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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2026-12 | FALKEN | Ensenada-Monterey Bay
Join FALKEN just across the border in Ensenada, Mexico, for the passage back north to Monterey Bay, California. You'll set sail after a day or two of briefings to learn the boat and meet the crew, then it's several hundred miles of ocean sailing in the Pacific! As with all 59º North trips, you're part of the crew - helm, navigate, manage systems, change sails and more as you and your shipmates steer FALKEN north.
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.
"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. The expression 'life-changing experience' is thrown around too loosely, but this one was for me. I'll be forever grateful to 59º North for this opportunity and I hope to sail with them again soon."
"I have been sailing for 60 years, mostly as an inshore one-design racer, and had never had the right boat, expertise, or opportunity to go far offshore. The Annapolis to Bermuda passage on ICEBEAR far exceeded my expectations—the skipper and mate were very knowledgeable, and ICEBEAR is a solid, sea-kindly vessel that is surprisingly fast in light air. Our crew of seven strangers became a cohesive, friendly, and competent group, and I’m grateful I got to put into practice the celestial navigation knowledge I gained from Andy and Mia’s 2020 seminar. I hope to make another passage with 59º North in the future."
"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."
"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."
"A fairytale on top of the world, traveling from charming island to island on our trusty steed and home, SPICA. Andy will need to get a wizard's hat for the next voyage."
"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."
"I really didn’t know what to expect on my trip. I knew it was going to be about 800 miles, the Bay of Biscay is notoriously challenging, and there was a remote possibility of orca attacks. Thankfully, we were safe, but the Bay of Biscay did not disappoint, and we logged more than 1,000 miles. Our skipper and mate, Nikki Henderson and Emma Garschagen, far exceeded any expectation I had, and at no time did I ever feel unsafe, which allowed me to fully take in every experience. I learned a ton, had a great time, and left with a new sense of confidence that I never expected."
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
A last hurrah
Under the dome of stars in a moon-less sky, each of us during our time at the helm used the most rudimentary celestial navigation, keeping a star or two lined up with the mast as a helper to following the heading range. It was a whole crew event to set the spinnaker, reef the mainsail and practice the heave-to in case of man overboard. Alex stressed that the key to success in all of these crucial activities is preparation. It was hugely satisfying to accomplish these tasks through teamwork. We share a constant good hearted back and forth full of stories, one-liners and comebacks that also means constant laughter.
One little bird!
Falken has almost rounded the Channel Islands and is cruising along splendidly about 100 miles offshore. Though several models predicted some slightly fresher winds today, we were met with a consistent 18-20 kts of pure bliss. It seems that from the moment we left the dock in San Francisco, there has been much laughter and conversation amongst everyone. The plan is to gybe in a few hours and begin our approach to Ensenada. As much as I do appreciate the jokes and intellectual musings, I equally appreciate the natural, silent moments we share at night, all of us on watch gazing up above to the shooting stars, constellations, and planets putting on their quiet show.
Birds and glows
The sun brought new wind and we were soon putting up the Yankee (jib) and turning off the motor. During the evening tradition of sharing “glums and glows” that follows the crew dinner, our Mate Ryan proclaimed it a “champagne sailing” kind of day. As Alex noted this evening, life goes by so fast that one of the very best things about his line of work is enjoying the passage of time in the slow lane of an ocean passage. But by tomorrow, the green blobs in the weather sailing app indicate we’re going to pick up some significant northwesterly winds and we’ll take them ever further south to the Channel Islands latitude. We’re all super excited for the knots to climb and to see Falken really run.
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).
More info will be coming out closer to the show!
Sailor's Social Party | Annapolis
Women's Happy Hour | Annapolis
The Quarterdeck
SEA·M’N·SHIP /ˈsēmənˌSHip/: “The skill in, and knowledge of the work of navigating, maintaining, and operating a vessel.”
