1/11
2 Dates
From US$962.50 today (US$3,850 total)
This 4-day sailing seminar in the U.S. Virgin Islands offers a practical introduction to coastal and offshore sailing. You’ll explore all three islands by boat, learn foundational skills, and return with confidence in your ability to cruise, charter, or simply sail with purpose in the Caribbean.
It may have winter in the title, but this instructional adventure won't require any cold weather gear. Some idyllic winter sun USVI sailing.
We believe real seamanship can’t be learned at a marina. Libra was built for the open ocean — and so was this program. Whether you're looking to gain confidence offshore, log serious sea miles, or chase the horizon just for the hell of it, you're in the right place. For over a decade, we’ve helped sailors step beyond the dock and into a full-spectrum passage-making experience. It’s hands-on and sometimes it’s rough & loud — but it’s real. Every passage is a team effort. There’s no standing back and watching here — you’ll be on the helm, trimming sails, navigating, standing watch, and learning what it really takes to move a boat. We meet you at your level, then build you up from there.
Real offshore and blue water cruising with a great owner skipper.
Your specific vessel is assigned based on your selected dates. All vessels meet our high standards for comfort and safety.
Bill Tripp - Custom Ketch
LOA: 60ft (18.2m)
Beginner
No sailing experience required. Perfect for newcomers.
Intermediate
Some sailing experience helpful. Comfortable on the water.
Advanced
Significant sailing experience required. Challenging conditions.
Active Crew Member
Full participation in all sailing activities.
Optional Involvement
Participate as much or as little as you like.
Passenger
Sit back and enjoy the ride.
No
All meals and cleaning are taken care of
18
Wind & Waves Weekend: A Virgin Islands Sailing Seminar Join us in the U.S. Virgin Islands for a hands-on, three-island sailing seminar designed to introduce you to the fundamentals of cruising, coastal navigation, and tropical seamanship. This 4-day loop from St. Thomas to St. John, St. Croix, and back offers a balance of protected waters, offshore sailing, and anchorage hopping — perfect for beginner and intermediate sailors looking to build skill and confidence in one of the world’s most beautiful sailing playgrounds. Whether you’re considering bareboat chartering, boat ownership, or just want to understand what it's like to live aboard a cruising vessel, this seminar gives you the knowledge, rhythm, and real-world experience to take the next step. Day 1: Welcome to St. Thomas – Orientation & Sail Prep We’ll meet in Charlotte Amalie on December 3rd, settle into Libra, and run through safety procedures, systems orientation, and sail handling basics. We'll have a crew dinner ashore that evening. Onboard learning includes: Boat walkthrough and line handling basics Intro to sail trim and helm control Safe anchoring techniques and mooring etiquette Day 2: Island-Hopping to St. John On our second day, we’ll sail from St. Thomas to Maho Bay, St. John — one of the most protected and scenic anchorages in the Caribbean. This segment focuses on coastal navigation, island-to-island routing, and mooring ball basics, with time to explore ashore. Training emphasis includes: Chart reading and GPS plotting Island weather patterns and microclimates Sail handling in light tradewinds Swim & snorkel break (optional) Day 3: Offshore to St. Croix – Bluewater Lite After breakfast, we’ll raise anchor and set course for St. Croix — a true open-water passage of roughly 40 nautical miles. This is your introduction to offshore sailing, including watch rotations 1 each hour, sail trim in ocean swell, and real-time navigation decisions. This offshore leg covers: Watchstanding and route tracking Radar and AIS use in open water Point-of-sail adjustments and reefing Confidence-building at the helm in real conditions We’ll arrive in St. Croix by evening, anchor, and enjoy dinner aboard and discuss the trip as a crew. Day 4: Return to St. Thomas – Debrief & Seamanship Wrap-Up Our final day (Sun) includes the return sail to St. Thomas, giving you a chance to apply everything learned over the weekend. Back in port, we’ll debrief, share takeaways, and celebrate your first steps into the cruising lifestyle. Why This Seminar is Special Sail All Three Virgin Islands – Experience St. Thomas, St. John, and St. Croix by sail Offshore + Coastal – A unique mix of short passages and open water sailing Cruising Foundations – Anchoring, mooring, sail trim, and real-time navigation Beginner-Friendly Environment – Designed for curious minds, future cruisers, and hands-on learners Life on Board Libra We’ll sail as a relaxed and collaborative crew. Expect short daily passages, mixed with hands-on learning, swimming, anchoring, and plenty of helm time. Each participant will rotate through steering, line handling, sail adjustments, and daily operations. Meals are simple, tropical, and communal — fresh fruit, grilled vegetables, pasta, and hearty proteins to keep the crew energized. Every night, we’ll anchor in a and enjoy the full rhythm of life aboard a working cruising yacht.
No optional extras
Tried and tested sailing experiences, from our pick of the world's best operators
All our trips are led by qualified skippers and sailing instructors
We only work with the most reputable sailing operators and yacht providers
Perfect for solo sailors looking to join a crew or groups wanting to charter
Our team is on-hand 24/7 to help you before, during and after your adventure
From US$3,850 per person
Secure your place today from US$962.50