Caribbean

The Islands You Never Knew

by Chris Caswell, Posted March 6, 2013

There aremany Caribbean islands that are just off the beaten path and are readily accessible for bareboaters looking for adventure, for something different or just to break out of the rut. Here’s a look at five islands you never knew you always wanted to visit.

Announcing the Winners of the 2013 Great Escape

by Meredith Laitos, Posted December 18, 2012

Each year, SAIL and St. Vincent and the Grenadines offer our readers the trip of a lifetime: a free charter in paradise on board a TMM Yachts charter boat. To win, readers submit their “Top Five Reasons” for chartering in SVG, and we sift through 1,000 essays to pick our winner.

Cat Christmas in the Caribbean

by Bill Springer, Posted December 14, 2012

Our hosts, John and Caroline Charnley, and my wife, Caroline, were already swimming in the cool, fresh water, but of course, I just had to jump in from the “cliff” (about 10 feet high) above the pool.

Win an Escape to St. Vincent

by Meredith Laitos, Posted October 19, 2012

Yearning to get away this winter on a Caribbean charter? You still have a week to win SAIL’s Great Escape contest: a free weeklong charter in St. Vincent and the Grenadines with TMM Yacht Charters.

Cowboys in The Caribbean

by Meredith Laitos, Posted July 16, 2011

Six weeks before we took off for St. Lucia, my nervous father texted me, “I’m buying some new clothes for the trip. Will I be okay in T-shirts and quick- dry tops?” “Sure!” I replied, “Think about buying some linen, too.” “Linen?” he texted back, “where on my body and where on a boat would I put linen?”

Spanish Virgin Islands: The Light Fantastic

by Tim Sheehy, Posted October 16, 2012

The thumbnail moon was below the horizon, making it tough to see the dust devils rising through the holes in the floor of the rusty Ford Econoline van as we careened down the bumpiest dirt road I’ve ever travelled.

Excessive Merriment & Hilarity in the BVIs

by Meredith Laitos, Posted October 15, 2012

The first time I met Julian Putley, I brought him a pair of shoes. We were shooting a video on bareboat sailing, and Julian’s boss didn’t want him to be barefoot on screen. “I’ll only wear these once,” he laughed when he saw them.

Secrets of St. Thomas

by Meredith Laitos, Posted July 9, 2012

When it comes to chartering in the Caribbean, St. Thomas has always stood apart for its convenient airport and top-notch shopping district in downtown Charlotte Amalie. But after Peter Nielsen’s exceptional experience at the St. Thomas Rolex Regatta, I wanted a taste of what else the island had to offer.

Race Charters in the Caribbean

by Amy Ullrich, Posted June 25, 2008

Amy UllrichCaribbean regattas aren't the sole province of locals and sailing journalists. Three big ones—the St. Martin Heineken Regatta (early March), BVI Spring Regatta and Sailing Festival (early April), and Antigua Sailing Week (late April)—have non-spinnaker charter divisions, and several charter companies allow their boats to enter.

Expert's Choice: Leeward Islands

by Chris Doyle, Posted August 8, 2008

Chris Doyle has been writing and updating the Cruising Guide to the Leeward Islands since 1989.FOOD AND DRINK» ProvisionsIf you decide to self-provision or just need to restock, it doesn't get better than in St. Martin, where the supermarkets are giant and waterside provisioning services ensure that superyacht guests (and you) are never