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The best Caribbean islands to visit in September offer the allure of hot, sultry weather in a season that is relatively quiet. During this month, expect most days to be adorned with blue skies and little cloud puffs.

Be ready, however, for occasional storms which typically manifest as short, sharp showers. These serve to cool the air in the early evening, providing trees and rainforests with a deep green gloss. More often than not, these refreshing downpours give way to intense, fiery sunsets.

Pick your destination carefully and there are many compelling reasons to visit the Caribbean in September. Kids are back in school, there are fewer crowds, and you’ll have glorious beaches to yourself.

Whether you’re in search of cocktails and cuisine, history and culture, dreamy beaches, or the delights of the underwater world, there’s no shortage of exciting islands to make your September Caribbean getaway unforgettable.

Puerto Rico

Street view of Old San Juan, Puerto Rico

Old San Juan, Puerto Rico

The glorious colors, sights, and sounds of Old San Juan are wonderful to explore at any time of year. The city is guarded by two fortifications, Castillo San Cristóbal and the imposing El Morro, which dates back to 1533 and gives a fascinating glimpse into the days of pirates and warfare.

Learn more about the culinary culture of San Juan with a Mofongo and Mojito experience. As well as a walking tour of Old San Juan, you’ll attend a cooking class to learn how to make this classic Puerto Rican dish of green plantains mashed with salt, garlic, broth, and olive oil, washed down with an ice-cold, minty mojito.

Aerial view of Escambrón Marine Park in Puerto Rico

Escambrón Marine Park, Puerto Rico

You can go snorkeling in Puerto Rico within the city limits, too. Escambrón Marine Park has a sandy beach and a gently shelving sea floor where the sand gives way to outcrops of brain coral. Here, you could spot brilliant blue tang, damselfish, and striped sergeant major fish.

St. Thomas

St. Thomas, one of the best Caribbean islands to visit in September

Charlotte Amalie, St. Thomas

Capital of the U.S. Virgin Islands, the pretty town of Charlotte Amalie on St. Thomas makes a great place to visit on a September vacation.

There’s tempting duty-free shopping and plenty to see in town, too. Try joining a culinary tour and tasting curried chicken and pulled pork tacos before learning how to craft the ultimate rum punch.

The underwater life is abundant in the U.S. Virgin Islands. For some of the best snorkeling in the Caribbean, head for rocky, uninhabited Buck Island, surrounded by coral reefs in shallow water teeming with tropical fish.

Turquoise waters of Magens Bay Beach, St. Thomas

Magens Bay Beach, St. Thomas

You may well see the occasional sea turtle drifting by, too. If you prefer to sunbathe on soft sand, pristine Magens Bay Beach is one of the best beaches in St. Thomas, backed by mangroves and dense tropical greenery, with arching coconut palms providing welcome shade.

Beach in St. John

St. John

Take a catamaran to sleepy St. John, much of which has been designated a national park. Spend time at gorgeous Honeymoon Beach, one of the most romantic beaches in the Caribbean.

You can explore ashore, or jump straight off the boat into the turquoise water. On the way back, sample rum punch as you relax to the rhythms of the Caribbean.

St. Maarten

St Maarten, one of the best Caribbean islands to visit in September

Grand Case, St. Maarten

St. Maarten is part Dutch and part French, and although there’s no border to cross, the two sides do have different characters.

In Philipsburg, on the Dutch side, you’ll find great shopping, while the French side is more about French labels, authentic patisseries, and fine dining, especially in the pretty village of Grand Case.

View from Sentry Hill, St. Maarten

Sentry Hill, St. Maarten

If the weather is fine, you’ll find sweeping views across the island from Sentry Hill on the Rockland Estate. Ride up on the two stages of the Sky Explorer chairlift to an elevation of 2,997 feet, from where you can see all the way to St. Barts, Anguilla, Saba, and St. Eustatius on a clear day.

Now, take your pick of adventures. The fastest way down is via the Flying Dutchman, the world’s steepest zipline, which whizzes you over the treetops in a flash, dropping 1,050 feet. The Schooner Ride, from the mid-station, is a specially designed track along which you “surf” in a big inner tube.

Airplane flying over Maho Beach, St. Maarten

Maho Beach, St. Maarten

Possibly one of the most eccentric activities in the whole Caribbean is to spend the day at Maho Beach, on the Dutch side of the island. This St. Maarten beach has an almost cult-like following among airplane spotters, as it’s just off the end of the runway of Princess Juliana International Airport.

Bask in the warm water or chill out with an ice-cold beer at the Sunset Beach Bar as enormous jets roar overhead to cheers from the crowd. Flight arrival and departure times are displayed on a surfboard, so you’ll know when to get in the water.


Sandy beach of Cane Garden Bay, Tortola

Cane Garden Bay, Tortola

The British Virgin Islands are warm and sunny all year round, with September being one of the hottest months. Head for the sweep of Cane Garden Bay, a beautiful beach backed by greenery, for a cooling dip and a rum punch.

Alternatively, take a trip across the water to sleepy Virgin Gorda and visit The Baths, a stretch of enormous, tumbled granite rocks along the shore.

Rock formations of The Baths at Virgin Gorda

The Baths at Virgin Gorda

Pick your way from one end to the other, clambering over rocks, through natural grottoes, and across shallow stretches of water. It’s great fun, and there are plenty of fantastic photo opportunities if you have a waterproof camera.

Read: Best Things to Do in Tortola

Grand Cayman

Aerial view of Stingray City, Grand Cayman

Stingray City, Grand Cayman

Grand Cayman lies in the northern reaches of the Caribbean and tends to receive fewer storms than some of the other Caribbean locations, making it one of the best islands to visit in September.

You could witness some cloudy skies and brisk evening downpours, but these clear the sultry air and provide respite from the late summer heat, and are seen as a bonus.

There are plenty of things to do in Grand Cayman, whatever the weather. Take a boat to Stingray City, where you stand on a shallow sandbar as docile stingrays glide around you, completely unfazed by humans.

Boardwalk at Queen Elizabeth II Botanical Park, Grand Cayman

Queen Elizabeth II Botanical Park, Grand Cayman

Or keep your feet on dry land with a visit to the lush Queen Elizabeth II Botanical Park and immerse yourself in nature among the orchids, tropical flowers, desert garden, and the traditional Caymanian cottage garden.

There’s a captive breeding program here for the blue iguana, so you may see these prehistoric reptiles basking in the sun.

People watching turtles at the Cayman Turtle Centre, Grand Cayman

Cayman Turtle Centre, Grand Cayman

You could also visit the Cayman Turtle Centre to see the efforts made to conserve endangered green turtles and learn more about this fascinating animal. There’s even a chance to swim and snorkel among the gentle turtles in Turtle Lagoon.

If culinary culture is more your preference, join a food tour of George Town, where you’ll enjoy sampling local rum and trying the Caribbean’s famous jerk spiced meat and fiery sauces.

Read: Best Caribbean Islands for Adventure


Aerial view of Punta Sur National Park, Cozumel

Punta Sur National Park, Cozumel

September brings consistently hot temperatures to Cozumel, so make plenty of time for cooling off in the soothing waters of the Caribbean.

Take a jeep tour to the quieter side of the island, where the long beaches of the Punta Sur National Park stretch along a narrow spit with a lagoon to one side.

Cozumel, one of the best Caribbean islands to visit in September

Playa Mia Grand Beach and Park, Cozumel

Or have a relaxed beach day at Playa Mia Grand Beach and Park, one of Cozumel’s best beaches. Here, you’ll find kayaks, water slides, a lagoon pool, and a bar with free-flowing cocktails.

Should you encounter a rainy day, head indoors for a chocolate-making workshop, where you’ll learn about the techniques used by the ancient Aztecs and Mayans who first cultivated cacao beans in Mexico. You’ll sample various types of chocolate, finishing with a magnificent chocolate martini.

Salsa making class in Mexico


Margarita workshops are popular here, as well—or why not learn to make salsa? Fun-packed classes teach you about Mexican cuisine and show you a few dance moves at the same time.


Aruba, one of the best Caribbean islands to visit in September

Eagle Beach, Aruba

Lying just off the coast of South America, desert-like Aruba is one of the best Caribbean islands to visit in September as it’s a considerable distance from the seasonal storm belt and generally basks in sunshine year-round.

Aruba has a different landscape from some of the greener islands further north. Aloe vera thrives in the dry landscape, and you can visit the Aruba Aloe Museum and Factory to learn about the healing qualities of this miraculous plant. Stock up on skin and haircare products in the factory shop.

Rock formations of Casibari, Aruba

Casibari, Aruba

Visit the Casibari and Ayo monoliths and climb up the rocks for perspective on the arid landscape and the island’s history—rock art dating back thousands of years has been found at Ayo.

The beaches in Aruba are spectacular, too. At Eagle Beach, the dazzling white sand is offset against the deepest aquamarine of the sea. It makes for an impressive shot if you capture the twisted form of the famous Fofoti trees in the foreground.

There’s great snorkeling and scuba diving in Aruba, too, with several wrecks to explore for the more experienced.


Bonaire, one of the best Caribbean islands to visit in September

Klein Bonaire

Sleepy Bonaire, like the other ABC Islands, basks in year-round sunshine in the far south of the Caribbean, the heat tempered by trade winds. While the sea and superb snorkeling are obvious attractions, you can try some different sports here, too.

Land sailing, for example, is easy to master and a fantastic rush. Sit back on a go-kart contraption attached to a sail, propelled at thrilling speeds by the wind. It’s one of the best things to do in Bonaire.

Mangroves of Lac Bay Park, Bonaire

Lac Bay Park, Bonaire

The island has impressive wildlife, and you can join a safari to Lac Bay Park, which has one of the best-preserved mangrove forests in the Caribbean. Here, you can spot pink flamingos, herons, wild goats, and iguanas before stopping for a cooling dip.


Clear waters of Knip Beach, Curaçao

Knip Beach, Curaçao

Enchanting Curaçao is a tiny slice of the Netherlands in the Caribbean, with what has to be one of the world’s prettiest waterfronts at Willemstad, the capital.

Gabled houses, many built by wealthy 19th-century traders, are painted in candy colors. Some of the colonial architecture reflects Spanish and Portuguese influences, as well as Dutch.

It’s no surprise that this scenic and historic spot is protected as a UNESCO World Heritage Site. Willemstad is a joy to wander around, with the curious combination of shopping for Dutch specialties like cheeses and Delft pottery and the hot Caribbean sunshine.

Pebbly Mambo Beach in Curaçao

Mambo Beach, Curaçao

Curaçao is encircled by white sand beaches, with plenty of places to cool off. Grote Knip is peaceful, with a thriving reef just offshore. Mambo Beach, close to Willemstad, has plenty of facilities, as well as introductory scuba classes.

For a true escape, take a boat to the uninhabited island of Klein Curaçao, home to some of Curaçao’s best beaches. Here, the sand is a dazzling white, and the water a deep aquamarine.

Tasting at the Landhuis Chobolobo, Curaçao

Landhuis Chobolobo, Curaçao

Back in town, if you’re looking for a souvenir to take home, head for the 19th-century Landhuis Chobolobo, home of the distinctive Blue Curaçao liqueur, a talking point at any drinks party.

While the liqueur is bright blue (which comes from a “brilliant blue” color that’s added after distillation), it actually has a delightful, bitter citrus flavor.

Colorful waterfront of Willemstad, Curaçao

Willemstad, Curaçao

Are you ready to set sail into the blue Caribbean for a September getaway? Browse our cruises to the Caribbean and book your dream escape.

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