Top Sailboat Shows: 2026 Edition
It’s no secret: we love sailing. From the breathtaking beauty of sailing the Caribbean to the friends you meet along the way, sailing the Virgin Islands on our ASA sailing courses is a unique way to experience island life.
But beyond the Virgin Islands, our captains and sailing instructors love seeing the latest industry trends around the world—and we think you will too! Here’s a look at the best sailboat shows in 2026.
Annapolis Sailboat Show
If there’s only one event you can attend in 2026, you should consider the largest in the USA—The Annapolis Sailboat Show. What started 50 years ago is still going strong—a 4-day celebration of sailing culture in the heart of the Chesapeake Bay.
The lively dock party features a who’s who of sailboat manufacturers, instructors, and sailing experts. Visit “America’s sailing capital” and meet Go Sail VI captain Genevieve, where you can learn more about sailboats on a beautiful October afternoon in the historic capital of Maryland.
Sausalito Boat Show
While only in its 3rd year, make no mistake about it—Sausalito is a destination for sailboat enthusiasts worldwide. Just across the Golden Gate Bridge from San Francisco, this charming Marin County town has incredible views and access to the Pacific Ocean and the San Francisco Bay.
From learning how to sail from expert instructors to enjoying music and food near the water, the Sausalito Boat Show is quickly becoming one of the must-attend events for California sailors.
Miami International Boat Show
The Miami International Boat Show kicks off on February 11, 2026, showcasing luxury yachts from around the world. The 5-day event is geared toward power boats, but there are typically a few dozen sailboats for sailing aficionados to check out, too. Seminars include tips on marine electronics, how to choose the right boat, and even fishing lessons.
Antigua Charter Yacht Show
Set in the UNESCO heritage site of Nelson’s Dockyard (a historic marina in the English Harbour) is the Antigua Charter Yacht Show. A few dozen yachts are spread around 3 marinas, allowing sailing enthusiasts to climb aboard some of the nicest boats in the Caribbean—last year’s highlight was the nearly 350-foot Black Pearl. Besides the incredible yachts and beautiful coast around the “Land of 365 Beaches,” we also look forward to the Concours de Chef and Tablescaping Competitions—cooking competitions that have taken on a life of their own.
Start Planning Your 2026 Sailing Vacation
It’s never too early to start planning for a sailing vacation in the Caribbean, USA, or beyond. Take Go Sail Virgin Islands ASA courses to prepare yourself for buying (or browsing) at some of the best sailboat shows in 2026.