Are you trying to choose an island to visit for a fun winter respite – and can’t decide which one because they all look wonderful!? It’s true, they all have stunning beauty and divine weather. To help you choose, we answer these FAQs based on our travel team’s professional experience and feedback from our travelers.

Q: Which islands are the prettiest, with sparkling turquoise waters, and made for relaxation?

A: Our favorites are Anguilla, Turks & Caicos, Antigua, the U.S. Virgin Islands, and St. Lucia due to their great beaches, natural beauty, and opportunities for tranquility. Lesser-known islands Martinique and Guadeloupe are beautiful French islands that we consider hidden gems. These all have great spots for snorkeling and other popular water sports.

Q: Which islands are the easiest to get to and around?

A: Part of enjoying a getaway is getting there easily. What’s better than leaving the cold in the morning and being on the beach by early afternoon! Several airlines offer direct flights from the NY area, otherwise a layover in Miami or Puerto Rico may be needed. Our preferred islands with direct flights from Newark include St. Thomas, St. Martin, Turks & Caicos. If you’d like to explore an island, renting a car is an option, otherwise in most cases taxis, shuttles and public transportation will take you where you need to go. Note, most islands have driving on the right, but for some, such as St. Thomas, it’s on the left.

Q: Should we stay at an all-inclusive resort?

A: If you prefer to spend your time within the resort grounds, partake in water sports and have on-site dining, then an all-inclusive vacation may be for you. Of the many options, we find Sandals and Beaches properties to best suit the needs of our clients – high-end accommodations with plenty of activities and good food. These resorts have prime locations on some of our favorite islands such as St. Lucia, the Bahamas, Antigua, and Turks & Caicos. As an alternative to all-inclusive, many of our clients enjoy small four- and five-star resorts in Turks & Caicos. Bermuda, the Bahamas, Anguilla. Antigua, or St. Martin.

Q: We can’t decide which island to visit. Should we take a cruise that stops at several ports?

A: Cruises are ideal for getting a flavor of different places while enjoying the benefits of traveling on a cruise ship – the accommodations, dining options, on-board activities and amenities are all pre-set and well-established. The only drawback is that you may not get as much time in a port as you’d like, but that only means you’ll have to go back another time for an extended visit!

There are many more considerations, such as:

Day trips – we recommend certain excursions to enhance an island visit. For example, if you’re staying on St. Thomas or St. Martin, take a boat ride over to St. John’s or Anguilla (respectively) for a day of extra tranquility and spectacular scenery.

Food – good restaurants can be found everywhere, but our favorite destinations for foodies are Anguilla, and any of the French-infused islands!

Adventure – zip-lining, scuba diving, parasailing and more – yes! Most Caribbean islands have active pursuits available for people of all skill levels.

Feel free to call and ask us your questions. Our consultants are ready to share their unique expertise in all-inclusives, independent island travel, cruising, and anything else you need to know to plan a Caribbean trip just right for your interests.