Is the Summer Offseason the Best Time to Visit the Caribbean?

The Caribbean’s classic proposition has always been the offer of a warm-weather escape when winter grips North America. That being said, real Caribbean aficionados know that summer in the islands is tough to beat. The intermittent rains can actually be quite refreshing, the crowds thin out, and there’s more ability than any time of year to book your favorite hotel and plant your lounge chair in the sand.

An influx of new commercial flights is making the journey quicker and more direct than ever. For 2024, Delta has added more than 1,000 new flights to the region direct from Atlanta, New York, Detroit, Minneapolis and Boston. If you’re coming from the West Coast, you can now fly direct to Nassau from Los Angeles on JetBlue, or from Seattle on Alaska Airlines. American Airlines just added a new route twice weekly from Miami to Ocho Rios on Jamaica’s north coast. And most interestingly of all, Caribbean Airlines is adding a route next month between San Juan, Puerto Rico, and Trinidad, with a connection in Barbados. In a region where interisland service has lagged behind international connectivity, this is a major step forward.

Signature Villa at the Cayo Levantado resort, Samaná, Dominican Republic / Photo: Courtesy of Cayo Levantado Resort

Smaller destinations are benefitting from major new flights. Antigua will add service to Miami on American, and JetBlue will increase its flight frequency from three times per week to daily. Turks and Caicos got a direct flight on Virgin Atlantic to London. Summer is also an ideal time to experience the Caribbean’s newest hotels, many of which feel like milestones.

First and foremost: Is Cancún becoming a well-being destination? The opening of renowned Spanish clinic Sha brings a dose of wellness to a region known for its all-inclusive.

Even those who are unsure about all-inclusive should check out the new Sandals Saint Vincent and the Grenadines. Nestled in its own private cove, this resort features several truly luxe two-story overwater villas. And over in the Dominican Republic, the new Cayo Levantado private island resort offers an all-inclusive experience that’s less about buffets and boozy pool bars and more about wellness programming such as aerial yoga and one-on-ones with personal trainers.

Sandals Saint Vincent and the Grenadines / Photo: Courtesy of Sandals Saint Vincent and the Grenadines

But don’t focus only on what’s new—summer could be the ideal time to visit the Caribbean’s grandes dames. This summer marks the 70th anniversary of Half Moon in Jamaica, which is in the midst of a multiyear renewal. A little over half of its villas will complete renovations this year, and the remaining will be finished next year. Nassau’s British Colonial, with more than 100 years of history, recently unveiled a massive restoration. And Rosewood Little Dix Bay added the stunning Villa Katsura into its mix—an exquisite four-bedroom, 23,500-square-foot oceanside estate on 2.74 private acres. Both new hotels and long-standing favorites alike tend to book up completely during the peak winter holiday season and school vacation weeks, so finding some rainy-season solace during the summer months might, in fact, be the best way to experience them. Just don’t forget your SPF—or your umbrella.