Most travelers think of the Caribbean as a winter escape—but off-season Caribbean travel is where the real magic happens. With fewer crowds, better rates, and vibrant local festivals, summer might just be the best time to go.

From world-class music festivals to culinary celebrations and Carnival-level pageantry, these are the warmer-weather weeks when the Caribbean throws open its doors and says, “Now it’s our turn.” You may sweat a little more — but you’ll get a front-row seat to the party.

Here are six reasons to consider heading south when everyone else is flying east.

Top Off-Season Caribbean Events This Summer

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Antigua – Antigua Sailing Week (April 26 – May 2, 2025)

With a beach for every day of the year and a proud sailing tradition, Antigua is a favorite among those who prefer authenticity and open water to the rhythms of an all-inclusive buffet. Sailing Week is the island’s time to shine, attracting elite crews, spectators, and sunset celebrations that go long into the night.

Getting There
No nonstop service from Chicago, but American Airlines offers convenient one-stop flights via Miami or Charlotte.

Where to Stay

• Hermitage Bay – A secluded collection of hillside suites and beachfront villas with outdoor showers, private plunge pools, and gourmet dining.
• Curtain Bluff – Long beloved for its all-inclusive ease and oceanfront elegance, this classic resort draws repeat guests with its two beaches and elevated service.

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Anguilla – Anguilla Culinary Experience (April 30 – May 4, 2025)

Anguilla is quietly one of the Caribbean’s most refined islands — a favorite among food lovers, celebrities, and those who prefer boutique beach escapes over cruise crowds. The Anguilla Culinary Experience brings together international chefs, local talent, and world-class beachfront dining for a celebration of flavor and island culture.

Getting There
Fly into nearby St. Maarten (SXM), then transfer to Anguilla by ferry or short puddle-jump flight. It’s a journey worth the extra step.

Where to Stay

• Cap Juluca, A Belmond Hotel – An icon of Caribbean luxury, with whitewashed Greco-Moorish villas, private beach access, and some of the most elegant beachfront dining in the region.
• Aurora Anguilla Resort & Golf Club – Freshly reimagined, this expansive resort offers gourmet cuisine, a world-class golf course, and a sleek, sophisticated aesthetic.

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Saint Lucia – Saint Lucia Jazz & Arts Festival (April 30 – May 11, 2025)

Saint Lucia is often thought of as the Caribbean’s romantic capital — for honeymooners, especially. But during festival season, it turns up the volume. The Jazz & Arts Festival draws international legends and local stars to open-air stages tucked between beaches and botanical gardens. Think jazz under the Pitons and sunsets that last as long as the solos.

Getting There
No nonstop flights from Chicago, but Delta and American offer easy one-stop options via Atlanta or Miami.

Where to Stay

• Jade Mountain Resort – An architectural marvel perched above the sea, known for its open-air sanctuaries and panoramic views.
• Sugar Beach, A Viceroy Resort – Nestled between the iconic peaks, this lush retreat offers elegant cottages and refined beachfront relaxation.

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Jamaica – Reggae Sumfest (July 13 – 19, 2025)

I really enjoy going to Jamaica. I’ve only ever been off-season, because I’m not a fan of crowds or peak-season prices. And yet… Reggae Sumfest might be the one reason I’d brave the buzz in July. It’s the biggest music festival in the Caribbean — a nonstop lineup of reggae greats and rising stars.

The streets pulse, parties spill out onto the beach, and the music pairs nicely with the jerk and Red Stripe. That’s really all you need in life, isn’t it?

Getting There
Direct flights from Chicago O’Hare to Montego Bay are available on American, United, and Southwest.

Where to Stay

• GoldenEye – The kind of off-the-grid cool that doesn’t try too hard. Beachfront cottages, lagoon villas, and cocktails that hit just right.
• Round Hill Hotel & Villas – Timeless, charming, and a favorite for decades. Think ocean views, old-school service, and quiet elegance.

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Saint Lucia – Carnival (July 17 – 23, 2025)

I attended a party on a beach in Saint Lucia once, but it was nothing like this. Carnival week is more than a celebration — it’s a full-on transformation. The streets fill, the volume rises, and suddenly it feels like the Rio party bus has arrived. Costumes, music, parades, feathers — it’s loud, joyful, and designed for dancing until you’re done.

Getting There
No direct flights from Chicago, but Delta and American offer connections via Atlanta or Miami.

Where to Stay

• Cap Maison – Tucked into the cliffs above Smugglers Cove, perfect if you want Carnival energy nearby but not on top of you.
• Ladera Resort – Perched between the Pitons, peaceful, dramatic, and completely open-air.

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Barbados – Crop Over (July 30 – August 5, 2025)

Crop Over started as a harvest celebration in the 1700s and has evolved into Barbados’s biggest and boldest festival. Today, it blends music, dance, parades, and pageantry with deep roots in Bajan culture. Grand Kadooment Day brings the feather-filled finale, but the week is packed with concerts, calypso competitions, and a sunrise party known as “Foreday Morning.”

Getting There
No nonstop flights from Chicago, but American offers one-stop service via Miami.

Where to Stay

• The Sandpiper – Elegant but understated, surrounded by gardens and just enough removed from the action to offer a breather.
• The House by Elegant Hotels – Adults-only and right on the Platinum Coast. All-suite, all relaxed, with champagne breakfasts and a loyal following.

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There’s more than one way to celebrate summer, and for those of you who follow the beat of a steel drummer, summer might be the best time of all to visit the Caribbean.

This is your reminder: the Caribbean doesn’t go quiet after spring break. In fact, for those who want color, culture, flavor, and the feeling that the tourists are gone and it’s the “if you know, you know” crowd — this is when it all comes alive.

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Need help planning your Caribbean escape?

Whether you’re dreaming of a summer festival, an off-the-grid beach stay, or a milestone-worthy resort, I can help you design a trip that makes it easy to say yes.
Click here to schedule a call and start planning the kind of Caribbean vacation you’ll still be thinking about long after the tan fades.

From “where should we go?” to “that was amazing,” I’m the one to make it happen—start to finish.

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About the Author

Karen Aikman is the founder of Live LARGE Travel, where she personally designs custom travel experiences tailored to her clients’ unique preferences. A seasoned traveler with a deep passion for exploration, she shares insider tips, expert insights, and destination inspiration both here on the Live LARGE Travel blog and across various platforms.

Whether you’re dreaming of a bucket-list adventure or a seamless luxury getaway,
click here to schedule a call with Karen and start crafting your next unforgettable journey.