The Best Caribbean Islands to Visit in the Fall

LT Globetrotter

June 22, 2023
Caribbean island beach

It’s well known that the Caribbean is an ideal destination to escape the worst of your winter woes. And it’s also a popular spring break destination for college students and families. But if you’re looking to avoid both the crowds and the high-season rates, visiting in the fall is a great time to go.

Although the temperatures are still perfect, September through November is considered the rainy season for some islands—hence the lower price point. But usually, visitors don’t have to worry about anything other than an occasional passing shower or a few cloudier days. Some islands on our list are even outside of the Hurricane Belt. And hurricane season ends in November—so visiting the first two weeks of December (still technically fall!) typically delivers both lower rates and great weather as your hometown temperatures start to plunge.

Plus, autumn is an ideal season to indulge in island culture, with various arts and music festivals, restaurant weeks, and sporting events.

Check out what you can do this fall on five incredible Caribbean islands.






Saint Lucia


Aruba in the fall

There are so many reasons to book Aruba any time of the year. But when it comes to fall travel, the biggest is that this gorgeous island has one of the lowest chances of rain in the Southern Caribbean. In fact, in October, Aruba has a lower chance of rain than some other islands during their driest months!

Visitors to Aruba can expect beautiful weather all year long. Plus, its small size means it’s easy to explore, making it an ideal island for vacationers who want to go beyond the resort. Soak up the sun on a white-sand beach in the morning, explore a rugged desert with tall green cacti and limestone cliffs before lunch, browse the colorful Dutch shops of Oranjestad in the afternoon, and snorkel before the sun sets. 

On the northwestern side, you can snorkel at Arashi Beach, Malmok Beach, or Boca Catalina, where you’ll meet barracuda, spinner dolphins, blue parrotfish, angelfish, and starfish. If you dive at daybreak, you’ll also have the opportunity to spot sea turtles.

View the Itinerary: 5 Romantic Days in Aruba



Family snorkeling

Also located outside of the Hurricane Belt, Curacao is a two-island nation located in the Caribbean Sea, approximately 40 miles from the coast of Venezuela. The main island is where most travelers stay and play, while the smaller island of Klein Curacao offers serene natural beauty that remains untouched. During fall, Curacao remains relatively quiet despite the influx of tourists during winter. This makes it the perfect time to explore the island's numerous attractions, including beaches and hiking trails, without having to deal with large crowds.

Curacao boasts a unique location and a diverse population of people from all over the world, where most locals speaking English, Spanish, Dutch, and Papiamentu (the native language). The capital, Willemstad, is beautiful with colorful buildings in Dutch colonial architectural style showing the diverse blend of cultures and African roots in this island nation. Plus, there are numerous UNESCO World Heritage Sites, with the entire downtown area classified as an open-air museum.

Curacao offers exceptional opportunities for diving and snorkeling with thriving coral reefs that are less crowded than other popular spots. With a visibility of up to 100 feet, you can see colorful fish and other marine life in the clear waters. Additionally, there are numerous shipwrecks to explore in the surrounding waters.



Barbados beach

The best part about visiting Barbados is its warm and sunny weather all year round, with temperatures between the mid-70s and mid-80s. The hurricane season in Barbados is officially from June to November, but most storms occur between August and late October. And even when it rains, it typically comes in short showers followed by sunny skies. However, Barbados is located far east in the Caribbean, so it is rarely hit by hurricanes. In fact, there has been no significant storm since 1955.

In fact, you’ll find plenty to do in Barbados during the fall, including the country’s famous Food and Rum Festival happening October 19th through the 23rd, and the Open Water Festival running from November 8th through the 12th. And since Barbados is famous for its friendliness, many visitors end up returning over and over again.

Barbados is known for its beautiful beaches, but it also offers a variety of other attractions. From its vibrant nightlife and the UNESCO World Heritage capital to hiking, golfing, festivals, and food, the island has something for everyone. When visiting Barbados, the beaches along the western and southern coasts have the calmest waters as they border the Caribbean Sea. The eastern side of the island is known for its giant waves and is favored by the experienced surfing crowd.



Jamaica waterfalls

With its lush rainforests, gorgeous beaches, and incomparable culture, Jamaica is a treat all year round. But some months are known for more rain than others. While September and October usually have the highest rain totals of the year, the skies clear for November. In fact, U.S. News & World Report states that the best time to visit Jamaica is between November to mid-December because of a combination of great weather and lower prices.*

In addition to perfect 80-degree days, late October and November are full of festivals and events in Jamaica. Traditionally it’s when both Restaurant Week and the Jamaica Food and Drink Festival occur. Along with tasting the island’s legendary jerk-spiced chicken and other traditional dishes, visiting Jamaica means spending your evenings listening to rhythmic reggae music.

During the day, you relax by the beach or pool, but there are so many possibilities to really make the most of your experience. Discover breathtaking landscapes as you wade in the pools at Dunn’s River Falls, swim in the bioluminescent waters outside of Montego Bay, or board a bamboo raft and drift down a river through the verdant rainforest.

View the Itinerary: 5 Days in Jamaica


Saint Lucia

Saint Lucia sea and mountains

In Saint Lucia, the fall season is more prone to rain due to its mountainous location. However, the rain showers are usually brief and are followed by beautiful blue skies above the perfect beaches and lush green foliage. October is a great time to explore the island, as it is dedicated to celebrating Saint Lucia's French Creole culture, heritage, and art. The celebration includes a wide array of events such as musical and theatrical performances, street fairs, seminars and lectures, art exhibits, and mouth-watering cuisines.

This popular honeymoon spot offers a perfect blend of romance and scenery. Visitors can enjoy breathtaking views of palm-fringed beaches and crystal-clear waters that are great for swimming, diving, and yachting. Beyond the shores, visitors can hike the iconic Pitons, take a Jeep tour, explore 19th-century architecture, and so much more.

On Friday nights, the streets of Gros Islet come alive with a variety of food, drink, music, and dancing, known as "jump ups." Don't forget to try the local delicacies, such as barbecued seafood and blackened corn on the cob.

View the Itinerary: 5 Days in Saint Lucia


Whether you’re ready to fall for the Caribbean in autumn or book winter and beyond, our expert travel consultants are here to curate the perfect vacation.


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LT Globetrotter

As fellow travelers, our people are always on the move discovering new destinations. On the occasions they take a break from exploring, they love to write up a few stories about their adventures before they leave for the next one, so you can enjoy expert tips, news, and recommendations to use for your own travels.