59º North Sailing
"Crisp stars overhead, the quiet rush of water below, all your troubles left ashore. Salt air, a hot meal on the stove, and the gentle motion of the boat rocking you to sleep in your cozy seaberth.
From the first time we sailed over the horizon and discovered the freedom and sense of purpose the sea can bring, we knew we wanted to share that experience. Out there, people come together in a way they rarely do on land. You’ll leave the dock as strangers and return as Shipmates - a bond shared only by those who have gone to sea together.
Come sail with us. Hold fast to your dreams."
sail offshore on bucket-list adventures
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2027-1 | FALKEN | San Diego-San Jose del Cabo
The first passage of 2027, and we can't wait to get back to sea! FALKEN starts her journey back to the home waters of the Atlantic as we head south from our off-season quarters in San Diego towards Mexico and the Baja Peninsula. Escape the northern winter with some warm Pacific breezes. This passage might have the highest chance of seeing wildlife as any of ours, so get your whalewatching binoculars out!
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.
2027-6 | 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.
REAL SAILING & REAL PEOPLE
You know what's cool about 59º North? We sail actual offshore routes, that require real planning, real strategy, and our crew (that's you, we hope!) to truly hands-on sail the boat. But maybe more importantly, there is a real person writing this marketing text! That's right, everything on this site was brainstormed and designed by me, Andy Schell, co-founder & one of the Lead Skippers at 59º North Sailing. So keep that in mind as you peruse the site.
We're confident that we offer the very best offshore sailing adventures in the world, combined with the best & most unique experiential education through our limited annual workshops. Co-Founders Mia, August & I run all aspects of the business, from the intial customer signup process (shout-out to Mia), to boat maintenance and staff selection right on up through actually sailing with you at-sea. We've all got real skin in the game, and that matters to the quality of your experience out there. We flat-out care more.
Our small group of professional sailing staff are close friends, selected by us for their work-ethic, knowledge, experience & humanity. What we offer in terms of real-world sailing expeditions & educational workshops, events & online courses cannot be duplicated and you'll find it nowhere else. We hope you'll join us on the high seas for the adventure of a lifetime.
"The trip delivered on all my expectations and more. I wanted to experience sailing beyond my current boundaries, apply my skills, and learn from those around me. I felt able to embrace the whole experience because we had an excellent 59º North team that shaped us into a great crew on a well-prepared boat. If you are seeking ocean wisdom, you could not be in better hands."
"This passage was literally my first time sailing. My goal was to get as far as possible from my daily life and desk-bound comfort zone, and Andy assured me I would be looked after. I could not have asked for a better skipper (thank you, Jon), better crew mates, or a more enjoyable passage. I'll be forever grateful to 59º North for this opportunity, and I hope to sail with them again soon."
"I highly recommend the experience of doing a passage on ISBJØRN. I gained valuable offshore experience on a fine boat, learned how Andy and Mia competently manage their boat, learned about celestial navigation, and had a great time doing it. Completing ISBJØRN's first back-to-back 200 mile day passage was a smokin' fast bonus!"
"The experience was more than I hoped for in every way. I felt completely at home on the open water in our mighty vessel and with a wonderful crew that quickly became family. All of the staff at 59º North were kind, professional, fun, knowledgeable, and friendly. I will be back!"
"There are so few opportunities in our lives, unless we seek them out, for adventure, exploration, and personal challenge. Doing hard things results in personal satisfaction and makes life meaningful. If people don't understand that and want more creature comforts than 59º North trips offer, then they're not the right people for you. Keep doing what you're doing and there will be plenty of crew who share your values wishing to join you."
"It was such an experience! Meeting all the people and being part of the crew is something very special. We were so lucky to spend the passage on FALKEN; the nature and weather gave us the best, and I really wish it could have lasted longer."
"I sailed on ISBJØRN in March 2024 from Bergen to Tromsø and it was fantastic. 59º North truly lived up to expectations—Mia and August were always helpful, and our skipper Jon Amtrup did a fantastic job, balancing safety with giving everyone the right tasks and space. We had incredible anchorages, great sailing, fun dinners, and unforgettable experiences under the stars on the North Sea. ISBJØRN is a wonderful boat with character, and I highly recommend the trip."
WHY 59º NORTH?
ambitious sailing schedule
The best boats
WOMEN BUNKS GUARANTEED
Professional, well-paid staff
knowledge & community
Why it costs what it costs...
NEWEST BLOGS
The gobbledygook of sailors
We sailors can come across as a cryptic bunch. Similar to almost all niche endeavors, it boils down to efficiency, safety and tradition. There are so many "ropes" and so much gear on a sailboat, that trying to identify them by descriptive terms just wouldn’t cut it. We’re in one of the best learning environments available to offshore sailors, and mistakes are a part of the process.
Dive on in
Life aboard Adrienne is hot and sticky. It was hilarious how fast we all started moving once we heard we might go for a swim in the ocean. With our captain’s blessing, we started jumping in, hooting and hollering, grinning like children on a carnival ride. It was simple and delightful and also mind-boggling to be bobbing and washing in the great ocean under a clear sky with nothing around but our floating home and each other. But the deeper cleaning of this ocean plunge will certainly linger for days.
Death on the high seas
I’m not going to lie - I really miss my dog. As we’re just now approaching Cap Verde (two thirds of the way) I can’t help but think of all the wonderful things that happen on a trip like this; strangers become friends, terror turns into confidence, and ignorance into knowledge. It’s not for everyone. But if you do decide to cross some of most isolated spaces on the planet in a small boat, you’re definitely in for a mighty interesting ride. And next time I’ll bring my dog with me. 😊
You are the crew
You don’t need to be a seasoned sailor to join us; 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.
IRL Events
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).
Women's Happy Hour | Annapolis
Sailor's Social Party | Annapolis
59º North's annual Annapolis Boat Show party returns at J/World Annapolis in Eastport, featuring free food and drinks (beer by Heavy Seas), networking with sailors and crew, and deck tours of WOODWIND II. All proceeds, with a minimum $25 ticket, benefit Matt Rutherford and Nicole Trenholm's Ocean Research Project.
The Quarterdeck
SEA·M’N·SHIP /ˈsēmənˌSHip/: “The skill in, and knowledge of the work of navigating, maintaining, and operating a vessel.”
