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4. San Juan-HAVANA-Key West: // 1,100 Miles & 15 Days // $6,000 // 1 Available

$6,000 // 15 days

It's official - we're sailing back to Havana in 2019! This is by far our most popular passage, and we are already on a waiting list. To add yourself to the waitlist, complete the registration form and indicate that in your first passage choice. We'll advice what your place is in line.

Passage Logs & Photos from 2016


Mia and I recently discovered Puerto Rico, cruising aboard Isbjorn in fall of 2015, and it's GREAT! The locals are awesome, the food is excellent and cheap, and the scenery is stunning. So for that reason, we've decided to make Puerto Rico our Caribbean base for 2019. We'll be meeting the Havana crew in Old San Juan. It's super cheap to fly into San Juan too, and a visit to Old San Juan is a must on your way to the boat! See details below...

  • Join the boat in San Juan, Puerto Rico on April 10 to get introduced to life onboard, and plan for an April 11 departure. We'll likely anchor out in San Juan harbor on Night 0 to get acclimated to life aboard. Details on travel logistics and hotel arrangements will be sent once you sign up.
  • We'll set sail and point the bow west towards the Old Bahama Channel, stopping only perhaps for a swim along the way before making landfall in HAVANA!
  • After a few days visiting the historic capital of Cuba, we'll make the 90-mile hop overnight and back to Key West.
  • Crew must leave the boat by April 25, once we arrive in Key West. Details on hotels and flights our from KW will be provided on registration.


  • Fly into San Juan, which has direct flights from a lot of major US airports and at a very reasonable fee. Southwest recently added routes to San Juan, so be sure to check there too.
  • It's a quick taxi ride to Isbjorn from the SJU airport, we encourage you to explore the Old town of San Juan a day or two before joining Isbjorn.
  • Fly out of either Miami (MIA) or Ft. Lauderdale (FLL) for the cheaper option, or from the small airport in Key West and connect.

How to Join

To register, complete the Offshore Passage Registration by clicking the 'Register Now' button above or at the bottom of the page. You'll be asked to complete the  form - make sure you hit submit. Indicate 'Leg 4, Puerto Rico - Havana - Key West 2019' as your preferred passage. 

Once we receive your registration, you'll be sent an invoice for 50% of the balance, due immediately. The final 50% of the balance will be due 60 days prior to the passage date. Terms and conditions are in the registration form, and you'll be asked to agree to them before submitting your deposit. Please read them carefully.


The trip is $6,000.00 per person, which includes everything you need on the boat, plus the following:

  • Use of a Helly Hansen 'Inflatable Racing' PFD with integrated harness.
  • Use of a double-tether for moving around on deck
  • Isbjörn Sailing crew t-shirt or 59º North hat or visor (your choice at registration).
  • All meals, snacks and drinks while on the boat, including beer, wine and rum while in port.
  • Pillows and sheets onboard.
  • Large collection of books onboard, including novels, sailing classics and sailing reference books, in hard copy.
  • Online tracking for friends and family at home from YB Tracking.
  • Handling of paperwork for entering Cuba.
  • Custom and immigration fees for entering & departing Cuba.

Optional Extras:

  • Extra t-shirts, hats and visors for sale onboard ($20.00)
  • Custom embroidered Helly Hansen crew polo shirts with your name and/or the passage route embroidered on them ($60.00). Available in red, white, navy or black.
  • Any Helly Hansen clothing and sailing gear offered at 10% off their retail price. Visit for their online catalog. Can have stuff custom embroidered with the Isbjörn Sailing logo.

What the price DOESN'T include:

  • Transportation to and from the boat.
  • Personal toiletries & clothing.
  • Sleeping bag.
  • Foul-weather gear (see packing list for details).
  • Meals and drinks ashore.