Six Ways to Experience the Annapolis Sailboat Show

October 9–12, 2025 | Downtown Annapolis, MD

Each October, the sailing world drops anchor in Annapolis. Whether you’re outfitting a bluewater cruiser, fine-tuning your raceboat, looking for the perfect daysailer, or just dreaming from the docks, the Annapolis Sailboat Show is where you will connect, explore, and be inspired. With an incredible range of boats, gear, experts, and experience, the show offers something for every kind of sailor. Here are six ways to make the most of your visit:

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The Dreamer: Step Aboard, Imagine the Possibilities

Maybe you’re planning your first charter. Maybe you’re ten years out from retirement. Or maybe you’re just in it for the salty air and sleek lines. Whatever the reason, the show delivers plenty to inspire— a huge diversity of boats including decked-out catamarans, and stunning monohulls, and the best people-watching on the waterfront. 

New to sailing? You’re not alone. The Annapolis Sailboat Show is an ideal launch point, with beginner-friendly boats, intro-level seminars, and a welcoming crowd. Climb aboard a pocket cruiser, try a sailing dinghy, or ask the questions you’ve been Googling for months. You can even sign up for an introduction to sailing complete with an on-the-water session in the popular First Sail Workshop. Everyone starts somewhere—and this is the place to do it.

Come walk the docks and join the party.

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The Seeker: Learn Something New

Learning is a crucial part of sailing, and the Annapolis Sailboat Show offers many opportunities to start and expand your skills. Beginners may join hands-on classes like First Sail Workshop, while more experienced sailors can attend expert-led seminars through Cruisers University or take part in the popular Offshore Emergency Medicine Class. Daily free seminars from industry partners cover topics such as navigation, weather, boat systems, and cruising techniques. No matter your experience level, there is always something new to learn, and the show is a great place to do it.

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The Cruiser: Find the Boat That Feels Like Home

Cruisers come to Annapolis to see what’s new, compare liveaboard-ready designs, and get hands-on the latest gear. It’s the ideal setting to explore tech, talk with vendors who understand passagemaking, and step aboard boats built to go the distance. Whether you’re prepping for your next crossing or planning your first season aboard, you’ll find the tools, knowledge, and support to make it happen.

The Cruisers Creating Content Booth has evolved from a small group of top creators into a vibrant, bustling hub at the show. Creators from around the globe gather here to connect, collaborate, and share their passion for sailing. From Youtube content to informal dockside chats, this is your chance to connect with the storytellers who may have inspired your own journey into the sailing lifestyle. Ask questions, swap experiences, and find new motivation from those who do it full time.

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The Gearhead: Get Your Hands on the Hardware

Riggers, sailmakers, electricians, and tech reps are all here—and they speak your language. From windlasses and watermakers to MFDs and sail handling systems, Annapolis offers a rare chance to compare top-tier gear side by side. Don’t just read the spec sheet—talk to the people who built it.

Explore a wide range of marine equipment designed for all kinds of sailors. Cruisers will find reliable watermakers, autopilots, and sail handling systems for long passages. Racers can check out lightweight carbon spars, high-performance sails, and advanced race electronics. Day sailors and weekend adventurers will discover easy-to-use navigation tools, durable rigging, and innovative deck hardware. Even if you’re not a sailor yet, the show offers plenty to enjoy, from stylish sailing apparel to fun gear and accessories.

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The Racer: Chase the Edge

Annapolis is a goldmine for hardcore racers. Compare high-performance hulls, talk sail inventory with loft reps, and check out the latest in foil design, carbon spars, and race electronics. Whether you’re racing weeknights or preparing for your next offshore A-to-B, you’ll find the tech, talent, and tools to stay ahead of the fleet.

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The Traveler: Choose Your Next Destination

Charter companies from around the world converge in Vacation Basin, ready to help you plan your next adventure. Talk to experts about bareboat, flotilla, or fully crewed options in the Med, the Caribbean, the South Pacific, and beyond. While you’re there, step aboard some of the beautiful monohulls and spacious catamarans available for charter and speak directly with company representatives to find the option that’s right for you. You don’t have to own a boat to live the sailing life—you just need the right escape plan.

Annapolis offers more than just a world-class boat show. Explore its historic streets, dine at award-winning restaurants, sip drinks at waterfront bars, and take in the charm of a town that lives and breathes sailing. Turn your visit into a weekend and see why sailors return year after year.

Ready to Find Your Course?

From first-timers to lifelong sailors, Annapolis offers something for every kind of sailor—and every kind of sailing.

Attend The Show