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.
"My time on FALKEN crossing the Atlantic was highly rewarding and incredibly enjoyable. The trip was routinely challenging and always a lot of fun, allowing me to stretch myself and enjoy being absent from the rest of the world for a time. Unforgettable."
"This was my second trip with 59º North, and once again it was absolutely fantastic. The crew quickly became a friendly, supportive team, and living in close quarters felt natural and easy. Jon set the perfect tone as skipper, sharing his knowledge with clarity and patience, and Mia’s behind-the-scenes planning made everything seamless. Sailing with 59º North is about growing as a sailor, sharing adventure, and making lasting memories."
"This was my second trip with 59º North, my first being a fantastic heavy weather crossing of the Irish Sea on ISBJØRN. I signed up for the Canary Islands to Caribbean trip, thrilled to be chosen as crew. The attention to detail in equipment, vessels, and crew at 59º North is world class, making ocean sailing both safe and unforgettable. I will definitely be sailing again with 59º North."
"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 truly enjoyed the entire experience. I went to gain confidence and understanding of offshore sailing, build my skills as a sailor, and have fun—this trip did not disappoint. Our captain, Paul Exner, had a relaxed and friendly coaching style, walking us through decision points and sharing his thought process, which was invaluable. I loved sailing on ISBJØRN; my only regret was that the trip had to end. Thanks to 59º North for such a dynamic experience!"
"I'm still processing everything I saw, felt, learned, and experienced over those 17 days, but there are a few things I wanted to express before the land sickness wears off and I return to my landlubber life. Your Skippers and Mates created an environment of calm, comfort, and confidence that washed away any apprehension I had about joining seven strangers on a 1600-mile round trip. I am blown away by their depth of knowledge, not only of sailing but also in teaching a crew of widely different experience levels without a hint of condescension. I would not hesitate to sail with them again, and we're already scoping out future dates on the cal."
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
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. 😊
Eleven Snippets from Adrienne
This list of little moments might just shed some light on all the other stuff happening out here as we make this massive journey together. The back aft deck takes on many roles, like a salon (Anton gave Naxo an award winning haircut), a butcher shop (Kif cleaned his first fish), a yoga studio, gym and a dance club (Manot is an excellent DJ - and Captain and Katelyn keeps us moving wither energy and enthusiasm). Culinary magic happens nightly in a tiny galley by three amazing chef - sailors. Big thoughts, life's questions, personal histories, paths taken and talk of family (pets too) are shared. I'm beyond grateful to be a part of this little community in the middle of the Atlantic.
The Wheel Keeps on Turning
Helming is basically steering the boat by hand. Helming is so completely unlike driving anything else. How each of us put all this information and sensation together to guide our hands and keep Adrienne going where we want to go - to stay the course as the saying goes - is as different as the individuals on this boat. Well there you have it helming as described by six people who approach the same basic task with highly varied perceptions, feelings, and even emotions.
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.”
