Set Your Course for Annapolis

October 9–12 | Annapolis, Maryland

Welcome, Sailing Magazine readers! Whether you cruise across coastal waters, race on inland lakes, or tow your boat from one adventure to the next, the Annapolis Sailboat Show is where your story intersects with the global sailing community. The docks are packed with bluewater cruisers, performance monohulls, and trailerable racers from top builders—offering something for every type of sailor.

A Waterfont Unlike Any Other

Each October, Annapolis transforms into the world’s largest in-water sailboat show. More than 175 boats, 500 exhibitors, and two miles of floating docks fill the historic harbor and City Dock area. Tucked between brick-lined streets and the U.S. Naval Academy, the show offers a walkable, waterfront experience that’s as charming as it is expansive.

Learn More about the Show

Big Adventures, Small Footprints

For sailors who tow between lakes or launch from local ramps, the Annapolis Sailboat Show features an impressive lineup of trailerable sailboats—compact on the road, mighty on the water. From the timeless Sandpiper 15 and Sakonnet 23 to the sleek Storm 18 and high-performance Saffier 27, these small boats offer big possibilities. Racers can explore the hydrofoiling Birdyfish and one-design favorites like the MacKay VX One and VX Two, all proof that big sailing dreams can fit right in your driveway.

Check out the Boat List

Come for the Boats, Stay for the Camaraderie

More than a boat show, Annapolis is a reunion. Join seminars led by seasoned seafarers, get hands-on with the latest gear, and trade stories dockside with sailors from every corner of the map. You’ll leave with new ideas, new gear, and maybe even a new crew.

Attend the Show

Plan Your Trip

Fall brings crisp breezes and serious sailing energy to Annapolis—making it the ideal backdrop for the biggest show of the year. After exploring the docks, unwind in the walkable Historic District, where pubs, shops, and seafood spots line the cobblestone streets. Find travel tips, hotel deals, and everything you need to make the most of your visit to America’s Sailing Capital.

Start Planning Your Visit