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Mar 12-20
US$4,850
3 spaces available
This northbound passage offers an in-depth tour of the Windward and Leeward islands, starting with a tropical exploration of the Grenadines before transitioning into a series of offshore legs north to Sint Maarten. The route is designed for hands-on navigation, day sails with frequent stops in the southern islands, and extended offshore runs as the trip progresses. The itinerary includes a mix of island-hopping, customs formalities, and continuous watch rotation, making this passage ideal for sailors looking to combine real-world passage-making with time spent exploring the Caribbean’s island chain from sea. What a great opportunity to try before you buy a boat, or charter, the inside info learned from Libra about the islands and connections you will make are priceless.
Sailing from Grenada to Sint Maarten is a create way to authentically experience the Eastern Caribbean and the cultural shifts from island to island.
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 Departure: Grenada Primary Route: Grenada – Carriacou (Tyrell Bay, customs/immigration exit) – Bequia – The Grenadines (Mayreau, Union Island, Canouan as time permits) – St. Vincent – St. Lucia – Dominica – Les Saintes (Guadeloupe) – Sint Maarten Estimated Distance: 430–500 nautical miles, depending on exact routing and anchorages Key Points: Initial tropical island exploration, northbound offshore/coastal navigation, progressive increase in passage length, final long leg to Sint Maarten Passage Breakdown Grenada to Tyrell Bay, Carriacou & the Grenadines Crew briefing, vessel checks, and weather review in Grenada before departure Short sail to Carriacou (Tyrell Bay) for customs and immigration exit Daytime passages through Bequia and the Grenadines, with opportunities for anchorages and local exploration (Union Island, Mayreau, Canouan) Island-Hopping Northbound Coastal and offshore legs north through St. Vincent and St. Lucia Possible stops for crew rest and resupply based on schedule and weather Active log keeping, navigation, and watch rotations maintained throughout Final Legs: Dominica, Les Saintes & Sint Maarten Continuing north to Dominica and Les Saintes (Guadeloupe), with landfall for customs, provisioning, and time ashore as conditions allow Final long overnight passage north to Sint Maarten, arrival and trip debrief at marina Training Focus Coastal and offshore passage planning, including customs/immigration requirements at Carriacou and other islands Navigation using GPS, chartplotter, radar, AIS, and paper charts Watchkeeping: helm, lookout, log entries, and routine system checks Anchoring and harbor maneuvers in varied Caribbean anchorages Sail handling, reefing, and sail changes for changing wind and sea conditions Fatigue management and night watch procedures on longer legs Expected Conditions Winds: E–ESE trades, 15–25 knots typical for late March; lighter winds or local gusts possible in acceleration zones Seas: 4–8 feet in open channels, moderate chop between islands, generally calmer in southern anchorages Weather: Mostly sunny with trade wind cumulus, isolated brief squalls, high humidity and warm temperatures Hazards: Small boat and ferry traffic near islands, squalls in channels, strong currents and acceleration zones Why This Passage is Relevant Combines day sailing in tropical islands with longer offshore and overnight legs Offers practical experience in Caribbean customs and immigration procedures Builds skills in real-time navigation, watchstanding, and vessel management Ideal for sailors seeking both coastal cruising and advanced mile-building
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$4,850 per person
Secure your place today from US$1,212.50