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I spend much of my year flying in the Caribbean, and I’ve noticed a huge change in what travelers are actually looking for. For decades, the standard fare for a tropical vacation was to book a flight and shuttle to a giant, walled all-inclusive mega-resort and never leave the property. And believe me, I get it. One of my favorite trips last year was going to Cabo and rotting by the pool at Garza Blanca.
But sometimes I get tired of the convenience of that cookie cutter. I do raw, authentic magic.
If you want to experience what the Caribbean should actually feel like – living cultures, incredible historic architecture, and local economies that aren’t just manufactured tourist traps – you should leave the mega resort strip.
Here are 7 charming, under-the-radar Caribbean cities and towns that I’m putting on everyone’s radar for 2026. (PLUS an interactive quiz at the end of this article to find out which one is perfect for you!)
1. Santo Domingo, Dominican Republic
America’s first city
When I want deep, immersive history, I skip the walled mega-resorts entirely Punta Cana and head straight to the Zona Colonial in Santo Domingo. It is the oldest continuously inhabited European settlement in the Americas, and it is not without reason that it is on the UNESCO World Heritage List.
Why I love it: Walking around here I feel like I’ve stepped onto a 16th century Spanish film set. The cobblestone streets are lined with breathtaking colonial architecture, shady squares and ancient ruins that are organically integrated into a thriving modern city.
My strategy: I always skip the huge hotels here and book a boutique place. I like to spend my evenings eating at intimate courtyard restaurants and listening to live bachata near the Ruinas de San Francisco.
2. Christiansted, St. Croix (US Virgin Islands)
The historic promenade harbour
Instead of the heavily commercialized cruise ship ports of St. Thomas, I always point people south to Christiansted on St. Croix. It has a Danish colonial history all its own and an incredible, raw authenticity that can’t be found anywhere else in the region.
Why I love it: This is the ultimate unpretentious, historic waterfront city. The streets are lined with shaded, covered walkways and striking yellow 18th-century Danish buildings. Seeing the perfectly preserved Fort Christiansvaern, right on the harbor, never gets boring.
My strategy: Since it is a US territory, I I don’t even have to take my passport out of my bag to visit. My perfect day here involves walking the Christiansted Boardwalk for a fantastic waterfront dinner, grabbing a cocktail made with local Cruzan Rum, and booking a catamaran day trip to the pristine Buck Island Reef National Monument for world-class snorkeling.
3. Port Elizabeth, Bequia
The retro-nautical harbour
Bequia (pronounced beck way) is the second largest island in St. Vincent and the Grenadines. I always describe it to my friends as a snapshot of what the Caribbean was like thirty years ago.
Why I love it: There are absolutely no chain hotels, no mega-resorts, and no huge corporate coffee shops here. Instead, Port Elizabeth is a hub for international yachts and sailboats, giving it a surprisingly cosmopolitan yet completely relaxed atmosphere.
My strategy: I spend most of my time walking the Belmont Walkway. It’s a stone coastal path that allows you to walk seamlessly from the bustling city center to the pristine white sands of Princess Margaret Beach. I highly recommend grabbing your own rum punch Cocos and watch the sunset Jack’s Bar.
4. Deshaies, Guadeloupe
The volcanic fishing village
Located on the wild, mountainous Basse-Terre wing of the French Caribbean, Deshaies is an unassuming fishing village that has managed to balance international television fame (it’s the filming location for the BBC show Death in paradise) with robust ecological conservation.
Why I love it: This is my go-to spot when I’m longing for deep green tropical rainforests, volcanic landscapes and authentic Euro-Caribbean culture over flat, manicured beaches. The coastlines here, like Grande-Anse, are spectacular and completely devoid of intrusive high-rise hotels.
My strategy: English isn’t spoken much here, which I actually love because it acts as a great natural filter against mass tourism. I usually brush up on a few basic French phrases before I go so I can confidently order local specialties such as acras (fried seafood fritters) and a powerful one Ti’ Punch in a bistro on the beach.
5. Portsmouth, Dominica
The Eco-Luxe Vanguard
Dominica is known as the ‘Nature Island’, meaning it trades traditional lounging on white sand for dramatic black sand, boiling lakes and deep jungle rivers. The secondary city, Portsmouth, is currently pioneering a new wave of high-end, sustainable eco-luxury that I’m mildly obsessed with.
Why I love it: Located on the edge of Cabrits National Park, Portsmouth combines historic British garrison ruins with ultra-luxury, low-density resorts such as Secret covewhere your villa is built from sustainably sourced hardwood, directly into the jungle cliff face.
My strategy: 2026 is the year I tell everyone to go. Dominica’s long-awaited new international airport will finally open in 2027, and I expect the island to explode in popularity as it gains more air transportation. I like to use Portsmouth as my base camp for a guided canoe trip down the hauntingly beautiful, mangrove-lined Indian River.
6. St. George’s, Grenada
The culinary and carnival epicenter
The capital of ‘Spice Island’ is built around a beautiful horseshoe-shaped harbor known as the Carenage. It’s a total sensory overload of colonial architecture, spice markets and incredible waterfront dining.
Why I love it: St. George’s takes advantage of its volcanic soil and herb growing heritage to foster an elite, highly localized culinary scene that I can’t get enough of. You can eat world-class fusion, or grab an authentic bowl of ‘Oil Down’ (the national dish) at a regular place like Patrick’s Local Homestyle restaurant.
My strategy: If you want my top recommendation for cultural immersion, book your trip for August 1-11, 2026, for Spicemas. Be prepared to wake up before dawn on Carnival Monday for J’ouvert, where we immerse ourselves in oil and paint and dance through the streets to primal Jab Jab music.
7. Willemstad, Curacao
The Bohemian Dutch Caribbean area
You’ve probably seen photos of Willemstad’s Handelskade: the iconic row of vibrant, candy-colored Dutch colonial buildings along the harbor.
Why I love it: Although the main harbor is beautiful, for me the real magic happens just outside the old city gates in the Pietermaai district. It’s a highly walkable, bohemian enclave packed with jazz bars, boutique hotels and cutting-edge restaurants, housed in restored 18th-century mansions.
My strategy: Because Curacao is outside the traditional Caribbean hurricane belt, the weather is extremely predictable year-round, so I never worry about booking a trip here. For nightlife, I like to base myself in Pietermaai and rent a car to explore the cliff jumping on Grote Knip beach during the day.
Take this quiz now to find out which one is perfect for you!
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