7 Overlooked Cities in the Caribbean Worth Visiting

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We all know the heavy hitters. You’ve probably looked at flight deals Punta Canachecked the resort prices Montego Bayor maybe you even braved the cruise ship crowds Nassau.

And hey, I get it: I love a classic “sun, sand, and drink in hand” vacation as much as anyone (looking at you Cabo!)

But sometimes the resort strip just doesn’t cut it. Sometimes you want to go where the locals actually live and walk through streets that feel like real places instead of movie sets built for tourists.

There is a huge shift happening in travel right now. We see more and more travelers trading in the mega-resorts “travel slowly”experiences that are authentic, a little rougher and a lot more memorable.

If you want to escape the crowds this winter, these 7 Caribbean cities are the hidden frontiers you need to know about, curated by our Travel Off Path team.

1. Caye Caulker Village, Belize

If your blood pressure is running high, this is the cure. Caye Caulkers motto is literal “Go slow,” and it is not just a suggestion; it’s a way of life. There are no cars here, just sandy streets filled with bicycles and golf carts.

Located just one mile within the Belize Barrier Reefthis city has resisted the high apartment buildings you see elsewhere. Instead, it’s all pastel-colored wooden houses and a “barefoot everywhere” vibe. The center of the action is “The Split”—a channel created by a hurricane where you see the Lazy lizard bar. It’s the perfect place to enjoy a Belikin beer and swim in the clear water.

While Belize is becoming a hotspot digital nomadsCaye Caulker retains a bohemian soul. It is too unbelievable affordable– you can feast on fresh grilled lobster at a street stall for a fraction of what you would pay in Tulum.

2. Grand Case, Sint Maarten

While the Dutch side of the island is famous for its casinos and nightlife, the French side hides the truth “Culinary capital of the Caribbean.” Big deal is a city of beautiful dualities. During the day it is a sleepy fishing village with a quiet, turquoise bay that is much more relaxing than the busy Orient Bay.

But at night? The city is transforming. You have an incredible mix of high end French bistros sit right next to it “Lolos”—local open-air barbecue areas.

You can enjoy a world-class wine dinner and a huge plate of ribs and johnnycakes in one evening Sky is the limit the next. If you are a foodie, this is your pilgrimage.

3. Charlestown, Nevis

If you’re tired of port towns that are all duty-free jewelry stores and T-shirt shops, Charlestown feels like a relief. It is widely regarded as one of the best preserved colonial cities in the Caribbean.

We’re not talking about fake facades; this is the real deal, with Georgian stone buildings that have withstood centuries of hurricanes.

There are no traffic lights here and the atmosphere is dignified and peaceful. It is also the birthplace of Alexander Hamilton (yes, that Hamilton), and you can visit his childhood home.

4. Portobelo, Panama

This one is for the history buffs who want something raw. Located on the Caribbean coast of Panama, Portobelo was once the ‘Treasure House of the World’, where silver from Peru was loaded into Spanish galleons.

Today it is one UNESCO World Heritage Sitebut don’t expect manicured lawns and counters. The black coral stone ruins of the forts are atmospheric and moody and still line the bay Sir Francis Drake was buried at sea.

But the real heartbeat here is the Congo culturea vibrant Afro-colonial tradition that is alive and well on the streets. It’s less about lying on the beach and more about feeling the pulse of history.

5. Windward, Saba

Saba is often called ‘The Unspoiled Queen’, and for good reason:it has no beaches. I know, that sounds like a dealbreaker for the Caribbean, but hear me out. Because there are no beaches, there is zero mass tourism. And if you still want to get in the water, this is one of the BEST places in the Caribbean to go diving.

Windward looks like a European mountain village that has fallen into a tropical rainforest. It’s clean, tidy and located 400 meters above sea level, which means it’s cool and misty.

This is the walking capital of the region, home to the Mt. Landscape path. Getting here is half the fun (or fear, depending on how you look at it), since you’re on the the world’s shortest commercial runway. It keeps the crowds at bay and the atmosphere pristine. Moreover, the Staying here is cute and dreamy.

Our very own Upgrade Editor, Liz Fox, spent some time on Saba last year and had the time of her life. Read all about it here.

6. Port Elizabeth, Bequia

Part of St. Vincent and the Grenadines, Bequia is the darling of the hunting world.

Port Elizabeth is one of those rare towns that faces the sea instead of turning its back on it. The harbor is always full of sailboats, which gives the city a cosmopolitan, nautical energy.

The best way to see it is the Belmont Walkwaya stone path that runs along the coast. You can walk straight to the white sand from the city center Princess Margaret Beachstopping at bars along the way. Make sure you check out Bar onea floating bar in the bay.

Since there’s no major jet airport here, you won’t find the three-day weekend crowd; everyone here has made a journey to arrive, which creates a great sense of community.

7. Deshaies, Guadeloupe

If you’ve ever seen the BBC show Death in paradiseyou already know Deshaies—it is the filming location for the fictional town of Honoré. But despite its TV fame, it remains a modest fishing village at heart.

Located in the wild, volcanic Basse-Terre regionit’s a world away from the flat resort strips. The Grande Anse Beach nearby is perhaps one of the best in the Caribbean: golden sand, deep green palms and no hotels cloud the view. Moreover, the botanical gardens here are world-class.

Be aware that not much English is spoken, so brush up on a few French sentences before ordering your acras and Ti’ Punch.

Tyler Fox

Tyler is our editor-in-chief and writer. After years of reading, writing, and obsessing about travel (while traveling as often as possible, of course!), he wants to give readers the best and most balanced experience possible when exploring the site.