The Most Beautiful Towns In The Caribbean

The Caribbean is known for its white sands, palm fringed beaches and crystal clear waters. It is also home to some of the most beautiful, historic and culturally rich towns in the world. Colonial architecture dominates the urban landscape thanks to the rich history of these often contested islands. Georgian houses, Napoleonic forts, Dutch buildings and old churches sit comfortably in the breathtaking tropical scenery. Take a walk with Culture Trip to discover the most beautiful towns in the Caribbean.

Old San Juan, Puerto Rico

Old cobblestone streets, beautifully vibrant colored buildings and colonial architecture make exploring old San Juan a must for any visitor. The UNESCO site of Castillo San Cristóbal is the largest fortification built by the Spanish in the New World. Castillo San Felipe del Morro, also a UNESCO site, is a splendid 16th century citadel and a popular first stop for many visitors. Restaurants, bars, galleries and shops nestle into the picturesque streets of the old town. Best explored on foot, the streets of old San Juan offer a glimpse into Spanish old world charm with a tropical Caribbean backdrop. Be sure to visit the bar at the Barranchina restaurant, 104 Fortaleza St, the birthplace of the Pina Colada.

Old Havana, Cuba

Willemstad, Curaçao

Willemstad is a tropical Dutch must-see. The little capital of Curaçao is famed for its historic centre and is one of the most picturesque towns in the Caribbean. This is another UNESCO world heritage site, where Dutch, Spanish and Portuguese colonial architecture dominate. Willemstad is one of the most visually pleasing Caribbean towns to visit with floating markets, draw bridges and street cafes. Just for a moment it could all have you believe you’re in Amsterdam.

Oranjestad, Saint Eustatius

The historic town of Oranjestad is the capital of the pretty Dutch island of Sint Eustatius. The lower part of the town, closest to the shore, has many charming old ruins and some dive shops near the harbour. The upper part of the town is the commercial centre; US dollars are the common currency in this Dutch Special Municipality. A 17th century fort keeps watch over the waterfront with historic cannons. Oranjestad also has a Jewish cemetery and one of the oldest Synagogues in the western hemisphere. The old colonial buildings share the space beautifully with traditional Caribbean style buildings, lending a particular charm. This lovely town makes a good base for hiking and snorkeling, too.

St George’s, Grenada

The sweet smell of spices perfume the Grenadian air, so it’s no surprise that it’s known as ‘the Spice Isle’. Cinnamon, nutmeg, lemon grass, turmeric and cloves grow in abundance in Grenada’s rich, fertile hills. Originally French, Grenada was ceded to Great Britain in the 18th century and the town renamed St George’s. To one side is the sea and inland a horseshoe of hills including an old volcano crater. Georgian buildings overlook the most beautiful inner harbour known as the Carenage. Deservedly known as one of the most beautiful Caribbean towns, St George’s contains many buildings of historic interest and is best explored on foot.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.