A Landlubber’s Guide to the 2025 Annapolis Spring Sailboat Show - April 25-27

Though March 20th is the official first day of spring, the Chesapeake’s inhabitants often turn to other indicators to mark the turning of the season. For some, it’s the osprey coming back to the Bay. For others, it’s the Orioles returning to the Yard. Daffodils bloom. Spring peepers peep. Woodcocks dance. But for sailors – perhaps the Bay’s most idiosyncratic species – the start of spring is marked by the Annapolis Spring Sailboat Show. 

Given that Annapolis is the US’s self-appointed Sailing Capital, the event’s significance should come as no surprise. Sailors come to stock up on gear, shop for sailboats, take part in seminars, and hobnob with their fellow blow-boaters. That said, it isn’t just for sailors. Part of the appeal is akin to that of bird watching – seeing the transients return from their southern migration in their full sailing gear plumage. The other aspect is that it’s quite a bit of fun, regardless of your affinity for sailing. 

With its unique mix of history, outdoor activities, dining options, and entertainment, Annapolis is a great family destination. The Spring Sailboat Show is no different. Kids love looking around boats, and there are plenty to explore at the show. Exhibitors are always happy to let kids roam as long as you keep an eye on them (and their hands aren’t too sticky), and BoatU.S. has loaner lifejackets at the gates for the little ones who forgot theirs at home. Plus, there will be a selection of small boats on shore to pique their interest in sailing. On the opposite end of the spectrum, there's a 80-foot catamaran to board as well as high-tech foiling boats. Located right in the heart of downtown Annapolis, the show also serves as a great launchpad for a day in the capital. 

For those interested in trying sailing, there’s no better place to start. The show’s First Sail Workshop offers a great introduction to the sport with a 45-minute classroom session followed by 90 minutes of on-the-water instruction. Additionally, there will be free seminars covering everything from sailing with kids to celestial navigation.  

Guests 21 and older may enjoy the all-new No Wake Zone. Along with live music and a fashion show, the area will feature cocktails, desserts, and tastings from a selection of Maryland based wineries and distilleries.  

If you prefer a sit-down meal, downtown Annapolis is just steps away, where a wide selection of waterfront restaurants and cozy taverns offer everything from casual fare to gourmet dining. For a true local experience, grab a basket of fries from Pip’s Dock Street Dogs or sip a cocktail at The Choptank with an overview of the show. 

For history enthusiasts, the show’s location in downtown Annapolis offers the perfect opportunity to explore one of America’s most storied maritime cities. A short walk from the show, you can visit the United States Naval Academy, where guided tours provide an inside look at the lives of midshipmen. Additionally, you can get a view of the magnificent Annapolitan skyline from the water with a tour from Watermark or aboard the Schooner Woodwind. The nearby Maryland State House, the oldest state capitol still in continuous legislative use, offers a fascinating glimpse into the nation’s past. If you prefer a more leisurely stroll, the charming streets of the historic district are filled with colonial-era homes, boutique shops, and art galleries. 

The Annapolis Spring Sailboat Show is more than just an event – it’s a celebration of the sailing community and a harbinger of the better weather ahead. Whether you come to shop, learn, or simply enjoy the festive atmosphere, you’ll find something to love. And even if you have no intention of ever hoisting a sail, you might just find yourself charmed by the spirit of the sea. So, don your deck shoes, soak up the maritime culture, and welcome spring the Annapolis way. 

Find tickets and additional information at AnnapolisSpringSailboatShow.com.