City break to beach bliss: Pairing USA cities with Caribbean shores

When you’re flying westwards for a city break in the USA, make the most of your long-haul flight across The Pond and pair American city life with Caribbean beach bliss.

The USA city and Caribbean island combinations are almost endless, whether you want to double down on an active break, search for a cultural juxtaposition, or crave pure relaxation after your city explorations. Here are some of our favourite pairings, from the full thrill and chill combo, a deep dive into two contrasting culinary scenes and the perfect duo for non-stop family fun.

New York and Grenada

For a holiday of true contrasts, pair New York with Grenada. After a fabulously fast-paced few days pounding NYC's streets and avenues, there’s a peacefulness to the Spice Island of Grenada that you’ll be ready for. It’s lesser developed than other Caribbean isles, and you’ll find heritage chocolate factories and spice plantations when you venture out from the pampering resorts. As you take a rainforest walk past lakes and waterfalls, the city streets you left behind will feel every inch of the 2,000 miles distance. And just like the vast choice of hotels in New York, from the trendy to the traditional, you can choose resorts in Grenada that range from the rustic Mount Edgecombe Boutique Hotel to the modern minimalism of Silversands Grenada.

New York and St Lucia

Swapping New York for the Caribbean doesn’t mean you have to dial down the action when you reach sandy shores. You'll discover a different world of adventure by taking a five-hour flight to St. Lucia from New York. Instead of ascending towering skyscrapers like The Edge or One Vanderbilt, you'll climb the Jacquot Trail for treetop views. Strolls along the High Line will transform into invigorating hikes through the rainforest. Horse-drawn carriage rides in Central Park will give way to exhilarating horseback rides along the beach, and you can compare and contrast a cruise along New York’s East River with a sunset cruise to St Lucia’s Rodney Bay.

Miami and Dominica

Named one of the best places to unwind by Lonely Planet, Dominica is having a moment in the spotlight. It’s a Caribbean island that’s flown under the radar of UK travellers for a while now, partly because you can’t fly directly from London. Connect in Miami but make the most of your layover by staying a few nights in the Magic City first to experience two destinations in one trip. Spend a few days getting swept up in the frivolities of South Beach, or take it easy in a calmer neighbourhood like Sunny Isles Beach or Coconut Grove. 

Then it’s easy to get to Dominica from Miami — it’s just a three-and-a-half-hour flight from Florida, so you can have breakfast in the famous News Café on Ocean Drive and a sunset dinner in the Caribbean, with no time difference to acclimatise to.

New York and Barbados

New York and Barbados make the perfect pairing for food lovers, where you can complement the fine dining of Manhattan with Barbados’ top restaurants. Find yourself dining with a city skyline view one day and across the ocean from one of Barbados’ legendary restaurants the next — longstanding favourites The Lone Star and The Cliff have unwavering reputations as does the Bajan Blue Sunday brunch at exclusive Sandy Lane. But it’s not all fine dining in these locales. Handheld street food in NYC (think pretzels and hot dogs) is part of the fabric of city life, and beachside bolthole Oistins Fish Fry is a Barbadian institution. And after you’ve joined a food tour in New York (a neighbourhood eating tour of Brooklyn comes highly recommended), you can try a Bajan street food tour in Bridgetown.

Las Vegas and Mexico

Fun-filled Las Vegas and Mexico’s Riviera Maya are a match made in heaven. Both locations lay on excitement and excess — as you leave the endless brunch buffets and over-the-top entertainment in the mega-resorts of Vegas behind, you’ll find yourself similarly spoilt by all-inclusive resorts like Secrets Maroma Beach Riviera Cancun or at Hotel Xcaret Mexico, which has more restaurants than you may have time to try. Plus, you have the parks of Xcaret with its ziplining, adventure courses, and water parks at your fingertips. This is an ideal combination for couples, groups of friends, and families alike — just be sure to pick the right resorts to suit your tribe.

Boston and Aruba

Boston might be the gateway to the glorious beaches of Cape Cod, but for year-round warmth, flying to Aruba may be a more tempting option if you’re visiting Boston in the cooler months. 

After walks through Boston following the Freedom Trail that tells the story of the Revolutionary period, a five-hour flight brings you to this delightful Dutch Caribbean island, less than 20 miles from the Venezuelan coast. It’s blessed with palm-lined white sand beaches in the south, but if Boston has whetted your appetite for exploration, there are excellent hiking routes in the east of the island.


If you’d like to pair a big-hitting US city with relaxation by the coral-filled Caribbean Sea, get in touch. We'll talk you through our suggested combos, handpick your hotels and put together a trip that’s perfectly planned for you. 

This feature was updated on 12th February 2024. The information within this feature is correct to the best of our knowledge at the time of print. Feature by Anna Hann.

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