Lately we’ve been talking about the state of summer fares. And if you’ve been poking around in Google Flights lately, you know that story is an…interesting one. Domestic flights are up roughly 20%. Europe fares are looking sky high, especially for June and July. Oil prices aren't helping anyone.
But there's a bright spot: The Caribbean is quietly on sale.
Yes, hurricane season runs June through November, and it's usually enough to spook a meaningful chunk of travelers away from the region in summer. Airlines know this, so they price accordingly. The result: While the rest of the world gets more expensive during summer, the Caribbean is releasing dirt-cheap fares that are difficult to ignore.
What most people don't realize, though, is that "hurricane season" is a blanket term that doesn't tell the whole story. Not every destination carries the same risk. Some sit below the hurricane belt and see little more than the occasional afternoon shower. Others have no real off-season to speak of. And a few are showing so much deal availability right now that they’ve got us seriously questioning a European summer altogether (think $200s–$300s roundtrip).
If you've been wanting to get away this summer but balking at what it's going to cost you, this could be your chance. Here's where we'd point you. (And if you’re interested in getting to the Caribbean on points and miles, keep an eye out for tomorrow’s Going with Points newsletter!)
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Want the closest thing to a guaranteed deal? This is it. Puerto Rico has no true off-season, which means availability is wide and consistent across most departure airports throughout the summer. Add in that it's a US territory—no passport required, no currency exchange, no international roaming—and it becomes a shockingly low-friction trip for a shockingly low price.
But don't let the easy logistics fool you into thinking it's a watered-down experience. Puerto Rico is incredibly varied. San Juan’s colorful streets and fortress walls are the obvious starting point, but venture further: the bioluminescent bay at Vieques, the sprawling pink salt flats of Cabo Rojo, the largest cave system in the Western Hemisphere at Cavernas del Río Camuy. On the northern coast, Arecibo has a restaurant row worth building a feast around. And in the south, Ponce has 18 museums and a 19th-century coffee plantation you can tour.
Oh, and the piña colada was invented here.
Sample deal we’ve recently sent: Little Rock and Vail to San Juan for $233–$351 roundtrip (July)
Learn more in Going’s local guide to Puerto Rico.
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Jamaica is popping up in our data in a big way right now, with nearly three times as many deals as we're seeing elsewhere in the Caribbean. Okay, Jamaica. You’ve got our attention.
Yes, it sits within the hurricane belt, so there's some weather risk in summer. But cheaper flights, fewer crowds, and the island at its most lush and green is an easy trade-off for many.
The food alone is worth the trip. Start with ackee and saltfish in the morning, then jerk smoked over pimento wood for lunch, and a pour of rum from Appleton Estate (distilling since 1749) in the evening. Beyond that, there are 200 miles of beaches, waterfalls around every corner, and a cultural richness—from the Maroon mountain communities to the Bob Marley Museum in Kingston—that many visitors only scratch the surface of.
Sample deal we’ve recently sent: Spokane, Champaign-Urbana, and Rochester to Montego Bay for $352–$392 roundtrip (various dates July–August)
Learn more in Going’s local guide to Jamaica.
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The Dutch Caribbean: Aruba, Bonaire, and Curaçao |
Many travelers don't know that the Dutch Caribbean sits south of the hurricane belt entirely. The weather risk that keeps people away from the broader Caribbean in summer doesn't apply here in the same way. Airlines discount them anyway because most travelers lump them in with everywhere else. Hey, we’ll take it!
Each island has its own personality. Aruba is flat, dry, and reliably sunny nearly every day of the year. It’s also purpose-built for beach holidays, with a visitor repeat rate of 65%, the highest in the Caribbean. Bonaire is quieter, a world-class diving destination. Curaçao is full of character, with Dutch colonial architecture, 100-plus nationalities reflected in its food scene, and some of the best snorkeling in the region. Any of them would be a smart summer call.
Sample deal we’ve recently sent: Cleveland to Aruba for $375 roundtrip (June–July)
Learn more in Going’s local guide to Aruba.
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Trinidad tends to escape the average traveler's radar, precisely why it's worth putting on yours. It sits near the southern tip of the Caribbean, well outside the traditional hurricane belt, with the same favorable weather as the Dutch Caribbean. What it trades in famous beach resorts it more than makes up for in culture. Trinidad is the birthplace of calypso and soca music, home to one of the world's great carnivals, and a serious food destination in its own right. Also, a seriously affordable one right now.
Sample deal we’ve recently sent: Miami and Phoenix to Trinidad for $295–$396 roundtrip (various dates July–August)
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Cartagena sits on Colombia's Caribbean coast rather than an island, but it earns its place on this list easily, as it’s below the hurricane belt, offers great value once you’re on the ground, and is visually stunning, full stop.
The walled old city is a UNESCO World Heritage Site with bougainvillea-covered balconies, cobblestone streets, and history in every nook and cranny. Just outside it, Getsemaní has become one of the best neighborhoods in the city for street art, hotels, and nightlife. Your obligatory lunch—whole fried fish, coconut rice, and a coconut limeade—will be as good as the scenery. Nobel Prize winner Gabriel García Márquez launched his writing career here (his home still stands in the city center). The city feels so incredibly rich, you won’t believe you got there for such a steal.
Sample deal we’ve recently sent: Boston and Pittsburgh to Cartagena for $335–$344 roundtrip (June)
Learn more in Going’s local guide to Cartagena.
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