
59º North Sailing
sail offshore on bucket-list adventures

"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."


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.



Where we sail
Since 2015, 59º North boats have sailed far and wide, covering most oceans of the world and sailing with a range of skippers and mates and over 1,000 crew from all walks of life and from all over the world. Have a look at our impressive stats below, which update automatically!
171,196
185
1,037
6
21
27
13
4
16
2
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


2026-2 | WOODWIND | Chesapeake Adventure Cruise
Join the WOODWIND for the passage back to Annapolis after the Great Chesapeake Bay Schooner Race! This had been an annual event for many years (and Andy has done it twice while working as a deckhand in 2006 & 2007), but it's been on hiatus for a few years, and now that 59º North has taken ownership of WOODWIND, we're bringing it back! You'll join the boat in Norfolk the day after the race crew depart, and we'll plan an adventure cruise back up the Bay. As the route is only 130 miles, we'll have time to sail and explore, gunkholing up secluded creeks on the Eastern Shore and visiting some quaint Chesapeake towns in the less-crowded fall season. The weather this time of year usually allows for good sailing conditions and crisp mornings and evenings on anchor. This is a wonderfully unique passage on a fabulous, classic schooner, join us!


2027-8 | FALKEN | ARC Europe: Annapolis-Bermuda
We first sailed with ARC Europe back in 2017 on ISBJØRN, so it's high time we re-join the cruising rally on FALKEN! Andy & Mia used to be the event managers on the rally back in the day and we know the route well. You can signup for the full rally, or each individual leg. We'll start on the Chesapeake Bay and meet the northbound rally fleet in St. George's, Bermuda. This is one of 59º North's "classic" offshore routes from hometown Annapolis, across the Gulf Stream to the 'Onion Patch!'


2027-11 | FALKEN | ARC Europe: Sao Miguel-Oban
Our last leg with ARC Europe, as we split with the main fleet and head north, while the majority sail east for Portugal. With a rhumb-line distance of 1,800 miles, nearly as long as the Trans-At itself, this is an awesome and challenging passage towards Northern Europe and the British Isles. We'll stay west to skirt the Azores high, and should have favorable winds for the majority of the sail north, but will have to contend with passing depressions as we sail up the west coast of Ireland, aiming for landfall in Oban, Scotland, single-malt heaven for you Scotch lovers!
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.”


















