The Caribbean has a magnetic pull that keeps us coming back year after year. So I thought I would dedicate a blog post ranking all the Caribbean islands we have visited and some of our thoughts of each slice of paradise.
The Caribbean is a treasure trove of stunning islands, each offering its own unique charm, from pristine beaches and crystal-clear waters to vibrant cultures and hidden adventures. After exploring several of these tropical paradises, we’ve decided to rank the islands we've visited based on our personal experiences. Whether you're seeking a relaxing escape, thrilling activities, or a deep dive into local culture, this list will guide you to the perfect Caribbean getaway. Let's dive into the ultimate island showdown!
We’ll keep this post updated as we explore more islands, adding new destinations to the list with each visit!
CUBA
Time of visit: December
Ideal trip length: 10 days
Rating: 9/10
An explosion of colour and culture combined with delicious food, warm sunshine and gorgeous waters - what’s not to love? We spent 12 days in Cuba and it was the perfect amount of time for a bit of everything city, beach, colonial towns and cigar country.
Don't miss: Havana, Trinidad and Viñales
SINT MAARTEN
Time of visit: June
Ideal trip length: 5-6 days
Rating: 8/10
Sint Maarten. Saint Martin. Half French and half Dutch, but somehow still quite American 😂 we loved how much there was to do on the island, allowing for packing a lot into your trip outside of lounging on a beach. Despite visiting in June we had warm sunny days most of the time, and any rainstorms we experienced lasted only an hour at the most.
Don't miss: The beautiful murals of Philipsburg. Oh and Maho beach definitely has the trippiest airplane landing experience!
SAINT BARTHÉLEMY
Time of visit: June
Ideal trip length: 1 day
Rating: 6/10
This is where the celebrities come by, we were told. Prepare for exorbitant prices everywhere, but then again, it’s catered to the clientele. Small island, perfect for a day or two, and easily combined with St Martin for a 2-for-1 holiday. We visited as a day trip from St. Martin via ferry and rented a car to explore the island. It wasnt for us, but I know many people who have really enjoyed their time here.
Don't miss: Eden Rock, the seafront property that has been a symbol of luxury travel in the Caribbean for decades.
ANGUILLA
Time of visit: June
Ideal trip length: as much as you can manage
Rating: 20/10
You might have guessed by now that we did a little island hopping during our trip to Sint Maarten. Just a half hour away by boat from Sint Maarten - and to be honest when we arrived we weren’t so sure about the island. A lot of it is just empty. But once we got to the beaches - Oh. My. God. Outside of the beaches there’s not much to do, but with sands like this you’ll not want to do anything else. We’d go back in a heartbeat!
Don't miss: Cap Juluca, a bit of a splurge but worth every penny. Oh, and the Anguillan sunsets are absolutely epic!
CURACAO
Time of visit: December
Ideal trip length: 4-5 days
Rating: 9/10
Take a quintessential street in Amsterdam and pop it in the Caribbean - and the result is Curaçao. Colourful colonial buildings, artsy city center, and gorgeous beaches dotted across the island. I really do think its very very underrated. In addition, while the Caribbean has a reputation for being pricy, Curacao stands out as one of the most affordable.
PUERTO RICO
Time of visit: December
Ideal trip length: 7-8 days
Rating: 8.5/10
If I had a stereotype about Caribbean lifestyle, it would be PR. Colourful colonial buildings, beautiful beaches, slow island life. What's not to love? We weren't a big fan of El Yunque which is touted as a must-visit in literally every PR blog we read, but the rest of the island has a lot to offer.
Don't miss: Old San Juan, Rincon and the west for beautiful sunsets, Vieques for Mosquito Bay, and Culebra for the best beaches in the region
DOMINICAN REPUBLIC
Time of visit: January
Ideal trip length: 5 days
Rating: 7.5/10
Known for its stunning beaches, all-inclusive resorts, and vibrant culture. With diverse landscapes from the tropical Samaná Peninsula to the historic city of Santo Domingo, it offers a perfect mix of relaxation and adventure. I will admit we read some scary stories about safety in Punta Cana and given that this was my babymoon, we choose to stay in an adults only all-inclusive for the entirety of our time here. So given that all we wanted was R&R, DR met our expectations, but we could tell there was a lot more to the country than what we experienced.
Don't miss: the chance to enjoy stunning all-inclusive beach resorts at a fraction of the cost of typical Caribbean vacations.
U.S. VIRGIN ISLANDS
Time of visit: January
Ideal trip length: 7 days
Rating: 7/10
The US Virgin Islands are actually made up of 3 islands - St Thomas, St John's and St Croix - and a week here will give you enough time to fully explore one island or see a bit of St Thomas as well (chances are that you will arrive/leave the USVI through St Thomas, as it is the biggest island and has the international airport). We spent most of our time in St. John, which boasts crystal-clear waters, white-sand beaches, and excellent snorkeling. Oh, and lots of national parks for hiking too. Quite a diverse island holiday!
Don't miss: the beautiful Gallows Point Resort for a home away from home in the USVI
As we wrap up our island ranking, it’s clear that each Caribbean destination has its own unique allure and charm. Whether you're drawn to the tranquil beauty of a secluded beach or the vibrant energy of a bustling town, the Caribbean offers something for every traveler. We hope our rankings help you find your perfect paradise and inspire your next tropical adventure. Stay tuned for updates as we continue to explore and discover new islands to add to our list!
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