Sailing the Tropical TrailSailing Course from Bermuda to St. Thomas

What will the type of sailing be like?

The Tradewind Run: Bermuda to St. Thomas Sail south into the tropics on this classic offshore passage from Bermuda to the U.S. Virgin Islands. Covering approximately 850 nautical miles, this route follows the traditional tradewind track used for generations by offshore sailors and delivery skippers. With 6 to 7 days at sea or more, this passage offers consistent breeze, deep ocean sailing, and the reward of arriving in the Caribbean by sail. You'll cross latitudes, navigate shifting wind belts, and ride the northeast trades into the turquoise waters of the Virgin Islands — a journey that blends challenge, rhythm, and reward. Departing Bermuda — Into the Open Atlantic We’ll depart St. George’s, Bermuda on November 14th, heading south into the deep Atlantic. This passage begins in cooler weather and transitions quickly into the warmer tradewind zone, offering a tangible sense of crossing into a new region of the world. In the first days, you’ll focus on: Adapting to Libra’s 3-on, 6-off watch system Helm work and sail trim in offshore conditions Navigation using radar, AIS, and celestial cues (we'll get the sextant out for this one) Settling into offshore routines and energy management Sailing the Trades — Steady Wind, Starry Nights By Day 3 or 4, we typically reach the northeast trade winds, which provide steady breeze and consistent sailing. This is the classic “tradewind run on L65 (delivery route)” — long rolling swells, starry skies, and reliable wind on the beam or quarter. You'll gain experience in: Beam and broad-reach sail trim Weather routing and adjusting course for efficiency Sailing by wind angle for long periods of self steering Logbook and position reporting Standing watch underway The Final Approach — Landfall in the Caribbean As we close in on the Virgin Islands, you’ll help with landfall prep, navigation into island waters, and the excitement of arriving under sail, you will smell the land distinctly after a long offshore passge like this. Depending on timing and routing, we may anchor in the evening or arrive at sunrise for customs clearance in Charlotte Amalie, St. Thomas. Why This Passage is Special Tradewind Offshore Sailing – Steady breeze and long ocean miles make for a perfect offshore rhythm Ocean-to-Caribbean Transition – A satisfying progression from cool ocean nights to tropical sunshine Hands-On Seamanship – Bluewater experience, sail handling, watchstanding, and route planning Iconic Arrival – Sail into the Caribbean the way it was meant to be done: by sea Life on Board Libra As with all offshore passages, you’ll rotate through Libra’s 3-on, 6-off watch schedule, learning every aspect of life at sea. Expect helm time, lookout, sail changes, logbook duty, and galley shifts. We function as a unified crew, supporting each other through the rhythm of the passage. Meals are hearty and practical: Meats, fresh bowls, pasta, rice, snacks, and hot drinks during the night watches. The Mate will ensure the crew stays fueled and focused throughout the journey.