Nowhere on Earth is there a more abundant and eclectic mix of vacations in such close proximity than the Caribbean. While that’s a great problem to have, it does beg the question, which is the best Caribbean island?
The answer depends on what you want from your vacation. Romance, family friendly, adventure, water sports, culture – all and more are catered to. Here are my favorite Caribbean islands for any vacation along with the best time of year to visit.
Criteria used to choose the best Caribbean islands
Although these recommendations are based primarily on my experiences of the islands, I have also used a range of other data to support their inclusion. Yes, postcard-perfect beaches, glowing seas, mouthwatering cuisine and the like are important. But so too are other important influencing factors.
Safety and stability
It’s important to feel safe on vacation and the truth is, some islands are safer than others. My choices factor in crime rates and political stability.
Accommodation options
From unique individual properties to budget stays, luxury hotels to all-inclusive resorts. For beachside charm, try the many hotels a short stroll from Negril Beach in Jamaica. If it’s a zero-effort all-inclusive you’re after, it’s hard to beat Punta Cana in the Dominican Republic.
Activities and attractions
Natural and manmade, from beautiful beaches and epic diving spots to the best bars and restaurants. Looking for buzzy nightlife? Trinidad and the Bahamas, where celebrities often visit, might fit the bill.
For adventure, head to Jamaica where you can cruise rivers on bamboo rafts and zipline through forests. The US Virgin Islands is a great place to take kids with its family-friendly resorts.
Accessibility and flight costs from the US
If you’re in Miami or Fort Lauderdale, you’re just a short flight from Nassau, Puerto Rico and the Bahamas. Depending on the island you’re visiting, you could be there in under two hours. You can also find flight deals from major cities like New York to the Bahamas or the Dominican Republic, or from Los Angeles to Jamaica.
When is the best time of year to visit Caribbean islands?
With year-round good weather it’s almost always the best time to visit the Caribbean islands! It’s typically driest in winter and early spring, which makes this peak season. Temperatures are typically lovely and humidity is low, which makes activities and adventuring more fun. Peak season does mean more crowds and higher prices, but the payoff is the incredible atmosphere and busy roster of festivals and events.
The major hiccup is hurricane season, which typically runs from June to November. This doesn’t mean the Caribbean is a no-go in these months, it just means you have to pick a suitable destination. Trinidad and Tobago, Curaçao and Aruba are all good bets.
How do you choose the best Caribbean island for your needs?
Here’s a quick comparison of the key things to know before you decide which Caribbean island best meets your needs.
*Safety ratings are based on U.S. travel advisory levels, where 1 indicates the safest conditions and 4 represents the highest risk.
The best Caribbean Islands
Whether you’re traveling solo, as a couple or family, looking for adventure or luxury, diving or dining, there’s a Caribbean island that fits the bill.
1. The Bahamas
Best for: Nightlife – especially in the capital, Nassau. The Bahamas offer a great mix of daytime fun and nighttime indulgence. To make the most of the former, my advice is to avoid too much of the latter.
No Bahamian visit is complete without a trip to swim with the pigs at the aptly named Pig Beach on Big Major Cay. Up the ante and swap pigs for nurse sharks with a swim at Compass Bay in the Exumas. Continue the theme nearby with a snorkel trip through the cathedralesque caverns of Thunderball Grotto underwater cave system. Named for its appearance in the Bond film, it’s renowned for its exceptional aquatic life and extraordinary light.
As the sun sets, Arawak Cay sizzles to a soundtrack of its world-famous Fish Fry and live music from its open-air stage. Sunday nights are the standout, when locals and tourists gather over conch fritters, rum punches and reggae beats. At the opposite end of the scale, the Atlantis Casino and Aura Nightclub are an exercise in excess and decadence – dress to impress and bring your wallet.
For partying, it has to be Spring Break around March and April. Be aware, it will be very busy so expect to pay a premium for flights and hotels – but the parties are legendary. KAYAK data shows September is the cheapest month for accommodation with average low nightly hotel prices around $476. Peak season January sees prices rise to an eye-watering average high of $1,092 a night.
2. Jamaica
Best for: Adventure and enjoying the great outdoors. Jamaica is blessed with a landscape built for fun, from mountain to shore – and it’s not just the adrenaline-focussed activities that are adventurous. Try eating a scotch bonnet smothered chicken wing or ten!
Start in-land and up high in the Blue Mountains where ziplines fly high over waterfalls and bike and hike trails snake towards spectacular summit views. Visit coffee plantations, try a homestay and, on Mystic Mountain in Ocho Rios, ride through the rainforest in a snowless bobsleigh in honor of the famous Jamaican Olympic team.
Follow the rivers to the beach. Be it a relaxed bamboo raft along the Martha Brae (rum punch in hand) or high-adrenaline guided climb at Dunn’s River falls. Round off your day with a sundowner at Rick’s Cafe near Negril, or join the cliff-divers making a splash out front and keep the adventure going.
Jamaica swelters in high summer, so to make the most of its bountiful outdoors, aim for the winter months. Hotels are cheapest in September according to KAYAK data, with an average low nightly cost of $336. And they’re at the priciest in peak season February, when average high nightly prices more than double to $795.
3. Barbados
Best for: Anyone with a big appetite. Barbados is foodie heaven – Caribbean and Creole cuisine rubbing shoulders and spices in a mouthwatering mashup, be it fine dining or food truck. And all the while, the island’s most famous output adds a (rum) punch to every meal courtesy of Mount Gay, the world’s oldest commercial rum distillery.
You’re spoiled for choice island-wide with an endless array of bars, rum shops, fine dining restaurants and food trucks. On Friday nights, Oistins Bay Gardens is the place to be for the fish fry, an extravaganza of aquatic cuisine cooking up everything from marlin to mahi-mahi. Get there early to pick up scraps from the fish market and feed the turtles from the pier.
From November 6th to 9th, the Food & Rum Festival sends the aroma of fine food across the island’s southwest. Dive into the best local and international foods and rums, cooked up by a raft of celebrity chefs.
The late fall and winter months are perfect for the Barbadian climate. Still warm, but not so hot as to put you off all the lovely food waiting to be tasted. KAYAK data points to October as the cheapest month for hotel stays with an average low rate of $331 a night. January is at the expensive end with average highs of $945.
4. Dominican Republic
Best for: Making the most of the ocean. The Dominican Republic is a water sports paradise, rich in waves, wind and whale watching. It’s also renowned as one of the best islands in the Caribbean for all-inclusive vacations thanks to its many superb resorts.
The north coast is my preferred area for the best water sports. A road trip along its length could see you learning to kite surf in Buen Hombre to the west before heading east to the buzzy surf town of Cabarete.
Follow the coast all the way east to the tip of Samaná and the European enclave of Las Galeras, where lovely hotels and fine restaurants dot the sides of long, lonely dust roads. From January until late March, humpback whales gather offshore to breed and birth.
Peak season is long and runs from December to April. I prefer the late spring months with their warm, dry weather and lighter crowds – especially along the north coast. According to KAYAK data, September is the cheapest month for hotels, with average low prices of $251 a night. January sees prices peak at an average high of $531. Comparably, these are some of the lowest rates in the Caribbean, making the Dominican Republic a good budget option.
5. Puerto Rico
Best for: An easy vacation from the US mainland. As an unincorporated US territory, American citizens can fly to Puerto Rico without a passport. It’s also one of the best Caribbean islands for culture, nowhere more so than its atmospheric old capital, San Juan.
San Juan’s Old Town is colorful, historic and rich in the culture of the island. Dating back to 1521, its eminently walkable streets are a canvas of polished colonial architecture juxtaposed against the city’s fast run towards modernity. Stroll cobbled streets to palm-fringed beaches towered over by ancient fortresses. You could – and should – spend days immersing yourself in it.
Swap culture for nature at the El Yunque National Forest to the city’s southeast. Tropical, dense and teeming with life, its hiking, swimming and horseback riding are a welcome relief from city streets.
September is the best time for cheap stays with average lows of $261 a night according to KAYAK data. The highest average night prices come in February at $688 a night. Like its close neighbor, the Dominican Republic, high season runs from December to April but expect San Juan to be buzzing year round.
6. Saint Lucia
Best for: Unadulterated romance. Saint Lucia is the best Caribbean island for couples thanks to its focus on wellness that manifests in some truly gorgeous hotels. It’s also home to perhaps the Caribbean’s most iconic natural phenomenon in the UNESCO-listed Pitons. These volcanic spires erupt spectacularly from the sea to dominate the skyline.
Saint Lucia is the spa capital of the Carib and its natural wellness experiences are second to none. That’s in no small part down to the island’s unique geological assets where sulphur-rich volcanic features have created a booming industry.
There’s no better way to earn a massage than with a hike. Take an easy stroll to stunning views along the Tet Paul Nature Trail or a more challenging climb up Gros Piton. As reward, head for the world’s only drive-in volcano at Sulphur Springs to slip into its naturally heated mud baths. Follow it up with a signature volcanic mud massage at one of the many spas.
Undoubtedly a year-round destination, high season runs mid-December to mid-April but I prefer the shoulder seasons April to May and October to November. Days are equally sun-filled and the views just as crystal clear, but with far fewer visitors it only feels more romantic. For the cheapest hotel rooms, consider late September when KAYAK data shows average lows of $649 a night. Come March, average highs climb to $1,266 a night.
7. Turks and Caicos
Best for: Miles of perfect, powdery beaches. Among the most tranquil and pristine of the Caribbean islands, the Turks & Caicos are often, somewhat lazily, compared to the Maldives. This is mostly down to their focus as a luxury destination, where it’s hard to call them apart. But for North Americans, Turks & Caicos are thousands of miles closer to home.
Seclusion is the name of the game and beyond the main island of Providenciales, there are many small islands and tiny bays to revel in just that. Governor’s Beach on Grand Turk, Mudjin Harbor and Bambarra Beach on Middle Caicos all fit the bill nicely.
The big hitter beaches are all on Providenciales though – none more famous than Grace Bay. Some 12 miles of white sands and bath-warm seas stretch along its northern bight, dotted with incredible resorts. Regularly famed as among the world’s best, it’s easy to see why. Round out a day frolicking in sun and sea with a sunset dinner at Infiniti Restaurant for some of the finest seafood on the islands.
When it comes to beach lazing, the hotter the better, I say. That means for the beach capital of the Carib, dry and high season reigns supreme. From December to April, expect hot, sunny days, gorgeous temperatures and not even a rumour of rain. Which goes some way to explain the nightly average highs of $2,454 for a hotel in December. That’s the most expensive of all the islands in this article according to KAYAK data. September, the cheapest month, will still cost you an average low of $894
8. Saint Barthélemy
Best for: Exclusivity, or rather, seeing and being seen. Better known as St. Barts (or Saint-Barth to the locals), this tiny French-speaking Leeward Isle is a haven of luxury and exclusivity, and a favorite hangout for celebrities.
Considering its diminutive size, St Barts packs a lot in. From the sophistication of its French-influenced culture to the rawness of its wild beaches and windswept cliffs, it’s always impressive. Cross paths with turtles and nudists on the silken sands of Plage de Gouverneur. Swim and snorkel the coral reefs of Plage de Colombier. Get away from everyone and everything at remote Plage de Saline.
The main show happens in the capital, Gustavia, where money talks and bigger is definitely better. Don’t be put off by the mega yachts, designer boutiques and personal shoppers – there’s plenty of local culture and history to enjoy too. It’s all just polished to a very high shine.
January to April are peak season in St Barts with great weather and thinning crowds after the rush. March is my choice for the best balance, mixed in with some great events like the always fun St. Barths Bucket Regatta, taking place March 12th to 15th in 2026.
September sees the lowest average hotel prices of $639 a night, from KAYAK data. December is the most expensive month with average highs of $2,378.
9. British Virgin Islands
Best for: Taking it easy, preferably with the family on the deck of a yacht. The BVIs as they’re known are one of the world’s great sailing hot spots. Across its 50-plus islands spreads a giant aquatic playground, brilliant for families to explore.
The BVIs are uncompromisingly laid back, which is a big part of their charm. Rent or join a yacht to mooch lazily from island to island. Calm waters, sheltered bays and incredible sea life are the perfect canvas to introduce kids to the wonders of the ocean. My favorite is the lesser-developed Ginger Island.
On Virgin Gorda, don’t miss the famous Baths – incredible swimming and snorkeling grottoes shaped by 70-million-year-old volcanic rocks. Take the trail to Devil’s Bay for an exhilarating adventure to a secret beach. Go early or late to avoid the crowds.
December to April is peak season. Not only for the guaranteed sun but because this is when the trade winds are at their most consistent. Perfect for sailing, then. If you’re not boat-bound, consider May, June or November when prices are lower, crowds (a little) lighter and the weather is still close to perfect.
KAYAK data shows September is the cheapest month with average hotel lows of $491 a night. February sees prices peak with nightly highs of $1,429.
Tips for finding and booking flights to the Caribbean
FAQs
In most cases, US citizens will not need a visa to visit the Caribbean islands. However, typically you must present a passport with at least six month’s validity beyond your departure date.
In addition to the Virgin Islands and the Bahamas, there are a couple of lesser-known islands that are great for families with younger children. One that stands out is Dominica. This is a great place for kids to experience nature, as you can walk one of its many nature trails to see the local wildlife or visit the botanical garden to see native plants. There are also pretty beaches on this island, most of which are less crowded, making them more comfortable and safer for parents traveling with young children.
Alongside Saint Lucia covered in this article, Antigua is a great choice for unfettered romance on one of its 365 beaches. One for every day of the year, then.
Yes, the Caribbean is largely safe to visit according to recent US travel advisories. Most Caribbean countries fall into the Level 1 advisory, which indicates the lowest level of risk. Countries at a Level 2 rating include Dominican Republic, Turks and Caicos and the Bahamas. Jamaica is a Level 3 advisory and only Haiti is classified as Level 4, meaning you shouldn’t travel to the country.
The official hurricane season runs from June 1st to November 30th, although Mother Nature doesn’t always stick to that schedule. Hurricanes can pop up as early as May although this is quite rare. There are several countries that lie outside of the hurricane belt including Aruba, Curaçao, Barbados, and Trinidad and Tobago.
Price data in this article is based on average hotel rates in Barbados over the past 12 months and is accurate as of June 2025. Rates may vary depending on demand, availability, and booking date.
