Finding My Favorite Caribbean Island

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The number one question I get when people find out we travel to the Caribbean annually is “What is your favorite Caribbean island?” It’s a natural question to ask but far from easy to answer. While we’ve had the great fortune to visit a lot of islands in the Caribbean, we haven’t visited any of the Virgin Islands (US or British), the Bahamas (are they even considered Caribbean?), the Caymans, TCI or any of the Windward islands among many others. There are simply too many to visit and doing only one trip a year limits your opportunities. Still, it’s a fun question to ponder but even if I had visited all of the islands of the Caribbean, I don’t know that I would be able to answer it definitively.
Picking a favorite Caribbean island is like picking your favorite child. Since I only have one kid, picking a favorite is easy for me but if you have a lot, similar to the islands of the Caribbean, you recognize that each one has characteristics and personalities that are special and make each one individually unique. Each island in the Caribbean has something to offer that would entice you to visit. Here are some of the islands I’ve visited and a few reasons why they might be considered a favorite.

View from Roy's Bayside Grill, Sandy Ground, Anguilla

St. Kitts: If you’ve followed the blog for any length of time, you’ll know that St. Kitts has long a been a favorite of mine. A beach bar utopia with more monkeys than people, the addition of the Christophe Harbour development on the southeast peninsula brings a whole new personality to the island. Don’t like the beach? It’s also mountainous with an extensive rainforest and plenty of history for the more studious among us.

Nevis: St. Kitts’ sister island, Nevis is the Caribbean of the past that a lot of people yearn for – pristine and quiet. Plus, it’s home to Sunshine’s Killer Bee cocktail and that alone should make it a destination of choice.

Antigua: One of the few islands we’ve visited twice, it’s a favorite for its many beaches (one for each day of the year), maritime lifestyle and Sunday evening sunset parties at Shirley Heights. There are moments that are unforgettable – watching the sunset over English Harbour from Shirley Heights is one of those. It will be etched into your mind and you will take pause to be thankful for the chance to witness it.

Barbuda: Beautiful and nearly deserted pink sand beaches. ‘Nuff said.
Aruba: I mean really, it’s Aruba, the island paradise that the Beach Boys yearned for. It calls itself the happy island and you can’t be anything but happy while on this beach paradise. The blues seem bluer and the whites appear whiter. After a few days here, you’ll be wondering why the Beach Boys didn’t name their song “Aruba” instead of “Kokomo.”

Barbados: As far south and east as you can go and still be in the Caribbean, the west coast of Barbados, also known as the Gold coast for the sunsets and money that blanket its beaches, is as stunning as the east coast is wild. A little known fact – Barbados has the 15th highest population density in the world which says enough in and of itself – people come to this crowded rock and never leave. Barbados will do that to you, giving you the cosmopolitan city-like feel a lot of other Caribbean islands can’t replicate.

Cozumel: Not to leave the eastern Caribbean region out of the conversation, Cozumel is a snorkeling and scuba lover’s dream. I’ve done it and it lives up to the hype. Throw in the easy ferry ride access to Playa del Carmen and the Riviera Maya and Cozumel’s options are limitless. And it’s also the place one of the best days of my vacation took place – a round the island beach bar crawl on mopeds, or our “little hawgs” as we preferred to call them. It’s a must when on the island.

Isla Mujeres: An often unthought-of Caribbean island due to its proximity to Cancun, Isla Mujeres offers a laid back Caribbean island vibe that you won’t find anywhere in the bright lights big city atmosphere of its big sister. A short 25 minute ferry ride from Cancun, you’ll forget you’re sitting in the shadow of one of the most popular tourist destinations in the world as you sip margaritas on the white sand of Playa Norte and watch the sunset slowly dip behind the horizon with a handful of your newest friends. Let me put it this way – when I go back to Cancun, I won’t be staying in the hotel zone. I’ll be headed straight for the ferry and my secret island escape.

St. Martin/St. Maarten: One of the subjects of our most recent trips, this two country island offers anything and everything you would ever want in the Caribbean. There’s a reason it’s always filled with cruise ship passengers – people simply love it.

Anguilla: What can I say – Tony Bennett may have left his heart in San Francisco but I left mine in Anguilla. I was told before my trip that a visit to Anguilla would be life changing and it was. I can’t stop thinking about the island, its natural beauty and its people. Much like Aruba calls itself the happy island, Anguillians refer to their home as the friendly island and the moniker fits. I felt like I was home in Anguilla and I can’t sound a more ringing endorsement than that.

Do you have a favorite island in the Caribbean and if so, what is it about the island that separates it from the rest? Let me know in the comments – the best part about coming back from vacation is planning the next one and you could help me determine my next destination!

Author: Tom W.

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6 Comments

  1. Yes, it is like picking a favorite child! Love Virgin Gorda for its natural beauty, Barbados is a long time fav for the food, nightlife and things to do, Curacao for its beautiful colors, and the family islands of The Bahamas – smooth waters that look like glass. St Lucia is so beautiful – looks more like a pacific island – oh I could go on and on 🙂 Great article!

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    • Thank you very much, Linda! Appreciate the feedback. I’ve only been to Barbados on your list but I’ve heard so many great things about the other locations. So many islands, so little time!

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    • Great point, Sonja. Two different cultures on one island. Hard to beat that!

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  2. British Virgin Islands. I love Virgin Gorda beaches.

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    • Hard to argue with that choice, Holly! Cheers!

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