Guide to Attending the Annapolis Boat Shows

The fall season means a lot of different things to people: fall leaves, pumpkin picking, cozy coffee drinks, and Halloween. But in Annapolis, most locals and boaters think of October as Boat Show Season.

Before we ever kept our boat in Annapolis, we visited Annapolis each October to see the latest sailboats and equipment.  Now that we keep our boat here and live in town, we’ve attended Annapolis Boat Shows for at least a decade and, more recently, worked the show as part of the crew.

Whether you live here or you’re just visiting, nothing quite compares to watching Ego Alley transform overnight and fill up with hundreds of boats every fall. If you’ve never been, the Annapolis Boat Shows are a world-famous event that attracts boaters and spectators from all over the world.

As always, we’ve made every effort to keep this article accurate at the time of publication, but show details can change quickly due to weather and year-to-year changes and conditions. Always refer to the official Annapolis Boat Show site for the most up-to-date information.

Annapolis Boat Show: Our  Guide to Making the Most of The Show

The historic Annapolis City Dock and the waterway known as Ego Alley are normally home to a handful of boats along the docks by the waterfront restaurants, as well as a few slips and the water taxi stand, and boaters cruising up and down the alley to see and be seen from the local restaurant decks. During boat show season, however, this space transforms overnight, thanks to a skilled and synchronized crew.  Docks that have been waiting in storage are floated in, and all new boats are directed in as the space transforms into a floating marina packed with everything from dinghies, daysailers, and cruising catamarans.

Annapolis Sailboat Show vs. Annapolis Powerboat Show

If you’re not a boater and you’re just going to the show for fun, you may not fully understand the all-encompassing term Annapolis Boat Show and the difference between the Annapolis Sailboat Show and the Annapolis Powerboat Show. The Annapolis Boat Shows are two separate shows held back-to-back in October. There are also smaller boat shows that take place in the Spring and across the Bay Bridge in Grasonville.

The Powerboat Show– officially called the United States Powerboat Show — now comes first in October, typically the first full week of October, and this show is a chance to see all the powerboat favorites that are very at home on the waters of the Chesapeake Bay.

This year, 2026, the Powerboat Show will be October 8-11. At this in-water show, you’ll see motor yachts, trawlers, family cruisers, center consoles, and inflatables, as well as small trailerable boats on land (aka on the hard) that are still available to board.

Unlike the Miami Boat Shows, the Annapolis powerboat shows keep to smaller boats and motor yachts under 50 feet or so; the megayachts and superyachts, as seen in Miami, aren’t part of the show. There are also tents of vendors here at the powerboat show with gear and equipment made especially for powerboats. During a short changeover after the last day of the show, the powerboats will leave, the docks will be reconfigured, and the sailboats will arrive.

The Annapolis Sailboat Show takes over the same space with sailboats of every sort and is considered the bigger of the two shows, since there are many more boats and attendees, and also because Annapolis is known for being the sailing capital of the world.  In 2026, the Sailboat Show will be held from October 15- 18.  The Sailboat Show really shows the range of hull styles, from monohulls, catamarans, and other multihulls to racer-cruisers and ocean-going yachts from builders around the world. Each show has its own tickets, so you’ll need to purchase tickets for each show and day individually.

There’s also a smaller Annapolis Spring Sailboat Show every April at the same City Dock location, which is a nice lower-key show to attend if you’re able to make the trip twice a year, and the Bay Bridge Boat Show in Grasonville near Kent Island, put on by the same organization.

Getting There By Boat

Many boaters and cruisers plan their trip south in late summer and early fall around not only hurricane season and weather windows, but also with the aim of arriving in Annapolis in October for the boat show, especially the sailboat show.

Between long-distance sailors and a few local boaters who want to attend by boat, the mooring fields fill up quickly and need to be reserved in advance during boat show weeks. The usual slips in Ego Alley are occupied by the boat show, and City of Annapolis moorings are first-come, first-served, so plan your travel accordingly. You can find out more about the Boat Show restrictions and available mooring fields via the Annapolis Harbormaster’s website.

If you don’t mind being at anchor, there’s also an anchorage on the Severn, just outside Spa Creek near Horn Point, but this is a very windy and choppy spot, especially with busy boat traffic and gusty fall weather.

Local marinas like Annapolis City Marina, the three Safe Harbor Marina locations in town (formerly Mears, Port Annapolis, and Eastport Yacht Center), and others sometimes have transient slips available, but still plan and reserve early.

If you’re planning to be at the mooring balls and dinghy into the show, be aware that some usual dinghy landings at Ego Alley and Prince George St. Dinghy Dock will not be open, but a dedicated dinghy dock at the end of Shipwright St. will be available for boaters to use. You’ll have to walk a bit from that dock to get to the show gates.

Another easy way to get to the show from the moorings or the Eastport side of town is to use the Water Taxi, which will pick you up at your position in the mooring field and stop at Annapolis City Marina, Carrol’s Creek, and other locations. Because of the show, the stops might be slightly modified and will be more crowded than usual because of the number of passengers. If you’re on your boat, you can also hail the Water Taxi on 68 and be picked up right on at your boat.

Places to Stay

If you’re planning to stay in Annapolis during the show, the hotels book up quickly with visitors and vendors who have come into town for the show. The Annapolis Waterfront Hotel on Compromise Street is located right in the middle of the show action, near the main gates, and hosts several events and seminars.

Other downtown hotels like The Westin, The Hilton Garden Inn, The Graduate, and others on West Street provide a place to stay that is about a 15 -25 minute walk to the show. The Historic Inn on State Circle, as well as the Gibson’s Inn near the USNA gates, and other hotels, boutique hotels, and bed-and-breakfasts. The Boat Show has a list of several hotels close to downtown, but space is very limited.

Many boat show attendees also opt to rent a house with friends or family through Airbnb or VRBO, and Annapolis usually has great options, since many local residents rent out homes for the boat show, Commissioning Week, and other family events at USNA.  However, like everything else, most rentals go quickly, so again planning ahead for where you’ll stay is a great idea.

If you’re out of luck staying right downtown or close by on West Street, there are other hotels farther outside of town in areas like Riva and closer to Edgewater, which will require you to either Uber in or drive in and use the designated parking.

Parking

Parking is perhaps one of the biggest concerns when attending the boat show, even for seasoned visitors. Downtown Annapolis is small, historic, and already has parking issues on a day when the show isn’t in town. Additionally, the show takes up some of the parking areas for the vendor and exhibitor tents, so parking anywhere close to the show is nearly impossible.

Our advice is to skip trying to find street parking anywhere near City Dock altogether, and plan to park in the official show parking, which is about 2 miles away at Navy-Marine Corps Memorial Stadium on Taylor Avenue. The show runs a free shuttle continuously from this lot to the main show gate on Compromise Street, about an hour before the gates open until an hour after closing. The show recommends that you reserve your parking spot ahead of time through the parking app rather than showing up and hoping for the best, since the lot does fill up on weekends. You can reserve parking or can get more details about the official show parking situation here.

There are some parking spots that pop up in Eastport, where the Elementary school runs a paid parking lot after 3 pm on Friday through the weekend. There’s also a paid hourly lot outside Carrol’s Creek, which is a quick walk or water taxi to the show. On-street parking is very hard to come by in any section of town, but occasionally you might luck out. Still, pay close attention to signage if you go this route, since fines can be steep. Whichever way you arrive, give yourself extra time; road closures around the Historic District start days before the show opens and stay in effect through breakdown.

What to Wear

While some boat shows have become see-and-be-seen events that bring out a few designer labels and a bit of old-money yachting style, as most boaters know, comfort is key, and a basic T-shirt and shorts are perfectly acceptable boat show attire.

Of course, you’ll want to dress for the weather, which in October in Annapolis can change drastically. The “usual” boat show weather can range from a hot, sunny 85-degree day with clear blue skies to a rainy, cold, damp 50-degree day with flooded docks. The daily weather report will tell you whether you’ll feel most comfortable in a crisp button-down and shorts or a wool sweater, foul-weather gear, and waterproof boots.

Obviously, you’ll want to check the specific forecast for the days before you go, but layers are usually your friend. A t-shirt or tank under a lightweight sweatshirt, shirt, or sweater, paired with shorts, pants, or jeans, is a comfortable way to dress for mid-fall temperatures and make it through the chilly morning and sunny afternoon. If rain is expected later, stash a raincoat or shell in your bag or tie it around your waist, or pick one up at Helly Hansen or other vendors selling foul-weather gear.

Aside from comfort and warmth, the most important fashion consideration at the boat show is footwear. As most boaters know, grippy, non-marking soles are important on the water. Even if you’re not planning a sea trial, you’ll want some stable footwear for navigating the docks, which can be a bit rocky, especially at the outer docks of the show if it’s a choppy or high-traffic day. That said, if you’re planning to tour some of the boats—and we assume that’s what you’re there for—you’ll be asked to remove your shoes when boarding.

The no shoes aboard rule means an easy-on, easy-off slip-on shoe, sneaker, or sandal is usually your best bet. Another thing to keep in mind is that the most popular brands of boating shoes will be worn by many attendees, so if you’re the owner of a popular style of Sperry topsider, Olukai flip-flop, or other boating brand of shoe, you might want to label your shoes in some way so that you can easily determine which pair is yours in a pile of similar styles.

Also, if walking around barefoot on the boat that many others have toured sans-shoes feels a bit off-putting, pair your look with socks or keep an easy-to-slip-on pair in your back pocket to slip on when down below.

You’ll also want sunglasses, sunscreen, and perhaps a hat, since on a sunny day the sun can sneak up on you. Bringing a reusable water bottle is a great idea for hydration, and there are refill stations are available throughout the show.

Days of the Boat Show

Whether you’re attending the Powerboat Show or the Sailboat Show, the day of the week you attend can make a big difference.

For both boat shows, Thursdays are usually VIP days for VIP ticket holders or VIPs, as designated by brokers who may give tickets to serious buyers. For both VIP and General admission, you’ll need to enter at the gates and show your ticket. You’ll get a wristband or handstamp and a map.

The VIP day is meant to be quieter and slower, giving the brokers and prospective boat owners time to talk and walk through the boats they’re considering at a slower, uninterrupted pace.

On the Friday of both shows, the show is open to general ticket holders and gets a little busier and more festive.The lines to get in are longer, so plan on waiting in line for a little bit.

The Saturday of both shows is the busiest day, as you might expect, since it’s the weekend and those who can’t attend on the weekdays will be making their way to the show. Saturday night is usually when most brokerages hold their parties, which are typically by invitation only for owners, so expect the show to wrap up promptly at closing time as various brokers prepare for the after-hours parties.

We’re not sure what the plan is for this year, but in years past, the boat show itself, or a local publication, also hosts a party which is open to all attendees. It used to be on top of Pusser’s, but since Pusser’s is no more, we’re not quite sure what the party plan is, or if there even is one!

Sunday is a busy day, but it’s also the last day of the show, so it can be a good day to get deals from vendors who don’t want to pack up all their wares and floor displays and might be eager for a sale. Close to the closing time of the show on Sunday, you’ll see everyone actively packing up, because the show runs on a tight timeline, especially the last day of the Powerboat Show, where all the boats have to depart to make way for the Sailboat Show setup that starts immediately. So don’t start your first conversation with a vendor or broker at 4:45 pm on Sunday.

What to See and Do Once You’re Inside

If you’re attending for fun and just to browse the boats, take your time milling the docks and hopping aboard anything that appeals to you.

If you already own a boat or you’re thinking of purchasing one, then your approach to the boat show might be different.

If you’re a current boat owner and not looking for a new boat, you might be there for the vendors. If so, you’ll want to be a little organized before you go. Bring notes on the equipment you’re looking for, plus any product numbers, SKUs, and models you have questions about. Bring all your boat specs as well, so you can easily tell whether a product is suitable for your boat. It’s also a good idea to research pricing beforehand so you know what’s a good boat show deal and what isn’t.

Buying at the Boat Show

If you’re hoping to buy a boat at the boat show, you’ve likely been doing some research beforehand. Reading up on the boat manufacturer’s site, watching YouTube videos, and joining owner groups on Facebook or Instagram is a great way to start gathering information on the boat you’re considering.

If you’re very serious, reach out to the brokers for your boat before the show and let them know you’ll be coming ready to purchase. That way, they can set aside time to see you and prioritize your visit. You’ll also want to have all your necessary financial information ready to go.

You might also be looking to join a boating vacation club with fractional boat ownership like the Moorings offers. Again, do your research and make sure you have all your financial information on hand and ready to make a purchase or down payment.

Browsing the Show

If you’re just in the browsing stage and trying to figure out what type of boat is for you, these shows are an amazing opportunity to see a huge variety of makes and models and get familiar with some of the specs and signature styles of each manufacturer. Once you’re through the show gate, we still recommend getting familiar with the slip and dock layout to help you decide. Some brokerage boats are scattered in among the new boats, so you’ll want to take a close look at the show map so you know which slips belong to yacht brokers versus manufacturers.

If you’re just there to tour the boats and not purchase anything, still be ready to register and sign up to see certain boats, possibly wait in line, or schedule an appointment to tour some of the more exclusive listings. Brokers are usually happy to have people tour their boats, but serious buyers will probably take precedence.

As a newcomer, you may not realize that some boats are privately owned boats that have been lent to the broker for the show, so obey all the signs about not opening cabinets or sitting on beds in these boats, because they are personal property.

Attending Seminars

If you’re attending to build your skills rather than just look at hulls, Cruisers University runs alongside the fall Sailboat Show with classes on everything from diesel maintenance to heavy-weather sailing, and it includes show admission for the days you’re enrolled, but there is a tuition fee.

There’s also an Offshore Emergency Medicine class with life-saving techniques for offshore sailors. Newer sailors might be interested in the First Sail Workshop, a hands-on session that gets you actually out on the water working through open-water boat handling and precision docking with an instructor rather than just watching from the dock.

There are also free daily seminars on nautical education topics like chart reading, provisioning, and route planning that don’t require any advance sign-up, which is a great way to fill an afternoon between boat visits. Check out and register for the seminars that are of interest to you here. This year, the classes are held up the street from the show at Historic Inns of Annapolis, the Governor Calvert House, at 58 State Circle.

Meet & Greets

At the Sailboat Show, there are also lots of meet-and-greets with sailing celebrities, aka Cruisers Creating Content, who have made a name for themselves through YouTube, Instagram, and sometimes Bravo boating shows. The times for these meet-and-greets run according to a schedule and are held in a dedicated area of the show. If the cruiser you want to meet has a huge following, expect to wait in line to say a few words and have a photo op.

Boat Show Etiquette

We’ve been to enough shows to have a few opinions about boat show etiquette, and most of it comes down to simple courtesy. Here are a few tips:

Don’t linger in a companionway or cockpit chatting once you’ve seen what you came to see; there’s almost always a line of other people waiting behind you, and the crew showing the boat appreciates it when visitors keep moving.

Always wait to be invited on if there’s a broker managing the flow of traffic. If there isn’t, just make sure that there’s room for you aboard; otherwise, wait until a few others have left the boat. It can get very crowded quickly aboard some of the smaller boats.

Getting off and on some of the boats can be tricky, so offer a steadying hand if you see someone who needs a little help.

Remember, the show docks are floating on the water, so they can be rocky and unstable, especially on windy days. Always walk cautiously, but also keep the flow of traffic moving. If you see someone you know and want to have a chat, make every effort to stand to the side.

If you’re seriously interested in a boat, speak to the reps, and the broker or builder rep will usually give you far more time and special attention than a passerby gets.

And if you own a boat yourself, don’t be surprised if someone who is considering a boat like yours or another boat owner strikes up a conversation with you in line with questions about your shared experience of ownership.  It’s a great way to share your knowledge, learn something new about your boat, and become part of your unique boating community.

That said, you’ll also probably want to keep from saying anything too disparaging or negative about any boat while you’re on board, since the builders and brokers are right there, and you might be affecting the outcome of potential sales. Educated opinions and constructive feedback are usually always welcome, but unvarnished and unfounded opinions might not be.

We said it earlier, but it’s worth repeating: while you can walk the docks with a drink, leave it back on the dock landing while touring the boats themselves. Leave any food and beverages, like coffee, that could spill and stain at the boarding docks or registration area; you don’t want to bring anything on board that could damage the boat.

As we mentioned before, follow any signage on the boat asking you to stay off the beds or keep cabinets closed, since these are either privately owned vessels on loan for the show or sold to a buyer.

Also, while some visitors take videos and photos for content creation or to remember specific boat details, try not to take too long filming or block major walkways while taking photos.

Places to Eat and Drink

When you’re on your feet for several hours at the show, you usually work up quite an appetite. There are a few food options within the show itself, namely The Fleet Club, which is usually a members-only club for members of the Armed Forces, opens up its space, and the members man the stoves and grills to offer their famous Pit Beef sandwiches and a few limited menu offerings.

The Fleet Club also offers beer, canned seltzer drinks, soda, and Cruzan Killers – the Fleet Club’s alternative to the official drink of the boat show – The Painkiller. The top deck of the Fleet Club is a great spot to get a bird’s-eye view of the show, and a great place to watch the show tear down when all the boats depart.

Speaking of Painkillers, this is the first year that the world-famous Pusser’s is now closed. The old Pusser’s space is now occupied by Marmo and Armada, two new Atlas Group-owned restaurants, so we’re not quite sure what will be happening with the official boat show beverage that used to pour so freely. We’re also not sure if the decks of these two restaurants will be serving any boat show specials since the decks are next to the show, but we’ll keep you posted. We know that Armada makes a Painkiller Margarita, but we’re not quite sure if some other vendor has been tapped to bring in the official Painkiller drink that has been synonymous with the boat show for years.

If coffee is more your thing, we have suggestions for that as well. One of the most frequently asked questions my husband fielded while working the show was, “Where can I get a good cup of coffee?” Close to the show, we recommend Storm Brothers, which, as of late September 2026, has begun offering breakfast bites and coffee as a result of its neighboring coffee shop, Bitty and Beau’s, closing as of mid-September 2026. There’s also Rise Up located in the Market House, very close to the show. We’ve written up a guide of the Best Coffee Spots in Annapolis, if you’re looking for a coffee shop anywhere within Annapolis.

Back at the show, there are a few food trucks located at the Dock Street side of the show layout for lunch, but if you want something heartier and more of a sit-down experience, you can leave the show, head out to a restaurant, and come back.

Our favorite spots close to the show are Pip’s for delicious hot dogs and cheesesteaks,  Iron Rooster for burgers, Dock Street for fish and chips or crab cake, McGarvey’s for oysters and sandwiches, Federal House, and Middleton’s are also nearby.

The Secret Spot in Market House offers great pizza (but last we knew they were sold as whole pies, not by the slice), and there’s an Oyster Bar inside as well. Chick and Ruth’s Delly is another classic Annapolis lunch stop just up the street from the boat show. For a classic, nautically on-theme stop a bit farther away, cross the Eastport Bridge and head to The Boatyard. Here’s our list of favorite bars in Annapolis; most offer a quick bite to eat, and all are great stops after the show for a drink and dinner.

Enjoying Downtown Annapolis

Part of what makes the Annapolis Boat Show experience special is that it all happens in a town worth exploring on its own. Main Street and Dock St. are lined with historic brick, hip and delicious restaurants, and boutique galleries and small shops that are fun to visit after the show or between stops.

The area also has a lot of history, plus the Naval Academy, so there’s plenty to see outside the show if your visit allows.

There are also many other restaurants on the Eastport side of town, like the Boatyard. Adam’s Ribs, Davis’ Pub, Blackwall Hitch, Rumhouse, and Vin 909, as well as Lewnes and Carroll’s Creek. They range from casual sit-down places to fine dining, but all are busy for the show, so make a reservation ahead if you can.

More Coastal Travel and Annapolis Things to Do

We’ve written a few guides on places to eat in Annapolis, and we’ll be adding more along with things to do in our city!  Check out these recent posts if you’re looking for the Best Pizza in Annapolis or Best Seafood Restaurants in Annapolis. We have plans to add our picks for the best Restaurants in Annapolis, the best places for breakfast in Annapolis, and more. If you travel up and down the East Coast as we do, you might also like our posts on our favorite places to eat in St. Augustine and favorite restaurants in Marathon, Florida. Also, follow us on Instagram and keep up with our adventures!