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Sailboat Racing in Anguilla happens throughout the year and is all about harnessing of the island's natural splendor and the talent of the island's inhabitants to be world class.

No better way to celebrate the 4th than with a day sail adventure off the northeast shores of our home island of St. Croix, U.S. Virgin Islands.

Sailing Virgins, the sailing school born of the sexy, non-stop party at sea that is The Yacht Week, employs a chill method of instruction that's heavy on getting you up close and personal with the Caribbean's natural wonders, culture, nightlife, and irie vibes.

A few years ago, I was lucky enough to catch much of the beauty and fun to be had at the Black Point Regatta. One thing I missed, and now desperately want to experience is perhaps the most uncommon aspect of the event: the ugly. Specifically, the "world famous" Ugly Man Contest.

A long day of intermittent lounging, swimming, splashing around, and laughing along the pristine and perfectly crescent-shaped white sand paradise of Deep Bay, Antigua is drawing to a close.

Sailing the BVI's has always an adventure, but perhaps even more so now. It makes every day more rewarding than ever. Every day more of an opportunity to support this special destination. And, of course, the best way to rediscover these islands is with a bareboat or skippered charter from our friends at Sunsail.

A scintillating display of world class seamanship, speed, and man's/woman's insatiable appetite for competition, Antigua Sailing Week presents about as thrilling an experience as I've ever enjoyed at sea.

Sea conditions offshore Grace Bay Beach in Providenciales, Turks and Caicos are generally as calm as they come in the islands, yielding nice, long sessions of ultra-smooth sailing.

Phenomenal sunsets play out daily across the Caribbean, though I can hardly imagine any more spectacular than this one at Salt Whistle Bay in Mayreau, the smallest of the inhabited islands of The Grenadines.