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12. ICEBEAR: Tortola (BVI)-St. Bart's-Antigua // 250 Miles // WAITLIST


Skipper: Andy Schell
Mate: Mia Karlsson

Extend your Thanksgiving holiday and come sailing in the Caribbean! Join ICEBEAR, our Swan 59, in Tortola for the passage south and east to Antigua!. We'll sail to Ile Fourche & St. Bart’s on the way, so it will be a combination of island exploration and proper, Caribbean ocean sailing!

We sailed this route in 2016 & 2017 on ISBJORN, and it’s one of our all-time favorites.. Normally, it's upwind all the way, against the prevailing easterly trade winds. But in 2016, we sailed out of the harbor in Road Town after the sun went down, and almost miraculously sailed through the night on starboard tack, the wind from the south, which is extremely rare in that neck of the woods at that time of year.

Once we depart Tortola, we'll aim east. There is no set itinerary, but several places we can stop along the way. The French side of St. Martin is always a fun place to visit, and definitely the classier side of the divided island. Ile Fourche, the gorgeous, deserted marine park that belongs to St. Barth's is another popular stop where we often go ashore before the dawn for a sunrise hike up the moon-like landscape.

Antigua is the easternmost island in the Leeward Islands, so it's all upwind from St. Martin or St. Barth's. Good thing ICEBEAR is such a windward thoroughbred! Depending on timing, we can make landfall in Antigua in Jolly Harbour on the island's west coast, or sail another 30 miles or so around to the south and into Falmouth Harbour, the epicenter of the Caribbean superyacht scene.

This passage is classic Caribbean trade wind sailing, taking in some of our favorite destinations en route to Antigua. You'll love it!

The Route


  • November 30: Join ICEBEAR in Tortola, BVI at 1700. Dinner with the group either ashore or onboard.

  • Dec. 1: All-day safety briefing & boat orientation (plus some swimming & beach time!). Dinner onboard, early bedtime.

  • Dec. 2: Depart BVI for Ile Fourche (part of St. Bart’s). Overnight, upwind sail.

  • Dec. 4: Sunrise hike on Ile Fourche (wake-up at 0500!). We’ll land the dinghy on the beach in the dark then set out up the steep rocky slopes of one of the islands five peaks, making it to the top in 30 minutes or so and early enough to watch the sun rise over the Atlantic Ocean. In the afternoon we’ll daysail down to Gustavia, in the heart of St. Bart’s harbor.

  • Dec. 5: Day ashore in Gustavia, the (formerly Swedish!) capital of St. Bart’s and one of the French Caribbean’s most beautiful towns.

  • Dec. 6: Depart for Antigua. Overnight sail down to Falmouth Harbor on the island’s south coast.

  • Dec. 7: Arrive Falmouth / day ashore or exploring.

  • Dec. 8: Crew depart ICEBEAR in Antigua by 1200 noon.

Travel Logistics

  • Either fly into St. Thomas (STT) and take the ferry to Tortola, OR fly right into Beef Island (EIS) where you can literally walk from the airport down to the beach in Trellis Bay where ICEBEAR will be waiting on anchor.

  • Fly out of Antigua (SJU), which has direct flights to Miami & New York/Newark where you can connect to other major US cities. Flights to and from Europe as well.

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 '2019-12: BVI-St. Bart’s-Antigua' 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.

Cost & What You Get

The trip is $3,400.00 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

  • ICEBEAR 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 ($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).

Blogs from 2017

What to Expect Onboard


Other Important Passage Info