There’s a misconception that all Caribbean islands are the same. However, as someone who’s been traveling to the Caribbean for almost two decades, I’ve found that each island has its own distinct food, festivals, and cultural traditions.
After visiting 20 Caribbean islands, I can see why the area is such a hot spot for tourism. Here are the five islands I’d love to return to and the two I’d skip next time.
St. Lucia is home to fun wellness activities and great food.
Though St. Lucia is typically billed as a romantic destination, I visited on a solo trip and had a blast exploring the island.
Some of my favorite activities included a mud bath in Sulphur Springs, a rum and chocolate tour, and an afternoon boat ride past The Pitons.
St. Lucians also have some great street food and love to have a good time. During my stay, I headed to the lively Friday night Gros Islet street party for grilled conch and fried fish straight off the boat.
St. John has gorgeous beaches.
I spent my 15th wedding anniversary on St. John, the smallest of the three main US Virgin Islands. One of the highlights of my stay was a beach day at Trunk Bay.
The beach is located inside Virgin Islands National Park on St. John, and though there’s a small entry fee, it’s worth every penny. The beach is framed by lush mountains, and towering palm trees dot the wide, sandy shore. In short, it’s paradise.
St. John isn’t a hub for partying or late-night entertainment, but the island’s gorgeous sunsets and natural setting are ideal for honeymoons and special anniversary trips.
Dominica is perfect for hiking and exploring natural attractions.
Nicknamed “the nature island,” Dominica is one of the Caribbean’s best-kept secrets.
One of my favorite excursions was a hike to Trafalgar Falls, a pair of stunning waterfalls about a 20-minute drive from the island’s capital city, Roseau.
I also rode horseback on the island’s black-sand beaches and floated on an inner tube through Titou Gorge, a cave with a hidden waterfall and swimming hole.
Turks and Caicos are great for decompressing on the beach.
There’s a reason Turks and Caicos are a magnet for celebrities and socialites, but you don’t have to be an A-lister to enjoy the islands.
Providenciales is the most populated island in Turks and Caicos. Provo, as some locals call it, offers a laid-back, tranquil beach vacation. Most hotels on Provo are located along Grace Bay, a picture-perfect stretch of pearly white sand and turquoise water.
Water sports like jet skiing, snorkeling, and clear-bottom kayaking are popular, but I was content to spend most of my days alternating between reading on the beach and cooling off in the pool.
Grenada is a snorkeling hot spot with a unique national park.
During my stay on Grenada, I encountered lots of warm and inviting locals, who would strike up conversations and ask how I was enjoying my visit.
Besides visiting the popular Grand Anse Beach, I booked a day tour to Grand Etang National Park to check out Grand Etang Lake, a freshwater lake surrounded by a lush rainforest.
I ended my stay on Grenada with a snorkeling trip to Molinere Underwater Sculpture Park to see the submerged sculptures.
However, Grand Cayman was one of the priciest islands I’ve visited.
Grand Cayman has a lot going for it: beautiful resorts, delicious food, and a flight from Miami that’s under two hours.
The soft white sand and sparkling turquoise water of Seven Mile Beach have also helped make Grand Cayman a popular vacation spot.
But when I visited, I experienced a bit of sticker shock since US currency doesn’t go as far as it does on other islands. The Caymanian dollar has a fixed exchange rate, and one Caymanian dollar is worth $1.20 USD.
I’ve visited more affordable islands with equally stunning beaches — like Klein Curaçao Beach in Curaçao, Crane Beach in Barbados, and Palm Beach in Aruba.
Grand Bahama left me wanting more.
One of my first trips to the Caribbean was to Grand Bahama via a ferry from Fort Lauderdale. My husband and I stayed on the island for about a week, filling up on fresh conch and visiting the Port Lucaya marketplace.
Although I enjoyed the laid-back stay, I’ve found that other Bahamian islands have more to see and do.
If you want to be closer to the action, I recommend skipping Grand Bahama for New Providence, which is home to top-notch restaurants and hotels, historic landmarks like Queen’s Staircase, and the annual Junkanoo parade.
This story was originally published in May 2024 and most recently updated on July 22, 2026.
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