
59º North Sailing
sail offshore on bucket-list adventures

“59º NORTH was founded on a simple vision — to explore the world’s oceans & landfalls in safety & style on cool boats with cool people. We are passionate about traditions of the sea, and share our love for the philosophical aspect of ocean sailing with our eclectic crew. Sign up to sail with us, and hold fast to your dreams."
P.S. - We hope you enjoy the new website experience! Hold Fast!


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


2026-14 | FALKEN | Ensenada-San Diego | Sail Training
Our last passage of 2026 is one of our popular Sail Training passages on FALKEN. While all of our trips involve extensive seam'nship & sail training aspects, this one focuses primarily on just that. As it's a pretty short distance between the start port and end port, it gives us the flexibility to sail further offshore and set the boat up for all points of sailing, practicing upwind/downwind, spinnaker flying, some celestial sights and more.


2026-1 | WOODWIND | Great Chesapeake Bay Schooner Race
The first-ever 59º North passage onboard the 74-ft. schooner WOODWIND! In reality, this passage is a long-time coming, and has a lot to do with the origins of 59º North. Andy sailed in the Schooner Race twice when working as a deckhand on WOODWIND in 2006 & 2007, and to this day it's one of his favorite experiences.


2026-13 | FALKEN | Monterey Bay-Ensenada
FALKEN heads further south down the west coast with a 500-mile hop to Ensenada, across the southern USA border and into Mexico's Baja Peninsula! As we head south the air temps will heat up while the water temps remain California-cool. This is a great passage for those needing a shorter time away from home and easy travel logistics, but want to get offshore.
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.”


















