• Jessica White

How to pick the perfect Caribbean destination for you

6 of my favorites based on what you care about most.

There are so many choices of islands and resorts in the Caribbean, it can make your head spin. With hundreds of options, it can seem impossible to choose one, and then it may still be uncertain whether the one you picked is somewhere you will actually enjoy.

This is where I come in. I help my clients focus in on their vacation priorities to help match them with the best destination fit for them. With insider expert knowledge, I am able to address questions that people didn’t even know they had - Is seaweed a problem on the island? Has the resort been recently renovated or is it a bit worn? What is the damage after a hurricane?

Below are some of my favorite destinations all based on what you are looking for from your island getaway:

For pristine beaches: TURKS & CAICOS

If you imagine yourself sunbathing on a white sand beach with crystal-clear turquoise waters, T&C would be your version of paradise. Grace Bay Beach is consistently ranked one of the best beaches in the Caribbean (and the world), and it does not disappoint. T&C has so much to do on the island, from water activities, to restaurants and nightlife – making it is the perfect destination for couples or families seeking your quintessential island getaway.

Where to stay: The Palms and the Shore Club are some of my favorites right on Grace Bay Beach. For a little seclusion Amanyara is the perfect choice. Whichever you choose I can ensure you get free breakfast and some other VIP perks by booking through JWT!

To wine and dine among celebrities: ST. BARTHS

St. Barths has become a hot spot for the rich and famous – and for good reason. This French-speaking island boasts some of the best dining and shopping in the islands – along with gorgeous beaches and wonderful resort options. There is no better place to eat and drink your way through award-winning restaurants, relax on one of the many beaches, all while watching the sparkling yachts go by.

Where to stay: To see and be seen stay at the famous Eden Rock, for a little more seclusion I recommend Le Sereno. Another fantastic option that also has beautiful villas is Cheval Blanc (photograph below).

For the best value for your dollar: RIVIERA MAYA, MEXICO

Riviera Maya is one of the easiest destinations to reach, with many direct flights from the US, and also has a huge variety and number of accommodation choices – which all adds up to a great value for your money and the perfect option for a quick getaway. Whether you are seeking ancient ruins, unique cenotes, authentic Mexican cuisine, or simply a beach getaway – you can find it in Mexico.

Where to stay: Since there are tons of options, where you stay really depends on what you are looking for – I love Hotel Esencia (pictured below) for a boutique, authentic feel, Nizuc for convenient luxury close to the airport, and Mayakoba for a unique jungle paradise. For a fun adults-only, food-focused resort try Unico 2087. Last but not least, Riviera Maya is also home to one of my favorite all-inclusive resorts in the Caribbean – Grand Velas.

For jungle and adventure: ST. LUCIA

St. Lucia offers some of the most unique landscapes in the Caribbean. With towering pitons, lush jungles full of waterfalls and wildlife, and waters perfect for snorkeling or fishing, St. Lucia is perfect for active travelers. To top it off, the island has some of the most romantic resorts in the world – making it a perfect honeymoon destination.

Where to stay: For a romantic getaway in a three-walled suite where you really get to be one with nature, I recommend Jade Mountain or Ladera. For the best beach and prime location, you cannot beat Sugar Beach Viceroy.

For those who like unlimited entertainment: BAHA MAR, BAHAMAS

Baha Mar is a fantastic new addition to Nassau island – and often called Vegas on the beach. Baha Mar is the ideal destination for those who love to have fun, want lots of options to entertain themselves, and might fear they would get bored sitting on the beach. Baha Mar has over 30 dining options, a huge casino, multiple pools, an extensive art gallery, and so much more. The complex is a destination in itself with three distinct resorts, and is a great option for both families and couples.

Where to stay: There are three hotels located at Baha Mar – Grand Hyatt, SLS and Rosewood. The Grand Hyatt is by far the largest, and best if you want to be in the middle of the action. The SLS is all about style and luxury, whereas the Rosewood is the smallest and most exclusive, for those who want to escape the crowds to their own private space.

TO get away from it all: ANGUILLA

This lesser-known island of Anguilla is a wonderful getaway if you want a stunning beach, amazing dining options, and chill island vibes. To get to Anguilla you fly into St. Martin then take a short boat ride to the island. Since Anguilla is under-the-radar, you get a sublime beach destination with an authentic island culture, without all the crowds.

Where to stay: Anguilla has some of my favorite luxury resorts. I adore the brand-new Four Seasons Resort as well as the Belmond Cap Juluca. For golfers, head to CuisinArt Golf Resort & Spa.

The Caribbean can be very overwhelming because there are SO many choices. Part of my job is navigating through all the options to help match you with the perfect destination for you.

Not sure where to go or ready to get your next Caribbean vacation on the books? Reach out to me at

Happy travels!


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