The first summer Alison Morris Roslyn and Scott Roslyn spent in the Caribbean, they were apprehensive. They were getting married at the Rockhouse Hotel & Spa in Negril, Jamaica, in July 2013. And they wondered—would it be too hot, too rainy?
Those doubts disappeared the moment they landed. The trade winds were blowing, the skies stayed clear; even though a heat wave pushed temperatures into the triple digits, Alison says that was part of the fun. “We danced the night away and everyone ended up in the pool to cool off at the end of the night,” she says. Now, the couple returns nearly every summer for their anniversary—and Alison even wrote a children’s book about their favorite getaway spot.
A lot of people think of the Caribbean as a place to escape winter, but savvy travelers know that the warm season is actually the sleeper hit, delivering serious advantages, like better value, fewer crowds, calmer waters, and festive celebrations.
“Everything about traveling to the Caribbean in the summer is awesome,” says Alison. “It’s less hectic. It’s cheaper. And you never have to worry about your flights getting canceled because of a Northeast snowstorm.” Although June, July, and August fall within the region’s hurricane season, travelers can minimize risk if they play it smart.
Here’s why you should plan your summer escape to the Caribbean.

In terms of weather, the Caribbean may be a better destination than the Mediterranean during the summer.
Courtesy of Royce Fonseca/Unsplash
It’s not too hot
Yes, the Caribbean is warm in the summer. But so is Europe—often with no sea breeze. Constant trade winds keep the Caribbean islands pleasant. “With climate change, the idea of seasonality has changed completely,” says Jack Ezon, founder of luxury travel planner Embark Beyond. “In the Mediterranean, which used to normally be beautiful in summer, the weather is now extremely hot—sometimes more humid and hot than in the Caribbean. So you could go to St. Bart’s and have that [French] St. Tropez–style experience without the overcrowding and overheating.”
Culture comes alive in summer
While the high season may have the hype, summer has the soul. Throughout the region, the warmer months bring plenty of cultural events. In Barbados, the Crop Over festival (July to August) marks the end of the harvest season with a swirl of parades and calypso beats.
In the Bahamas, Goombay Summer Festivals pop up throughout the islands, including Eleuthera and the Abacos, celebrating local culture with dance, food, and music. Nassau’s Junkanoo Summer Festival is a colorful carnival that takes place on the Saturdays between July 7 and August 4. There are also music festivals like Jamaica’s legendary Reggae Sumfest (July 13 to 19).

Not all Caribbean islands are within the hurricane belt, a region in the Atlantic Ocean prone to hurricanes.
Photo by Rabih Shasha
Hurricane season isn’t a deal-breaker
Hurricane season officially runs from June through November, but the riskiest period is typically from late August to early October. That leaves a solid window for safer summer travel in June, July, and early August. Another thing to consider: Many southern Caribbean islands, such as Aruba, Bonaire, Curaçao, Barbados, and Grenada, are outside the hurricane belt and are historically less affected.
More good news: Some Caribbean resorts offer flexible booking policies to guarantee peace of mind. For example, the Palms on Turks and Caicos has a 100 percent refund policy in the event of a hurricane threat; the resort even has provisions for tropical storms.
However, forecasters are predicting an above-normal Atlantic hurricane season this year, so purchasing travel insurance is a smart bet. According to InsureMyTrip, the most common pitfall is buying a policy after a storm is named. More tips: Book your insurance early, save all your documentation, know what your policy covers, and don’t wait to file a claim if your plans are impacted.

During summer, Caribbean waters are exciting to explore—both in the daytime and at night.
Photo by Words As Photos/Shutterstock (L); courtesy of Krystal Basas/Pexels (R)
The water is warm and calm
The Caribbean Sea is at its calmest and clearest in summer, making it perfect for water activities. In the Cayman Islands, June is a highlight for divers, with peak fish activity on the reefs and top visibility at spots like Little Cayman’s Bloody Bay Wall, one of the world’s best dive sites.
Summer is also turtle nesting season in places like the British Virgin Islands, where the creatures are protected and monitored through conservation programs such as the Association of Reef Keepers. On Peter Island—a private island resort that recently reopened after a major restoration—you might spot turtles nesting along the beach or swimming in the shallows offshore.
Another bit of seasonal magic: On Vieques, an island off the coast of Puerto Rico, the bioluminescent Mosquito Bay glows brightest from June to August, and the calm waters are ideal for kayaking. The best (and most sustainable) way to see this phenomenon is in a glass-bottom kayak tour with an outfitter like Aqua Sunset Tours.
Travelers can get a better value
Off-season in the Caribbean means hotel rates dip, flight prices decrease, and luxury resorts roll out tempting deals. Case in point: Tamarind Hills Resort and Villas on an oceanfront bluff in Antigua is offering up to 35 percent off its Tamarind Studios from July through October, with perks like breakfast and private Jacuzzis.
On St. Lucia, an annual summer sale—running for more than a decade—has helped transform the island into a year-round destination. This year’s promotion, “Summer Saint Lucia Style,” includes deals on properties around the island, including Ladera Resort, a spot overlooking the iconic Pitons (40 percent off plus up to $200 in credits), and the Fond Dux Eco Resort, set within a UNESCO World Heritage site (35 percent savings).
In St. Bart’s, this season is all about fewer crowds, quieter beaches, and events like Gustavia Day and Bastille Day that celebrate the island’s French Caribbean heritage. There are ample special offers: Stay four nights at Le Barthélemy Hotel & Spa, and you’ll only pay for three. Book a three-night stay at Eden Rock, and you’ll get extras like round-trip transfers, breakfast at Sand Bar, a car rental, and free water sports.
Jamaica’s Rockhouse Hotel has two great ways to save this summer: The “Longer Weekend” deal gives you a free night when you book four, while the “Sky-Rock” promotion offers 30 percent off a six-night stay split between the cliffs of Rockhouse and the beachside vibes of sister hotel Skylark.