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.

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.

Flotilla Adventures

by Meredith Laitos, Posted October 4, 2011

Looking for a new way to enjoy a charter sailing vacation with friends and family? Join SAIL on a Flotilla Adventure in the British Virgin Islands, where a SAIL host will guide you through a week of fun and relaxation with new friends. Traveling aboard a fleet of Sunsail charter boats out of Tortola, we’ll explore BVI hot spots, visiting old favorites and discovering new

December Sunsail Flotilla

by Sail Staff, Posted October 3, 2011

Looking for a new way to enjoy a charter sailing vacation? Join SAIL on a Flotilla Adventure in the British Virgin Islands, where SAIL host Chris Museler will guide you through a week of fun and relaxation.

2 by 2

by Dawn Dupree, Posted September 27, 2011

Conventional wisdom has it there can be only one captain on a boat, and that skippering by consensus never works. When it comes down to the wire, one voice must be heard above all others, or chaos will ensue. Well, that’s obviously a male viewpoint. My friend Pip and I share a passion for sailing and adventure, and we’ve done some offshore racing and family cruising, but neither of us had ever