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.
"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."
"I’ve sailed with 59º North four times—each has been a unique and gratifying experience. Sailing with like-minded folks, captained by the best in the biz, in well-maintained vessels has been the highlight of my 40-year sailing career. I’ve learned so much about sailing and myself on my 59º North adventures."
"Having sailed on ISBJØRN in 2019, I was excited to join another 59º North passage and finally sailed on FALKEN for the trans-Atlantic in January 2025. The 17-day passage was an incredible experience, sharing sailing knowledge and cultural perspectives with a diverse crew. FALKEN felt extremely safe and comfortable, and the care 59º North puts into both the voyage and post-trip details is outstanding. I came away with new friends, unforgettable memories, and a whole new level of sailing experience."
"I signed up for this passage hoping to spend an extended period offshore, learn new skills, increase my competencies and confidence, and sail with amazing crew mates—and this passage completely exceeded my expectations. The 59º North team brings impressive skill, experience, wisdom, and fun to each passage and crew, which is a huge part of why I returned for this second passage in twelve months. I recommend 59º North to all of my sailing friends who want to learn about offshore passage-making in a thorough and hands-on way from true professionals."
"Sailing from San Diego to Cabo San Lucas with 59º North Sailing was an outstanding experience that I would recommend to anyone seeking offshore sailing combined with exceptional instruction and seamanship. The lead crew, Andy, Mary, and Ryan, created a professional and welcoming environment focused on safety, preparation, and teamwork. I came away with much more confidence in offshore sailing and a deeper understanding of ocean passagemaking. 59º North delivers an authentic offshore experience, expert leadership, and an adventure that builds both skills and confidence."
"At 65, I was anxious about my first ocean passage from Antigua to Bermuda, but 59º North provided a unique opportunity to experience the magic of passage making while learning new skills. Mia Karlsson was inspiring and supportive while sailing FALKEN and cooking amazing meals, and Captain Chris Kobusch brought a wealth of knowledge and experience. This was truly the experience of a lifetime."
"Mark and I signed up for a multi-night sailing adventure and ended up with a life-altering week of utter delight. Alex and Mia created an atmosphere of trusting, loving community the second we boarded FALKEN, and we still can’t believe how they trusted us with their beautiful boat and the crew’s lives. We learned about sailing, charting, trimming sails, and working in teams with strangers, and experienced everything from flat calm to huge swells, dolphins, and whales. We’ve been off the boat for four days and are already obsessed with going on another leg—what a week, 59º North!"
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.”
