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4. ICE BEAR & ISBJORN: San Juan-Key West: // 1,100 Miles & 15 Days // $5,500 // 5 Available

$5,500 // 15 days

This will be the first passage of 2019 with BOTH BOATS. We'll sail in company from San Juan-Key West, with a stop in the Dominican Republic en route for some coastal cruising. Note that the Havana stop has been CANCELLED due to legal issues. More info below.

Mia & Andy will be aboard ICE BEAR. Simon Borjeson & a mate TBD will be onboard ISBJORN.

Ice Bear: 2 Crew Space Available
Isbjorn: 3 Crew Spaces Available

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 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 boats 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 perhaps for a swim along the way and cruise the Dominican Republic before making landfall in Key West.

  • Along the way, we’ll stop over in the Dominican Republic for some coastal cruising, exploring, maybe some diving (optional), before continuing on 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.


What follows is the letter we sent to all registered crew on the reasoning for cancelling the stopover in Havana:

Hi Gang,

Greetings from Pennsylvania. We've got some changes to the upcoming Puerto Rico to Key West passage next year that we need to inform you of.


  • Due to forces out of our control, we are NOT stopping in Havana.

  • The trip remains ON, same dates, same start/finish ports, lower price (now $5,500).

  • All crew will be offered a full refund if they decide to cancel, no questions asked.

  • Instead of Cuba, we are looking into stopping over in the Dominican Republic or the Bahamas. We will stay on the boats for these stopovers instead of booking a house ashore, and instead do some coastal cruising before continuing on to Key West.


The long story short is that as we had feared, we cannot legally go to Cuba on EITHER boat next year. Shortly after we announced the trip back in 2017, the current administration has cracked down on the 'People-to-People' travel concession, and the rules continue to be vague and changing. We were hoping something would change for the better in the interim. Alas, it hasn't and we're worried if anything, it'll go the other way and make it even harder still to go to Cuba. We didn't want to find that out at the last minute next spring, so decided to change our plans now.

Furthermore, the boats would be uninsured in Cuban waters. So there is too much to risk both to us and the business, but also to you all as Americans. We could not get a satisfactory answer from anybody on how to do this properly, and combined with the insurance issue decided to cut our losses and re-work the trip.

We ARE still doing the passage - same dates, same start & end, San Juan-Key West. Instead of Cuba we’re looking at stopping over in the Dominican Republic or possibly the Bahamas, and will have details more on that in the coming weeks.

All crews from both boats will have the option to cancel the passage for a full refund, no questions asked. We hope you stay onboard anyway, as it’ll still be 1,000 miles of downwind, offshore sailing! But we understand Cuba was a big draw. The trip will also cost less than originally stated - instead of $6,000, it will now be $5,500. If you stay on, this difference will be reflected in the balance payment due 60 days out.

We're sorry to give you this news but it’s out of our hands unfortunately. If we were cruisers we'd probably still go - but we’ve got too much at stake to push the limits and I don’t want to be made an example of.

Thanks you all for understanding, and don't hesitate to call or email us if you have any questions - we're in the USA until Oct 30 and available to talk on 484-269-3358.


Andy, Mia & Simon


  • 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 - Key West 2019' as your preferred passage. Also indicate which boat you'd like to be on - ICE BEAR or ISBJORN.

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 $5,500.00 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.

Optional Extras:

  • Extra t-shirts, hats and visors for sale onboard

  • Custom embroidered Helly Hansen crew polo shirts with your name and/or the passage route embroidered on them. 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.