The Best Places for Pizza in Annapolis, MD

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 visit these restaurants by calling or checking their websites 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 the 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 on the edge of Eastport, but it’s also a spot for delicious farm-to-table offerings, salads, and a wine bar that makes 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 that needs to be saved just for special occasions. Getting a seat might mean a wait; however, 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, 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 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 our conversations with their team members, we learned that Timber has several other DMV locations, including one in DC and two in Virginia, making the move to Annapolis a natural extension of the business. They also just opened a new location in Edgewater.

Their wood-fired approach and bright, sunny space at their new West Street storefront had people lining up for 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 it 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 ordered frequently – especially while moving or on those nights when cooking didn’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 — it 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, but it also 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.

Secret Spot

25 Market Street, Annapolis, MD secretspotannapolis.com

Secret Spot is a new pizza establishment that opened a few months after we first published this post, and it definitely deserves a mention among the best pizza spots in Downtown Annapolis.

Secret Spot is a little bit hidden inside their stall at the Market Space food court on Market Street in Downtown Annapolis, across from Ego Alley and Middleton’s. The Secret Spot can be found in a stall towards the back of the building.  We had a chance to try this pizza when someone brought a few pies to a party we were attending, and we were impressed. It was a classic Neopolitan style. We had the margarita and loved it for the generous dollops of mozzarella and whole basil leaves.  If you’re Downtown and need a quick slice or a whole pie, it’s worth seeking out the Secret Spot!

Rocco’s Pizzeria

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

Rocco’s Pizza is unpretentious yet 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 shop, we were ordering Rocco’s subs and pizza for several weeks during the move.

Rocco’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 can feel a little rushed, and you might have to wait a bit for someone to pick up 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 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 of those unique-to-the-establishment pizzas that should be tried, even just for the novelty. Sandwiches, salads, and kids’ menu offerings are also available.

Service was very friendly, but the bar floor needed a bit of a wipe-down, as it was covered in 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 in Annapolis

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 Annapolis 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!

Update: There are a few new pizza places that have moved to the area that we need to try.  We can’t wait to check out the new Positano restaurant that opened in West Annapolis in the beautiful space where Agave used to be.  Additionally, we recently learned that Luna Blu has a great selection of pizzas, so we’re eager to try those. We’ve also heard that The Right Slice in the Annapolis Mall is a hidden gem for pizzas. We plan to visit these spots soon and we’ll update our list and pictures when we do!