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The 12+ Best Caribbean Islands To Visit in 2023 [Month-by-Month Guide]

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Lori Zaino
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Lori Zaino

Senior Content Contributor

54 Published Articles

Countries Visited: 58U.S. States Visited: 40

Lori is an intrepid traveler who loves creating itineraries that exude “luxe on a budget.” She’s written for CNN, NBC, The Infatuation, and more, and loves to muse about points-fueled trips to Sri Lan...
Edited by: Jessica Merritt
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Jessica Merritt

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94 Published Articles 514 Edited Articles

Countries Visited: 4U.S. States Visited: 23

A long-time points and miles student, Jessica is the former Personal Finance Managing Editor at U.S. News and World Report and is passionate about helping consumers fund their travels for as little ca...
& Keri Stooksbury
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Keri Stooksbury

Editor-in-Chief

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Countries Visited: 47U.S. States Visited: 28

With years of experience in corporate marketing and as the executive director of the American Chamber of Commerce in Qatar, Keri is now editor-in-chief at UP, overseeing daily content operations and r...

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With hundreds of islands, the Caribbean offers an array of destinations for travelers seeking a vacation with sand, sun, and crystal clear waters. Located just southeast of the U.S., it’s relatively easy to get to many Caribbean destinations from numerous U.S. hubs.

From family-friendly islands to honeymoon destinations, affordable escapes, and seasonal options, these are the best islands to visit in the Caribbean.

Why Visit the Caribbean?

A Caribbean vacation offers travelers a fun-in-the-sun getaway, but there’s also so much more to get out of a Caribbean vacation. Caribbean vacationers can explore history, culture, cuisine, adventure, and incredible natural landscapes, such as volcanoes, waterfalls, bioluminescent bays, and unique flora and fauna.

It’s easy to get to the Caribbean from many U.S. destinations and airports, and U.S. travelers don’t have to worry about jet lag like they would when visiting islands like Fiji or Bali.

Divers and snorkelers may find the Caribbean especially enticing, as it’s home to some of the most exotic marine life in the world, as well as sea turtles and whales. The islands are also known for having friendly and welcoming locals, as well as iconic Carnival celebrations and festivals throughout the year.

When To Visit the Caribbean

Although the Caribbean islands have a hot and tropical climate year-round, it’s important to understand that most destinations have 2 main seasons: rainy and dry. The dry season from December to May is usually when visitors can enjoy the best weather. The rainy season is from June to November and includes the Atlantic hurricane season. The months of the edges of each of these seasons are considered the shoulder seasons.

Visiting during the rainy or shoulder season may offer better deals on airfare, activities, and hotels. Rainy season could mean sunny skies most of the day with an occasional tropical rain shower, or it could bring a hurricane.

These Are the 12 Best Caribbean Islands To Visit

The Caribbean is divided into 3 groups: The Bahamas, Greater Antilles, and Lesser Antilles. Although The Bahamas aren’t technically in the Caribbean Sea, these islands are still considered part of CARICOM, the Caribbean Community. Also, Turks and Caicos is part of the Lucayan Archipelago alongside The Bahamas.

However, most travelers aren’t too particular about such distinctions, so we’ve included both The Bahamas and Turks and Caicos in our roundup. After all, these islands offer what most Caribbean travelers are seeking, such as crystal clear waters and fine white sands.

Read on to learn about the best places to visit in the Caribbean and what type of traveler each island caters to, as well as the best Caribbean islands to visit by season and month.

1. Best Caribbean Island To Visit on a Budget: Jamaica

Jamaica Beach Shack
There’s nothing like kicking back with a Red Stripe at a local beach shack in Jamaica. Image Credit: Peggy und Marco Lachmann-Anke via Pixabay

Excepting Jamaica’s luxurious Sandals resorts, the island can be a rather affordable destination for travelers who want a budget Caribbean vacation. Low-cost air carrier Spirit offers cheap flights from Fort Lauderdale (FLL) or flights with a layover in FLL from hubs including Chicago (ORD) or Dallas (DFW) for less than $280 round trip on select winter dates.

A quick search on Booking.com revealed many hotels under $100 per night, such as the charming Westender Inn, an oceanfront property with a pool and garden. For under $200 per night, you can lounge on the crystalline sands of the Sand and Tan Beach Hotel in Ocho Rios or enjoy grand sea views at the Hotel Grand A View.

Once in Jamaica, there are plenty of affordable activities to do during your stay. Lounge on the blissful Seven Mile Beach (which, despite its name, is actually only 4 miles long), or pop into a reggae bar to listen to the locals jam from your hammock.

Hot Tip:

If you’re really in the market for an affordable escape, use your points and miles to fly to the Caribbean— we detail the best ways to do so.

2. Best Family-Friendly Caribbean Island: The Bahamas

Family on a beach in Bahamas
Many islands in The Bahamas have clear, calm waters ideal for children. Image Credit: Trent Erwin via Unsplash

From pirates to marine life to endless fun in the sun, The Bahamas offers everything a family with young children, teens, or even older adults could ever want. The massive resort complex Atlantis on Paradise Island, home to 5 different hotels, offers family-friendly services like stroller rentals, plus kids 6 and under eat free. There’s also an on-site water park and kids’ club activities. Teens will love the Atlantis underwater video arcade and the teen-only nightclub.

Meanwhile, Nassau is one of the best Caribbean islands for kids, thanks to its interactive Pirates of Nassau Museum, a fit for kids of all ages. You can get up close and personal with wildlife, such as flamingoes at Ardastra Gardens, a wildlife center that also features pigs, monkeys, and other animals. And it’s not just the most developed islands in The Bahamas that cater to kids. The serene stretches of soft sands and calm waters on islands like Exuma or the Abacos are some of the best Caribbean Islands to visit with toddlers, ideal for little kids to run, play, and shout to their hearts’ content.

3. Best Caribbean Island To Visit for All-Inclusive Resorts: Dominican Republic

Sanctuary Cap Cana Marriott All Inclusive
Sanctuary Cap Cana is a Marriott all-inclusive resort in Punta Cana, Dominican Republic. Image Credit: Marriott

One of the best Caribbean Islands to visit for all-inclusive hotels is the Dominican Republic, thanks to resort areas like Punta Cana, La Romana, and Puerta Plata, all home to numerous resorts that offer all-inclusive packages.

Punta Cana has endless options for all-inclusive travelers, whether you’re on your honeymoon or on the hunt for a family-friendly all-inclusive resort. Choose from the luxury of the Sanctuary Cap Cana (a Marriott resort), the contemporary, family-friendly Hyatt Ziva Cap Cana (home to a water park), and the Hyatt Zilara Cap Cana (adults only), plus 2 new Hyatt Sunscape Resorts opening in 2024 and an all-inclusive, adults-only W Punta Cana coming in 2025 (one of the first all-inclusive W properties in the world).

If you’re hoping to book a Hyatt resort in the Dominican Republic for your next Caribbean getaway, you can save 40% when booking by December 13, 2023.

Hot Tip:

What does all-inclusive mean? Find out how to get your money’s worth at an all-inclusive hotel in our detailed article.

4. Best Caribbean Island To Visit With Friends: Anguilla

Gorgeous Scilly Cay
If you’ve ever wanted to dine with your friends on a tiny island, do so at Gorgeous Scilly Cay off Anguilla. Image Credit: Gorgeous Scilly Cay

Anguilla is known as one of the friendliest islands in the Caribbean, which means visiting with friends will be lots of fun. You can interact with locals at the beach parties of Sandy Ground Beach and enjoy participating in the local culture, including Anguilla’s Carnival celebrations, which happen each summer and include boat races, street jams, and parades. The U.S. State Department has also named Anguilla one of the safest Caribbean islands (marked as a Level 1) to visit, so you and your friends should be able to frolic freely without worry.

Anguilla has quite a bit of diversity in what to do on your vacation. Of course, there are those stunning Caribbean beaches, like the picture-perfect Shoal Bay or the pinkish-hued sunsets of Mead Bay. Friends can also hit up art galleries, visit museums, go snorkeling or diving, birdwatch, and share a meal on the famous island of Scilly Cay, a tiny island home to the Gorgeous Scilly Cay Restaurant, where you can dine on local grilled lobster or Caribbean-inspired surf and turf.

5. Best Caribbean Island To Visit on a Honeymoon: St. Lucia

St. Lucia
The Pitons are a romantic, beautiful backdrop for St. Lucia honeymooners. Image Credit: Nick Fewings via Unsplash

One of the best Caribbean islands for a honeymoon, St. Lucia’s breathtaking scenery, gorgeous hotels, and impressive natural wonders make it the perfect Caribbean island to visit as a couple. Visitors can admire the island’s emblematic backdrop, the moss-covered Piton Mountains that seem to rise directly out of the sea. Choose from world-class resorts such as Jade Mountain, home to its own chocolate farm and laboratory, and Hyatt’s all-inclusive Zoetry Marigot Bay, flanked with verdant foliage.

Pigeon Island National Park is one of the best spots on the island for couples who want to experience history, a wooded islet home to former British forts. Nature buffs should explore the cascading waterfalls, dense rainforest, and sulfur springs near Soufrière.

Hot Tip:

The only thing better than a honeymoon in St. Lucia is a free one. You can redeem World of Hyatt points to stay at Hyatt’s AMR Collection properties across the Caribbean. To stock up on Hyatt points, apply for The World of Hyatt Credit Card or earn flexible points that can transfer to the World of Hyatt program with a card such as the Chase Sapphire Reserve® or Chase Sapphire Preferred® Card.

6. Best Caribbean Island To Visit for Endless Beaches: Antigua

Antigua Beach
Antigua is the island for beachcombers. Image Credit: Nici Keil via Pixabay

The Caribbean is indeed known for having some of the most beautiful beaches in the world. But not every island is created equal, and some have more beaches and better beaches than other destinations. Antigua wins for quantity when it comes to beaches, with around 365 different sandy stretches — you could spend a year there and never go to the same beach twice!

However, the large number of beaches can make it difficult to decide which ones to visit, especially if your trip is just a week long and not a year. We recommend Half Moon Bay, a crescent-shaped stretch of sand with a reef for snorkeling. Ffryes Beach is the one to visit for photos of sparkling sands and transparent waters, especially beautiful around sunset.

7. Best Caribbean Island To Visit for First Timers: Cayman Islands

Cayman Islands
The Cayman Islands is perfect for first-timers who want a resort experience or an exotic, tranquil escape. Image Credit: Ronny Rondon via Unsplash

Between the 3 different Cayman Islands, first-time travelers can get a true taste of what a Caribbean vacation is all about. Grand Cayman, the largest and most popular of the 3, is the perfect place to start, offering visitors a more curated, traditional resort stay and access to perfect Caribbean sands and waters, as well as plenty of dining, amenities, and activities. We love the Kimpton Seafire Resort & Spa, an IHG resort located directly on the famous Seven Mile Beach.

Those looking for something more off-the-beaten-path will also find it in Cayman on the other 2 smaller islands: Cayman Brac and Little Cayman. Both of these islands are known for offering incredible marine life accessible to snorkelers and divers, plenty of solitude, and a general far-flung, deserted island feel.

8. Best Caribbean Island To Visit Solo: British Virgin Islands

BVI Tortola
BVI is a safe and enjoyable destination for solo travelers and beyond. Image Credit: Dietmar Lichota via Unsplash

Some Caribbean islands are safer than others, and solo visitors should feel comfortable heading to the British Virgin Islands: Tortola, Anegada, Virgin Gorda, and Jost Van Dyke — plus more than 50 other tiny islands and cays. It holds the lowest travel safety advisory rating (a 1) from the U.S. State Department. This means travelers should exercise normal caution.

Often referred to as BVI, these islands offer comfortable and luxurious resorts like the Rosewood Little Dix Bay or Scrub Island Resort, Spa & Marina (unfortunately, no longer affiliated with Marriott) for those that want to relax in style. There are also plenty of secluded beaches and hidden spots to hide away from more mainstream tourism.

Solo travelers who want to make new friends should head to Cane Garden Bay on Tortola, a picturesque stretch of white sands that features beach bars and hotels with live music, happy hours, and other activities. Another must-see is The Baths in Virgin Gorda, a mix of sea boulders, hidden coves, and white sands accessible by land or boat. Consider heading there first thing in the morning or later in the day to beat the day trippers. For a bit more solitude, consider Anegada, a quieter island known for its wildlife and peaceful beaches.

Hot Tip:

Don’t have a passport but really want to visit the Caribbean? You can visit the U.S. Virgin Islands (USVI), which became U.S. territories in 1917: St. John, St. Croix, and St. Thomas.

9. Best Caribbean Island To Visit for Luxury: St. Barts

Eden Rock
Luxury hotels like Eden Rock are ideal for luxury travelers. Image Credit: Eden Rock

St. Barts isn’t the easiest Caribbean island to access, which is why high-profile celebrities and athletes often vacation there to get away from the general public and shutter-happy paparazzi. An overseas territory of France, the island oozes French sophistication combined with Caribbean glamour.

Besides the many exclusive luxury hotels, such as Eden Rock, a seafront property that offers sophisticated amenities like yacht rentals, and the Rosewood Le Guanahani, which feels intimate and secluded, thanks to its 66 rooms and suites, it’s also a paradise for shoppers. Thanks to duty-free status, you’ll pay a lot less tax on luxury goods on the island.

10. Best Caribbean Island for History and Wildlife Buffs: St. Kitts and Nevis

St. Kitts
The Brimstone Fortress is a nod to St. Kitt’s history. Image Credit: Derrick Miller via Pixabay

While the 2 islands of St. Kitts and Nevis boast blissful beaches, lush rainforest, and coveted Caribbean waters, the destination is also ideal for those who want to understand more about the culture of the Caribbean. St. Kitts was Great Britain’s first settlement in the Caribbean. Nevis featured the region’s first hotel, the Bath Hotel, which dates back to the 18th century. These days, when it comes to hotels, we favor the elevated Park Hyatt St. Kitts Christophe Harbour.

Learn more about the island’s history at the Brimstone Hill Fortress National Park, a UNESCO World Heritage Site. Animal lovers may also enjoy the fact that this island is home to hundreds of free-roaming vervet monkeys. Just don’t get too close to them! Between the months of June and September, visitors can spot 3 different species of turtles hatching: the hawksbill, the leatherback, and the green turtle.

11. Best Caribbean Island for Adventure Travelers: Dominica

The pool at the InterContinental Dominica
Dominica has lush tropical foliage and plenty of sun. Image Credit: IHG

Known as the nature hub of the Caribbean, Dominica’s viridescent landscape is home to extensive rainforests, tree-covered mountains, dramatic gorges, inviting freshwater lakes and hot springs, and even active volcanoes. The island’s landscape is decidedly unique, from the bubbling saltwater rising up from the sea floor at Champagne Beach to the sulfur springs of Wotten Waven, rumored to have healing properties.

With 3 national parks on the island, there’s much to do in the way of hiking, whether it be to reach a secret waterfall, wander through a cloud forest, or just enjoy dramatic views of the island’s memorable landscape. You can enjoy some of the island’s best natural wonders right from the hotel if you stay at the InterContinental Dominica Cabrits Resort & Spa, which overlooks the Caribbean Sea and the greenery and volcano of Cabrits National Park.

12. Best Caribbean Island for Top-Rated Beaches: Turks and Caicos

Grace Bay
Grace Bay has been repeatedly voted one of the best beaches in the world. Image Credit: Pine Cay Beach via Unsplash

Turks and Caicos has some of the very best beaches in the Caribbean, with the whitest, finest sand, and clearest, most enticing waters. Although some may argue that Turks and Caicos isn’t really a part of the Caribbean, we’re including them in this roundup. With 40+ different islands, this archipelago has plenty of sand to go around — and all beaches are public, so you can visit as many as you’d like.

Grace Bay is probably the most famous beach on the islands, often snagging the top spot on best beach lists. It’s home to a reef system, and a portion of it is part of the Princess Alexandra National Park. Long Bay Beach’s winds are ideal for kiteboarders, while families should head to the lagoon waters of Half Moon Bay. AvGeeks should head to Pine Cay Beach, where you can feel the breeze from landing airplanes landing at and taking off from the Pine Cay Airstrip, though definitely don’t expect to spot any 747s.

Best Caribbean Islands To Visit in Winter and Spring

Grenada
Grenada is one of the lesser-visited Caribbean islands, the perfect spot to avoid crowds during the busy winter peak Caribbean travel season. Image Credit: Hugh Whyte via Unsplash

The Atlantic hurricane season runs from June until the end of November, so winter and spring are the best times to visit almost any of the Caribbean Islands if you’re looking for sunny, dry weather.

However, with peak season comes peak prices and high crowds, so if you’re visiting during prime time, you might want to consider one of the more affordable Caribbean islands (Jamaica or Dominica) to stay within budget, or one of the more obscure Caribbean islands (Grenada or St. Vincent and the Grenadines) to have a crowd-free Caribbean winter escape.

Best Caribbean Islands To Visit in Summer and Fall

Curacao
Curaçao is part of the ABC islands that sit outside the Atlantic Hurricane Belt. Image Credit: Jorgen Hendriksen via Unsplash

The ABC islands of Aruba, Bonaire, and Curaçao sit outside of the Atlantic hurricane belt, so they’re less susceptible to major or damaging storms. These are the best places to visit if you’d like to escape to the Caribbean in the summer, which coincides with hurricane season.

The best southern Caribbean islands to visit include St. Vincent and the Grenadines, Barbados, and Grenada, as well as Trinidad and Tobago. These islands are closer to Latin America and are usually less likely to get hit by a hurricane, though they’ve all seen their fair share of intense tropical storms.

Just remember, there are no guarantees when it comes to nature, so if you want to minimize the risk of hurricanes or other tropical storms, visit the Caribbean during the dry season (December to May). The highest risk of hurricanes is from August to October, so you may want to consider avoiding those months in the Caribbean if you’re worried about bad weather.

Hot Tip:

If you visit the Caribbean during the summer months, make sure to get travel insurance. Don’t forget that many popular credit cards come with travel insurance — we detail some of the best in our guide.

Best Caribbean Islands To Visit by Month

Beyond just hurricanes and budget, there are certain times of year when it’s ideal to visit specific Caribbean islands. From underwater visibility to whale migrations to iconic cultural celebrations, these are the best islands to visit in the Caribbean each month.

Best Caribbean Islands To Visit in January

Grenada sailing
January is the perfect month for Caribbean sailing. Image Credit: Hugh Whyte via Unsplash

Foodies should head to the Cayman Islands in January for the Cayman Cookout, which brings together revered chefs, mixologists, and spirits connoisseurs from around the world (January 9 to 15, 2024). This year’s event also includes a musical performance from the Goo Goo Dolls.

Grenada is another island to visit in January (and the beginning of February), as the destination hosts Grenada Sailing Week. The event (January 28 to February 2, 2024) consists of sailing races and lots of parties back on dry land.

Hot Tip:

January is one of the sunniest and driest months in the Caribbean, so you’ll likely have excellent weather on all of the islands. Just book ahead to get the best prices, and know that you may encounter crowds this month and in the months following, especially around spring break.

Best Caribbean Islands To Visit in February

Trinidad and Tobago Carnival
Trinidad and Tobago’s Carnival is an annual event to remember. Image Credit: Holger Woizick via Unsplash

It’s prime sperm whale season throughout the Caribbean, but especially in Dominica between November and March. Head out on a boat around areas like Scotts Head, Roseau, Layou, and Point Round to admire these gentle giants — just make sure not to lure the animals. You may also spot spotted and spinner dolphins.

For those that want an iconic Carnival experience outside of Brazil, Trinidad and Tobago’s Carnival event (February 12 to 13, 2024) is famous worldwide, featuring parades, partying, and some of the most elaborate costumes you may have ever seen.

Finally, celebrate the leap year and welcome in the month of March with the St. Maarten Heineken Regatta (February 29 to March 3, 2024), home to 4 days of sailing and lots of cuisine and Heineken beer.

Best Caribbean Islands To Visit in March

Diving in Bonaire
March is an excellent time for calm seas and extended underwater visibility. Image Credit: Jesse van Vliet via Unsplash

March is another perfect month in the Caribbean, with smooth seas for sailing and excellent visibility for diving and snorkeling. Head to Antigua for the Superyacht Challenge (March 11 to 17, 2024) to see boats race for the win.

Or, focus on the delights of the underwater world, diving and snorkeling around the Turks and Caicos Barrier Reef, Grenada’s Molinere Bay Underwater Sculpture Park, or Bonaire, where the capital of the island, Kralendijk, translates to coral reef.

Best Caribbean Islands To Visit in April

Cuba trumpet player
Cuba in April is magic. Image Credit: Jessica Knowlden via Unsplash

April brings continued sunshine to the Caribbean, as well as the BVI Spring Regatta and Sailing Festival (April 1 to 7, 2024), home to sailing and lots of fun.

For a unique Caribbean experience, let’s not forget about Cuba, a country a few hundred miles away from Florida. April brings the island’s Afro Cuban Dance Festival (March 30 to April 9, 2024) to Havana. U.S. citizens can travel to Cuba if they meet one of the 12 categories of travel set by the U.S. government, which include things like educational activities, support for Cuban people, public performances, and workshops.

Best Caribbean Islands To Visit in May

Antigua Sailing Week
Antigua Sailing Week is the island’s most notable event. Image Credit: Antigua Sailing Week

May is an excellent month for travelers looking for the best Caribbean islands to visit on a budget — although there’s just slightly more rainfall, the prices are usually more affordable, and the crowds start to dissipate. It’s the perfect time to visit St. Lucia thanks to the St. Lucia Jazz and Arts Festival (April 30 to May 9), which blends jazz, blues, R&B, swing, calypso, and Latin music with cuisine, dance, craft markets, and more.

This month also brings one of Antigua’s most notable events: Antigua Sailing Week (April 27 to May 3, 2024).

Best Caribbean Islands To Visit in June

Bahamas
Pineapple lovers should head to the Bahamas in June. Image Credit: AJ Garcia via Unsplash

As the Atlantic hurricane season gets its start, the ABC islands, which have more stable and drier weather, become more popular as they reside outside the Atlantic hurricane belt. This is why heading to Bonaire’s Rum Week (June 12 to 17, 2024) is the optimal plan for travelers who want a trip focusing on Caribbean spirits, cigars, cuisine, and sunshine.

Pineapple lovers should travel to The Bahamas for The Bahamas Pineapple Festival (June 7 to 8, 2024). Here, you can chow down on this flavorful fruit alongside other Bahamian desserts and beverages.

Hot Tip:

Concerned about the possibility of a hurricane? Consider getting one of these cancel for any reason travel insurance policies.

Best Caribbean Islands To Visit in July

Carnival
July is a festive time in the Caribbean, with Carnival celebrations happening on a number of islands. Image Credit: Bash Visual via Unsplash

July is a month for celebration in the Caribbean. Enjoy Carnival celebrations in St. Vincent and the Grenadines (Vincy Mas, July 4 to 10, 2024), St. Lucia (July 10 to 17, 2024), and Antigua (July 26 to August 6, 2024).

St. Kitts and Nevis celebrates Restaurant Week (July 13 to 23, 2023), where restaurants around the island will offer special menus around a theme ingredient. The upcoming festival’s ingredient is pineapple.

Finally, Jamaica gets festive with its Reggae Sumfest (July 16 to 22, 2024), featuring nonstop concerts and events.

Best Caribbean Islands To Visit in August

Tortola on BVI
BVI celebrates its Emancipation Day in August each year. Image Credit: Matt Briney via Unsplash

Brave the heat and humidity to attend Anguilla’s Summer Fest (August 1 to 11, 2024), celebrating the 50th anniversary of the island’s Carnival history. Events include the Miss Anguilla competition, boat races, concerts, parades, and more.

Both the British Virgin Islands and St. Kitts and Nevis honor their Emancipation Days in August. To celebrate, these destinations feature several days of music, parties, and more.

Best Caribbean Islands To Visit in September

Hurricane season lasts about half the year. However, the most common time for cyclone activity is around September 10, according to the National Hurricane Center. Still, that doesn’t mean storms will definitely occur around that time. If you’re willing to brave the possibility of hazardous weather (most often intermixed with plenty of sunshine), September happens to be prime turtle-hatching season on many Caribbean islands. Spot them on islands such as Aruba, St. Kitts and Nevis, The Grenadines, and even in Mexico, Florida, and Puerto Rico, too.

Best Caribbean Islands To Visit in October

Remember, even during the peak of the Atlantic hurricane season, the ABC islands often see much less inclement weather, so October is a good time to visit.

If you’re willing to brave a bit of rain, visit St. Lucia, which celebrates its Creole Heritage Month in October. Festivities begin October 1 with Oktoberfest and end on the last Sunday in October to celebrate Creole Day. Or, vacation in Barbados, known as the birthplace of rum. The island celebrates its Food and Rum Festival each October.

Best Caribbean Islands To Visit in November

Cayman Islands Pirates Week Festival
There’s nothing more emblematic of the Caribbean than pirates. Image Credit: Cayman Islands Pirates Week Festival

November welcomes the final month of hurricane season, so you may see clear skies as the end of the month approaches. Families and adults alike can celebrate at the Pirates Fest in the Cayman Islands. It’s celebrated on all 3 islands (Little Cayman, November 3 to 5, 2023; Grand Cayman, November 9 to 19, 2023; and Cayman Brac, November 24 to 26, 2023). The merriment includes parties, cultural events, turtle releases, costumes, dancing, and plenty of pirate fun.

Those looking for a slightly higher-brow experience than “Yo ho ho and a bottle of rum” can find it in St. Bart’s. The annual St. Barth’s Gourmet Festival (November 7 to 12, 2023) welcomes top chefs and hungry foodies from around the world.

Best Caribbean Islands To Visit in December

Christmas beach
Why not spend the holidays at the beach this year? Image Credit: minfl3 via Pixabay

Spending the holidays in the Caribbean is the ideal winter getaway. The weather starts improving, so those in search of winter sun will find warm and drier conditions in nearly all of the Caribbean Islands. However, we suggest a visit to The Bahamas, where 16 of the islands celebrate Junkanoo, which includes dancing, music, and elaborate costumes. The festival occurs on the day after Christmas annually.

Meanwhile, the U.S. Virgin Island of St. Croix celebrates the Crucian Christmas Carnival, which begins in December and culminates on Kings Day, which is January 6.

Hot Tip:

If the beach and sunshine don’t inspire you around the holidays, consider a trip to Europe, home to some of the world’s best Christmas markets, instead.

Final Thoughts

With so many islands in the Caribbean, it’s easy to find the right one for you. Whether you’re on a budget, looking for the best beaches, or want to travel in a specific month or season, the wide range of Caribbean islands offers something for every traveler.

Frequently Asked Questions

What Caribbean island should I visit first?

Most Caribbean islands are ideal for first-time visitors, but we suggest heading to the Cayman Islands, which offers a little bit of everything. Islands such as the U.S. Virgin Islands are also easy for first-timers, as you don’t need a passport, and most locals speak English.

What is the cheapest and safest Caribbean island to visit?

One of the most affordable Caribbean islands is Jamaica. Dominica, a more under-the-radar destination, is also cheaper. Visiting any of the Caribbean islands during the low season (June through November) means you may get better prices. The safest Caribbean islands are the British Virgin Islands, ideal for solo travelers, and Anguilla, which markets itself as a very safe Caribbean destination.

Which is the nicest part of the Caribbean?

If you’re looking for a luxury vacation, the nicest part of the Caribbean may be St. Bart’s, an island frequented by the rich and famous. If you’re traveling with your family, The Bahamas is the best Caribbean island to visit with toddlers, children, and teens, with lots to do and see.

Where is the prettiest place in the Caribbean?

The prettiest place in the Caribbean is debatable. Antigua and Turks and Caicos are known for beaches, while islands like Bonaire may be most beautiful underwater, with extensive marine life. If you love natural wonders like waterfalls, hot springs, and rainforests, St. Lucia and Dominica are 2 of the prettiest Caribbean islands.

Lori Zaino's image

About Lori Zaino

Lori is an intrepid traveler who loves creating itineraries that exude “luxe on a budget.” She’s written for CNN, NBC, The Infatuation, and more, and loves to muse about points-fueled trips to Sri Lanka, Sicily, and Myanmar.

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