Caribbean Island Guide: How to Choose the Right Island For Your Vacation

Caribbean Island Guide: How to Choose the Right Caribbean Island For Your Vacation

Millions of beach-ready tourists flock to the sunny islands of the Caribbean every year; but with so many places to choose from, how do you know which one is best for you?

Whether you're an adventure seeker looking to hike the mountains and dive with the stingrays, or you're researching where you can indulge and relax near the beach on some luxury Caribbean vacations, this Caribbean Island Guide will help you decide where to go based on your style, travel schedule, and budget. Browse the islands below, grab your sunnies and bathing suit, and get ready to book your ticket!

 

1. Antigua

Antigua (and Barbuda) is the ideal place for people who can’t stay in one spot the whole time. You’ll have the chance to go beach hopping and island hopping every day if you visit this yachting destination. There are also lots of options for accommodations and activities for any budget.

Best For: Beach Lovers, Sailors & Boating, Families, and Couples
Accessibility from US and Canada: Easy to get to with daily flights from most major airports
Price Range: $$$

 

2. Aruba

If your ideal vacation involves lounging around the beach 24/7, this is your destination. Aruba’s beaches are among the world's finest with crystal clear waters and white sand along the coastline.

Best For: Beach Lovers, Affordable Travel, Couples, Families, and Watersports
Accessibility from US and Canada: Easy to get to with daily flights from most major airports
Price Range: $

 

3. Bahamas

Probably one of the most popular destinations in the Caribbean for family travel. Besides the popular Paradise Island (home to the Atlantis Resort), there are actually a ton of other hidden gems where visitors can experience diving, quiet beaches, and luxury villas.

Best For: Families, Affordable Travel, and Diving
Accessibility from US and Canada: Extremely easy to get to with frequent, daily flights from most major airports
Price Range: $$

 

4. Barbados

The island of Barbados is perfect for people who are looking to explore outdoor activities at a lower cost than some of its neighboring islands. Some of the beaches offer perfect waves for surfing or windsurfing. Golfers can also come and indulge here as Barbados offers some really exquisite golf courses (it was actually the destination for Tiger Woods’ wedding).

Best For: Affordable Travel, Beach Lovers, Surfers, Golfers, Couples, Families, and Foodies
Accessibility from US and Canada: Easy to get to with daily flights from most major airports
Price Range: $

 

5. Cuba

For a truly exotic and foreign experience in the Caribbean, you’re going to want to head to Cuba right now. The rumors are true... The island really looks as if it has just been unleashed from a time capsule from the 1950s, but there is still so much untouched beauty that visitors can explore. There are beaches to visit, urban adventures to explore, delicious food to indulge in, and lots of music to dance to. Head there quick before they ruin it with Starbucks and McDonalds!

Best For: Adventure Travel, Music Lovers, History Lovers, Couples, Foodies, Beach Lovers, and Affordable Travel
Accessibility from US and Canada: Becoming easier with the increase in flights as travel restrictions ease. Currently some flights from most major airports
Price Range: $

 

6. Puerto Rico

I might be biased because my family is from here, buttttt.... Puerto Rico is one of the best (if not THE best) destinations in the Caribbean IMO. You have some of the most gorgeous beaches in the world (just Google Flamenco Beach), the only rainforest in North America, colorful streets and nightlife, casinos and live music, delicious food and tons of rum, surfing, and so much more! Plus, you don’t even need a passport to come here if you’re a US citizen!

Best For: Beach Lovers, Families, Couples, Singles, Foodies, Surfing, Water Sports, Outdoor Adventures, Hiking, and Golfers
Accessibility from US and Canada: Extremely easy to get to with frequent, daily flights from most major airports
Price Range: $$

 

7. Dominica

Dominica is the perfect destination for people who are looking for something different than the typical “beachy” Caribbean destination. The terrain and geography of Dominica provides visitors the perfect landscape for outdoor adventures. Think hiking, waterfalls, diving, mountainous rainforests, natural hot springs or mud baths. It’s been dubbed the “Nature Island.”

Best For: Outdoor Adventures, Hiking, Watersports & Diving, and Couples
Accessibility from US and Canada: Will most likely have to connect on a flight from a nearby island, like Puerto Rico
Price Range: $$$

 

8. Dominican Republic

While Dominican Republic has traditionally been known as a great budget-friendly destination, recent developments have turned this popular Caribbean island into a luxury escape for all types of travelers. You can enjoy affordable all-inclusive beach resorts, hidden getaways in the forest, or luxurious colonial-style villas in the city.

Best For: Affordable Travel, Beach Lovers, Families, Urban Travel, Couples, Luxury Travel, Golfers, and Outdoor Adventures
Accessibility from US and Canada: Extremely easy to get to with frequent, daily flights from most major airports
Price Range: $

 

9. Curacao

The two largest appeals of coming to Curacao are the diving/snorkeling excursions and the cuisine. The beautiful bays and colorful urban landscapes aren’t too bad either!

Best For: Watersports & Diving, Outdoor Adventures, Urban Travel, Families, Foodies, Affordable Travel, and Couples
Accessibility from US and Canada: Moderate with a (likely) layover in a nearby city or island
Price Range: $

 

10. Trinidad and Tobago

These sister islands are like a yin and yang in that they can offer visitors two completely different experiences. Trinidad, which is home to one of the world’s biggest Carnival celebrations, is a much bigger island and has some of the best nightlife, music, and culture scenes. Tobago, on the other hand, is much smaller and home to lush rainforests, sandy beaches, and a relaxing natural environment. You really get the best of both worlds by visiting these sister islands.

Best For: Music Lovers, Outdoor Adventures, Watersports & Diving, Foodies, and Hiking
Accessibility from US and Canada: Moderate with flights into Trinidad from most major airports
Price Range: $$

 

11. Cayman Islands

Heading to the Cayman Islands can feel a lot like visiting places in Southern Florida. Vacationers can enjoy outdoor activities, such as snorkeling and diving (especially at Stingray City, where you can actually swim with them too) or lounging on pristine beaches (like Seven Mile Beach). You can also go golfing or dine at upscale restaurants, like Chef Eric Ripert’s restaurant.

Best For: Watersports & Diving, Beach Lovers, Affordable Travel, Foodies, Families, and Golfers
Accessibility from US and Canada: Easy to get to with daily flights from most major airports
Price Range: $$

 

12. US Virgin Islands

The US Virgin Islands are comprised of 3 main islands—St. John, St. Thomas and St. Croix—as well as some other smaller, minor islands. St. John and St. Croix are a bit less developed that St. Thomas, so here you’ll be able to explore the natural landscape and parks a bit better (think horseback riding, hiking, and snorkeling). St. Thomas is great for people who enjoy the mega-resort vibe and the commercial comforts of the US.

Best For: Beach Lovers, Outdoor Adventures, Families, Couples, Water Sports, Hiking, and Affordable Travel
Accessibility from US and Canada: Easy to get to with daily flights from most major airports and ferries available from St. Thomas to reach other islands
Price Range: $$

 

13. British Virgin Islands

If you’re into sailing or boating, this is your destination. Visitors often explore the British Virgin Islands by these modes of transportation, making it great to explore all the little caves and bays around the terrain. People who enjoy snorkeling and diving will also find paradise among the islands here.

Best For: Sailors and Boating, Watersports & Diving, Couples, and Families
Accessibility from US and Canada: Will most likely have to connect on a flight from a nearby island, or find a flight into Tortola. Can also take a ferry from St. Thomas.
Price Range: $$$$

 

14. Turks and Caicos

If you’re looking to relax near some of the most beautiful beaches in the world, then Turks and Caicos is your place. The islands are surrounded by crystal clear waters and beautiful coral reefs to explore. Turks and Caicos is also wonderful destination for visitors looking to be pampered and treated by some of the best health and wellness retreats and resorts in the Caribbean.

Best For: Beach Lovers, Health & Wellness Retreats, Watersports & Diving, Couples, Families, and Luxury Travel
Accessibility from US and Canada: Easy to get to with daily flights from most major airports
Price Range: $$$

 

15. Jamaica

Jamaica is undoubtedly in the middle of a rebirth period right now. The island, which was once known as the home of reggae music and Bob Marley (and also for being a frequent cruise ship port), is quickly coming onto the scene as a perfect Caribbean getaway for any type of traveler. You can still come to experience the incredible music scene, but you’ll stay after you fall in love with the local cuisine, the natural landscapes and terrain, the idyllic beaches, and the luxurious resorts.

Best For: Music Lovers, Foodies, Beach Lovers, Affordable Travel, Outdoor Adventures, Couples, Families, and Golfers
Accessibility from US and Canada: Easy to get to with flights from most major airports
Price Range: $

 

16. St. Martin/St. Maarten

This lively island is shared with between the Dutch and the French, thus offering a very unique cultural experience on both parts of the island. The French side offers a more laid back and charming vibe, while the Dutch side offers a more boisterous and vibrant feel. There are also tons of restaurant choices because of these two unique cultures that sit side by side.

Best For: Cultural Travel, Foodies, Beach Lovers, and Urban Travel
Accessibility from US and Canada: Easy with flights from most major airports
Price Range: $$$

 

17. Anguilla

Foodies and beach lovers who are looking for a luxury low-key vibe will find paradise in Anguilla. You’ll find everything from hole-in-the-wall food shacks to five star dining and just about any cuisine you’re looking for. The beaches are also spectacular, with some of the most famous being Shoal Bay, Meads Bay, Maundays Bay, and Junks Hole.

Best For: Foodies, Beach Lovers, Couples, and Luxury Travel
Accessibility from US and Canada: Moderate with ferries departing from St. Martin
Price Range: $$$$

 

18. Grenada

Grenada is somewhat of an untouched beauty in the Caribbean. This little island is perfect for a beach vacation getaway where you won’t have to deal with hoards of tourists and bustling crowds. The rainforest also offers a great escape into nature, while St. George’s (the capital) looks like a mini replica of the Italian Riviera.

Best For: Beach Lovers, Couples, Outdoor Adventures, Hiking, Couples, Families, Foodies, and Relaxation
Accessibility from US and Canada: Moderate with some direct flights from major airports and some with connecting flights
Price Range: $$$

 

19. Guadeloupe

This little island is one of the Caribbean’s best-kept secrets. This French territory is home to some incredible beaches, quaint seaside villages, and an exquisite culinary scene. It’s a great spot for people who want to vacation without the side of tourists.

Best For: Beach Lovers, Couples, Foodies, and Families
Accessibility from US and Canada: Will most likely have to connect on a flight from a nearby airport or island
Price Range: $$

 

20. Haiti

Haiti has been faced with some challenging times in recent years—from political unrest to natural disasters. There is still some natural beauty around the island, but the rich African culture and history really makes this place a great destination for travelers who are interested in exploring those subjects. If you're interested in giving to the greater good during your trip, you might want to consider visiting Haiti to participate in mission or aide work as well.

Best For: Cultural Travel or Mission/Aide Work
Accessibility from US and Canada: Will most likely have to connect on a flight from a nearby airport or island
Price Range: $

 

21. Martinique

Francophiles and French-speakers will likely enjoy a trip to this French-Creole destination. Visitors can enjoy isolated beaches, world-class cuisine, and a lovely, historic port with 17th century buildings that make for a colorful and lively town.

Best For: Francophiles, Foodies, Couples, Hiking, and Beach Lovers
Accessibility from US and Canada: Moderate with few major airports offering daily flight options, although more are starting to offer them
Price Range: $$

 

22. St. Kitts and Nevis

St. Kitts and Nevis is another pair of sister islands that offers visitors fun outdoor activities and hiking, historic, pirate-era landmarks, and great golf courses.

Best For: Outdoor Adventures, Hiking, History Lovers, and Golfers
Accessibility from US and Canada: Will most likely have to connect on a flight from a nearby island, like Puerto Rico
Price Range: $$

 

23. St. Lucia

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St. Lucia is known for being the ultimate honeymooner’s destination of the Caribbean. It offers breathtaking views of its mountains, great hiking terrain, lush waterfall and rainforest trails, and botanical gardens. But if you come here to just kick it on the beach, you won’t be disappointed either.

Best For: Couples, Beach Lovers, Outdoor Adventures, Hiking, Watersports & Diving, and Luxury Travel
Accessibility from US & Canada: Easy to get to with daily flights from most major airports
Price Range: $$

 

24. St. Vincent & the Grenadines

This string of islands is probably the least visited area of the Caribbean, but it offers a lot for a particular type of traveler. These islands are great for divers and people who love boating and sailing, which works out well for them since it’s not overly congested with tourists.

Best For: Diving, Sailors & Boating, and Adventure Travel
Accessibility from US & Canada: Will most likely have to connect on a flight from a nearby location and can travel to surrounding islands by boat
Price Range: $$

 

25. St. Barts

Visiting St. Bart’s is the ultimate luxury destination in the Caribbean and perfect for people who are really looking to indulge. This French-speaking island is popular with the A-list crowds because of its luxury accommodations, beautiful beaches, high-end shopping, and fine dining establishments. You can expect expensive yachts, private luxury villas (that come with a private butler), crazy nightlife, and the occasional celebrity sighting.

Best For: Luxury Travelers, Foodies, Couples, and Beach Lovers
Accessibility from US and Canada: Will most likely have to connect on a flight from a nearby island, like Puerto Rico or Antigua
Price Range: $$$$

 

Have you ever been to the Caribbean? What is your favorite destination and why? Comment below with more tips!

This post is in collaboration with Luxury Retreats. All opinions are my own.


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