This Puerto Rico City Is the Hottest Urban Getaway in the Caribbean This Summer

Americans are getting ready for summer vacation — but it’s not just beaches they’re after.

According to new data from Hilton.com, urban destinations are seeing a surge in travel interest. And leading the way in the Caribbean is San Juan, Puerto Rico, which Hilton has identified as the region’s top urban getaway for the summer.

While beach locales continue to trend overall, Hilton’s data shows that more travelers are also gearing up for “summertime in the city” — looking to combine the buzz of an urban escape with tropical surroundings.

The region’s top city retreat right now

San Juan’s inclusion among Hilton’s top trending destinations underscores the city’s growing appeal: a mix of colonial charm, vibrant culture, and easy access to the coast, all wrapped into one of the Caribbean’s most dynamic cities.

Hilton has a broad, growing portfolio of hotels in San Juan proper, both the signature Caribe Hilton and other hotels with varying service and space options.

Hilton’s San Juan portfolio

At the Caribe Hilton, history and leisure meet just outside the walls of Old San Juan. This is where the piña colada was born, but it’s not just about cocktails — it’s about lounging in a hammock beneath swaying palms, with the ocean close enough to taste the salt in the air. You’ve got your own stretch of beach, a garden filled with parrots and peacocks, and a pool scene that feels straight out of a vintage postcard. And when you’re ready to explore, the city’s history is just a short walk — or a long wander — away.

The Condado Plaza Hilton is a front-row seat to the rhythm of San Juan. Wedged between the ocean and the lagoon, it’s where kayaks glide by in the morning and the nightlife hums after dark. There’s a mid-century glamour to the place, but it doesn’t try too hard. You could sip a coffee on your balcony and watch the day unfold, or you could plunge into the Atlantic before breakfast. Either way, it’s about flow — the kind of vacation where city energy and coastal ease melt together.

At the Embassy Suites by Hilton San Juan – Hotel & Casino, it’s all about the unexpected mix. The location — in Isla Verde — means you’re close to one of the city’s best beaches, but there’s a Vegas-adjacent buzz in the lobby. You walk through the atrium and suddenly you’re not just in a hotel, you’re in a scene: tropical plants, clinking glasses, and the low murmur of a roulette wheel somewhere in the background. It’s playful, it’s colorful, and it’s exactly the kind of place where a city summer comes alive.

If you’re looking for somewhere else to stay, check out our guide to the best hotels in San Juan, which covers everything from luxury resorts to hip boutiques.

Flying to San Juan

The island’s tourism renaissance has been buoyed by cheap, abundant airlift from just about every US mainland city you can think of. That hasn’t changed in recent years. 

You can flights from Miami to San Juan on Spirit right now for $175 roundtrip, and from Newark on Frontier for just $192 roundtrip, according to Google Flights.