Caribbean Sailing

Sailing the Caribbean

Sailing the Caribbean promises awe-inspiring moments almost constantly—from the turquoise waters your vessel plies, to the pristine anchorages, and, of course, the many characters you’ll meet along the way. There’s just no better way to experience the West Indies than aboard a sailboat. To be in your personal space, in the personal spaces of your boatmates, and be attached to the vast natural world that surrounds you. Whether at the helm with the wind in your face, or laying out on the hammock in the middle of the night staring up at the Milky Way, or just idly snorkeling after a long crossing — these moments and many more are what sailing the Caribbean offers.

Last updated by Patrick Bennett on .

More about Sailing the Caribbean

Fort Amsterdam, St. Maarten
St. Martin/St. Maarten

Fort Amsterdam, Sint Maarten – Sadly Decaying 17th Century Stronghold

Like the continued coexistence of the Dutch and French in SXM, the combination of Dutch and Spanish styles in Fort Amsterdam make it unique.
3
Shares
Buck Island sailing
🇻🇮Buck Island

2021: A Summer Like No Other for Buck Island Sailing

Summer 2021 is shaping up to be an unprecedented one for Buck Island sailing adventures, though not in a manner that suits procrastinators...
1
Shares
Christmas Sailing St Martin / St. Maarten
St. Martin/St. Maarten

Sailing the Caribbean for Christmas – All I Want; This or Any Year

Sailing the Caribbean for Christmas, is there a better way to spend the holidays? Trading burning-cold breezes for salty sea air.
0
Shares
Remote Working In Style from Buck Island, St. Croix
🇻🇮St. Croix

Remote Working In Style from Buck Island, St. Croix

As remote working setups go, this floating "office" anchored curbside at Buck Island just off the northeast coast of St. Croix is tough to beat.
151
Shares
Baie à Ferret
🇭🇹Haiti

Baie à Ferret – Mooring in the Footsteps of Henry Morgan

Baie à Ferret. Île-à-Vache. Haiti. At first blush it seemed plucked straight out of some classic pirate novel. The perfect hurricane hole.
0
Shares
Prune Bay, St. Croix
🇻🇮St. Croix

Pining for Prune Bay Breezy Beach Fun in St. Croix

Prune Bay just off the northeast shores of St. Croix is a prime spot for all sorts of wind-driven water sports – sailing, kiteboarding, windsurfing.
129
Shares
S/Y Columbia
🇻🇮St. Thomas

S/Y Columbia Shining Bright in St. Thomas

The S/Y Columbia is no ordinary ship. Constructed in 2014, the ship is a jaw-dropping replica of a legendary fishing vessel of the same name.
315
Shares
USVI Charter Yacht Show
🇻🇮St. Thomas

On The USVI Charter Yacht Show and Taking a Different Tack

The USVI Charter Yacht Show is the premier event to get up close and personal with the multihulls, monohulls, and motor yachts of the Virgin Islands
71
Shares
Ice Cream Boat Making a Delivery in St. Martin
St. Martin/St. Maarten

Lily’s Ice Cream Boat Sails On in St. Martin

There's a lot of encouraging news coming out of French St. Martin these days. The icing atop the news for me: Lily's Ice Cream Boat sails on!
85
Shares
see more
Send this to a friend