Sailing the Tropical Trail
Bermuda & U.S. Virgin Islands · Caribbean
Next: 13 - 23 November 2026
1 date in November
$7,550
12 trips to choose from, with berths from £2,875.
Bermuda & U.S. Virgin Islands · Caribbean
Next: 13 - 23 November 2026
1 date in November
$7,550
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Where you'll sail
See where each trip goes and when it next sails, then pick the one that fits your dates.
This 850 to 900-nautical-mile offshore passage from Bermuda to St. Thomas offers 6 to 7 days of steady tradewind sailing and real-world offshore experience.
This 4-day sailing seminar in the U.S. Virgin Islands offers a practical introduction to coastal and offshore sailing.
Embark on an unforgettable Bluewater journey from the heart of the US Virgin Islands to the lush spice island of Grenada.
This passage provides a classic northbound Caribbean training opportunity, traveling from Grenada to Sint Maarten with multiple potential island stops along the way.
This passage offers a classic southbound transit of the Lesser Antilles, traveling from Sint Maarten to Grenada with a focus on French-influenced islands along the way.
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…
This passage focuses on extended offshore sailing, covering a direct non-stop leg from Sint Maarten to St.
This passage offers a mix of offshore sailing and historical exploration. Departing Grenada, the route features a layover in the historic town of St.
Covering roughly 900 nautical miles nonstop from Sint Maarten to Bermuda, this passage takes you directly north into the open Atlantic.
This classic offshore passage covers approximately 650–700 nautical miles from St. George’s, Bermuda to Newport, Rhode Island, featuring a full Gulf Stream crossing and real-world…
Sail the Portuguese coast aboard Libra on a weeklong passage from Lisbon to the Algarve, combining coastal sailing, historic ports, dramatic headlands, protected anchorages and…
Sail offshore from Portugal to the Canary Islands aboard Libra on a 10 day Atlantic passage from Faro to Tenerife.
About the operator
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.
Your home at sea
Where you'll sleep, eat and learn the ropes for the whole trip.
Bill Tripp Custom Ketch
Vessel Overview: Libra is a 60-foot custom center-cockpit ketch built in 1969 by Abeking & Rasmussen and designed by William H. Tripp Jr., one of America’s most respected yacht designers of his era. From her elegant lines to her rugged fiberglass construction and capable offshore performance, Libra has always stood apart. Over five decades and many tens of thousands of offshore miles, she has proven herself as a serious sailing vessel. Originally commissioned for global voyaging, Libra now serves as the flagship of Sail Libra’s offshore training program, carrying sailors on passages from the Caribbean to North America and across the Atlantic to Europe. Refitted and continuously upgraded, she blends the enduring qualities of classic yacht design with modern systems and real offshore capability. Design Heritage: Libra was born from the work of one of the most influential American yacht designers of the twentieth century and built by a shipyard known for uncompromising craftsmanship. William H. Tripp Jr. was a Long Island–based naval architect whose designs helped shape modern offshore sailing. He was known for boats that balanced performance, strength, and practicality at sea, favoring seakindly motion and manageability over trends or dockside appeal. Tripp was an early advocate for fiberglass as a serious offshore construction material and played a significant role in its acceptance for large ocean-going yachts. Among his most notable works is Ondine, a custom racing yawl whose hull form and proportions became legendary in offshore sailing circles. Ondine’s success in ocean racing, including repeated victories in the Newport to Bermuda Race, established Tripp’s reputation for fast, powerful, and well-balanced hulls that could perform across a wide range of conditions. That racing pedigree directly informed his later cruising designs. Tripp’s influence extended well beyond custom race boats. He worked closely with Hinckley to develop the Block Island 40, which evolved into the Hinckley Bermuda 40, one of the most enduring and respected cruiser-racers ever produced. He also designed several major production yachts for Columbia Yachts, including the Columbia 57, blending offshore capability with interior volume in a way that was ahead of its time. Libra’s hull was drawn from this same design lineage. She carries the DNA of Ondine’s powerful yawl form, adapted for long-range cruising and extended offshore work. The result is a balanced hull with a long waterline, generous displacement, and proportions that favor speed, comfort, and control in open ocean conditions. That design was executed by Abeking & Rasmussen in Bremen, Germany. Founded in 1907, the yard has more than a century of experience building high-quality yachts and specialized seagoing vessels. Their reputation rests on structural integrity, precision craftsmanship, and vessels built to operate reliably in demanding environments. Libra reflects that tradition, combining German engineering with Tripp’s offshore-focused design philosophy. Libra was one of Tripp’s later custom designs, completed shortly before his death in 1971. Today, after decades of sailing and continuous refit, she remains true to that original intent. She is not a reinterpretation or a modernized copy. She is the real thing, refined and maintained, still doing exactly what she was designed to do: sail offshore, carry her crew safely across open water, and reward good seamanship.
Meet the crew
The people behind Sail Libra, with every mile they've logged on SailTies to back them up.
@rrayfield
Owner · United States
Latest voyages
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Cancellation and refund terms shown on every trip page before you pay a deposit.
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A cracked shroud 250 miles from the Rolex Middle Sea Race finish, three volcanoes in one campaign, and why Robert Šarić of Veruda Sailing School trains his crews on the Adriatic.

A Tall Ships bursary put Elouise Pemberton to sea at 19. Twenty years on she is working through all thirteen Challenge yachts, logging every mile on SailTies.

Jenny Whelan sailed 46 legs and 1,800 nautical miles around Britain with her partner Pete, their dog Svea, and an AI chatbot, logging every leg on SailTies.
Yes, and most people do. Trips are sold by the berth, so you join a crew rather than needing to bring one. Cabins are shared with someone of the same sex unless you book a whole cabin.
It depends on the trip, and every listing says which level it is written for. Beginner trips assume you have never sailed; advanced trips assume you can stand a night watch without supervision.
The berth, the skipper and crew, and the running of the boat. Flights, insurance and most meals ashore are not. Every trip page lists what is and is not included before you pay.
The operator's cancellation terms are published on the trip page before you pay a deposit, so you can read them before you commit. They vary by operator and by how close to departure you cancel.
The skipper decides the route, and changing it is normal seamanship rather than a problem. Trips are very rarely cancelled outright; when they are, the operator's terms say what happens.
Independent charter businesses and skippers we either know personally or have been recommended by past customers. Their registered business details are available upon request. All trips are checked before they go live.
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