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The best Caribbean islands for a romantic or family vacation

Updated on April 10, 2013
Caribbean islands
Caribbean islands

Island breeze

The first question to answer is what do you mean by best? What do you like to do? How much do you want to spend? Would you rather be on an island with just a few people or lots of people?

Best means different things to different people. Some of the questions you must answer is what time of year do you want to go? What activities do you enjoy? What's your budget?

Here are some general comments about a few of the various islands.


  • One of the most beautiful places in the world.
  • Quaint. Lots of things for families to do.
  • Lots of shopping, sightseeing, fine dining. There are so many things you can do, you will not be bored.
  • Has a strong British influence. They drive on the wrong side of the road (like they do in England), which is difficult to get used to.
  • You will not be able to rent a car and drive around. You will need to take a taxi or you can rent a motor scooter. But the roads are winding, lots of round-abouts, lots of blind curves and plenty of views of the ocean.
  • It is further north than most of the other islands so the water is much cooler; swimming season is May through September.


St. Thomas

  • A U.S. possession and a fairly large island.
  • Not as picturesque as Bermuda but still very tropical.
  • Lots of shopping, night life and plenty of fine dining. Plenty of things to do and see.
  • You could take the ferry over to St. John's or do some day sailing. You will not need a passport.

St. John

  • Beautiful. Lots of tropical growth.
  • Sparsely populated.
  • Limited number of things to do and see. Limited nightlife.
  • Some great snorkeling and swimming.
  • If you are looking for quiet, this is the island for you.

U.S. Virgin Islands: St. Thomas and St. John


  • Not well developed. Not that much to do on the island.
  • Mainly a place for chartering sailboats.
  • A British Island so you will need a passport and must pass through customs.

Virgin Gorda

  • Primitive but beautiful.
  • Isolated and very little to do.
  • Yacht club is very expensive.
  • Not for most folks.

British Virgin Islands: Tortola and Virgin Gorda

The Bahamas

  • Tourist island.
  • Lots of hotels, dining, and night life.
  • Great beaches.
  • Not as beautiful as St. John or St. Thomas, but probably a little less expensive.

Grand Cayman

  • Noted for its 7 mile beach with great snorkeling.
  • Expensive.
  • Not a lot of attractions other than the beach and the turtle farm (which you can smell way before you get there).
  • Rum Point is a very isolated section of the island. You can find seclusion around Rum Point.
  • Good duty free shopping.

Tropical beach
Tropical beach

Most of the islands have great bargains on such things as china, perfume and liquor.

It all comes back to what your individual taste and preferences are. If I had to choose just one, it would be Bermuda. It has the most charm and character if you are looking for something other than the beach. If you are just looking for a beach, St. Thomas would probably be my pick. Getting away from everyone with no budget worries, I would go with St. John's, St. Peter or Virgin Gorda.


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  • amy jane profile image

    amy jane 10 years ago from Connecticut

    Thank you for answering my question! We have been to the Cayman Islands, and really love it there (for the snorkeling and scuba), but it is a long plane ride from the North East and not ideal for a shorter trip. Bermuda sounds perfect! :)