Every fall, Annapolis turns into a floating festival of sails, stories, and seafaring spirit—and even if you’ve never hoisted a halyard (let alone know what one is), you’re welcome to come aboard. Whether you’re a lifelong sailor or a certified landlubber, the Annapolis Sailboat Show (Oct. 9–12, 2025) is the perfect excuse for a Chesapeake Bay escape.
Here’s why this iconic event should be on your calendar:
1. Annapolis Turns into a Floating Village—And You’re Invited
City Dock becomes a walkable marina, with two miles of floating docks lined with boats from around the world. You’ll need a ticket to enter—but once you’re in, the harbor is yours to explore.
2. Boats as Far as the Eye Can See (and Yes, You Can Climb Aboard)
From sleek catamarans to pocket cruisers and bluewater dreamboats, you’re welcome to step aboard, chat with dealers, and imagine your life at sea.
3. It’s Not Just for Sailors—It’s for Anyone Who Loves the Water
Even if you’ve never set foot on a sailboat, this show is packed with exciting exhibits. Think high-tech gear, sunset charters, luxury lifestyle products, and great people-watching. You can even get an introductory on-the-water lesson at the First Sail Workshop.
4. Mimosas, Music, and Maritime Vibes in the VIP Lounge
Looking for a little luxury? The AXOS Bank VIP Experience includes breakfast, open bar, and comfy lounge space with front-row views of the show.
5. Be Inspired by World Travelers and Weekend Adventurers
The Cruisers Creating Content crew is back—YouTubers, bloggers, and podcasters who live life afloat. Meet them in person and pick up tips for your own adventure.
6. Learn a Thing or Two—Even if You’ve Never Tied a Knot
Free daily seminars cover everything from navigation apps to cruising the Great Lakes. No experience needed—just curiosity.
7. Plan Your Dream Getaway in Vacation Basin
Thinking Caribbean charter or a tour of the Med? The show’s travel hub features charter companies and destinations ready to help you plot your next adventure.
8. The Perfect Excuse for a Fall Escape
October in Annapolis is magic. Golden leaves, brick-lined streets, sailboats at every turn, and the best seafood on the Bay.
9. Eat, Drink, and Stroll Through the Heart of America’s Sailing Capital
Bookend your boat show experience with dockside drinks, live music, and shopping in one of the East Coast’s most walkable historic towns.
Ready to come aboard? The Annapolis Sailboat Show runs October 9–12, 2025. Visit AnnapolisSailboatShow.com for tickets, parking tips, and the full lineup. See you on the docks.
