2027-5 | FALKEN | Cayman Islands-Key West
(Note that we offer a % discount if you pay by cash/bank transfer.)
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.
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?
ambitious sailing schedule
The best boats
WOMEN BUNKS GUARANTEED
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."
"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."
"Before 59º North I didn't know my bowsprit from my binnacle and suffered from low sailing esteem. After two weeks of 59º North, what a difference! As a longtime podcast listener, I arrived for my Bermuda to Horta transatlantic with high expectations, and they were all not just met but exceeded. I could not imagine a skipper and mate more professional and enthusiastic than Andy and Emma."
"Mark and I signed up for a multi-night sailing adventure and ended up with a life-altering week of utter delight. Alex and Mia created an atmosphere of trusting, loving community the second we boarded FALKEN, and we still can’t believe how they trusted us with their beautiful boat and the crew’s lives. We learned about sailing, charting, trimming sails, and working in teams with strangers, and experienced everything from flat calm to huge swells, dolphins, and whales. We’ve been off the boat for four days and are already obsessed with going on another leg—what a week, 59º North!"
"Having sailed on ISBJØRN in 2019 from Puerto Rico to Key West, I was excited to join another 59º North passage. Meeting the crew in Las Palmas for the trans-Atlantic passage on FALKEN was a fantastic experience, sharing cultural perspectives and sailing knowledge with people from six different countries. I learned so much, from safety procedures to specialized sail trimming, and made great friends on that journey."
"The trip delivered on all my expectations and more. I wanted to experience sailing beyond my current boundaries, apply my skills, and learn from those around me. I felt able to embrace the whole experience because we had an excellent 59º North team that shaped us into a great crew on a well-prepared boat. If you are seeking ocean wisdom, you could not be in better hands."
"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."
THE BOAT
Farr 65
'
FALKEN
'
🇬🇧
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.
packing lists & notes
Packing Notes
Start here when planning your packing for sailing with 59º North. This list includes the general basics for all of our passages. The passage-specific packing lists offer more details.
Tropical Offshore Packing List
This will be a tropical passage, so expect hot & humid conditions and light, sun-protective clothing! There's not much shade on any of our boats, so you'll want sunscreen, hats & visors. Good chance for a mid-ocean swim if conditions allow. Check the specific packing list for more details, but generally these passages are HOT!