30 Jan - 6 Feb
US$5,200
2 spaces available
This passage provides a classic northbound Caribbean training opportunity, traveling from Grenada to Sint Maarten with multiple potential island stops along the way. The focus is on continuous offshore and inter-island experiences, active night watches, and exposure to a range of navigational and weather scenarios as we move up the Windward and Leeward island chains to Sint Maarten. Routing and specific stops will be adjusted based on real-time weather, sea state, and crew input. Any of Libra's North and South passages through the Caribbean are a great intro to either bringing your own boat, or chartering. You get to experience the entire easter Caribbean conditions in one passage.
Meander your way through the Windward and Leeward Isles on a truly authentic sailing adventure.
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
Route Overview Primary Route (and possible stops): Grenada – Carriacou & the Grenadines – St. Lucia – Martinique – Dominica – Les Saintes – Deshaies (Guadeloupe) – Sint Maarten Estimated Distance: 475–500 nautical miles, depending on stops and routing Key Points: Coastal and offshore navigation north along the island chain, multiple overnight passages, variable stops at anchorages depending on timing and weather. Passage Breakdown Grenada to Carriacou & the Grenadines Crew briefing, vessel checks, and weather review in Grenada before departure First leg to Carriacou and through the Grenadines, with anchoring opportunities at Union Island, Mayreau, or Bequia based on timing Watch rotation (3 hours on, 6 hours off) established immediately, all crew involved in navigation, log keeping, and sail handling Up the Island Chain (Windwards & Leewards) Successive offshore legs north along the Windwards and into the Leeward Islands Potential anchorages or brief stops: – St. Lucia – Martinique – Dominica – Les Saintes (Guadeloupe) – Deshaies (Guadeloupe) Multiple overnight sails required to cover distance and manage weather windows Navigation includes coastal piloting by day and open-water passages by night Final Approach to Sint Maarten Final overnight passage north to Sint Maarten, with arrival and customs check-in at the marina Crew dinner ashore at Lagoonies Bistro Training Focus Offshore and inter-island passage planning: route selection, waypoints, and safe harbor identification Practical navigation: use of chartplotter, radar, AIS, GPS, and visual references Watchkeeping: helm, lookout, sail management, log entries, and system checks Night operations: navigation, safety, lighting protocols, and fatigue management Sail management: headsail changes, reefing, downwind and reaching techniques for variable trade wind angles Real-time weather assessment and route adjustments based on forecasts and conditions Expected Conditions Winds: E–ESE trades, typically 15–25 knots in open water; possible gusts in squalls and acceleration zones between islands Seas: 4–8 feet in open channels, moderate to rough at times, with shorter-period chop between the islands Weather: Mostly clear with trade wind cumulus, brief squalls possible especially near island channels, warm and humid throughout Hazards: Traffic in coastal approaches, occasional fishing gear, squall lines, and strong currents between certain islands Why This Passage is Relevant Combines continuous offshore sailing with multiple island landfalls Requires active night watches and real passage-making skills Broad exposure to navigation scenarios: open water, coastal, and inter-island Ideal for sailors seeking multi-day watch experience and mile-building under realistic conditions You get to experience the entire easter Caribbean conditions in one passage
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$5,200 per person
Secure your place today from US$1,300