Choosing the best sailing school in the Virgin Islands can feel overwhelming until you know what actually matters. If you’re searching for sailing schools with the best reviews in the Virgin Islands, the highest-quality sailing experience, and reliable support from the moment you reach out to the day you step off the boat and beyond, Go Sail has you covered. Here’s what makes Go Sail the best sailing school in the Virgin Islands.
American Sailing Courses
The Best Quality Sailboats Available to Charter
Your classroom is the ocean and your boat matters. Go Sail uses well-maintained, high-quality sailboats that are ideal for both learning and comfort. You won’t be training on outdated or poorly equipped vessels. Instead, you’ll gain hands-on experience on boats that reflect what you’ll actually want to sail in the future. All our boats come with air conditioning, water makers, and spacious cabins. Learn more about the boats we charter here.
Fountaine Pajot Elba 45
Innovative Design Meets Performance and Comfort
🔶2021-2025 Catamaran sailboat models
🔶 4 private cabins, each with en-suite bathrooms option
🔶 3 private cabins, each with en-suite bathrooms option
🔶 Water maker, air conditioning, and generator
🔶 Helm integrated with a large sun lounge for skippers to remain part of the social scene
Clear, Transparent Pricing on VI Vacations
No surprises. No hidden fees. No confusing packages.
We believe that pricing should be straightforward. Every course clearly outlines what’s included, so you know exactly what you’re getting before you book.
We offer special discounts throughout the year and also reward our alumni with exclusive pricing on future bookings.
World-Class ASA Instructors
The heart of any great sailing school is its instructors, and ours are among the best in the world. American Sailing awarded three Go Sail instructors with Outstanding Instructor awards in 2024. Go Sail was the only ASA school with three outstanding instructors awarded that year!
Our American Sailing certified instructors bring deep experience, professionalism, and a passion for teaching that shows in every lesson. They don’t just help you pass a certification, they help you become a confident, capable sailor.
You’ll get personalized instruction, practical knowledge, and real-world sailing skills you can trust.
Captain Jalil Jacallen
“We’ll go where you want to, and do the things you’ve been dreaming of.”
Captain Jalil grew up in Alaska, the son of an engineer on ocean-going tugs and fishing vessels. Captain learned to sail in the Åbo archipelago in Finland while in grad school, and has been sailing his own boats ever since. In 2017 he retired early from software consulting and started sailing professionally right here in St Thomas, USVI. The Captain has made several off shore passages to share stories about. He is very knowledgeable about the local history and ecology, and loves to share sea time with fellow enthusiasts of wind, water, and wildlife.
Captain JT Quinn
“The sea has a way of showing us what we’re capable of, one tack at a time”
Captain JT first started sailing while living in New Zealand. He is an expert American Sailing instructor. He brings not only years of cruising experience from the Virgin Islands, US Virgin Islands, Spanish Virgin Islands, he has also spent time working on yachts all along the Atlantic Coast, Caribbean, and the Med. He has crossed the Atlantic Ocean, sailed to every island in the Caribbean, and transited the Panama Canal. Whether it’s long, open water passages or cruising the islands, JT loves to share his stories and knowledge about sailing.
Corey Roy
“I really like just passing what I know on to people so they can go experience what I have.”
Driven by a lifelong love for the water, Corey Roy transitioned from a career on nuclear submarines to working full-time on historic tall ships. After earning his captain’s license and transitioning into the world of luxury yachts, he became a certified American Sailing instructor. He now shares his passion and expertise with students in the Virgin Islands, finding fulfillment in teaching others to navigate the oceans he once only saw from beneath the surface.
The Sailing School with the Best Reviews in the Virgin Islands
We don’t just say we’re the best sailing school in the Virgin Islands. Our students say it for us.
Our reputation is built on consistently exceptional experiences, from first-time sailors to seasoned adventurers advancing their skills. When people search for sailing schools with the best reviews in the Virgin Islands, Go Sail stands out because of our personalized instruction, supportive environment, and unforgettable locations.
How Go Sail Compares to Other Sailing Schools in the Virgin Islands
Go Sail stands out at the best sailing school in the Virgin Islands because we consistently have:
- More availability
- Reliable communication
- High-quality luxury boats
- Consistent 5 star reviews
- Expert ASA Sailing Instructors
If you’re looking for a sailing school that combines professionalism with a genuinely welcoming experience, Go Sail delivers on every level.
Ready to get started? Your best days on the water are closer than you think.
Availability That Works for You
One of the biggest challenges with sailing schools in the Virgin Islands is limited scheduling. At Go Sail, we’ve built our programs to offer more availability and flexibility. Whether you’re planning months in advance or looking for a last-minute opening, we provide options that fit your schedule. If you have more flexible availability, check out our exclusive offers page to save hundreds on your sailing vacation!
Real People, Real Responsiveness
When you contact Go Sail, you’ll be directly connected with a real person who understands sailing, knows the programs inside and out, and can help you choose the right course for your goals. Oftentimes, you’ll get our founder and CEO on the phone!
If you have questions about certifications, trip timing, or experience level, you can be sure we will respond quickly, thoughtfully, and with clarity. We believe planning your sailing experience should feel exciting, not frustrating.
Captain Genevieve Evans
“Salt is the cure for everything, sweat, tears, and the sea.”
Captain Genevieve (G) is the founder of Go Sail Virgin Islands and Go Sail Flathead Lake in Montana. As the lead instructor trainer for Go Sail VI, Captain G feels that good sailing captains are good leaders with good communication, understanding, empathy, planning, organizing, listening, and command of the situation.
Captain G is originally from Montana. She has raced, taught, and sailed in Montana, the Virgin Islands, Hawaii, Martinique, St. Lucia, the Bahamas, and Belize on small and large cruising monohulls and catamarans for over a decade.
Tyler Evans
“The whole point of this vacation school is ease— not feeling overwhelmed with the details and being able to focus on enjoying your time.”
Tyler is a craftsman at heart, drawn to timeless skills like carpentry, blacksmithing, and knife making. He discovered sailing in 2014 and was hooked by the challenge, navigation, and thrill of exploring the unknown—even dreaming of the Bermuda Triangle. As Operations Manager at Go Sail, he brings his operational expertise from 14 years in the brewing industry and love of adventure to ensure every sailing vacation runs smoothly.