
59º North Sailing
sail offshore on bucket-list adventures

"59º North Sailing was built on a simple belief: that there is magic over the horizon, and its best shared with like-minded people. The allure of a dark night watch, the salt air, that cozy seaberth, a warm, one-pot meal & endless stories with your shipmates. The clarity of purpose & sense of togetherness that only emerges miles offshore.
If you feel that pull, come sail with us. Hold fast to your dreams."


OFFSHORE SAILING
The best offshore sailing adventures in the world, open to everyone. You don’t need to be a seasoned sailor; you do need to be curious, engaged, and willing to be part of the team. As a paying crew member, you’ll take part in every aspect of running the boat: helming, sail handling, navigation, weather routing, etc, all the small decisions that add up to a safe and successful ocean passage.
We’re not a formal sailing school. We teach seam'nship the way it’s been taught for centuries—by doing it, for real, in real conditions, with experienced staff who care deeply about safety, quality, and the people on board.
Inclusivity matters to us. We reserve at least two bunks on every passage for women sailors and we work hard to create an environment built on respect, trust, and genuine care for each other.
If you’re looking for a polished vacation, this may not be it. If you’re looking for meaningful challenge, real responsibility, and an unforgettable experience at sea—you’re in the right place.



Professional
& safe
We are a dedicated team qualified to the highest MCA Yachtmaster Ocean standards, adhering to the strictest of safety regulations. Our boats are commercially coded per flag-state regulations and have the highest-industry-quality safety & comms equipment.
Our skippers and mates are the best in the business, with hundreds of thousands of ocean miles between us, several passages to 80º North in the High Arctic, a handful of circumnavigations, many equator crossings and landfalls in some of the most far-flung ports on earth. But better yet, all of our staff are genuinely kind & passionate human beings, the key ingredient to leading a group of strangers on an offshore voyage.



sail offshore


2027-6 | FALKEN | Key West-Bermuda
It's 1,200 miles from Key West to Bermuda, with a little hitch in the route to get around the Bahamas. This is a longer, more challenging passage out into the Atlantic proper, where we'll have to plan the weather just right while we're in the Gulf Stream for the first portion of the voyage until we can turn east past the Abacos. You'll get all kinds of weather on this trip as we transition through the Horse Latitudes — cold fronts coming off the continent, easterly Tradewinds at the start, and deep ocean swells once clear of the Bahamian islands.


2027-5 | FALKEN | Cayman Islands-Key West
Join FALKEN in Grand Cayman for the run around the west end of Cuba and on up to Jimmy Buffett's spiritual home in Key West, Florida. It's been almost ten years since we last sailed into Key West and it's one of the more memorable landfalls as you sail past Mallory Square and into Key West's historic seaport.


2027-4 | FALKEN | Panama-Providencia-Cayman Islands
FALKEN starts her Atlantic season in earnest and gets some new landfalls in on this first passage. If you zoom in on Google Earth, you'll find a small group of islands that sit more or less on the rhumb line between Panama and Grand Cayman. "What's that?!" we thought, when planning the passage. Providencia, a small Colombia outpost in the middle of the Caribbean Sea and an irresistible stopover en route to Grand Cayman!
CREW TESTIMONIALS
IRL Events
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Celestial Nav Workshop | Annapolis


Annapolis Boat Show | Annapolis
Every October Andy, Mia & friends and family of the 59º North team come to our spiritual home port for the annual Boat Show festivities, and we’ll be back in 2026! The Annapolis Sailboat Show dates in 2026 is October 15 - 18, 2026 (Thursday - Sunday, 4 days).
More info will be coming out closer to the show!
The Quarterdeck
SEA·M’N·SHIP /ˈsēmənˌSHip/: “The skill in, and knowledge of the work of navigating, maintaining, and operating a vessel.”


















