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5. ICE BEAR & ISBJORN: Key West - Bermuda // 1200 Miles & 11 Days // $4,500 // WAITLIST


Our second passage of 2019 on BOTH BOATS! ICE BEAR & ISBJORN will sail in company from Key West to Bermuda, following the outline below. Mia & Andy will be aboard ICE BEAR. Simon Börjeson & Ben Doerr will be onboard ISBJORN.

ICE BEAR: Waitlist
ISBJORN: Waitlist

Two classic sailor's paradises in one trip! This is a long ocean passage from Key West into the Atlantic and towards Bermuda. We'll start by threading our way north into the Gulf Stream and around the Bahamas, before angling northeast and into the Atlantic Ocean proper, for a classic landfall at the 'Onion Patch.'

This passage will include variable weather and the potential for heavy weather as we get further offshore. We've allowed some time for weather delays, but it's a long enough ocean passage that once offshore, we'll have to take what nature throws at us, so be prepared!


  • Join the boat in Key West. Feel free to fly down a few days early and spend a few nights ashore if you'd like to explore.

  • We'll plan to set sail on May 2nd (weather dependent) and point the bow east and into the Gulf Stream sailing along Florida and up the coast, around the Bahamas and northeast into the Atlantic towards Bermuda.

  • Crew must leave the boat by May 12, once we arrive in Bermuda. If we arrive earlier than that, you're welcome to stay onboard until May 12. Details on hotels and flights to Florida and from Bermuda will be provided on registration.


  • Fly into either Miami (MIA) or Ft. Lauderdale (FLL) for the cheaper option, or from the small airport in Key West and connect.

  • Fly out of L.F. Wade International Airport, Bermuda, a 15-minute taxi ride to the airport from St. Georges, where we'll be heading to on arrival.

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 5, Key West - Bermuda 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 $4,500.00 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.