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6: ICE BEAR & ISBJORN: Bermuda - Annapolis // 750nm & 10 Days // $4,200 // WAITLIST

$4,200.00 / 10 Days

Our 3rd 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. Paul Exner and a mate TBD will be onboard ISBJORN.


Join Isbjorn in historic St. Georges, Bermuda, a UNESCO World Heritage city, for the 750-mile jaunt back to her home waters on the Chesapeake. Bermuda is one of the classic sailor's landfalls, and a place every sailor needs to visit at some point. The harbor is filled with boats coming and going, especially at this time of year, and you know they've had a long sail just to get there. And Bermuda is the only place where you can buy Gosling's 'Family Reserve Old' Rum - so load up the bilges with some of the finest sailor's rum in the world to bring back to family & friends on the continent!

It'll be the first time Isbjorn has sailed back to Annapolis since 2016, and should make for an exciting reunion.

The passage back from Bermuda is usually reasonable weather this time of year, but it's long enough that you never know what it'll be like by the time we reach the Gulf Stream, so be mentally prepared for changing conditions as we head west. It'll be a warm-weather trip, maybe a little cool in the evenings offshore. 

The biggest challenge with this trip is timing the Gulf Stream crossing - ideally, you'd like to pick a weather window for this part, but since the GS is a good 600 miles west, it's sometimes hard to get a forecast accurate that far out. So we do our best and take what we get when we get there.


  • May 18: Join the boat in St. Georiges, Bermuda

  • May 19: Planned departure from Bermuda, weather dependent. Non-stop offshore trip to Annapolis, MD.

  • We'll enter the Chesapeake Bay in the south and sail the 120nm up the bay to Annapolis.

  • May 26-27: Planned arrival to Annapolis, but depending on the weather it can be faster (or slower). If we arrive early, you are welcome to stay onboard and explore Annapolis until May 28th.

  • May 28: Crew depart Isbjorn at noon.

Travel Logistics

  • Fly into L.F. Wade International Airport, Bermuda, a 15 min taxi ride from St. Georges where you'll meet Isbjorn. If you like to explore Bermuda before joining Isbjorn, check out for accommodations ashore

  • Closest airport to Annapolis is Baltimore (BWI), or any of the DC airports. A quick taxi ride to Annapolis. We will let you know exact location in Annapolis closer to the trip.

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 6: Bermuda - Annapolis 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 $4,200.00 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).