Spanish Wall Beach, Rincón, Puerto Rico
Dudes and dudettes flock to this semisecret beach in winter for steady six-to-seven-foot waves. The Atlantic and Caribbean meet at Rincón (which means “corner”), so it has great swells all around. If the surf at Spanish Wall looks bad, head to nearby Domes or Antonio’s. At night, a beach bonfire can turn into a rave at the drop of a wetsuit.
Saline Beach, St. Barts
Elder naturists still swear by the southern end of Orient Point beach on St. Martin, but the young beautiful Parisians have moved their firm buttocks on to Saline. Nude, topless, clothed—anything goes on this gorgeous, secluded beach.
Hol Chan, Caye Caulker, Belize
This marine reserve has been closed to fishing for eighteen years, so the barracuda, grouper, snapper, and nurse sharks are muy grande, and the barrier reef—the world’s second largest—is spectacular. The resorts on Caye Caulker and neighboring Ambergris Caye can set up dives or snorkel trips ($35 to $110 per person).
North Lee Bay Beach, Fallen Jerusalem, BVI
This 30-acre uninhabited island is a national park and bird sanctuary donated to the BVI government by Laurance Rockefeller. Head to the secluded beaches on the north side for some much-needed alone time, and plan your escape early, because there’s nowhere to stay.
Cupecoy Beach, Sint Maarten
The Caribbean’s British colonies and American-influenced islands are not particularly homo-hospitable, but the Dutch part of Sint Maarten is as permissive as you like. Cupecoy pulls in attractive men between 18 and 45. If you’re looking for a sex beach, just ask around; this isn’t it.
Pinney’s Beach, Nevis
The Four Seasons Resort here is a popular destination for many Fortune 500 CEOs. With any luck, you’ll be ordering piña coladas alongside Steve Jobs.
Pink Beach, Harbour Island, Bahamas
Far from the casinos and cruise ships, the ocean is clean and calm, and this three-mile stretch of sand beach is a perfectly pink powder that slowly eases into the turquoise sea. Grab a drink at Chris Blackwell’s Pink Sands hotel and pull up a chaise longue for the evening show.
Mullins Beach, St. Peter Parish, Barbados
After a dip in the 80-degree sea, pull up a lounge chair at Mullins Beach Bar on the west coast and get completely hammered—no one on this soothing, extremely safe, post-college-age island will mind, as long as you’re not obnoxious. When you need a change of scenery, head down the beach to Cocomos, where the beer is served icy cold and bands play most afternoons.
Seven Mile Beach, Negril, Jamaica
Scoring pot on this beach in the northwestern corner of the island is a cinch—it doesn’t take much more than a significant gaze to get approached. You should pay about $25 for an eighth; the police look the other way. Bonus: Seven Mile is consistently rated as one of the top beaches in the Caribbean.
Seven Mile Beach, Grand Cayman, Cayman Islands
With an average winter water temperature of 80 degrees, and just about the calmest water outside a swimming pool, this gorgeous five-and-a-half-mile-long powdery white beach is a great bet for the water-wing crowd. Big resorts (like the brand-new Ritz-Carlton and the recently remodeled Marriott) dominate the beach, but none of it is private.
Grand Anse, Grenada
Within walking distance of most resorts, this wide, under-populated two-mile-long beach with white sand all the way into the ocean is reason enough to hop a plane to Grenada. The young medical students from the not-quite-top-tier school at St. George’s University who sun themselves here are an extra incentive.
The JC Beach, Eleuthera Island, Bahamas
Your best bet for coral formations, perfectly intact conchs and starfish, and prized bivalves in extraordinary hues is to comb the two-mile stretch of beach that lies along the James Cistern settlement between Hatchet Bay and Governor’s Harbour. Hurricanes tend to push piles of shells onto the shoreline, so this should be a great season for shelling.
Platinum Coast, Barbados
The beaches along Barbados’s west coast are prime territory for famous guests of high-end villas and resorts like Sandy Lane, where Cindy Crawford, Hugh Grant, and Tiger Woods have all recently stayed. The star power is especially rampant during the Christmas–New Year holidays.