Caribbean Vacation Packages

Best time to take a trip to Caribbean

The Caribbean features a tropical climate with sunshine year-round, making a Caribbean vacation worthwhile no matter what time of the year. The region experiences dry and wet seasons, plus much warmer months, so the best time to visit boils down to whether you prefer perfect weather or lower hotel rates.

January to May tend to be drier months, and are more popular with travelers -- especially in January. From early spring through summer, more rain and hotter temperatures (plus cool trade winds) make this an ideal time to find great deals on a Caribbean vacation. Hurricane season officially spans from June through November, and early December is the best time to go for low hotel rates and few crowds.

Insider tips for Caribbean travel

Try The Fish Fry restaurant in Nassau

Try The Fish Fry restaurant in Nassau near Arawak Cay for authentic Bahamian conch salad, fried fish and cold Kalik beer.

Rent a scooter in Bermuda

Rent a scooter in Bermuda for great exploration, with stops in Dockyard, Hamilton City, St. George and the famous Swizzel Inn.

Eat at Scotchie’s in Montego Bay and Ocho Rios

Eat at Scotchie’s in Montego Bay and Ocho Rios for fantastic Jamaican jerk food, plus traditional fried dough and breadfruit.

Do the Dolphin Cay Deep Water Swim at Atlantis

Do the Dolphin Cay Deep Water Swim at Atlantis and snorkel alongside a dolphin using your own water scooter.

Buy some bling in St. Martin

Buy some bling in St. Martin, where you’ll find some of the best deals on silver and gold in all of the duty-free Caribbean.

Things to do in Caribbean

Aruba

For a more exclusive, arid take on the Caribbean, make your way to Aruba. Indeed expensive, the tradeoff comes with notorious hospitality, year-round temperatures in the low 80s, and a pleasantly dry climate. Explore miles of pristine beaches, stroll the main town of Oranjestad or try your luck at Stellaris Casino. On Tuesday night, the weekly Bon Bini Festival is a treat.

Bahamas

This 29-island nation with its hundreds of cays and thousands of islets also brings its share of beaches, resorts and adventure, like a snorkel or dive with a Stuart Cove’s tour. Visit Atlantis on Paradise Island, the islands top attraction, with six resorts, 11 pools, thrilling water park rides, dolphin swims and one of the world’s largest open-air marine habitats.

Bermuda

Famous for its astonishingly pink-sand beaches, Bermuda brings luxe resorts and adventure from snorkeling at Elbow beach to glass-bottom boat tours. Play golf or explore the fantastic Crystal and Fantasy Caves featuring a 55-foot, clear-blue underground lake. For nightlife, head to the capital City of Hampton.

Cayman Islands

Set along the deep Cayman Trench lie the three Cayman Islands. Grand Cayman is top dog, especially for families and 5-star living along Seven Mile Beach. Shop the malls, dine in style or keep it Caribbean with a trip to Stingray City. For less glitz, dive into the natural, local landscapes of Cayman Brac. Little Cayman both lives up to and defies its name with its small size and world-famous dive site, Bloody Bay Marine Park.

Dominican Republic

R&R is easy to find with all-inclusive resorts fronting white sand beaches, blue waters and famous dive sites. But eco-adventure is just as accessible with inland mountains, waterfalls and tropical forests. Visit Santo Domingo to walk the historic and happening Colonial Zone, considered the oldest city in the New World. Altos de Chavon, Lago Enriquillo and Isla Catalina are other showstoppers.

Jamaica

In Ocho Rios, dive world-class reefs or take a tour to the Dunn’s River Falls, complete with a marketplace at the top. Ride on horseback at Chukka Cove or push the limits with Montego Bay’s Flight of the White Witch Canopy Tour. In Negril, kick back at Rick’s Café and watch divers plunge from 35-feet above or relax at the lesser known gem, Floyd’s Pelican Bar.

Puerto Rico

This tropical paradise is equal parts modern and historic. Stunning white sand beaches cater to every desire, including the calm Luquillo Beach, surfer-friendly Playa Higuer and Playa Esperanza or snorkeling. Roam the cobblestoned streets of Old San Juan or the 16th Century El Morro citadel. Or venture below to Rio Camuy Cave Park to witness the third largest underground river in the world.

St. Lucia

Both serene and stunning, St. Lucia presents breathtaking peace and earth-shattering natural wonders. Known for beautiful beaches -- and more recently its glamorous resorts -- there’s more under the surface than the iconic Pitons. Hike the immense rainforest, explore Diamond Mineral Falls (believed to have healing powers), or take the road to the world’s only drive-in volcano.

United States Virgin Islands

Pulsing with West Indies vibes and calypso beats, the U.S. Virgin Islands consists of three main islands. St. John offers a pristine environment coveted for its beaches and snorkeling in Trunk Bay. A popular port of call for many cruise ships, St. Thomas is the place for shopping. St. Croix brings a balanced mix with beautiful coasts and rainforests, famous dive sites and nightlife.