Discover Go Sail Virgin Islands Posts

One of the most exciting aspects of the sailing industry is coming together with other sailboat owners, vendors, and—of course—sailors! Sailboat shows are an excellent place to learn more about the latest and greatest sailboats, ask questions to industry experts, and make friends along the way.  If you plan to visit a sailboat show, it’s…

The 2025 Annapolis Sailboat Show has wrapped up and Go Sail took away so many great experiences from the show. Here are a few of the 2025 Annapolis Sailboat Show highlights we recommend sailors learn more about if they weren’t able to make the show this year! The Best New Sailing Gear of 2026 Cruising…

The Annapolis Sailboat Show is one of the premier sailing events anywhere in the world. It’s the largest sailboat show in the USA and takes place in “America’s Sailing Capital”. Not sure what to expect? Take a look at some useful information about the popular event in Chesapeake Bay!  What Are the Dates of the…

The Caribbean Sea is arguably the best sailing destination in the world. It has warm weather, champagne sailing conditions, and incredibly scenic places to drop anchor. It’s also home to some great sailboat events in 2026, making for a spring break or winter getaway.  Read about some of Go Sail Virgin Island’s favorite Caribbean sailboat…

The Basics The boat: “Endless Joy”, a 2024 Lagoon 46 Crew: Captain JT (instructor)   ASA Students: Ron and Larien (with Lynn and Lois along for the ride) Courses Completed:  ASA 101 (Basic KeelBoat), ASA 103 (Basic Coastal Cruising), ASA 104  (Bareboat Cruising), ASA 114 (Cruising Catamaran) Day 1: Along for the Ride Captain JT met…

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…

William Whitacre found his way to sailing through the military. Not through a deployment but instead, through a veteran’s yacht club. The Chaos Bay Yacht Club. It all began a handful of years ago, one of his military friends invited him out to the invite-only yacht club for a sail to see if he would…

The Annapolis Sailboat Show is almost here, and Go Sail Virgin Islands is looking forward to attending once again. If you aren’t familiar with the fall event, it’s 4 days of fun for sailors of all levels. You can shop for the latest sailboats, meet other boating enthusiasts, and chat about anything from new gear…

The Virgin Islands’ weather is generally more predictable than a lot of popular sailing locations. However, this doesn’t mean you shouldn’t plan ahead.  Sailing conditions can change quickly, so it’s always important to understand the basics of weather safety before setting sail. Here’s a look at some frequently asked questions about the weather in the…

The Virgin Islands are often described as having “champagne sailing” due to the normally calm conditions and the picturesque Caribbean Sea. For most of the year, the BVI and USVI are an excellent place to learn how to sail, with gentle breezes and small swells.  But as with much of the Caribbean, it’s important to…

Donna wouldn’t recommend how she learned to sail to any of the students she teaches now. “I learned how to sail by myself,” she laughed. “I put the sails up within a couple weeks of buying [a sailboat in Connecticut] and just figured it out on my own. I bought some books and just tried…

The Basics The boat: Phoenix, a 2020 Fountaine Pajot Saba 50 Crew: Captain JT (instructor)   ASA Students: Andy, Elaine, Daniel, and Sally Courses Completed:  ASA 101 (Basic KeelBoat), ASA 103 (Basic Coastal Cruising), ASA 104  (Bareboat Cruising), ASA 114 (Cruising Catamaran) Day 1: Two Couples’ Cruising Dream Daniel and Sally and Andy and Elaine all…