Make the Most of the Annapolis Sailboat Show in 3 Days

What is the Annapolis Spring Sailboat Show?

The Annapolis Spring Sailboat Show provides a local, fun, and accessible entry point to the sailing lifestyle. Located in the heart of America’s sailing capital, the event offers opportunities to take part in graduated learning experiences, buy boats from local dealers, and start sailing that weekend.

Adapt to the Sailing Lifestyle

Kick off the weekend by diving into all things sailing at the Annapolis Spring Sailboat Show. Browse a vast selection of new and used sailboats, ranging from high-performance racers to luxury catamarans. Take advantage of the First Sail Workshop, a perfect introduction for beginners looking to get hands-on experience with an expert instructor. 

For a true waterfront experience, head to Carrol’s Creek Café or Boatyard Bar & Grill. Both offer fresh seafood, stunning views, and a lively nautical atmosphere. 

What Else to Dive Into

Step away from the docks and into history with a guided tour of the Maryland State House or a leisurely stroll down Main Street. Stop by local shops like Hobo Bags and Capital Teas for unique finds.

Dine at O’Leary’s Seafood Restaurant, known for its upscale yet cozy ambiance and top-tier crab cakes. Wrap up the night with a drink at Pearl, neat, up, on the rocks no matter how you shake it.

Where to Stay (And Dream of Sailing)

More Boats, More Adventure

Start the day with a seminar on navigation, where classes cover topics ranging from the basics (rules of the road, docking, knot tying, reading the weather) to advanced skills (racing, watermakers, celestial navigation). Then, climb aboard more boats to compare your dream vessels side by side - with a wide selection of new and used sailboats – ranging from 80’ cruising catamarans to hydrofoiling racing dinghies.

Relax in the No Wake Zone, where you can enjoy live music and sample Maryland-made spirits, including craft whiskey, rum, and wine (guests 21 and older only). Grab a bite from local food vendors or visit Iron Rooster for an all-day brunch. 

What Else to Dive Into

Venture a little farther and explore BWI Trail for lush outdoor adventures, perfect for a scenic bike ride. If you’re a history buff, visit Historic London Town & Gardens in Edgewater for a peek into colonial Maryland. 

For an upscale dinner, Lewnes’ Steakhouse in Eastport offers a fantastic steak and seafood selection. Looking for a laid-back vibe? Forward Brewing serves up local craft beer and casual eats in a cozy neighborhood setting. 

Where to Stay (And Dream of Sailing)

Seize the Last Day

Use your last morning to finalize any boat deals, pick up must-have marine accessories from local vendors, and sit in on one last free seminar. 

Enjoy waterfront brunch at Blackwall Hitch, known for its crab hash and Chesapeake benedict, or visit Miss Shirley’s Café for Southern-inspired fare. 

Take a scenic drive down to Galesville or Deale, where charming marinas and quiet coves offer a relaxing way to wrap up your weekend. 

Set Sail!

The Annapolis Spring Sailboat Show is more than just a boat show—it’s an immersive experience in the world of sailing, set in one of the most charming and historic cities on the Chesapeake Bay. For more to do, explore our website and purchase your boatshow tickets!

This event is proudly sponsored by Visit Annapolis and Anne Arundel County.

Co-written with Ryan Gullang of Annapolis Boat Shows.