearly every town near Annapolis, so it’s easy to find the one closest to you.

Boatyard Bar & Grill

400 Fourth St, Annapolis, MD 21403 boatyardbarandgrill.com

Boatyard is known for boat drinks, crab cakes, oysters, and fantastic seafood offerings that highlight the best of Maryland cuisine.  That said, when we’re not ordering the sandwiches, salads, or seafood, we’ve quite often ordered the pizza from Boatyard.

Not only is it really good pizza, it has the added benefit of being the perfect small size for two when you just want a little bit of pizza with another appetizer or salad.  Possibly the best feature is their cauliflower crust which is their unique gluten-friendly offering that is tasty enough to order even if you aren’t gluten intolerant. Like everything else on the extensive menu, there are flavorful toppings available and the pizza at Boatyard is delicious!

Pasticcio

150-F, Jennifer Rd, Annapolis, MD 21401  pasticcioannapolis.com

When we’re over in the Jennifer Road area of Annapolis, out near the Westfield Mall doing errands near Trader Joe’s and Home Goods, Pasticcio is a delicious and nearby stop. These homemade pizzas are topped with very fresh ingredients and come in 14 and 16-inch sizes as well as square options. There are also different crust types including a Sicilian thin crust and Grandma’s style so that you can customize your pizza experience.

At the recommendation of others, we tried the  Grandma Margarita, which had a generous helping of basil, cheese, and sauce. We would love to try the Chicken Parmigiana as well as a slice of regular cheese for comparison next time. Pasticco also offers entrees, salads, and fresh subs.

Rocco’s Pizzeria

954 Bay Ridge Rd, Annapolis, MD 21403  roccospizzashop.com

Rocco’s pizza is unpretentious, but still quite delicious, and it is the go-to spot for a generously sized classic pizza. It’s a great freshly made option that stands well above the chains like Papa John’s or Domino’s. In fact, we probably wouldn’t have survived our move to Annapolis without Rocco’s. Each night before we unearthed our pots, pans, and plates and before we had time to grocery we were ordering Rocco’s subs and pizza for several weeks during the moving transition.   R

occo’s pizzas are generously sized, and have the classic pizzeria taste. It’s another pizza spot great for feeding a crowd with varying tastes, and will always hit the spot if you want a classic  New York pizza preparation. You can also get gluten-free and Sicilian crust varieties as well as pizza by the slice, which is a handy option for lunch or a quick snack.

Rocco’s also offers pizza delivery. Rocco’s phone line is often busy with delivery orders, especially on weekends and near the holidays, so service sometimes feels a little uneven and you might have to wait a bit for someone to pick up the phone during the busier times. The subs are also great at Rocco’s – we usually go for the classic Italian Cold Cut.

Neo Pizza + Taphouse

220 Harker Pl Suite 145 , MD 21401 neopizza.com

If you’re over near the Annapolis Town Center shopping area and looking for a bit of pizza, Neo is a popular option. We only visited once, and while the pizza and atmosphere were fairly customary. The bar seating option was particularly nice since Neo offers some great local craft beers, and it’s a nice place if you’re dining solo. In fact we were so impressed with the beer selection and our Caesar salad that the pizza was competing for that attention rather than standing out. Neo stands for “Never Expect Ordinary”- and to that end, they are known for their specialty pizzas and are one of the spots we tried that offers a gluten-free crust.

We went with the Goodfellas pizza on our visit and would order that or the Florentine or the Margarita again.  The Philly Cheesesteak or the  Chesapeake option also looks like one unique to the establishment pizzas that should be tried even just for the novelty of it. Sandwiches, salads, and kids’ menu offerings are also available.

Service was very friendly, but the bar floor needed a bit of a wipe-down since it was full of crumbs from the lunch rush and previous patrons. While it’s not the first stop on our list, we know so many others who swear by it, especially because of the gluten-free options and the convenient location, nearby parking, and proximity to the gym, shops, and residences around Town Center so check out the menu and see if it’s for your taste buds!

More Fun Things to Eat and Do

We’ll be covering more fun things about Annapolis including the best bars in Annapolis, the best coffee shops in Annapolis, and the best seafood restaurants in the area. We’ll also share with you fun things to do in Annapolis. If you’d like more coastal dining ideas check out our ideas for the best restaurants in St. Augustine, Florida.

We hope this guide to pizza places in Annapolis has helped you find a slice of pizza you love!

We have visited Saint Augustine– the nation’s oldest city–three times in the past two years.  The second time we stayed for a whole month! Thanks to those experiences, we’ve had the opportunity to learn more about the great food scene in St. Augustine, indulge in some wonderful meals, and discover what we think are some of the best places to eat in St. Augustine.

When trying to find the best restaurants in St. Augustine, we feel like we get to live like locals when we stay in our Thor Gemini RV, making Anastasia State Park our temporary home. There are a few different areas of the city that are home to some wonderful dining areas. We’ll share some great places to eat the beach area of Anastasia Island, the historic downtown, Lincolnville, and the waterfront areas along the river and out towards Vilano Beach.  We hope this helps you find a few fun restaurants to visit when you stay in St. Augustine!

As always, menu items, and hours can change frequently. You may want to confirm details before you go by calling or checking their website, or social media pages.  All images and opinions are our own. 

Best Places to Eat When Visiting St. Augustine Florida

St. Augustine is a place full of history and a variety of restaurants. As a waterfront city there are many seafood restaurant offerings but there’s also fine dining, Southern comfort food, and some Cuban-inspired fare as well. Here are a few of the St. Augustine restaurants we’ve enjoyed, and we hope you will too!  We’ve presented these in a bit of random order but with some of our favorites first.

St. Augustine Fish Camp

142 Riberia St, St. Augustine, FL staugustinefishcamp.com

Upscale fresh coastal seafood favorites, and cocktails in a beautiful waterfront location

We’ve eaten at the St. Augustine Fish Camp each time we’ve visited St. Augustine. Our first visit to Fish Camp was when we stayed in St. Augustine for only a few days, and the next time it was one of our first stops!

Fish Camp has a few other locations in coastal Florida, but it’s still not what you’d ever call a chain, each space is unique with well-crafted dishes on the menu that feature the local fare.

The decor at St Augustine Fish Camp is upscale nautical, open, and modern, and it is an immediately welcoming spot close to the water. We chose the back bar where the seats offer a little hideaway from the main dining room but still afforded us a water view.

Our bartender, who we had as our server on both visits, was a fantastic steward of the place. He was a great conversationalist and kept all the bar patrons happy and engaged while mixing and serving delicious craft cocktails and pouring perfect pints.

Shrimp and grits from St. Augustine Fish Camp

As native New Englanders, we were impressed to see the fried clams offered, but we ultimately decided to go with the local cuisine and picked the Shrimp and Grits. It was so good the first year, we just repeated the order in year two. So much for branching out; maybe next year!

The menu is a pleasing mix of fresh seafood favorites with local and multi-coastal influences. As we mentioned we saw North to mid-Atlantic favorites on the menu like clam chowder, cod, and blue crab next to southern-style dishes like Oyster Po Boys, Shrimp, and Grits, Low Boil for Two, and Fried Green Tomatoes.

Fish dip appetizer 

There are also some Carribean-inspired dishes like the conch fritters and Mediterranean-style plates like fried octopus. There are also burgers, and delicious pork and chicken entrees if anyone in your party doesn’t favor seafood. We highly recommend this spot if you’re seeking a great atmosphere and delicious food.

Asado Life

173 Shipyard Way, St. Augustine, FL 32084 asadolife.com

Upscale waterfront restaurant that offers a fine dining and Argentinian grilling experience that is not to be missed!

The open-flame outdoor grill at Asado Life

Asado Life was a new restaurant for us to visit in 2024, and we will certainly make it a point to return on all of our future trips to St. Augustine. Asado Life is named for and inspired by the traditional Argentinian method of barbeque.

Chef Matthew Brown has taken this BBQ method and turned it into the overarching theme of the restaurant: experience grilling. The dinner menu consists of a Prix Fixe menu of chef’s selections which are posted seasonally on their website.

The fixed price offerings for the Waterfront dinner range from the Asado Trio for $59, all the way to the Tomahawk rib eye for two for $169. There are also lunch options and seating at the bar.

The Waterfront dinner is by reservation only, and reservations are booked out well in advance.  Since we decided to go last minute with friends, we didn’t have reservations so it gave us a great opportunity to experience the lunch offering.We were extremely impressed by the meal itself, the portions, atmosphere, and overall experience.

At lunch,we ordered the Grilled Asado Trio for two along with the classic Pisco Sour. Our friend who joined us is originally from South America, and he verified that both the Pisco Sour and the meat was prepared both authentically and perfectly. The Asado trio was all that we expected and more. The Argentinian steak was so flavorful and perfectly complimented by the seasonings, and chimichurri sauce as well as the open flame method of cooking.

The Asado Trio

We sat outside with a fantastic view of the River as well as the outdoor open flame grills, and high-end barbeque equipment that is the foundation of the Asado Life brand.

Since we were there during lunch, we could see the chefs preparing some of the prix fixe offerings for the dinner service over the open flame. The open terrace, as well as the inside bar, is decorated in an upscale coastal style of the restaurant. Both areas are beautiful spots to spend time.

Interior bar sand dining pace at Asado Life

If you’re not in the mood for a meat-centric meal, Asado Life also offers burgers, sandwiches, salads, and small plates. You can also shop the market for prime cuts of meat, spices, sides, and much more.

Whether you make a reservation for one of the prix fixe dinners, enjoy lunch, or even just pick up some seasonings and prepared food from their market, we think the Asado Life is the good life!

River  + Fort

12 Avenida Menendez, St. Augustine, FL 32084  riverandfort.com

Steak and seafood in an unforgettable atmosphere with beautiful views 

As you drive down the Avenida Menendez you can’t miss the fort — Castillo de San Marcos — and the Mentdoz River — and across from both of those is one of St. Augustine’s newer restaurants and a fine dining experience: River and Fort.

This restaurant has an amazing atmosphere. The multi-level space features a ground-floor open dining terrace,  spacious dining rooms high ceilings, and plenty of windows and porches showing off the view. There are also welcoming bar spaces on each level and a popular rooftop deck.

Seared scallops and chow chow with red pepper gastrique

While it was the rooftop deck and the outdoor lounge area that we had seen online and encouraged us to go in, it was actually the only disappointing aspect of the space. The rooftop deck doesn’t have the best view of the fort and the water, but it still has the gorgeous design elements that are present in every area of this space. The menu is also limited to flatbreads and pizza on the rooftop.

Since we wanted to have the full steak and seafood experience the restaurant is known for, we opted for an early dinner and craft cocktails. We ordered the seasonal cocktail– the Sage Blossom– which was a delicious combination of strawberry puree, sage syrup, and St Augustine rum and Pimm’s.

The Stuffed New York Strip from River & Fort

For our meal, we splurged and ordered the stuffed New York strip and the seared scallops. Both were dishes to remember, both for their incredible presentation well-balanced flavors, and perfect preparation.

The menu offers wines by the glass and craft cocktails along with a full bar and wines but the bottle.

River + Fort is a definitely fine dining experience, with the best cuts of meat and fresh fish prepared with sophisticated pairings, but they still cater to the whole family with a kid’s menu and classic dishes.

Whether you go here for a drink or enjoy a full meal, it’s a fine dining experience in a gorgeous building with a beautiful view.

The Rooftop at River & Fort offers flatbreads and cocktails

The Floridian

72 Spanish St #3638, St. Augustine, FL thefloridianstaug.com

Floridian-inspired tiki cocktails and fresh farm-to-table food with a Southern twist

The Floridian is located on historic Spanish Street in downtown St Augustine and is another local treasure we had on our list of spots we wanted to try. Some of the Foodie RV YouTubers we follow had raved about the food there and they were right to do so!

The Floridian’s menu philosophy revolves around using the finest local ingredients to craft Southern comfort food with a modern twist. The result is a menu filled with upscale comfort food that pays homage to the rich food culture of the local farms in Florida and the cuisine of the South.

Beet Salad with the Catch of the Day

We ordered the Citrus Beet Salad with the Catch of the Day and the Not Your Momma’s Meatloaf sandwich and enjoyed both of those tremendously. The restaurant’s atmosphere is fantastic. It’s a sophisticated and aesthetically pleasing mix of old Florida style with bold tropically themed wallpaper, rattan details, retro decor finds, and beautifully chosen details from the tables to the plates and tables.

Not Your Momma’s Meatloaf

The cocktails were out of this world. We tried the Garden Gimlet and Saturn in Crosshairs cocktail which were two of the best drinks we’ve ever had.  The service was efficient and welcoming, echoing the warmth and hospitality that was apparent in every aspect of this place.

Beachside Diner

451 A1A Beach Blvd, St. Augustine, FL 32080  beachsidediner.com

Classic brunch and breakfast options with brunch cocktails in a lively beachside diner

When we are staying at Anastasia in our RV, we don’t want to have to pack up the RV to go out to for a meal–especially breakfast– so we are always eager to find restaurants that we can bike or walk to.

The Beachside Diner is located on A1A in the beach district of St. Augustine on Anastasia Island. It’s about a 7-minute bike ride from our campsite at Anastasia State Park.

Waffles with fruit 

This diner is a clean, cheerful, and welcoming modernized 1950s-style dinner that serves a fantastic breakfast and offers brunch cocktails. There’s a whole menu dedicated to their creative takes on Bloody Marys!  It gets crowded at breakfast, but we didn’t have to wait long for seating.  The breakfast offerings are fantastic. We had the 2-2-2-2  which is exactly the kind of full breakfast combination with pancakes, eggs, and sausage that we always crave, but can rarely find!

We also had the chicken fried chicken – another delicious and somewhat hard-to-find combination. We were tempted by the cocktail offerings but saved it for our second visit where we had the waffles which were as visually gorgeous as they were delicious and the biscuits and gravy which we loved! Highly recommend this as a breakfast or brunch spot.

Beachcomber Restaurant & Bar

2 A St, St Augustine Beach, FL 32080  beachcomberstaugustine.com

Beachfront dining with excellent cocktails and island-style seafood, burgers, and salads.

The Beachcomber is one of our favorite places to bike from where we stay in Anastasia State Park. St. Augustine has some great bike paths, and taking some of the back roads from the State Park to A1A  will get you to the Beachcomber in just a few minutes.

Island-inspired cocktails are a specialty at The Beachcomber

The Beachcomber is an amazing little beach bar and restaurant right on the sandy entrance to the beach. You can sit outside at the picnic tables and outdoor covered patio that have a nice view of the dunes and water.

We love sitting at the bar since all the doors are open and the beach atmosphere very much carries into the bar space. We’ve gone for lunch, light mid-day food, and cocktails.

The bar makes a great Dark N Stormy, a drink called Changes in Latitude, and they are known for their Goombay Smash. All of the cocktails are great. We also enjoyed the Coconut Shrimp appetizer and the Big Fish Reuben.

It’s one of those places that really makes you feel like you’re on vacation. For a additionaly fun stop on the way home, there’s a little bar on the corner of A1a that is a fun spot to have a beer while being able to sit right on the street.

The Conch House

57 Comares Ave, St. Augustine, FL 32080 conchhousemarinaresort.com

A Caribbean-inspired eatery with great island-style drinks, outdoor seating, tiki huts, expansive decks next to a beautiful marina

We spend a lot of time in the vicinity of the Conch House because friends of ours keep their boat in the marina there. We are usually enjoying Bloody Marys or Painkillers at the fun bar decks that overlook the waterfront and marina. However, one day we decided to sit down and have a proper meal.

The Painkiller at The Conch House is authentically and perfectly made

The restaurant is known for its Caribbean-inspired menu, featuring a variety of seafood dishes, tropical flavors, and island-inspired cocktails. The menu often includes items like conch fritters, jerk chicken, and other dishes with a Caribbean twist.

Tiki style outdoor seating huts at The Conch House

One of the coolest things about The Conch House is the tree house style Tiki Hut seating with multiple level tikis that function as outdoor booths.

We got to sit in one of these, and we ordered the Shrimp & Grits, which our friends highly recommended, the hushpuppies, the Shrimp Anastasia seafood pasta, and a watermelon lime chili cocktail.

Shrimp and grits from The Conch House

The shrimp and grits were the spicy variety with tasso ham, so it wasn’t our favorite preparation, since the spicy ham overpowered the shrimp, but it was still good. The Shrimp Anastasia and the Watermelon cocktail were all delicious! The restaurant has a laid-back vibe, and with its outdoor seating options, tiki huts, and a waterfront deck, it’s a wonderful spot to enjoy Carribean-style comfort food while taking in the waterfront view.

Shrimp Anastasia seafood pasta

Ice Plant Bar

110 Riberia St, St. Augustine, FL  iceplantbar.com

 Craft cocktails and farm-to-table plates in the unique setting of a former working ice plant 

For a unique atmosphere and delicious cocktails, we love the Ice Plant Bar. Ice Plant is just a few steps down the road from St. Augustine Fish Camp and right next to St. Augustine Distillery. The interior is unlike any other restaurant, with a modern industrial feel, soaring ceilings, and a large open space, that has been carefully renovated to keep the historical details of the former ice plant.

Interior space at The Ice Plant

The Ice Plant Bar is known for craft cocktails and farm-to-table cuisine. Since St. Augustine Distillery is right next door, there’s a tasting room on the first floor of the Ice Plant in the distillery offering samples of local gins, vodkas, and bourbons.  For dining options, you can move upstairs to enjoy sitting at the tables in the open modern industrial space or outside on the small covered patio.

The Ice Plant Truck

The menu offers salads, sandwiches, southern dishes, and seafood like their famous blue crab beignets and smoked fish dip. What truly sets this place apart are the cocktails.

The bartenders here are mixologists creating drinks that are as visually appealing as they are flavorful. From classic cocktails with a twist to low and no-alcohol options mocktail concoctions, the drink menu is a work of art with ingredients like aloe, snap pea, rose hips and avocado seamlessly blended into magical cocktails.  One of our personal favorites was the Moonage Daydream, a cocktail that brilliantly captures the farm-to-table meets distilled botanicals.

Salt Life Food Shack

321 A1A Beach Blvd, St. Augustine, FL 32080 saltlifefoodshack.com

Cocktails, happy hour, and seafood favorites from the coastlines of the world in an upscale beachy atmosphere

After seeing Salt Life’s ubiquitous logo plastered on vehicle windows, and emblazoned on t-shirts, sunshirts, and other gear, we hadn’t associated the Salt Life brand with anything related to dining.

However, St. Augustine is home to one of the small group restaurants known as the Salt Life Food Shacks owned by the coastal fishing brand. We were pleasantly surprised to find that we enjoyed our experience there.

The name “shack” doesn’t really apply, since the restaurant is a beautiful modern 2-story building on A1A across from the beach. The contemporary surf-inspired decor, open-air bar seating, a great happy hour menu, delicious cocktails, and fast service made this one of our favorite happy hour stops during our time in Anastasia Island.

Salt Life’s menu unsurprisingly is ocean-inspired, offering a variety of coastal seafood dishes from many different saltwater environments from the New England Clam Chowder to Hawaiian-inspired Poke Bowls.

We went on a Thursday for their Oyster & Margarita specials where they offer 1/2 price margaritas 1/2 price Elevated Patron Margaritas and $9.99 for a dozen raw oysters, or 1/2  a dozen baked oysters. We also enjoyed their tuna roll and the shrimp brochette along with our order of the crab stuffed oysters and skinny and salty margaritas.

Prohibition Kitchen

119 St George St, St. Augustine, FL 32084 pkstaug.com

A vintage industrial-style atmosphere with live music nights, serving specialty hamburgers, American comfort food, cocktails, and boozy milkshakes 

One of the restaurants we knew we had to try was Prohibition Kitchen, located on historic St. George Street. The interior is a huge space with a vintage Prohibition-style speakeasy with industrial artifacts that give it a steampunk atmosphere.

Prohibition Kitchen specializes in contemporary American Gastropub food with a farm-to-table focus and a Southern twist. The sandwiches and burgers – including a build-your-own option are what they’re most known for.

The Prohibition Style Atmosphere at the bar at Prohibition Kitchen

We were there for lunch, so we had the PK Signature burger and the Bootlegger Burger with fried green tomato and pimento cheese, along with their famous boiled peanuts. We were also tempted by all the adult milkshakes we saw being served, but since we knew we had a day of walking and sampling other bites to eat, we didn’t indulge. From the baked mac ‘n’ cheese with add-ins to poutine, and hearty short rib dishes, we thought that the menu offers a range of delicious and hearty southern comfort foods that are perfect for lunch on a day spent touring St.Augustine.

The Bootlegger Burger

O’Steen’s

205 Anastasia Blvd, St. Augustine, FL 32080  osteensrestaurant.com

Known for: Casual fried seafood restaurant with classic Southern sides

O’Steen’s is a casual seafood restaurant right on Anastasia Boulevard, making it easy to get to from both the historic district of St. Augustine and the beaches. O’Steen’s was founded by the O’Steen family in the 1960s and has remained in the family ever since.  It’s now considered to be one of the must-visit spots in St. Augustine for any fried seafood lover.

The famous fried shrimp and sides at O’Steen’s

The menu at O’Steen’s is known for its focus on Southern-style and traditional seafood dishes; especially their famous St. Augustine Fried Shrimp. An important thing to note if you’re planning on going is that it is a cash-only restaurant. You can also enjoy crab cakes, clam chowder, various fried seafood, and Southern-inspired sides.

The Blue Hen Café

223 W King St Ste A, St. Augustine, FL 32084  bluehencafe.com

Hearty Southern biscuits and sandwiches and sides for breakfast, brunch, or lunch

The Yard Bird, a famous dish at the Blue Hen Cafe

This is a breakfast and lunch spot that my husband pedaled to on one of his bike trips into downtown St. Augustine.  The Blue Hen Cafe is known for its Southern comfort food, especially buttermilk biscuits and gravy, shrimp and grits, and fried chicken. The lunch menu features breakfast items along with a variety of substantial sandwiches. While he went with the famous Yard Bird  – a combination of buttermilk fried chicken, with onions, gravy, and collard greens for breakfast, our second pick would be the Fried Green Tomato BLT for lunch.

The Village Garden Food Truck Park

1480 S Old A1a S, St. Augustine, FL 32080  villagegardenftp.com

A collection of food trucks offering street tacos, salads, smoothies, coffee, and acai bowls 

One of the coolest things about staying at Anastasia State Park is the amazing combination of the natural setting of the park and ocean combined with the proximity to various attractions and restaurants. Right outside the park through the back exit down Nona and Papa Road is open only to foot traffic and bikes there’s a cut-through that takes you down a few neighborhood streets where Old A1A intersects with new A1A.

Budda Bowls and Salads are a way to get a quicky healthy meal in Anastasia Island

This little space is the permanent home to 4-5  food trucks including our favorite, Big Island Bowls. We mainly ate at Big Island Bowls, because getting fresh salads and veggies along with some healthy fruits is always tricky on the road. We loved the Shaka Bowl and the Hibiscus Bowl, along with the Spicy Thai Budda Bowl for a quick and easy lunch or early dinner.

One night also tried the street tacos and puffy tacos from both Kusina Colorado and the Birra Tacos from The Little Sombrero and had drinks from  The Good Karma Cafe.

Acai bowls are a specialty at Big Island Bowls

The drawback to these trucks is that not all are open, and there seems to be a lack of variety; specifically, there’s a surplus of taco and smoothie options, but it would be great to have a burger or barbeque truck to balance out some of the dining choices.

If you’re a fan of food trucks in general there’s no shortage in St. Augustine. There’s a coffee truck and a taco truck near the front entrance to Anastasia State Park, and there are some that show up in the parking lot when there are concerts at The Amp – the music venue next to the park. There are also many food trucks and food stands that come for the weekly farmers market on Saturday morning.

Blackfly

108 Anastasia Blvd, St. Augustine, FL 32080  blackflytherestaurant.com

Steaks and seafood prepared in fine dining methods in a relaxed bistro atmosphere

This restaurant’s name throws us off a little, as we tend to think of the frustrating gnat-like bug, and not the fine dining experience this place is known for. Of course, as many fishermen know, a blackfly is a fly fishing term, and the Blackfly sister restaurant is located in the Bahamas — so we’re lucky to have its counterpart in St. Augustine.

Friends of ours who also spend time in St. Augustine have insisted this is the place for a great meal, and they visit weekly! We were there for a late night after a day out, so we didn’t really get to experience the full expanse of the menu, but from what we saw there were so many excellent choices for seafood, as well as an extensive wine list.

We somewhat lamely had the pizza since we had eaten a large meal earlier that day, but we’d like to go back with the sole purpose of trying out their extensive menu. The pizza was fantastic, in a true margarita style with a delicious crust. The atmosphere of the bar and dining space was upbeat and welcoming and our friends splurged on rockfish and other entrees that looked fantastic, and probably more in line with what we’d order on a regular night.

We’d love to try the Wellington beef tips, and the Cocquille St. Jacques, as well as the seafood entrees like Blackfly Fried Shrimp and the Scallops Brandon or the catch of the day done in one of their excellent preparations. They also offer fine options like steaks and chops from their grill and an offering of desserts including the Celebration Cake which is perfect for a special occasion.

Andaman Asian Bistro

1935 A1A S, St. Augustine, FL 32080 andamanasianbistrofl.com 

A collection of Asian cuisine favorites including sushi, Thai dishes, and appetizers in a welcoming space

Pad Thai 

We were in the mood for Asian food and sushi after our month-long dining adventures that were heavy on comfort food, so one evening we biked the short distance from the back gate at Anastasia State Park, and used caution to cross over into a little plaza where Andiman’s is located.

This little spot is in a strip mall and has a welcoming small outdoor seating area. Inside, there are booths and tables along with a sushi bar. We ordered the pad Thai, the Andaman Platter which is an assortment of their best appetizers, and the Elton John roll.

The Elton John roll, one of the chef’s specialty rolls at Andaman

The dishes were excellent, with the beautiful presentation that one likes to see at a good sushi restaurant. All the food was delicious with fast and friendly service. While we wouldn’t travel to St. Augustine specifically for a visit to Andaman, it’s very nice to have it as an option within biking or walking distance to the park, especially when you’re craving pad Thai.

Pizza Time

124 St George St, St. Augustine, FL 32084

Unforgettable pizza with generous and creative Italian-entree-style toppings in a fast-casual environment

See the slices before your order. The line moves quickly!

Pizza Time has smartly marketed itself as “The Second Best Pizza in the US” thanks to its standing on TripAdvisor back in 2015. While we can’t prove ourselves that it’s true, this marketing tagline does have some really exceptional pizza behind it. If you’re looking for loaded gourmet slices with toppings you won’t find at most of the pizza chains and pizza parlors, Pizza Time is for you.

Burrata pizza

Be warned, it’s a cash-only spot and there’s a line and a fast ordering process where the efficiency of ordering is appreciated. There’s a rotating selection of pizza by the slice. These slices are loaded with options that sound more like entrees than toppings. The pizza toppings are rotating but on the days we were there, we were treated to toppings like lasagna, chicken parmesan, ravioli, meatballs, eggplant parmesan, along with full, heaping dollops of ricotta, mozzarella, and burrata. The generous toppings make for hearty slices.

Eggplant Parmigiana Pizza

At between $8 to $10 a slice for the heavier toppings, you can easily spend $20 on just a few slices, but they are delicious and not to be missed!

Sunset Grille

421 A1A Beach Blvd, St Augustine Beach, FL 32080 sunsetgrillea1a.com

Beachfront dining with a large menu featuring, seafood, pasta, and classic dining favorites, perfect for families

The Sunset Salad

Sunset Grill was another A1A restaurant, within a short bike ride from the State Park. It has an outside and multiple levels of seating. It has lots of Seafood options, as well as salads, sandwiches, pasta and “land food”.

On our first visit, we sat at the bar for a happy hour drink. We had the Sunset Salad with fish and Sunset Shrimp seafood pasta. We were impressed by both dishes and appreciated the friendly and efficient servers at the bar and the delicious Sunset Cocktail.

The Sunset Shrimp

We went again with a group of 5 of us when family was visiting, and we sat in the back room. Unfortunately, that time we had uneven service (it seemed like we were forgotten in that back room!), and our food didn’t taste as fresh and wasn’t presented as well.  This lead us to conclude that this spot could be a bit hit or miss. We’d go again, but wouldn’t make it a part of our must-visit destination each time we go.

Auggie’s Draft Room

3 St George St, St. Augustine, FL 32084  auggiesdraftroom.com

A self-serve tap house with affordable and tasty burgers

St George Street in St. Augustine is where the crowds go to take in some of the historic architecture of St. Augustine while browsing various shops and restaurants. It’s a busy and touristy pedestrian-only walkway. As we walk, we like taking lots of little breaks away from the crowds for food and drink.

The self-serve draft system at Auggie’s

We visited Auggies mainly because we had a coupon from the coupon book we picked up at the St Augustine Visitor’s Center, but we were also intrigued by their burgers and their unique draft system that allows you to pay by pour. The burgers were good and served quickly, and the open seating was a very nice atmosphere. The beers on the draft weren’t an exotic selection by any means – Bud Light was one of the selections — so we just had a few small pours and then headed to the St. Augustine Distillery tour that was right next door.

St. Augustine Restaurants We’d Love to Try

Even with this long list, there are still some classic St. Augustine restaurants as well as classic and world-famous spots that we haven’t visited yet. On our next visit we’d love to try these places that we’ve heard good things about.

Llama

We’ve heard Llama offers a fine dining experience of fantastic Peruvian food expertly prepared by their chefs using classically trained methods. The dishes are works of art and are meant to be an experience. The ceviche and the grouper in plantain leaves would be dishes we’d love to try.

Forgotten Tonic

We peeked at the menu here when dining nearby at getting some ice cream sandwiches at Peace Pie, and both the atmosphere and the menu looked fantastic!

Aunt Kate’s

This waterfront restaurant is located in the Vilano Beach area. and has a 100-year tradition of serving seafood baskets and entrees that are exactly the kind of food we love to eat on vacation.

Harry’s Seafood Bar & Grille

Harry’s Seafood Bar & Grille, is supposed to be a legendary spot nestled across from the Bridge of Lions across from the fort on one of the main streets of St. Augustine. We tried to get in twice, but unfortunately, it was packed and too long of a wait for our party. However,  we did get to quickly glimpse at the gorgeous courtyard garden. We’d love to have lunch on a leisurely day here in St. Augustine.

Colombia Restaurant

The Columbia Restaurant is part of a chain known as Florida’s Oldest Restaurants, and since St. Augustine is America’s oldest city, it’s almost like you’re getting double the history! The Columbia is known for award-winning Spanish and Cuban cuisine. This location is also known for its impressive architecture with an open two-level style courtyard and tile-lined space and fountains. Everything from the famous 1905 salad to the Cuban sandwiches for lunch, tapas, or one of their seafood or steak entrees served in the traditional Spanish style all sound delicious to us!

More Ideas for Where to Eat

If you’re looking for more ideas for where to eat in Florida, check out our best places to eat in Marathon, Florida.

We’ll also be soon writing more about our experiences camping at Anastasia State Park in St. Augustine as well as our picks for the best bars in St. Augustine, and where to enjoy some sweet treats when visiting St. Augustine.

If you’re snowbirds like us, who go north for camping in the summer, you might also enjoy hearing about our travels further north camping in the Delaware Seashore as well as our adventures camping in Boothbay, Maine.

 

We’ve stayed in Marathon, Florida for several seasons camping in the Florida Keys at our home-away-from-home at Jolly Roger RV Resort. While we stay, we enjoy many of the local restaurants repeatedly. And, since everything in the Keys can be expensive, getting the most out of our dining budget becomes a top focus. of our Keys vacation.

If you’re looking for the best happy hours in Marathon, Florida, we’re sharing our guide to the happy hour deals we enjoy most when visiting the mid-point of the Florida Keys.

While we love a good meal, we especially appreciate a good deal on good food even more, that’s why we seek out as many happy hour specials as possible. Since we staying for an extended period in Marathon, finding good food at a good deal is not only a budget-friendly bonus, it’s one of our favorite things to research.

Thankfully, many Marathon restaurants are full of fantastic happy hour specials. That said, we’ve found it’s pretty hard to initially find and keep track of the happy hour specials day-to-day without visiting several sites, reading several reviews, and creating your own list of go-to places to find the best spot for happy hour each night.

In order to help you find those details — and to help ourselves keep track of these happy hour specials as well — we’ve created this guide to all of the Happy Hour offerings we’ve found in the Marathon. We’ve listed them in alphabetical order for easy reading.

As always, happy hour specials change frequently. While we have made our best effort to keep this list up to date, these deals are likely to change frequently or to be discontinued altogether,  you may want to confirm hours, and deals before you go by calling, or checking their website, or social media pages.  If you’re a restaurant in Marathon and you’d like us to make an edit or add your happy hour special to this list, get in touch with us via our Instagram!

 Quick Links for The Happy Hours in this Guide

If you’re looking for a specific restaurant, use these quick links to find their happy hour specials.

Jump to:

• Castaway Waterfront Restaurant + Sushi Bar
• Dockside Boot Key Harbor
• Florida Keys Steak and Lobster
• Havana Jacks
• Key Colony Inn
• Keys Fisheries
• Lighthouse Grill
• Porky’s
• Sparky’s
• SS Wreck
• Tiki 61

 1688 Overseas Hwy, Marathon, FL 33050 (Behind Bluegreen Vacations)

Barnacle Barney’s Facebook Page

3-5 pm Daily

$5.00 

Seasoned Fries

Chicken Mini Tacos

Pizza Logs

$7.00

Chips + Queso

Onion Rings

Sweet Potato Tots

Fried Cauliflower

Guacamole Bites

Creamy Mango Habanero Bites

$10.00 

Pretzel Bun Sliders (2) and Chips

Conch Fitters

Giant Pretzel with Cheese

$12.00

Blackened Tuna Bites

Fried Lobster Bites

Buffalo Wings with Blue Cheese

Barney Wings

Drink Specials

$2.00 off all alcoholic drinks

 

Barnacle Barney’s was a spot we tried for the first time this season. Located off of Overseas Highway, and behind the Bluegreen Resorts, this tiki bar meets sports bar has beautiful water views of the Gulf side of Marathon, outdoor seating that looks out on a few private islands nearby. It’s a great place to spend the afternoon.

If you’re a frozen drink lover, this is one of the few spots with frozen drink specials during Happy Hour.  Their take on the Key Lime Colada was one of our favorites. We also tried the sweet potato bites, the lobster bites, and the sliders that were on a happy hour special. The beer menu features local drafts from Florida Keys Brewing and Islamorada Brewing, with New England classic Narragansett Lager thrown in. In fact, the only drawback if you’re a domestic beer lover, and just want a Miller Lite or a Bud Light, is that all of the beers are local craft beers, except for the ‘Ganset.

Castaway Waterfront Restaurant + Sushi Bar

1406 Oceanview Ave, Marathon, FL 33050

castawaysfloridakeys.com

Happy Hours: 1:00 PM – 4:00 PM  (Closed Wednesdays)

$7.00 Food Specials

Chicken Wings

Fried Chicken Livers

Fish Fingers

2 Chili Dogs

4 PC Crab Rangoon

4 pc Lumpia

Chips and Pico De Gallo

4 PC Tuna Nachos

Spicy Tuna Dog

Spicy Tuna Crunch Roll

California Roll

Dragon Roll

Veggie Roll

Sashimi * Nigiri (3) pc per order

Drink Specials

Yuengling & Bud Light $2

12 oz Well Drinks $5

House Wine $6

Rum Punch $8

Sailors Sedative $9

Bloody Wilson $10

Drafts 1/2 Price 2-3 pm

The happy hour at Castaway Restaurant starts early and has an extensive offering, making it the perfect spot for a lunchtime happy hour, or to do some day drinking if you enjoy that sort of thing.

The Castaway happy hour is full of sushi and seafood options, including special rolls, tuna nachos, fish dip, beers on tap, and cocktails like the Rum Punch. Both indoor and outdoor bar seating is available.

Dockside Boot Key Harbor

35 Sombrero Blvd, Marathon, FL 33050

Dockside’s Facebook Page

Happy Hours:  3:00 PM – 7:00 PM

Food Specials
Sweet Potato Fries: $6

Fish Dip w/Chips: $7

Onion Rings: $6

3 Soft Pretzel w/whole grain mustard: $5.25

Wings (Buffalo/BBQ Ranch/Bleu Cheese): $7

Drink Specials

Well Drinks: $4

Domestic Bottles: $3.25

Bud Light Draft: $2.09

Wines: $3.25

 

Dockside Bar & Grill is located right next to the Boot Key Harbor marina area. It’s a great spot for looking out at the water, enjoying live music, and getting super-speedy bartending service while savoring their great happy hour specials. Deals include: well drinks for $4, Bud Light draft for under $3.00, and as well as tasty bar food at a discounted price. We love and usually order their fish dip and onion rings.

There is live music almost every night from both local musicians and national acts, so it’s well worth staying on past the happy hour specials.

Florida Keys Steak and Lobster

3660 Overseas Highway, Marathon, FL 33050

flkeyssteakandlobster.com

Happy Hours: 11:30 AM – 6:00 PM (Early bird until 5:30 PM)

Food Specials

$5.95

6 Chicken Wings

Mozzarella Sticks

Spinach Artichoke Dip

$6.95

Buffalo Shrimp

Potato Skins

$7.95

1/2 Pound Peel & Eat Shrimp

Calamari with Mango Sauce

Shrimp and Crab Ball

Prime Rib Kabobs

Tuna Tataki

JB Salmon Roll

 Drink Specials

All Well Drinks $5.00

Bud Light 3.00

Iguana Bait – Kolsch 4.50

Stella Artois – Pale Lager 3.50

Spearfish – Amber Ale 4.50

Funky Buddha Hop Gun – IPA 4.50

Featured Stout or Porter 5.00

Domestic 3.00

Import/Craft 4.50

Sailfish Sunrise City – IPA 4.50

Crazy Lady – Blond Ale 4.50

Blue Moon 4.50

O’Douls Non-Alcoholic Beer 3.75

Becks Non-Alcoholic Beer 3.75

Omission Lager – Gluten Free 3.75

Heineken Non Alcohol 3.75

Stella Apple Cider Gluten Free 4.00

3 Daughters Key Lime Cider 4.00

Canyon Road – Cabernet, Merlot, Chardonnay, Pinot Grigio, White Zinfandel
$5 Glass / $12 Half Carafe / $20 Full Carafe

Angeline Sauvignon Blanc 6.00

Moulin De Gassac Rose 6.00

Monte Degli Angeli Pinot Noir 6.00

Florida Keys Steak and Lobster is a must-visit spot for happy hour deals. Not only does it start at 11 am, but it also has some of the best deals imaginable. Florida Keys Steak and Lobster is one of the few restaurants in Marathon that aims to have a bit more of a fine dining experience rather than the typical tiki atmosphere.

The bar is windowless and therefore a little bit dark, so it won’t give you an island outdoor dining experience, but it will give you the chance to sample some delicious peel-and-eat shrimp, calamari, and have a beer for only $3!

We also adore their early bird dinner specials that start at 3:30. It’s ga reat way to have their salad, steak, and seafood dishes for less. Along with Key Colony Inn, this is probably one of the best cheap happy hour deals.

Havana Jacks

 401 E Ocean Dr, Key Colony Beach, FL 33051

havanajacksoceanside.com

Happy Hour 4 pm-6 pm

Food

The Giant Pretzel –  Bavarian salted pretzel served with beer cheese $15

Sesame Seared Tuna Wontons served with wasabi aioli with soy glaze $18

“House Favorite” TNT Shrimp tempura beer battered with boom boom sauce $15

George’s Shrimp Fritters $15

Tuna Tini Hawaiian-style tuna poke with avocado, onion, sesame seeds,  soy glaze,  and wontons $18

Edamame with sesame oil, sesame seeds, soy sauce $9

Coconut Shrimp coconut encrusted  with sweet chili sauce $15

Havana Wings mild, hot, guava BBQ or mango jerk or sweet chili served with blue cheese or ranch and celery

Drinks

$2 off all draft beer, domestic bottle beer, house liquor, and house wine.

The discount on beer and drinks is the real discount here — the food prices seemed a bit high to us. In addition to saving money on these drink specials, Havana Jack’s is a great open-air spot to enjoy live music and ocean views in their bar and outdoor lounge area that overlooks the Atlantic Ocean.

The Coconut Shrimp and Edamame were our happy hour picks, but like we said – $9 to $15 for simple appetizers isn’t exactly a deal. We also loved the Key Lime Colada here, but unfortunately, it’s not on the happy hour.

 

Key Colony Inn

700 W Ocean Dr, Key Colony Beach, FL 33051

kcinn.com

3:00 PM – 5:00 PM (Weekends 12:00 PM – 5:00 PM)

Food

$5 Fried Calamari

$5 Sesame Seared Ahi Tuna

$5 Shrimp Cocktail

$5 Tomato Bruschetta

$5 Caprese Salad

$5 Fried Mozzarella

$5 Mussels in creamy garlic sauce

$5 Cheese Pizza

Drinks

$5 Margarita

$5 Pirate Punch

$5 High Noon

$5 Espresso Martini

$5 Cappuccino Martini

$5 House Wine

$5 Bloody Mary

$4 Well Liquor

$3-$6 Beer

 

The Key Colony Inn’s happy hour is LEGENDARY and for good reason! You can get two drinks and two apps for $20! Those $5 espresso martinis! $5 full-size pizzas! And as you can see from the list, that’s just the start of it.

Additionally, the old-school Florida vibe of  Key Colony Inn located near the Key Colony Golf Club, lined with palm trees, is a classic location.

We love the Pirate Punch, as well as the caprese salad, shrimp cocktail, ahi tuna  ,and — of course — the pizza! These amazing happy hour offerings draw quite a crowd, so you’ll want to get there early for these deals, especially if you want to sit at the bar. Thankfully, the happy hour specials are available in the spacious dining room areas as well.

We are always stuffed after the $5 pizza, but we wanted to stay one of these days for an entree of one of their pasta dishes.

Keys Fisheries

3502 Gulfview Ave, Marathon, FL 33050

keysfisheries.com

 4:00 PM – 7:00 PM

Stone Crab Claw $15 each (Subject to availability and market prices)

Gulf Oysters $23 Dozen / $17 Half-Dozen

Fresh Tuna Poke Bowl $19

Stone Crab Chowder $8

$6 Bar Appetizers
Conch Ceviche
Tuna Sashimi
Crab & Spinach Dip
Smoked Fish Dip
1/4 lb Peel & Eat Shrimp

Upstairs on the deck at the Keys Fisheries Raw Bar (also now known as Shannon’s Crab Trap) is one of our favorite places to be in this world.  A beautiful breezy view of the gulf, great live music, great sunset views,  and an unbelievable deal on stone crab claws and toast at sunset make this one of our favorite spots and the perfect place for an early evening happy hour.

The happy hour specials here are mainly on food, but there is a $1.00 off on some beer and wine as well. Keys Fisheries is known for its fresh seafood, which is why we love their conch ceviche for happy hour.

In addition, we enjoy splurging on the Lime in Da Coconut cocktail or the Lobster Reuben (both are delicious, but not on happy hour specials). The bar also has super-friendly staff who go above and beyond to make your time at Keys Fisheries enjoyable. Be sure to thank them for their exceptional service!

Lighthouse Grill

1994 Overseas Hwy, Marathon, FL 33050

lighthousegrillmarathon.com

Happy Hours: 3:00 PM – 7:00 PM Monday – Friday

Food

Drinks

$2 off all Drinks

The Lighthouse Grill, the bar within Faro Blanco Resort, is a beautiful spot for an upscale happy hour experience. In addition to the food and drinks, we enjoyed the panoramic view of the marina and water.

While the happy hour specials don’t offer any huge bargains on dining, it was a nice way to sample some of their apps and drinks at a discount.

The cocktails are expensive (we paid $19 for a martini off the happy hour!), so it’s nice to have that $2 off option. We tried the Cuban Rice Balls for our app, thought it was delicious, and would order it again.

Porky’s

1410 Overseas Hwy, Marathon, FL 33050
3:00 PM – 6:00 PM
www.porkysbaysidebbq.com

Drinks

 $8 – The Following Classic Cocktails:

Mojito

Rum Punch Margarita

Pina-Colada

Pain Killer

—

$5 Sangria

Red or Sparkling

$5 Wine

Red: Cabernet, Merlot, Pinot Noir

White: Chardonnay

—

$5 Well Drinks

Pinot Grigio, Sauv. Blanc Sparkling: Moscato

Draft Beer

Andre Brut Champagne

$4 Bud Light

$5 Stella Artois

$4 Domestic Bottles

$6 Iguana Bait

Bud, Bud Light

$6 Islamorada Seasonal

Coors Light

$6 Marlin Wit

Miller Lite, Mich Ultra

$6 Funky Buddha IPA

Food

75¢ Peel ‘n’ Eat Shrimp (10 minimum) Served Chilled

$1.75/each Fresh Oysters (6 min)

$6 Pork Belly Bites w/Remoulade Sauce

$8 BBQ Pork or Chicken Sliders (3)

For Brisket (add $2); NC Pork or Mojo Pork (add $1)

$9 Smoked Chicken Wings (6)

(Buffalo or Spicy Thai)

$8 Fish Fingers

$8 Chef’s Tacos of the Day (2)

$9 Calamari

$9 Blackened Mahi Quesadilla

$9 Mussels Marinara

$9 Tuna Tataki

$8 Classic Roll / $8.50 Spicy Roll (choose Tuna or Salmon)

$12 Saku Tuna Nachos

 

Porky’s Bayside is in one of the many tiki huts on our happy hour list. This open air spot is off of Overseas Highway and one of the last stops before you cross the Seven Mile Bridge as you are on the way to Key West, but is still near Marathon.

This bar offers a casual atmosphere, marina side location,  and live music. We love that this happy hour includes good drink specials like a Pina Colada and a Painkiller – it’s hard to find good frozen mixed drinks on happy hour, but this place has a great selection of frozen and hand-mixed tropical cocktails.

 

The food is also a big draw for their happy hour offering. In fact, we have never dined for a sit-down meal here. We’ve only had happy hour food where we enjoyed the tacos of the day, the BBQ sliders, and the Mahi quesadilla especially. The only dish we didn’t enjoy were the pork belly bites which were too fatty and chewy for our liking.

The service behind the bar is excellent, with attentive and friendly bartenders.

Porky’s also have one of our favorite takes on key lime pie – a wedge of key lime pie with fried panko bread crumbs and raspberry sauce.  We’ve heard good things about the breakfast too, and the dinner menu is substantial.

Sparky’s

6850 Overseas Hwy, Marathon, FL 33050
4:00 PM – 6:00 PM daily (Closed Mondays)

www.sparkyslanding.com

Peel & Eat Shrimp and Wings $0.45 each

$1.00 off imports and drafts

$6.00 House Wine

$5.00 Domestic Bottles

$5.00 Well Drinks

 

Sparky’s Landing is one of our favorite restaurants in Marathon, and it was one of the best places in our article on The Best Restaurants in Marathon, Florida. Sparky’s features a large bar overlooking the water, outdoor waterfront seating, and a huge oversized tiki dining room. Sparky’s is a very popular spot; the bar is always packed, but it’s extremely hard to find a seat at happy hour, so arrive early!

The happy hour has been voted one of the best in Marathon, but to be honest we’re not sure why it gets this award. We find that it’s a very limited happy hour offering compared to some of the others we’ve mentioned here. The food specials are just the peel-n-eat shrimp and wings,  and if you don’t like either those (and one of us doesn’t at all!) you’re kind of out of luck for food. We prefer several of the other Marathon happy hours that offer a nice discount off of a range of small plates and appetizers from the regular menu.

 

The same goes for the drink specials, which are beer, wine, and well drinks. We love the specialty cocktails at Sparky’s, but since there’s no happy hour discount on those there’s no huge deal for us here on drinks either. We usually just settle for a beer or a rail rum and coke. Add to that the trouble with finding parking and bar seating after 4 and we’ve gone the opposite direction where we actually will avoid going to Sparky’s during happy hour, and go at 6:30 once happy hour clears out.

When we do go, we usually end up just ordering full-priced small plate or entree and drinks here – which, from their business perspective is probably great, but we’d really like to see a happy hour of a small menu that offers a discount on the delicious food the offer and at least one of the special cocktails that Sparky’s is known for before we would be able to give it our own little award for best happy hour.

SS Wreck

Hours: 3:00 PM – 5:00 PM
58835 Overseas Hwy, Marathon, FL 33050
www.sswreck.com

$8 – Special Menu

$1 OFF – Bottle & Draft Beers

$1 OFF – House Wine

$1 OFF – Well Drinks

$1 OFF – Seltzers

 

The S.S. Wreck was mentioned in our best key lime pie article for having the best key lime pie. But before we tried the delicious key lime pie, our first visit to “The Wreck” was for the happy hour.

Our first happy hour here was a bit of an uneven experience from a service perspective, with slow-to-arrive food and an overly-feisty waitress who gave us grief when we ordered water along with our drinks, and then forgot about us. After that first bad experience we have had some very good service there from the two servers who are most often behind the bar.

The day we went the special menu happy hour offering was nachos, and we just had 2 Coronas, so it was a pretty uneventful happy hour experience for us, but largely as a result of our own ordering. It’s not always clear what will be offered on the $8 special menu for food, but we appreciate the $1 off drinks. When not ordering from the happy hour menu,  we really enjoy the coconut shrimp, fajitas, tuna poke nachos from the regular menu as well as the legendary key lime pie!

Tiki 61

243 61st Street, Marathon, FL 33050

tropicalcottages.net

$1.00 off Beer, Wine and Canned cocktails

$1.50 off  Signature Drinks and Shots and Cocktails

 

Tiki 61 is located in the Tropical Cottages off of  Overseas Highway. Tropical Cottages are vacation cabin rentals, that are also home to a taco food truck called La Isla Tacos as well as a tiki bar called Tiki 61. Florida Keys tiki bars are one of the best things about the Keys, Tiki 61 is exactly the kind of atmosphere we love in the Keys.  It’s a local favorite, has live music, and there’s usually a seat somewhere. Tiki 61 and the Tropical Cottages were recently featured on Motel Rescue, and had an amazing makeover as a part of that process. The bar is now beautifully appointed with updated chic tropical decor. The cocktails are fantastic, and all of our favorites are on the daily happy hour which is $1.50 off signature drinks and $1.00 off beer, wine, and canned cocktails. We love the Painkiller, Rum Runner, Pina Colada, and the Strawberry Margarita. The tacos from the taco truck, aren’t a part of the happy hour, but grab a fish taco and then settle in for a few drinks during happy hour for a wonderful evening.

Places to Eat and Things to Do in Marathon Florida

We hope this helps you keep track of some of the best happy hour specials in Marathon, Florida. We’ll keep adding to this as our travels continue! Until then, save us a seat at the bar!

For more recommendations, check out our picks for the best restaurants in Marathon, Florida.

If you’re a camper or RV, also check out our thoughts on the best RV camping in the Florida Keys.

As with all of our posts, the information provided here was accurate to the best of our knowledge at the time of our visits to these restaurants. However, menu items, locations, hours, and availability are always subject to change. You may want to double-check specials, as well as restaurant locations and hours. All opinions are our own.

Except where noted, all images are photographed by and copyright of the editors of Currently Traveling. Use of our photos is prohibited without permission. None of this content was sponsored unless noted we always purchase our own food and beverages for all the dining experiences mentioned in this article.