Annapolis Boat Show: Sail Into the Week With Us!
The Annapolis Sailboat Show is almost here, and Go Sail Virgin Islands is looking forward to attending once again. If you aren’t familiar with the fall event, it’s 4 days of fun for sailors of all levels. You can shop for the latest sailboats, meet other boating enthusiasts, and chat about anything from new gear to new sailing spots you’ve discovered throughout the year.
Our Go Sail VI instructors had the time of our lives last year, and we can’t wait to go back! If you haven’t been to the event, here’s a quick guide to the Annapolis Sailboat Show 2025 to get you up to speed.
What to Expect at the Annapolis Sailboat Show
The best time to visit “America’s Sailing Capital” this year is between October 9-12. Not only can you experience some ghost tours and giant pumpkins scattered around the historic city for “Spooky Season”, but you can also attend the best sailboat show in the country.
For 50+ years, the bustling village and capital of Maryland has hosted the popular sailing boat festival, the Annapolis Sailboat Show. The occasion attracts well over 100,00 people who come to take a look at new releases from some of the industry’s most popular boat makers.
Aside from shopping for a new sailboat, this show offers fun for the entire family—with events, great restaurants, and even a chance to sail around the famed estuary. ASA-accredited sailors can take you on a 90-minute tour of Chesapeake Bay. If you find your sea legs, you can take ASA courses on a Caribbean vacation with Go Sail VI!
What to Eat at the Annapolis Sailboat Show
One of the best things about visiting Annapolis is all the great seafood. There are great places to eat all around town, and you can find food trucks and cocktails at the event.
If it’s your first time in town, the tourist favorite Chic & Ruth’s Delly is a must. However, we’ve found some other spots that you won’t want to miss.
Boatyard Bar & Grill
We can’t say no to the oysters at this local favorite opened by Chesapeake Bay native Dick Franyo. The Boatyard Bar & Grill is located right on Restaurant Row, so it’s a great place to go for happy hour before you try one of our instructors’ other favorite Annapolis restaurants.
Cantler’s Riverside Inn
Cantler’s Riverside Inn is the place to go for a soft-shell crab sandwich. It’s fresh, perfectly crispy, and has been a local favorite for decades. They also serve crab cakes, steamed clams, and dozens of other seafood specialties.
Iron Rooster
Breakfast is the most important meal of the day, especially when you’re sailing or shopping for a new sailboat. Iron Rooster is where you’ll want to fuel up for the festivities with lots of great dishes to choose from—but we can’t visit without ordering the chicken and waffles.
Where to Stay Near the Annapolis Sailboat Show
Annapolis is the oldest incorporated city in the United States, and you can feel the history as you walk around Main Street. It’s close to the action, and there are some great places to stay in the heart of the city.
The Maryland Inn
One of 3 of the Historic Inns of Annapolis, The Maryland Inn allows guests to stay in a famous hotel that has been in the center of the Maryland capital since the 18th century. The rooms are cozy with an old-world feel, and it’s a unique experience to stay inside one of the skinny brick buildings that downtown Annapolis is known for.
Learn the Ropes With Go Sail VI
Attending the Annapolis Sailboat Show is a great way to meet both new sailors and industry veterans. Reach out to Captain Genevieve before the event if you want to learn a little more about the show or talk about our ASA sailing courses in the Virgin Islands!