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This little Caribbean travel blog is over three and half years old now. In that time I’ve received countless emails from readers that share the same passion. Many of them have questions about the island, rum and why I point in all my photos. After awhile you begin to see trends and what people really want to know. I would say the most common question I get asked is…

What Caribbean island should I travel to?

It seems like a simple question, I could easily just tell the Castaway a couple of my favorite islands, wish them safe travels and to have a rum drink for me. But it’s not about me, it’s about them. It’s about what they like to do, what their idea of paradise is. Each person is different. That’s what makes the Caribbean so special, each island is different, each has its own unique personality.

Every time I get asked this question I immediately turn around and ask a few questions of my own. What do you like to do on vacation? Do you like to hike? Do you like to dive? Do you like to sail? Do you like to turn into a puddle of relaxation at a resort? Do you like to shop? Do you like to surf? There’s a million questions I could ask that would help to narrow down the perfect Caribbean island for that person.

Here are just a few Caribbean travel tips that will help you find the right island based on your interests.


Looking for the best spots to dive and snorkel? Belize, Bonaire and the Cayman Islands should be at the top of your list.


Looking for a romantic hideaway? A spot on Grace Bay on Providenciales in the Turks and Caicos or a majestic resort overlooking the Pitons on St. Lucia will fuel those fires of love.


Want a little nightlife in the Caribbean? Try San Juan, Puerto Rico or Dutch St. Maarten.


Want to get your hike on? St. John in the USVI is laced with trails. Dominica is a hikers dream with trails that take you deep into the interior to the Valley of Desolation. The interior rainforests of Puerto Rico and St. Kitts also have a lot to offer adventurous hikers.


Looking to raise the canvas for a week of island hopping? The British Virgin Islands, Abaco Islands of the Bahamas and the Grenadine Islands will satisfy your sailor’s soul.


Do you love to make your credit card scream mercy while on vacation? St. Thomas in the USVI and Nassau in the Bahamas are a shoppers delight.


Want to get lost? Want to relax where tourism hasn’t completely changed the island? To find a true Caribbean escape I would look into Nevis, Dominica, Grenada, Guadeloupe, Tobago, St. Vincent and the Bay Islands of Honduras.

These are some of the “personalities” of a few islands. By no means would I call myself an end-all-be-all expert. Other locations that I didn’t mention probably can be listed in some of these categories, but these are what I know and can help you choose a Caribbean destination that suits your idea of paradise.

I love receiving your emails and questions so keep them coming! Hopefully this brief list will help you choose a Caribbean vacation that fits you. Do you have any suggestions I didn’t mention, leave a comment below.



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About the Author: RumShopRyan

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty. To learn more, visit our About Us Page.