2024-6 | FALKEN | Jamaica-Cuba
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:
April 14, 2024
Crew arrive to FALKEN at 1300 in Port Antonio, Jamaica. 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.
April 16, 2024
Scheduled departure, weather dependent.
April 24, 2024
Latest date (12:00 noon) for crew to depart FALKEN from Havana, Cuba.
TRAVEL LOGISTICS
Port Antonio
Port Antonio marks a memorable chapter in our recorded passage history: a single landfall in 2024, when FALKEN completed her crossing here from Antigua that spring. Arriving on this lush northeastern coast of Jamaica after days of open Caribbean sailing gives the town its particular magic—the mountains of the Blue and John Crow ranges rise green behind the water, and the pace ashore feels a world away from the busier resort coast.
The harbor is unusual in that it is really two: a promontory divides the town's frontage into East and West Harbours, with the small, wooded Navy Island sheltering the western side. That island carries a long story of its own, careened and repaired by the British Navy in the 1700s and later, famously, owned for a time by actor Errol Flynn, who fell for Portland Parish and left his name on the modern marina at the heart of town. It's a place with deep maritime roots—historically a working shipping point for bananas and coconuts—that still welcomes visiting yachts.
With a day or two ashore, crew can wander the compact waterfront and old town, take in the twin-harbor geography from the higher ground, and explore beyond it: the celebrated Blue Lagoon lies just east, and the Rio Grande winds down from the mountains through classic rafting country. The nearby coves and small islands reward the curious sailor eager to see Jamaica from the water.
Airport Info
Norman Manley International Airport (KIN) in Kingston is the nearest major airport, about 1 hour drive from Port Antonio. There are also international flights arriving at Montego Bay Airport (MBJ), about 3.5 hours away by car.
Havana
59º North completed one recorded passage into Havana, when Falken arrived in April 2024 after a crossing up from Jamaica, and that single landfall marks our recorded history in this legendary Cuban harbor.
Guarding the entrance to one of the Caribbean's great natural harbors, Havana grew wealthy as the assembly point for Spain's treasure fleets, and its seafaring past is written into the stone forts that still flank the narrow channel. The Castillo de los Tres Reyes del Morro and the Fortaleza de San Carlos de la Cabaña rise over the harbor mouth, once linked by a chain that could be drawn across the water to seal the port at night. Inside, the sheltered bay opens into a working commercial and fishing harbor fringed by the old city, while the Malecón sweeps along the exposed Atlantic shore, taking the full force of northern swells when the weather turns.
Crew with a day or two ashore find Habana Vieja, a UNESCO World Heritage site, only steps from the water, its cobbled plazas and colonnaded streets easily explored on foot. The four historic squares, the maritime and colonial collections of the city's museums, and the fortress ramparts overlooking the channel all reward wandering. Live son and salsa spill from doorways in the evenings, and the seawall itself becomes a gathering place at dusk, where locals fish, talk, and watch the surf break against the ramparts.
Airport Info
José Martí International Airport (HAV) is located about 15 km from downtown Havana, with connections to the Americas and Europe.
Weather conditions
Expect a warm, tradewind passage with steady breeze on the beam and a lively, rolling sea—comfortable sailing for the most part, though you'll want your sealegs for those occasional sloppy patches as you reach across toward Cuba.
In-depth analysis, by WRI
WHY 59º NORTH?
ambitious sailing schedule
We sail upwards of 20,000 miles per year in all oceans of the world, and in over 200 passages, we've only been late by one day, one time! We've been able to accomplish this by properly planning our trips with enough time for weather windows, and allowing a few days in port between trips for staff to recover, re-provision and complete routine maintenance (most charter companies allow only a single day turnaround, which is insane!).
Every 4-5 trips we build in a 'fuse', where we have a 2-3 week maintenance period allowing us to take care of the boats in normal circumstances, or give a buffer should we get delayed by unforeseen circumstances prior to this break.
The best boats
We take pride in the maintenance of all of our boats, and hold ourselves to extremely high standards. We buy sails that will last for tens of thousands of miles, while holding their shape (unlike standard dacron); we carry lithium battery banks with high-output alternators so there's less time running the engine to charge at sea and killing the vibe; we carry enough sails to sail the boat to the conditons, whether that's heavy weather or light weather, to give you the full experience.
WOMEN BUNKS GUARANTEED
As a woman sailor, you will never be alone on a 59º North passage. We guarantee at least two women on every passage, and save those bunks before they sell out. If they don't sell, they're given away to women apprentices - yes, we put our money where our mouth is.
In fact, we rarely ever have to. 59º North passages have always been 'mixed' - not only by gender, but also by age, nationality, background, you name it. Back around 2022, we had a few prospective crew wondering if they'd be the only woman onboard. As that had almost never been the case, we decided there and then to guarantee it.
Our staff are also mixed gender as often as is logistically possible, and several times per year, on both boats, we run All-Women's passages, staffed and crewed entirely by female sailors to help further empower an often overlooked demographic at sea.
Professional, well-paid staff
Adventure sailing is the highest calling for most aspiring skippers who truly want to sail. Unlike superyachts, who spend most of their time in port, we spend most of our time at sea, and the real sailors who want to work in that envrionment are attracted to it.
Sadly, the industry-standard pay is extremely low, and offers little in the way of a safety net, or provisions for having family back home. We want to change that.
All of our professional staff are paid well above industry rates, and we sail on rotations of usually 6-week stints, so those of us with families and small kids ashore can be present as parents and partners while still living our dreams.
The truth is, most of us would do this job for free, and that's part of the "supply & demand" that sets the salary rates in our industry.
But at 59º North we value people above all else, and that starts with our staff, many of whom have been with us for years and will be familiar faces to those who return to sail with us again and again.
knowledge & community
When you sign-on to sail with us, your journey to ocean sailing starts the minute you click "Submit" on your signup form when we start the preparation process with you to go to sea. That includes:
- Extended FREE trial in our Quarterdeck seam'nship community & knowledge-base.
- Series of 3 newsletters leading up to your passage, including specific packing lists, gear discounts with our partners (including 25% off everything at Helly Hansen).
- 1-1 comms with Andy, Mia & August and our skippers if you have any questions before your trip.
Once you join the boat, you'll see why people sail with us again and again. But your experience doesn't end when the passage is over. You'll get:
- Exclusive earned patches for different milestones you've earned with us at sea.
- Sea-service letter/signed logbook if you're looking to earn miles towards a license.
- A final newseletter with photos and other useful information, including a copy of the handwritten logbook you kept while on the boat.
Why it costs what it costs...
Imagine you’re craving a burger.
On the same street, there are two restaurants. Both serve burgers. One is mass-produced to be fast & cheap. The other is made with carefully sourced ingredients by people who genuinely care about making a great burger (even great veggie burgers!). The bun is baked that morning. The onions are pickled in-house. The beef comes from a local farm. Every little detail is curated & intentional.
On paper, both have pretty much the same ingredients: a bun, a patty, cheese, onions, pickles and some sauce. They’re both burgers.
But nobody would argue that they taste the same or provide the same experience.
Offshore sailing is, weirdly, similar. You get out what you put in, and we put in a lot of effort to cross oceans in safety, in style, on-time and with passion.
At 59º North we obsess over and invest in the details: experienced career skippers, beautifully maintained boats & meticulous preparation, small crews, "teachable moments" and a culture of camaraderie.
Those choices cost more.
We know they’re worth it.
The end result of our "burger" is that it'll be the best-tasting burger you've ever had, literally life changing. Yes, you'll cross oceans, but the overall experience is what you'll remember for years to come, and what you'll want to return again and again for.
That's one tasty burger.
Hold Fast,
Andy | Skipper & Co-Founder
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
day 6
Last day of sailing today as we rounded the most westerly point of Cuba late last night. Its back to the coaching of the helm as many of the crew experience upwind conditions for the first time.
day 5
You can imagine my surprise to be awoken suddenly, wondering what emergency may have demanded my appearance on deck with such urgency. Fiona had been sent to undertake the task feared by many before her as she delivered the news that I must leave my dreamy wonderland of much needed rest…
day 3
Another cracking sail across to Grand Cayman where we picked up a mooring buoy off Georgetown in the early hours of this morning. Having woken early as instructed by the port security, we were able to clear in with ease as we temporarily came alongside the quay.
day 2
The pole made an appearance overnight as we waved goodbye to the lights of Jamaica that accompanied us for the first part of our passage yesterday. As always, the first night involved some coaching on the helm as each of our crew settled into life under sail aboard FALKEN.
Pre-Departure
Having reached Jamaica in remarkable time, given the almost perfect sailing conditions, the crew departed today but not before a number of mini adventures shoreside.












