The 20 Most Charming Beach Towns in the Caribbean

by Holly Riddle  |  Published February 11, 2019

TravelMag surveyed more than 300 travel writers, social media influencers and travel professionals, asking them to pick the most charming beach towns and villages in the Caribbean. While there are plenty of dreamy destinations to choose from, here are the 20 destinations that received the most votes.

Previously known as a surfer’s haven, Rincón, Puerto Rico, is gaining traction as a relaxing seaside retreat (Photo in collaboration with Discover Puerto Rico)

The Caribbean is a hot travel destination for globetrotters and once-a-year vacationers alike. The warm, sandy beaches and all-inclusive resorts beckon, tempting beach bums from around the world, especially those who live in colder climates. However, if one never ventures beyond the resort-filled, tourist-driven side of the Caribbean, they may never discover all the charm and character the islands offer.

Heading to the more remote towns and villages in the Caribbean, though, can be a daunting task: there are so many islands to choose from, so many exotic locales. TravelMag has made your search a little bit easier by surveying people in the know about the most charming destinations in the Caribbean islands. The catch? The area’s population had to be under 100,000. Locales on the Caribbean coasts of Mexico, Central America and South America were not considered.

So, where do the travel writers, the Instagram famous and the travel professionals go to get away from it all? In alphabetical order, here are the 20 Caribbean beach towns and villages that received the most votes for being the most charming.

Anguilla: West End Village

Luxury and local fun converge in Anguilla’s West End Village (Photo: Anguilla Tourist Board)

With a population of under a thousand people, Anguilla’s West End Village is certainly suitable if you want a bit of privacy and quiet time. The small village sits right where you’d expect: on the island’s west end. In addition to being home to the world-renowned Belmond Cap Juluca luxury hotel, it’s also home to more local-friendly spots, with seaside shacks serving freshly grilled seafood and drinks heavy on the rum and tequila. Enjoy it all alongside spectacular views of pristine white sands and crystalline waters.

Aruba: Savaneta

From a navy base to an Olympic training center, Savaneta can be both serious and seriously fun (Photo: Aruba Tourism Authority)

As the former capital city (until 1797), Savaneta claims a long history, evident in the island’s oldest surviving home, a 150-year-old mud hut. Now, the town is a base for the Royal Netherlands Navy and the Aruban Military, as well as an Olympic pool complex, where elite local and international swimmers train. Even so, you’ll find plenty of charm and a local, laid-back vibe with little pretension. A favorite hidden gem is Mangel Halto beach, flanked by mangrove trees and boasting shallow, calm waters protected by a barrier reef.

Barbados: Oistins

Oistins, Barbados, offers much to explore (Photo: mescal83 via Flickr CC BY-NC 2.0)

Oistins likewise has an extensive past. Here the Treaty of Oistins was signed in 1652, formally ending the skirmish between colonial settlers and the English Commonwealth over trade with the Netherlands. It’s not uncommon for travelers to be invited to join the locals for a weekend fish fry, which includes loads of fried seafood, music, dancing and even some shopping from the local craftsmen hawking their wares. The beaches of Oistins are also a good spot for plane spotting, as they sit right under the flight path of aircraft landing in Barbados.

Barbados: Speighstown

What can be better than a villa on the beach? (Photo: Pixabay)

Founded in 1653, Speighstown was once a hectic and busy port city. While the small town remains the second largest on the island, its importance in trade and political affairs has waned.   Now the quaint and somewhat forgotten feel lends a sense of having the entire place to yourself. Beyond the quiet beaches, travelers enjoy the historic architecture, eateries and shopping opportunities for local produce and handcrafts. Recently, a luxury marina development was added to the Speighstown landscape. Take advantage of this hidden gem before it begins to draw a larger tourist crowd.

Cuba: Trinidad 

Cuban color, right off the ocean (Photo: serena_tang via Flickr CC BY-NC-ND 2.0)

Known for its historical preservation, Trinidad is a must-see for Caribbean travelers seeking a destination with a truly remarkable historical facet. The oldest part of Trinidad, with its beautiful churches and colorful plazas, has been designated a UNESCO Heritage site. Beyond the vibrantly painted buildings, cobblestone streets and classic cars, travelers love the Cuban restaurants and museums. Plus, just a short drive from the center city, you can enjoy picturesque beaches and lush national parks. Whether you want to lie on the beach, explore Cuban culture, hike to the best views of the island or swim under waterfalls, you can do it all with Trinidad as your base.

Bahamas: Governor’s Harbour

Peaceful, luxurious and high-class Governor’s Harbour (Photo: The Bahamas Ministry of Tourism and Aviation)

Situated on Eleuthera, Governor’s Harbour is a quiet and peaceful town that harkens back to its 19th-century cultural roots. Lovely Victorian homes overlook the water, many of which now fulfill purposes other than that of private residence, from a library to a cafe. The town is best seen on foot, at a leisurely pace. Stop in some shops, sip a cup of coffee and rub elbows with the wealthy residents that have migrated to this peaceful and elevated spot in the Bahamas, a world away from locales that cater to party-driven tourists.

Grenada: St George’s

The Carenage in St. George’s (Photo: Heather Cowper via Flickr CC BY-NC 2.0)

 The small town of St. George’s acts as the capital city of Grenada. Recently becoming popular in the travel industry, it still manages to hold onto many older means of revenue, including its extensive spice production. While the presence of a university, sports stadium and international airport prove St. George’s is far from stuck in the past, the city still has many historic sites that are worth a visit, such as cathedrals from the early 1800s and Fort George. The Grenada National Museum lives within 18th-century French barracks and includes interesting historic items that range from whaling tools to Josephine Bonaparte’s marble bathtub.

Guadeloupe: Deshaies

Deshaies sits amongst lush rainforest (Photo: Pascal via Flickr CC BY-NC-ND 2.0)

While other island destinations still have remnants of colonialism and past religious influences, Deshaies gives travelers a different side of Caribbean history. Traces of its landscape look similar to what Christopher Columbus might have seen when arriving here in 1493. What’s more, the island was a popular spot for pirates. There’s even rumored to be buried treasure! The beautiful beaches are surrounded by lush, rainforest-draped hills. Further into town, alluring dining and drinking options await.

Guadeloupe: Saint Anne

It’s easy to see why travelers love Saint Anne (Photo: Wikimedia Commons CC BY-SA 3.0)

Saint Anne is likely the most tourist-driven town on Guadeloupe. Amidst the mostly agricultural region of the island, this lively spot stands out as an oasis of fun. Travelers love the spacious beaches, energetic night markets, exotic dining and array of water sports providers. At any time, you are just a few steps away from the calm waters, as well as the vendors serving up their local fruits and spices, as well as a variety of rum-based cocktails.

Jamaica: Negril

Whatever you desire from your Caribbean vacation, Negril delivers (Photo: Karen Maraj via Flickr CC BY-NC-ND 2.0)

A small and increasingly popular beach resort town, Negril caters to both travelers looking for a unique, budget-friendly Caribbean option and those seeking luxury. Resorts along the seven-mile beach offer varying degrees of privacy. Further away from the shore, you can find charming vendors and shops, dining options and fun nightlife. From white sand beaches to water sports, glass-bottom boat tours to bar crawls, Reggae music to jerk chicken, whatever you dream of for your Caribbean vacation, Negril delivers.

Martinique: Le Carbet

These same turquoise waters inspired the likes of famous painter Paul Gauguin (Photo: Antoine Hubert via Flickr CC BY-ND 2.0)

The village of Le Carbet was the first stop on Columbus’ last Caribbean cruise in 1502. Now, you can see much of Le Carbet’s history throughout the village, ranging from historic churches to a Paul Gauguin museum (dedicated to the painter’s time on the island) to a former sugar plantation. Other popular spots include Le Carbet’s zoological park and botanical garden. Of course, there are several beautiful beaches to choose from, like Big Cove Beach, known for its grayish sands and coconut trees.

Puerto Rico: Rincón

Rincón is a surfer’s paradise (Photo in collaboration with Discover Puerto Rico)

Rincón, situated in the northwest corner of Puerto Rico, is renowned for its surfing beaches, but there is no need to love surfing to enjoy a visit to this charming Caribbean town. The lodging options include beachfront resorts, boutique hotels, and bed and breakfasts. Local restaurants serve a mix of local and international cuisine. Beyond surfing, you can get moving through a range of activities, from peaceful yoga to adrenaline-pumping paragliding. If you plan your visit right, you might even get to catch one of the many local festivals, like the Whale Festival in March, the Coconut Festival in May or the Rincón International Film Festival.

Saint Barthélemy: Gustavia

Though its shipping and trade days are long gone, Gustavia’s waters are still filled with cute and characteristic boats (Photo: Luigi Rosa via Flickr CC BY-SA 2.0)

One of the primary towns on Saint Barts, Gustavia has a history of trade and shipping. The area’s eclectic architecture echoes of the international sailors it drew during its most formidable years. Among others, you can spot Swedish-built wooden and stone buildings, English churches and more Caribbean-style structures that mirror the architecture found elsewhere in the region. With its shipping and trade days long gone, Gustavia now aims to please visitors with a growing mix of boutique shopping and dining. The former tends to fall more in the luxury category, and you’ll spot many major European labels. As for the latter, expect high-quality dining with European influence.

Saint Kitts and Nevis: Basseterre

Despite a rough history, Basseterre still looks beautiful (Photo: Nevis Tourism Authority)

Even though it’s the capital of Saint Kitts and Nevis, Basseterre has a population under 20,000. One of the oldest towns in the Eastern Caribbean, Basseterre was founded in 1627, but then went on to face a tragic line of events, including colonial wars, citywide fires and earthquakes. Fortunately, remnants of the area’s history have been preserved. You can still find many of the older buildings in Independence Square, but head to The Circus for shops and dining.

Saint Kitts and Nevis: Charlestown

Find your slice of paradise in Charlestown (Photo: Nevis Tourism Authority)

Being the birthplace and childhood home of Alexander Hamilton is Charlestown’s claim to fame. This tiny village of just under 2,000 wears its history proudly, celebrating not only Hamilton, with the Museum of Nevis History in his birth house, but also nearly every aspect of Nevis culture and history, with many preserved structures and memorials. Mingle with the tight-knit community at the weekend roadside socials, where you are sure to find barbecue and live music. Whatever you do, get your dinner in before dark. This laid-back village shutters for the evening once the sun sets.

Saint Vincent & the Grenadines: Port Elizabeth

Port Elizabeth leaves little to be desired (Photo: St Vincent & the Grenadines Tourism Authority)

With its lush forests and calm beaches, Port Elizabeth sits on the island of Bequia. The blue-green water leading up to the small port is dotted with white yachts. In town, you’ll find that the boating tradition continues, as the area is still filled with expert boatbuilders. They are not the only craftsmen you will find, though; the artistic community in Port Elizabeth is strong and vibrant, making it easy to find unique, high-end souvenirs and gifts to take home. The culinary scene is likewise impressive, ranging from delicious local cuisine to French fine-dining, with seafood playing a primary role.

Trinidad & Tobago: Castara

Castara is known for its magical sunsets (Photo: Steve Bennett via Flickr CC BY-NC 2.0)

Castara sits on the northern coast of Tobago, with an easy-going, relaxed vibe. The beaches to the west boast beautiful sunsets, while the mountains to the east provide the perfect getaway for the outdoor adventurer. Tourism to Castara has increasingly grown over the last few decades, but the economy is still primarily dependent on fishing and agriculture. Because of this, travelers can expect a rich fishing culture, which means plenty of fresh seafood to adorn your plate at dinner.

Trinidad & Tobago: Maracas

Don’t miss a shark sandwich on the beaches of Maracas (Photo: neiljs via Flickr CC BY 2.0)

Maracas attracts true beach bums with its aquamarine waters, palm trees and white sands. The low waves make it a great place for board surfing, but the spacious beaches provide a quiet respite for those who want to relax rather than play. The beach is known for its many stands selling “bake and shark,” a Trinidadian street food made from fried flatbread filled with fried shark meat (with the shark caught right in the surf) and a mixture of sauces.

Turks & Caicos: Cockburn Town

Cockburn Town has certainly come a long way since its days in sea salt production (Photo: James Willamor via Flickr CC BY-SA 2.0)

Cockburn Town, the capital city of Turks and Caicos, is a small beach town that’s also the oldest permanent settlement in the country, originally founded by Bermudan sea salt producers. Beyond the pristine beaches, Cockburn Town is known for its colonial British architecture, scenic views and long history. Many of its cute vacation villas and small inns are historic buildings that have recently been restored and converted. Besides charm, these accommodations offer close proximity to local dining and shopping.

U.S. Virgin Islands: Cruz Bay

Kick back and relax in the U.S. Virgin Islands (Photo: U.S. Virgin Islands Department of Tourism)

On the West Coast of Saint John, Cruz Bay’s population is only a few thousand people, but it is the island’s largest commercial center. The people are hospitable and friendly, and there are many places to shop and dine. If you’re looking for entertainment, there is also a casino, but if you’re more in the mood to lay low, you’re in luck. The entire town seems geared toward relaxation. Life moves at a slow pace, but no one really seems to mind. Do as locals do and take your time, whether you are trying local cuisine, ambling along the many hiking trails or simply enjoying a drink on the beach.