Bareboat sailing in the Caribbean.

November 14, 2007 6:01 PM

Advice on bareboat sailing in the Caribbean. Four of us intend to spend a week sailing in the Caribbean in early February. Our group knowledge of the Caribbean is very limited. One of the group is a master sailor, so we should be able to rent a bareboat of our liking anywhere they're available. But with so many islands and so many boat rental places, it's hard to know how to decide on an itinerary. Suggestions?
posted by Jackson to travel & transportation (8 comments total)

We loved our ten-day jaunt through the BVIs. Enough fun sailing for the master sailor to have a ball, enough cruising (and great bars, ports, natural wonders and restaurants) for the rest of us more mellow folks. Tortola, Jost Van Dyke, Little Dix Bay... man, it makes me want to go back.
posted by nkknkk at 6:07 PM on November 14, 2007

Seconding the BVI.
posted by sanko at 6:52 PM on November 14, 2007

We're chartering over Christmas and New Years with Barefoot Yacht Charters out of St. Vincent and the Grenadines. They've been nothing but helpful and professional.

St. Vincent and the Grenadines are supposed to be great sailing, as the windward islands have more weather and the distances between moorings is relatively short.
posted by cior at 9:12 PM on November 14, 2007

I think the BVI will be the unanimous recommendation for non-hardcore first-time Caribbean cruising. You don't even need an itinerary, just gunkhole. Rather than picking a specific charter outfit, contact LateSail and let them help you pick a boat from among the (usually excellent) deals they have.
posted by nicwolff at 9:47 PM on November 14, 2007

OK, not unanimous :)
posted by nicwolff at 9:48 PM on November 14, 2007

The Grenadines are more rustic than BVI/USVI, though I have also heard they are "more beautiful." (My one chance to go we couldn't make it)

My going-on-elderly parents (very experienced sailors) are taking a vacation in the BVI with another couple right around now. They've spent lots of time in the Carribean and though I think the area around Turks & Caicos/bottom of the Bahamas was their favorite, they are doing BVI for the ease.

Their experiences in Barbados/Antigua/Insert 'wealthy'/'prestige' island name here were all pretty mediocre. Unless you just happen to be on a MegaYacht. Then, they are quite civilized.

I was once on Guadalupe and that was very very nice, though entirely in French (my beloved spent a lot of time looking at me and going, "huh-wah?").

Have fun.
posted by From Bklyn at 1:38 AM on November 15, 2007

Agree with the BVI answers, I did it a few months back on a 56ft
Hylas and it was a blast. If you have a master sailor on board, you will have some great days out, but there are also "Beer Boats" - 40ft catamarans usually rented out by 2 or sometimes three couples with no sailing experience - often they just run on the engine. You'll easily run the length of the archipelago in a day's sail. Some great places to check out - Jost van Dyke, Cane Garden Bay, Prickly Pear Island and The Spit - just about the perfect "desert island". We had our young kids with us, so we created an elaborate pirate treasure hunt with clues to our next destination and a final buried treasure. In any case, have a great time.
posted by Sk4n at 7:01 AM on November 15, 2007

nthing BVI. Beautiful, fun, and awesome for beginners. You can't go wrong.

As for charter companies, the Moorings is probably the largest, and has very nice boats (exclusively Bennetons, I think, if that makes any difference to your master sailor). As boats age out of the Moorings fleet, they transition to the Footloose fleet -- since their boats are older, their rates are obviously lower, but you spend more of your trip dealing with boat maintenance. There are other charter companies as well, but those are the two I have experience with.
posted by somanyamys at 12:41 PM on November 15, 2007