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.
SAILING STAFF
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The Passage
Rough itinerary
All 59º North passages are very much subject to weather. We pick our routes based on the "correct" time of year to be sailing in the different regions we visit, and we always build-in enough time to give us some margin for weather windows. The skipper has final say on departure dates and weather windows, but generally speaking, the intinerary for this passage will look like this:
March 14, 2027
Crew arrive to FALKEN at 1300 in Grand Cayman, Cayman Islands. FALKEN orientation followed by crew dinner. All crew stay onboard FALKEN.
Prep Days
Between the joining and departure dates, all pre-passage preparation, provisioning, and safety briefings will be completed. The specific pre-departure schedule will be outlined and posted onboard FALKEN by the skipper.
March 16, 2027
Scheduled departure, weather dependent.
March 21, 2027
Latest date (12:00 noon) for crew to depart FALKEN from Key West, United States.
TRAVEL LOGISTICS
Grand Cayman
Key West
Weather conditions
Mid-March on this passage usually feels warm and pleasant, with steady trade winds giving you a lively, downwind-leaning sail and a bit of swell to keep things interesting—generally settled, but always keep an eye out for the odd front sneaking down.
In-depth analysis, by WRI
WHY 59º NORTH?
The best boats
Professional, well-paid staff
knowledge & community
Why it costs what it costs...
"Our voyage was interesting because both ISBJØRN (which I was on) and ICEBEAR traveled the same route at roughly the same time. We had Matt Rutherford as our captain and Ben Doerr as first mate, and they were both chill, fun, and always happy to answer questions and provide advice. I feel I got the experience I need with the ocean and Gulf Stream to pilot my own boat from Florida to Bermuda in the future, which was exactly my goal. If you are looking for blue water sailing experience and a fun adventure, I highly recommend that you sign up with 59º North."
"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."
"It was such an experience! Meeting all the people and being part of the crew is something very special. We were so lucky to spend the passage on FALKEN; the nature and weather gave us the best, and I really wish it could have lasted longer."
"I'm AKA Andy’s Dad, so my opinion of the skipper may be slanted a bit. I admit to being wrong on my initial reaction to FALKEN—at first sight she seemed like a hard-to-handle race boat, but she is easy to handle and shrinks once you get used to her. The refit work done below is flawless, with comfortable bunks, a spacious galley, and plenty of storage. A trip with 59º North on any of their boats is truly a life-changing experience. Highly recommended!"
"59º North runs the most professional offshore training program you can find, and it shows in their professionalism, leadership, skill, and service. I felt honored to be part of the maiden voyage of FALKEN—she's a beauty, and the 59º North refit crew did an amazing job! Shout out to Nikki Henderson (Captain) and Alex Laline (Mate) for inspiring, knowledgeable, and caring leadership. I can't imagine having a better experience with any other."
"Adventure, education, majesty... I can't imagine a better pair to introduce people to the sublime enterprise of offshore sailing. This trip will always live amongst my cherished memories. Thank you!"
"Cruelling and unforgettable! I knew I would be inspired by Nikki and Alex—true professionals—but it was the inspiration I took from my crewmates that will stay with me for a lifetime. As a blue water cruiser, this experience definitely made me a better ocean sailor!"
THE BOAT
Farr 65
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FALKEN
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FALKEN is ideally set up for long-distance offshore sailing. We fully rebuilt the boat in 2022 to our exacting specifications and with the help of legendary yacht designer Bob Perry. She's comfortable belowdecks and each crew has their own dedicated sea berth & gear locker. On deck she has a huge cockpit which easily seats 10 people for our daily meals offshore, and allows for plenty of room to move about when handling lines and trimming sails. She's also easy to maintain, fast and fun to sail! FALKEN sails with 8 crew plus a Skipper & Mate and the occasional apprentice.