Where We Sail

Sail Libra doesn’t follow a set loop or stay in one region year-round. We move with the seasons and the wind, following the same patterns that offshore sailors have used for centuries. From New England to the Caribbean, across the Atlantic to Europe and back, every route we sail is timed for safety, learning opportunity, and the best conditions available.

Libra in front of St Lucia's Grand Piton

In the winter and early spring, we’re typically based in the Caribbean. Routes in this season range from island-to-island passages like St. Thomas to Grenada, to open-ocean runs like St. Martin to Bermuda. These sails are perfect for building offshore skills in warmer waters with steady trade winds and deep blue horizons. Many passages include stops in places like Guadeloupe, Martinique, or St. Lucia — but always with a focus on seamanship over sightseeing.

Libra at anchor in Maine

By late spring, we move north into the western Atlantic, often stopping in Bermuda before heading for Newport, Rhode Island. This is when we offer one of our most popular routes: the Bermuda to Newport Gulf Stream crossing — a classic offshore passage that teaches routing, weather interpretation, and heavy-weather sailing if conditions line up. From June through September, we explore New England and the Canadian Maritimes with passages to Portland, Maine, Block Island, Lunenburg, Nova Scotia, and around Long Island Sound. These summer trips often mix offshore nights with stunning coastal exploration, giving crew experience in varied conditions and tighter navigation.

Landfall after an Atlantic Crossing

In select years, Sail Libra crosses the Atlantic. Our Transatlantic expeditions typically begin in Newport or Bermuda, making way to the Azores, Portugal, and onward to Madeira, the Canary Islands, and Cape Verde. These routes are offered mid-year (June to September), timed to follow the best weather windows and traditional sailing routes. Later in the fall, we cross back westbound from Cape Verde to the Caribbean, usually arriving in St. Martin in early December to reset for the new season.

This seasonal migration gives our crew the opportunity to experience everything from short tactical legs to major bluewater crossings. Our schedule isn't about chasing the most comfortable conditions — it's about real offshore sailing, with all the challenges and rewards that come with it. Whether you're joining in the Caribbean, the North Atlantic, or on a transoceanic leg, you're stepping into a working passage with a clear purpose: learn, sail, and sail more.