The Best Weekend Getaways in the Caribbean

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We love a good weekend getaway -- they're the perfect cure when you're yearning for some relaxation, but have to be in the office on Monday. While you may think domestically when it comes to weekend trips, some destinations in the Caribbean are perfectly suitable for a quick jaunt. We rounded up six beautiful Caribbean spots that can be reached on nonstop flights from many U.S. cities, have excellent resorts not far from the airport, and of course, serve up lovely stretches of sand and warm sunshine. Check them out below.

1. Bahamas

Paradise Island Beach, Bahamas/Oyster

Paradise Island Beach, Bahamas

The Bahamas, an archipelago made up of over 700 islands and cays, is the most convenient Caribbean destination to reach from the U.S. Just 50 miles off the Florida coast, the Bahamas can be reached by ferry from Fort Lauderdale or plane from numerous cities. Direct flights are available from Miami, New York, and Dallas, among others. Of course, travel time isn’t the only allure — visitors will also enjoy gorgeous beaches, delicious seafood, friendly locals that speak English, world-class scuba diving, and casinos.

Our Bahamas Hotel Pick: While many travelers opt for one of the several Atlantis properties, we recommend staying at the quieter Ocean Club, A Four Seasons Resort, Bahamas, which gives guests free access to the amenities at the Atlantis. The 105 rooms and suites are incredibly luxurious and have massive bathrooms with separate walk-in steam showers and soaking tubs. The lovely grounds house three outdoor pools, a romantic garden and statuary modeled after Versailles, an 18-hole golf course, and a Balinese-style spa. 

2. Grand Cayman, Cayman Islands

Beach at Plantana Condominiums, Grand Cayman

Beach at Plantana Condominiums, Grand Cayman

Also offering nonstop flights from many U.S. cities, Grand Cayman in the Cayman Islands is a lovely choice for travelers wanting to spend much of their vacation swimming and sunbathing on the beach. For starters, Grand Cayman is home to one of the most spectacular beaches in the Caribbean — Seven Mile Beach. This public stretch has sparkling blue water and soft coral sand, plus it’s lined with (mostly upscale) hotels. Stingray City offers travelers a chance to swim with rays, and stellar diving sites include Bloody Bay Marine Park and Keith Tibbetts shipwreck.

Our Grand Cayman Hotel Pick: A tried-and-true favorite for many travelers, the upscale Grand Cayman Marriott Beach Resort sits on Seven Mile Beach. The 295 rooms here are comfy, and resort features consist of a well-sized pool, two international restaurants, a spa, and fitness center. Although perhaps more attractive to families than couples, all types of travelers stay here.

3. Punta Cana, Dominican Republic

Majestic Colonial Punta Cana

Aerial View of Majestic Colonial Punta Cana

All-inclusive lovers looking for a one-stop shop when it comes to their hotel should head straight to Punta Cana in the Dominican Republic. The year-round pleasant weather, calm and shallow water, well-regarded golf courses, and plethora of hotel options make Punta Cana a stellar weekend getaway destination. Plus, its international airport is close to most resorts, and offers daily direct flights from several U.S. cities. 

Our Punta Cana Hotel Pick: Set along stunning Bavaro Beach, the Majestic Colonial Punta Cana is an upscale all-inclusive resort with a family-friendly side and an adults-only side. Extensive features include a big pool complex, a spa, multiple restaurants, and nearly a dozen bars serving premium alcohol.

4. Montego Bay, Jamaica

Aerial View of Round Hill Hotel & Villas, Montego Bay

As the main airport is in Montego Bay, it’s wise to stick to this area of Jamaica if you only have a weekend to spare. Fortunately, this area is also gorgeous, and it has year-round beach weather, top-notch golf courses, and stellar fine-dining restaurants. Other pluses include the warm locals, omnipresent Jamaican culture, and some of the most attentive service found anywhere in the Caribbean. Nonstop flights are available from cities such as New York (four hours), Atlanta, and Orlando.   

Our Montego Bay Hotel Pick: Easily one of the top hotel options in all of Jamaica, Round Hill Hotel & Villas is a phenomenal luxury property with a small private beach. Accommodations include both Ralph Lauren-designed hotel rooms and stand-alone villas with kitchens and private pools. Dining is excellent, and all-inclusive packages are available to cut down on costs.

5. San Juan, Puerto Rico

Old San Juan, Puerto Rico

Old San Juan, Puerto Rico

Although Puerto Rico suffered devastating destruction from Hurricane Maria in 2017, the island — and San Juan specifically — are open for business. Puerto Rico’s capital and largest city still sparkles with its colorful Old Town, cobblestone streets, and multiple historic sights. A hopping nightlife scene, delicious coffee, and forest reserves are additional pros, plus U.S. citizens don’t need a passport to visit. Given that San Juan sits along the Atlantic coast, travelers will have to head to the southern part of the island for Caribbean waters, but nearby beaches are still attractive and good for surfing.

Our San Juan Hotel Pick: The 1950s-built El San Juan Hotel, Curio Collection by Hilton is considered a local icon, thanks to its storied past showcasing performances by Frank Sinatra and Nat King Cole. Today, it’s a chic and contemporary beachfront property with four pools, five restaurants, seven bars, a nightclub, and a luxe spa.

6. Providenciales, Turks and Caicos

Beach at Grace Bay Club, Providenciales

Beach at Grace Bay Club, Providenciales

A 37-mile chain of islands, Turks and Caicos is best suited for peace-seeking couples or laid-back families, and Providenciales is the main hub of hotels. In addition to striking beaches with crystal-clear water and white sand, visitors will find one of the world’s longest coral reefs here. Ample water-based activities include snorkeling, scuba diving, and sailing, while on land, travelers can go horseback riding or visit a bird sanctuary. This is also one of the safest destinations in the Caribbean. 

Our Providenciales Hotel Pick: The luxury Grace Bay Club is a top pick in Turks and Caicos for its stellar beachfront setting, variety of swish and well-equipped rooms, three outdoor pools — including an adults-only infinity option — multiple highly regarded restaurants, and kids’ club with free daily programming. Freebies include breakfast, non-motorized water sports, Wi-Fi, and bikes.

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