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2. Grenada-Virgin Islands // 500 Miles // 7 Days // 1 Available

  • chaguaramas trinidad (map)

$2,800 // 7 days


The following email is going out to everyone who is signed up to sail TO or FROM Trinidad with us in late January / early February. I just heard some unsettling news today that is forcing us to be flexible and change some plans for the trip.


In the past ten days, TWO sailing yachts on the route between Grenada and Chaguaramas, Trinidad were boarded by heavily armed Spanish-speaking pirates, likely from neighboring Venezuela. An 80-foot megayacht and a 32-foot family cruiser. Nobody was hurt, but lots of cash and stuff was stolen from the boat, and I'm sure the crew was in a bit of shock! You can read the news article that was just posted today here:

...and read a longer account from Noonsite here:

...and here's another piece from the Safety & Security Net website:


Given the news, I cannot responsibly continue ahead with plans on sailing to and from Trinidad. While the Trinidad & Tobago coastguard is probably amping up efforts to protect against this - their local economy relies heavily on the yachting industry, and this is far worse for them than it is for us - I still feel it's foolish to continue as planned.

Thankfully, Grenada is a nearby option on the way, in the 'safe' zone regarding piracy, and easy logistically to plan for. It'll shorten the trip by about 90 miles (12-18 hours or so) but add more time ashore to explore. I sailed there last year and the place is fabulous! Our new destination for the first trip will be St. Georges, Grenada, where we'll also departing from for the return leg.

I understand most if not all of you have already booked your flights into or out of Port of Spain in Trinidad. 59 North, Ltd. will either pay for your flight change, up to $250 per person, if that's possible, or buy you a ticket to/from Grenada. I did a quick search today and it's about $100-150 to fly direct from Grenada to Trinidad, and it's only a 40 minute flight.

Of course, if this change is too far from your original expectations, I'll offer a full refund if you choose to cancel the trip altogether, but cannot offer compensation for your airline tickets.


I hate to change things up again, especially for those of you who were so supportive of our change of plans to stop in Dominica on the way south, but this is the reality of the adventurous type of sailing you all signed up for! I sincerely hope you will all take this in stride and decide to stay on as crew. I'll do whatever I can to ease the logistical challenge of the change in plans. See below for new itineraries for both legs. 

If I don't hear back from you by end of day Monday, January 4, I'll call each of you individually to discuss options.


Trip 1: Virgin Islands-Dominica-Grenada
Jan. 23: Depart BVI bound for mid-way stop in Dominica (260 miles)
~Jan. 25/26: Arrive Roseau, Dominica. Clear customs and explore the island with Sea Kat! Option to do the Boiling Lake Hike, explore the Caribbean's best local market, go diving, etc etc!
~Jan/ 29/30: Depart Roseau bound for St Georges, Grenada (200 miles)
~Jan 31: Arrive St Georges
Feb. 1: Crew disembarks Isbjorn. Flies either on to Trinidad to connect home, or from Grenada if you can change your flight.

Trip 2: Grenada-Virgin Islands
Feb. 3: Crew arrives and joins the boat in St Georges (we will be at Port Louis Marina in St Georges town). You can either fly into Trinidad as planned and connect up to Grenada, or try and change your flight altogether.
Feb. 4: Depart Grenada bound for Virgin Islands (~500 miles)
~Feb. 7 or 8: Arrive Virgin Islands. If we sail fast enough, as we did last year on Serenity, we'll discuss the option to stop first in St Croix, USVI, before continuing on to Tortola.
Feb. 10: Crew disembarks and heads home!

Please feel free to ask me any and all questions. I appreciate your continued support and understanding in the change of plans!


This is a long ocean passage, and should be beam to broad reaching conditions most of the way, making for a fun & fast trip! We might even get a chance to hoist the spinnaker for a bit!

The mate for this trip will be none other than my old friend Clint Wells, who crossed the Atlantic with Mia and I in 2011! Hear Clint talk about that trip on the podcast. This is the return leg of the voyage south. If you'd like to book both passages, please contact Andy for special pricing.


This is the original itinerary, which has been changed (see above) due to piracy in Trinidad. Please disregard the below and read the email above!

  • Join the boat in Chaguaramas on February 2, for a planned February 3 departure.
  • We'll set sail and point the bow north to Tortola, stopping only perhaps for a swim along the way! Otherwise, it's 600 miles nonstop back to the VI, a proper ocean voyage.
  • Sail past some of the Eastern Caribbean islands, with a glimpse of the volcano at Montserrat a distinct possibility.
  • Crew must leave the boat by February 8, once we return to the VI. 

Travel Logistics

  • Fly into Port of Spain, Trinidad (POS) airport and take the short taxi ride to Chaguaramas, where Isbjörn will be at a local marina (TBD).
  • Fly out of either Beef Island (EIS) on Tortola (more convenient), or take the ferry to St. Thomas (STT) and fly from there (cheaper, but inconvenient).
  • If you fly from Tortola (EIS), you'll have to connect in either Puerto Rico or another major airport. EIS is very small and has only small planes.

Cost & What You Get

The trip is $2,800.00 per person, which includes everything you need on the boat, plus the following:

  • Helly Hansen 'Inflatable Racing' PFD with integrated harness.
  • Double-tether for moving around on deck
  • Isbjörn Sailing crew t-shirt
  • All meals, snacks and drinks while on the boat, including beer, wine and rum while in port.
  • Sleeping bag and pillow 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 for sale ($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.
  • Foul-weather gear (see packing list for details).