Best Caribbean Islands to Visit in 2020

Best Caribbean Islands | 50 States by 25

Whether you’re taking a cruise, lounging at an all-inclusive resort, or heading on an island-hopping adventure, a Caribbean island vacation is always a great time.

You’ll experience clear waters, secluded beaches, colorful bars, luxurious hotels, funky gift shops, unbelievable hiking trails, and fascinating historical tales. You’ll feast on some of the freshest seafood and fruitiest drinks you’ve had. You’ll come back with hundreds of postcard-worthy photos and memories to last a lifetime.

The question is – which Caribbean island is right for your next vacation?

Below you’ll find some of my personal favorite Carribean islands. Let me know what you choose!

Nevis Resort

What are the Carribean Islands?

The developed area of islands that sit between Florida and Venezuela are often confused with The Bahamas, but they are not the same. There are 7,000 islands in the Carribean. Popular Caribbean island destinations include:

  1. Anguilla
  2. Antigua
  3. Aruba (click for my full guide to Aruba)
  4. Barbados
  5. Barbuda
  6. Bonaire
  7. British Virgin Islands (Tortola, Virgin Gorda, Anegada, Jost Van Dyke)
  8. Cuba
  9. Curacao
  10. Dominica
  11. Dominican Republic
  12. Grenada
  13. Guadeloupe
  14. Haiti
  15. Jamaica
  16. Martinique
  17. Montserrat
  18. Puerto Rico
  19. Redonda
  20. Saba
  21. Saint-Barthélemy (Saint Barts)
  22. Sint Eustatius
  23. Saint Kitts and Nevis
  24. Saint Lucia
  25. Saint Martin/Saint Marteen
  26. Saint Vincent and the Grenadines
  27. Trinidad and Tobago
  28. U.S. Virgin Islands (St. Thomas, St. Croix, St. John, Water Island)

Other popular destinations like Bermuda and Turks and Caicos are technically part of the Lucayan Archipelago or The Bahamas, not the Carribean.

Puerto Rico

It’s easy to get lost at Senor Frogs and the fun, touristy nature of San Juan, but the island of Puerto Rico is beautiful in its own right. There’s so much to see and do; there’s no reason to restrict yourself to San Juan.

You HAVE to venture into the rain forest. It is one of the most beautiful things you will ever see. From weirdly entwined branches to colorful and exotic birds and flora, you’ll feel like you’re in Narnia.

Check out Old San Juan for cute little souvenir shops and American designer shops.

Must-sees in Puerto Rico:

  • El Yunque National Rainforest
  • Castillo San Cristobal
  • Flamenco Beach
  • Shopping in San Juan – check out the street markets!

St. Kitts and Nevis


Your journey to a Carribean island will almost always start out the same. You’ll leave the airport (or cruise dock) and walk into what looks like giftshop mecca. You’ll be greeted by a hoard of taxi drivers waiting to take your money. The city will be bright, colorful, and lively. However, this tourist entrance does not represent the whole of each island.

Sure, we’re talking about the Caribbean, so most islands will admittedly look pretty similar. However, St. Kitts and Nevis offer a unique opportunity. From St. Kitts, you can take a small boat over to the tiny island of Nevis.

Ferries can take as long as 45 minutes, while water taxis can get you to Nevis in less than ten minutes. Costs can differ but can be as cheap as $10 per ticket.

Sure, the entrance to the island is expecting tourists just like any other Caribbean spot. However, due to the island’s size, it’s naturally going to be less crowded and feel less like a tourist trap than some of the other islands. Nevis can be a beautiful place to spend a day.

Must-sees on St. Kitts & Nevis:

  • St. Kitts – Fairview Great House & Botanical Garden
  • St. Kitts – Cockleshell Beach
  • St. Kitts – Mount Liamuiga
  • Nevis – Lovers Beach
  • Nevis – Charleston Bath Hotel and Spring House

St. Thomas

Magen's Bay St. Thomas
Magen’s Bay – St. Thomas

One of the U.S. Virgin Islands, St. Thomas tends to be bustling with American tourists. Thankfully, like most islands, there are things to do other than hit every gift shop.

Must-sees on St. Thomas:

  • Magen’s Bay Beach
  • Blackbeard’s Castle
  • Coral World Ocean Park
  • Pirates Treasure Museum

St Martin/St. Marteen

St. Martin is unique because as small as it is, it is actually separated into two separate territories. One is Dutch-owned (St. Maarten), and the other is French (St. Martin).

As with the others, the duty-free shopping brings in most of their business, and the water is as clear blue as it could possibly get.

Must-sees in St. Martin:

  • Pinel Island
  • Boardwalk
  • Maho Beach
  • Lover’s Beach


Curacao Must Sees
Willemstad, Curacao

Curacao might be my favorite. The city of Willemstad makes you feel like you’re on the set of an animated Disney movie. There is color everywhere. There are fresh fruit stands and little tents where people sell sun hats and homemade baby clothes, and everything just seems so happy and right.

The Queen Emma Bridge between sections of the island capital of Willemstad moves, so that’s fun to watch, but definitely cross over and take some pictures while it’s stationary.

Must-sees in Curacao:

  • Willemstad/Punda/Queen Emma Bridge
  • Kenepa Beach
  • Playa Lagun
  • Shete Boka National Park
  • Curacao Sea Aquarium
  • Kura Hulanda Museum
  • Hato Caves

Which Carribean Island is Best?

I’ve barely scratched the surface in this blog, but here me out: most, if not all of the Caribbean islands on my list are going to have:

  • Snorkeling
  • Diving
  • Water sports
  • Beaches
  • Boat tours
  • ATV/Jeep tours

Most of them will also have adventure parks, great food, and beautiful walking or hiking trails. You’ll have plenty of opportunities for walking tours and guided day trips.

The question becomes which island sounds most appealing to you? Which photos most draw you in? Or, it might come down to which island is cheapest or easiest for you to get to.

Drop a note in the comments to let us know which island is YOUR favorite and how you’ll be exploring the Caribbean this year.

Happy travels!

This post was originally published on December 15, 2015, and was last updated on January 19, 2020.

Written by 

Travel Goals Club owner. Writer. Introvert. Overly obsessed with my two dogs and two cats.

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