October 9–12, 2025 | City Dock, Annapolis
Every October, Annapolis transforms into the beating heart of the sailing world. The Annapolis Sailboat Show isn’t just the largest sailboat show in the world—it’s the place where sailors and dreamers come together to climb aboard, learn, shop, and soak in the lifestyle. Whether you’re a lifelong cruiser or someone who likes the idea of cocktails on a catamaran, here are six reasons to make your way to City Dock this fall.
1. Climb Aboard Boats
The docks will be lined with everything from nimble daysailers to luxury catamarans and bluewater-ready cruisers, and you’re invited to climb aboard. This is your chance to wander cockpits, duck below decks, and imagine what it feels like to be at the helm. Want to compare layouts, check out rigging, or just see what it’s like inside a brand-new 50-footer? The Annapolis Sailboat Show makes it possible to tour more boats in one afternoon than you’d normally see in a season.
2. Vacation Basin
Not ready to buy a boat but curious about the lifestyle? Vacation Basin is your passport to sailing adventures. Sponsored by Cruising World, this popular section of the show is filled with charter companies and exotic destinations ready to help you plan your next getaway—whether that’s a bareboat charter in the BVI, a captained cruise in the Mediterranean, or a family week in the Chesapeake. Unforgettable vacations start at the Annapolis Sailboat Show.
3. Shopping
It’s not just about boats—though there are plenty of those. More than 500 exhibitors set up along the docks and under the tents, showcasing everything from high-tech electronics and custom sails to nautical artwork and coastal home décor. Need a new foul-weather jacket? Thinking about upgrading your chartplotter? The shopping at the Annapolis Sailboat Show is part retail therapy, part treasure hunt, and a whole lot of fun.
4. Educational Opportunities
Sailing may be a lifelong pursuit, but it doesn’t have to have a steep learning curve. The show’s educational programs are designed to give sailors of all levels the tools and confidence they need. New to sailing? Enroll in an on-the-water training program. First Sail Workshop lets you practice docking, sail handling, and navigation under the guidance of experienced instructors. Looking to sharpen your skills? Attend advanced seminars on cruising, safety, and maintenance.
5. Family Fun
The Annapolis Sailboat Show is more than a sailor’s playground—it’s a family-friendly day out. Kids love scrambling around cockpits and peeking into cabins, while parents can relax knowing there’s plenty to see and do off the docks as well. Vendors often have interactive displays, and the whole atmosphere is festive, with food, music, and plenty of ice cream within walking distance. It’s an easy way to introduce the next generation to the water—or just enjoy a fall day together by the Bay.
6. Exploring Annapolis
Of course, the show is only part of the draw. Annapolis itself is worth the trip. With its brick streets, colonial history, and lively waterfront, the city is a destination in its own right. After the show, stroll historic downtown, tour the U.S. Naval Academy, or duck into one of the many pubs and crab houses that give the city its charm. October is an especially magical time to visit, with crisp air, golden leaves, and the Chesapeake at its best.
Plan your trip now for October 9–12. Whether you’re dreaming of your first daysailer, shopping for gear, or simply enjoying a weekend getaway, the Annapolis Sailboat Show is where locals and sailors from around the world come to connect, explore, and celebrate life on the water.
Ready to come aboard? The Annapolis Sailboat Show runs October 9–12, 2025. Visit AnnapolisSailboatShow.com for tickets, parking tips, and the full lineup.
