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10 Best Caribbean islands to visit: Foodie favorites to family-friendly fun
Discover the 10 best Caribbean islands to visit for an unforgettable vacation, including Jamaica, the Cayman Islands, Anguilla, Grenada, and more.
With an abundance of stunning beaches, regal hotels, and, most importantly — island paradises — you might be struggling to figure out where to go in the Caribbean as a first-timer.
This guide includes the 10 best Caribbean islands to visit, each known for a unique feature. You’ll also find handy tips on when to visit, what to do to make the most of your trip, and how a Holafly eSIM can give you total relaxation in the Caribbean!
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1. Jamaica
Jamaica is full of natural beauty, including dramatic mountains, lush rainforests, and vibrant coral reefs. Given the rugged landscape and clear, turquoise waters, hiking, rock climbing, and diving are some popular activities here.
And let’s not forget about the beaches; Jamaica’s Seven Mile Beach is one of the most popular beaches in the Caribbean. One special thing Jamaica is known for is its vibrant nightlife, music festivals, and reggae tunes.
- Best for: Those who want an authentic taste of Caribbean nightlife
- When to visit: Jamaica is one of the best places to visit in December. Mid-December to mid-April are typically drier months and come in the shoulder season, so you won’t have to deal with larger crowds.
- Don’t miss this: Plan an excursion to the famous Blue Mountains. Grab some authentic Jamaican coffee while you’re there, and marvel at the idyllic views.
2. The Bahamas
One of the next best Caribbean islands to visit is the Bahamas, a tropical paradise. With its turquoise waters, white sand beaches, and more than 700 islands and cays to discover, you’ll find it’s a memorable getaway for all kinds of tourists.
From the vibrant streets of Nassau, rich in history and culture, to the pink dunes of Harbour Island, the Bahamas offers a range of activities perfect for both kids and adults. Enjoy world-class seafood and Bahamian friendliness while snorkeling or scuba diving among colorful coral reefs.
- Best for: Family getaways, group vacations, wedding crowds
- When to visit: The best time to visit the Bahamas for good weather is December to April. You can expect warm temperatures, plenty of sunlight, and little rain.
- Don’t miss this: Visit Aquaventure in the Bahamas, a 141-acre water park with a lazy river, Mayan-themed playground, long-winding waterslides, and the world’s largest open-air marine habitat with sharks, rays, eels, barracudas, and more.
3. Barbados
Barbados is a Caribbean treasure with the ideal fusion of stunning natural surroundings, a vibrant culture, and friendly locals. It’s also the birth country of a very famous singing sensation, Rihanna! Visit her hometown, Bridgetown (the dynamic capital and a UNESCO World Heritage Site), where she grew up in a three-bedroom bungalow and sold clothes with her father in a stall on the street.
Take in the island’s rich music, which includes calypso and reggae. If you’re a thrill-seeker, surf the renowned waves in Bathsheba; foodies can savor the island’s famous flying fish and rum. One thing we’d recommend is having reliable mobile internet in Barbados. This guarantees you stay connected, explore easily, and capture every priceless moment.
- Best for: Natural beauty, fantastic weather, and lively cultural scenes
- When to visit: Between December and early April is the best time to visit this Caribbean island. It’s the driest part of the year, and the high temperatures make it perfect for enjoying water activities.
- Don’t miss this: Explore Harrison’s Caves, an underground network of limestone stalactites and natural pools.
4. The Turks and Caicos Islands
Located southeast of the Bahamas, the Turks and Caicos Islands are a breathtaking Caribbean escape known for their white-sand beaches and some of the world’s most transparent waters. This paradise island is best for luxury getaways and world-class diving, with vibrant coral reefs teeming with marine life.
Visit Salt Cay, an island in the Turks and Caicos, home to one of the largest reefs in the world. Grace Bay Beach, often ranked among the world’s best, offers pristine shores, white sand beaches, and upscale resorts.
- Best for: Luxury getaways, world-class diving, and family vacations
- When to visit: The Turks and Caicos islands are especially enjoyable from December to May due to the dry season, meaning your chances of experiencing the perfect Caribbean summer are high.
- Don’t miss this: Grace Bay Beach and the Chalk Sound National Park (a vibrant teal lagoon, perfect for kayaking) are two must-visit locations in the Turks and Caicos.
5. Saint Lucia
This next island is one of the best Caribbean vacation spots. The beautiful St Lucia sits in the eastern Caribbean and is well-known for its striking scenery, rainforests, and the famous twin pitons. The tropical paradise, which offers everything from opulent resorts to outdoor experiences, is ideal for romantic retreats and nature enthusiasts.
Relax on the island’s golden and black sand beaches; take a hike to the summit of Gros Piton for breath-taking vistas, or soak in the sulfur springs. Sail down the coast, see the quaint town of Soufrière, or savor regional cocoa-infused delicacies and Creole food.
- Best for: Romantic getaways, adventurous excursions, and foodies
- When to visit: Like other Caribbean islands, the best time to visit Saint Lucia is from mid-December to mid-April. However, this is also peak season. To avoid tourist crowds, consider visiting between February and May.
- Don’t miss this: Known for being featured in Hollywood films like Doctor Dolittle (1967), Marigot Bay is also famous for its breathtaking beauty and historical importance.
6. Curaçao
Situated off the coast of Venezuela in the southern Caribbean, Curaçao (one of the ABC islands along with Aruba and Bonaire) is a lively island renowned for its unique cultural fusion, pristine waterways, and beautiful Dutch colonial architecture.
World-class coral reefs, secret beaches, and UNESCO-listed Willemstad make this island the ideal destination for history lovers and scuba divers. Through its food and vibrant festivals, discover the island’s distinctive Afro-Caribbean and European heritage.
- Best for: Those who enjoy historical architecture, picturesque landscapes, and sunny weather
- When to visit: The best time to visit Curacao is between May and November, especially for a budget-friendly trip. Otherwise, the island experiences the best weather from December to April.
- Don’t miss this: Stroll through the streets of Otrobanda, also a UNESCO World Heritage site, to view dozens of historical murals, sculptures, and art installations. Make sure you have mobile internet in Curaçao to explore and learn about its rich history easily!
Cayman Islands
The Cayman Islands, a tropical paradise in the western Caribbean, are well-known for their immaculate beaches, opulent resorts, and top-notch diving. Comprising three islands, the Cayman Islands are also perfect for an island-hopping excursion.
With some of the world’s top snorkeling and scuba diving locations, such as the famous Stingray City, Bloody Bay Wall, Eden Rock, and Devil’s Grotto, this location is ideal for divers and those who enjoy the ocean. While Cayman Brac and Little Cayman offer a more remote island getaway, Grand Cayman’s Seven Mile Beach is a sun-drenched paradise, perfect for beach-goers.
- Best for: Secluded beach trips, diving excursions, and history-lovers
- When to visit: The best time to visit the Cayman Islands is from December to April, when the Caribbean islands are blessed with sun-soaked days and minimal rainfall.
- Don’t miss this: Explore Cayman’s Crystal Caves, which have formed over millions of years. It’s one of Cayman Island’s newest attractions, previously located under the Caribbean Sea!
8. Anguilla
Anguilla, a hidden treasure in the eastern Caribbean, is renowned for its beautiful beaches, blue waters, and relaxed elegance. With some of the most pristine beaches in the area, such as Shoal Bay and Rendezvous Bay, this island is ideal for those who enjoy lounging around on the beach underneath the Caribbean sun.
Because it lacks cruise ports, high-rise luxury resorts, and casinos, Anguilla has a unique, laid-back vibe that is ideal for anyone who desires a relaxing trip to the Caribbean. Sail to neighboring islets for an off-the-beaten-path excursion, discover hidden coves, or savor fine dining, including fresh seafood and Caribbean flavors.
- Best for: Disconnecting from the hustle and enjoying a relaxing vacation in the Caribbean
- When to visit: The best time to visit the Cayman Islands is from December to April, when the Caribbean islands are blessed with sun-soaked days and minimal rainfall.
- Don’t miss this: Explore Cayman’s Crystal Caves, which have formed over millions of years. It’s one of Cayman Island’s newest attractions, previously located under the Caribbean Sea!
9. Grenada
Grenada, also known as the “Spice Island” of the Caribbean, is an idyllic paradise abundant in history, culture, and natural beauty. It offers thick jungles, cascading waterfalls, and some of the most stunning beaches in the area, including Grand Anse Beach. The island is currently a hidden gem and less visited, making it the perfect setting for romantic couple getaways away from the crowds and noise.
Book a romantic dinner to make the experience even more special for your partner. First, ensure you have stable mobile internet in Grenada, or planning could get tricky! Hike through Grand Etang National Park & Forest Reserve’s trails, explore the bustling St. George’s markets, or visit the first underwater sculpture park in the world.
- Best for: Couples, adventure-seekers, and beach enthusiasts
- When to visit: Visit Grenada from January to May to enjoy the sunniest and driest months. Although the country enjoys a hot climate year-round, you can expect some heavy rainfall from June to December (shoulder season).
- Don’t miss this: Explore Molinere Underwater Sculpture Park, now listed as one of National Geographic’s 25 Wonders of the World.
10. Dominican Republic
The Dominican Republic is the most diverse country in the Caribbean. It has the ideal balance of breathtaking beaches, fascinating history, and a lively culture. It is one of the most visited territories in the Caribbean and quite close to North America, making it the ideal Caribbean destination.
With everything from the white sands of Punta Cana to the lush mountains of Jarabacoa, this island is ideal for beachgoers and adventure seekers. One of the best things to do in the Dominican Republic is to discover the coral reefs, sea turtles, and tropical fish of the Caribbean in sites such as the Captain Kidd Shipwreck.
- Best for: Lounging on beautiful beaches, enjoying island parties, and exploring nature
- When to visit: A trip to the Dominican Republic will be best enjoyed between December and April, with fine weather and warm temperatures.
- Don’t miss this: Go whale-watching every year from December through April as humpback whales migrate from their feeding grounds in the North Atlantic to the warm waters off the coast of the Samaná Peninsula.
Enjoy total relaxation on the best Caribbean islands with Holafly
Without a reliable internet connection, no vacation is complete. From navigating new places and booking experiences to staying in touch and sharing memories, travelers and tourists rely on it for almost everything. Staying connected is just as essential as packing your passport to ensure a smooth and hassle-free trip.
A trip to the Caribbean Islands is all about sun, adventure, and relaxation, but staying connected via the best eSIMs is just as important.
Holafly’s Caribbean eSIM offers unlimited data, 24/7 customer support, and a quick set-up process that ensures you’re connected when you arrive in your tropical paradise.
Choose a plan between 1-30 days — the more days you include, the cheaper your Caribbean eSIM gets!
- 5-day trip: $34.90 ($6.98/day)
- 10-day trip: $59.90 ($5.99/day)
For those expecting an extended stay in the Caribbean, remote workers, or digital nomads, check out our monthly subscription service, Holafly Connect, and choose from three different data plans.
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Born and raised in Queens, New York, I'm a Psychology graduate with a passion for writing that I've been nurturing since 2019. Over the years, I've enjoyed creating meaningful content across various niches, including sports, hospitality, and career development. At Holafly, I focus on crafting useful and inspiring pieces to make your adventures more effortless. One of the best perks of this role? Creating travel content always seems to inspire my next vacation destination!
