Top 5 Caribbean Destinations to Visit this Winter

Winter can seem never-ending.  Two weeks straight of temps below 20 degrees?  No, thanks.  Instead, why not spend a few days soaking up the warm sunshine, with a refreshing drink in hand.  These are the top places in the Caribbean to visit this winter. 

Puerto Rico

Puerto Rico is back in business!  After suffering catastrophic damage last year during Hurricane Maria, the island is ready to greet visitors again.  With many of the roads and highways in good condition again, the much of the island is now accessible.  Spend a day learning about the commonwealth’s history and stroll the streets of Old San Juan.  Not sure where to stay?   Dorado Beach did not experience any structural damage during the hurricane and has renovated many of its ocean view rooms.  If you haven’t been before, make it point to take a hike in the El Yunque Rain Forest.  You’ll be rewarded with an amazing waterfall.  While in Puerto Rico, volunteer some time to rebuild local farms or clean beaches to help restore the island to its former beauty.

El Yunque Rainforest



Only have a few days for vacation?  Just a short trip from the East Coast, the Bahamas is a great spot for couples, singles, and families alike.  There are many activities in the Nassau area, or you can just relax on one of the island’s many beaches.  The much-anticipated new Grand Hyatt Baha Mar offers something for everyone.  Throw on our Crochet Cover Up to go from beach to lunch at the hotel. If you are looking for a vacation that is a little quieter, the island of Eleuthera delivers a slower pace.

Nassau Bahamas



One of Town and Country’s picks for trips this winter, Grenada is one of the Caribbean’s hottest places to vacation.  As compared to some other islands, it is not filled with as many tourists.  The beautiful beaches and rich culture make it a unique spot to spend your winter vacation.  If adventure is more your speed, Grenada offers waterfall hikes and scuba diving.   The waterfall and rain forest dune buggy tour highly rated. 




Home to 33 spectacular white-sand beaches, Anguilla is the perfect place to unwind.   The island’s rugged landscapes provide places to explore, hike, bike, or horseback ride.  While Anguilla did suffer some damage after Hurricane Irma, many of its restaurants and hotels have reopened so now is the time to visit.  Looking for a fun day trip?  St. Maarten is only 20 minutes away by boat.  Or, take a boat tour to snorkel at Little Bay.

Prickly Island Anguilla



Part of the ABC Islands (Aruba, Bonaire, Curacao), Bonaire is known for its coral reefs, and amazing scuba diving and snorkeling.  Bonaire also offers surfing and kite surfing for those looking to be active.     Make sure to check out the island’s downtown, Kralendijk, which is full of colorful and picturesque architecture.  Here you can shop at unique boutiques along Kaya Grandi, the main street.  One of our favorite rompers is the perfect choice for strolling the downtown.



Wherever your winter vacation takes you, be sure to check out our website for vacation fashion inspiration.  All you need is a bathing suit and towel, and you are all set for your winter Caribbean vacation. 

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