Top Destinations for a Caribbean Guys' Getaway

Surf and Sip in Barbados

You'll have ample opportunity to sample Barbados' famous rums whether you're on a tour of St. Nicholas Abbey or the Mt. Gay distillery or immersing in the famous party scene at St. Lawrence Gap. Plus, Barbados is one of the surfing and windsurfing capitals of the Caribbean and has one of the region's best horse tracks at the Barbados Turf Club for when you want to fire up a stogie and bet on the ponies.

Get Active in Puerto Rico

Puerto Rico is a great place for adventurous guys who want to get active on their vacation. You can visit the underground caves of Río Camuy Cave Park, the third largest underground cave system, where you'll take a guided walk deep into the caves.

Beach lovers will want to visit the western beaches of Rincón for sunbathing and surfing and if you want to do something unusual, go kayaking at Vieques' bioluminescent Mosquito Bay.

For clubbing, you can't beat San Juan, and Puerto Rico also offers plenty of high-energy sports, from boxing and baseball to the lure of the country's hotel-casinos. You can even do a cave rappel and zip line excursion near San Juan.

If you want to party every day of your vacation in Puerto Rico, try these party central type resorts like El San Juan with its on-site casino and expansive lobby bar. If you're visiting Ponce, and want a hotel that will entertain you once the sun goes down, the Hilton Ponce Golf and Casino Resort with casual bars and one of Puerto Rico's largest casinos, will fit the bill.

Celebrate in Trinidad & Tobago

If the guys are into girl-watching, Trinidad and Tobago have some of the most beautiful women in the world. In addition, Trinidad hosts one of the planet's biggest, loudest, and wildest parties—Carnival—every year, and you can pretty much find a soca-fueled "fete" any other week of the year, as well. 

Trinidad, around, Port of Spain is good for nightlife with bars, nightclubs, rum shops, dance clubs, and live music venues.

The Tobago Heritage Festival from July to August celebrates the island’s music, food, and dance. Tobago is home to some beautiful beaches—those on the north shore are great for swimming. Maracas Bay is home to the famous Bake and Shark stands, where they serve up fried flatbread filled with fried pieces of shark meat and topped with a variety of sauces.

In Tobago, most of the nightlife is found at the resort hotel bars and clubs.

Feel at Home in Aruba

Aruba is easy for Americans to love—you and your buddies will find plenty of ways to get here and lots that's familiar when you arrive. Activities abound whether you are on Palm Beach, named one of the world's best beaches by the Travel Channel, and looking to jet ski or join a pirate-themed rum cruise, or get down and dirty with a Jeep or ATV tour of the island's desert outback.

As far as places to stay, the Aruba Marriott Resort has an upscale, yet fun environment with Dutch-inspired architecture. Guest rooms are large and ideal for small groups to gather. On the premises is the Stellaris Casino, a 24-hour casino offering 26 gaming tables and a multitude of slot machines.

Nassau, Bahamas for Rum and Cigars

There's plenty to do in Nassau, the Capital of the Bahamas. You can enjoy a night out with the guys at the Graycliff Hotel and Restaurant situated in a historic colonial mansion. The hillside hotel in downtown Nassau has a chocolatier where you can sample and even try your hand at making chocolate treats and a cigar company where stogies are rolled by hand on site and can be paired with rum tastings.

The John Watling's Distillery, open daily, is located on the historic 1789 Buena Vista Estate. You can take a tour and sample Watling's small-batch, barrel-aged rums, which come in "pale" (white), amber, and "Buena Vista" five-year aged varieties.

And then there's the Pirates of Nassau Museum which will take you back to the times when pirates ran rampant in the Caribbean and were based in Nassau.