Uncrowded Caribbean Islands with Havana

Once the largest city in the Caribbean, until an earthquake struck in 1692 and submerged more than half the city, Port Royal today is a historically important settlement in Jamaica, which opened in early 2020 to cruise ships for the first time. Located at the end of an 18-mile long sand spit close to Kingston, Port Royal has a colourful history and was known for being a pirate hub in the Caribbean during the 17th century, earning it the nickname of ‘the wickedest city in the west’.

Today, the small town has some interesting historical sites, including Fort Charles, which was built in the 1600s and houses a small museum. In addition, the portion of the city that sank has been recognised as an important archaeological site. Jamaica’s capital, Kingston, was founded after the 1692 earthquake, and is around 16 miles from Port Royal. The vibrant city is known for being the birthplace of Bob Marley, who grew up in Trench Town, as well as the beautiful Devon House, a landmark of the city which serves some truly delicious ice cream.

UNESCO-protected Willemstad on Curaçao has narrow-gabled, 18th century houses in cool pastel shades, juxtaposed with intense yellows and royal blues. It’s akin to a carbon copy of Amsterdam, but with the gorgeous Caribbean climate thrown in.

The town has a number of intriguing museums worth visiting: the Curaçao Museum, the Maritime Museum and Kura Hulanda, which tells the history of the local slave trade. At Scharlooweg 77 is the house known as the 'Wedding Cake', a near perfect example of Dutch colonial architecture.

Willemstad is actually divided into two sections, Otrobanda and Punda, and both boast a rich, cultural heritage. They are connected by the Queen Emma Bridge, also known as the Swinging Old Lady, a floating, pontoon bridge powered by diesel, which swings open daily to allow ships in and out of the harbour.

Situated not far from the waterfront, the crowded streets of Punda are packed with smart galleries and shops, while nearby Pietermaai is alive with cool restaurants, bars and clubs. The island’s fantastic beaches are a true delight, with Santa Barbara Beach probably the pick of them all.

Basse-Terre, the main city on the island of the same name, is the administrative capital of French overseas region Guadeloupe, and the ideal place from which to explore all of the natural beauty that the island has to offer. Separated from Grand-Terre by a narrow river, the island of Basse-Terre is an ecological paradise, with the sprawling Parc National de la Guadeloupe in the centre of the island and one of the country’s most glorious beaches in the north.

The city of Basse-Terre sits in the shadow of La Soufrière, an active volcano reaching almost 1,500 metres high. Located within Parc National de la Guadeloupe, La Soufrière is the highest point in the Lesser Antilles. Another highlight within the national park is Les Chutes du Carbet, a series of waterfalls that cascade down through La Soufrière’s forested slopes. In the northwest of the island, Grand Anse beach in Deshaies is picture perfect. A kilometre stretch of glorious sandy beach that sits between the vibrant ocean and lush rolling hills.

With some of the oldest colonial buildings in the Caribbean, the elegant St. Kitts & Nevis capital of Basseterre is a beautiful town bursting with history. 

Established by the French in the 17th century, and claimed by the British following the Napoleonic War, much of Basseterre’s original Georgian architecture still stands and begs to be explored. The domed Old Treasury Building on the waterfront – now the National Museum – is worth a visit, as is the Victorian Berkeley Memorial Clock, a four-face, cast-iron tower that sits on the Circus, an original 19th century traffic roundabout. St George’s, an Anglican church originally built by the French, has been destroyed by fire several times, and was rebuilt to its present form in 1869.

Away from the town, visitors can take a tour to Brimstone Hill Fortress to admire magnificent views across the island, travel on the St. Kitts Scenic Railway – said to be one of the most attractive train journeys in the world.

Philipsburg is the capital of the Dutch half of St. Maarten, a Caribbean island amicably shared between Holland and France for centuries. The town is known as a shopper’s paradise, while its charming sandy beach, studded with colourful clapboard restaurants and outdoor cafés, is accessible via water taxi.

Front Street, Philipsburg’s long main street, is festooned with shops, but the alleys and courtyards down to Back Street are also worth exploring. There are some stylish restaurants, but the Lo-Lo huts, which sell grilled chicken, fish and cakes from home-made barbecues, are great for a cheap snack of authentic Caribbean food.

This tiny island was divided between the Dutch and French in the 1600s, as a bastion against the Spanish. This melting pot of rich cultures and old-world charm was supposedly divided up by someone from each country walking round the coastline in opposite directions until they met up again.

Two historic forts reflect the island’s colonial past: Fort Amsterdam, built in 1631 and soon after captured by the Spanish, offers fine views over Philipsburg from the original walls, and Fort Willem, built by the British during the Napoleonic War.

Havana, the capital city, major port, and leading commercial centre of Cuba, is famed for its colonial history and vibrant culture.The city is home to exquisite Spanish colonial architecture, classic American cars, irresistible rhythms of mambo and a confusing jigsaw of grand avenues and cobbled streets.

 A stroll around Habana Vieja, Old Havana, quickly reveals the audacious Latin atmosphere within the imposing coastal fortifications and intimate, traffic-free squares. At its centre, the buildings reflect the city’s vivacious architectural mix: the Castillo de la Real Fuerza, the iconic National Capitol Building, the Baroque Catedral de San Cristóbal, and the Plaza Vieja are all worth the effort to uncover.

The art culture is one of the city's biggest revelations, and Cuban creativity is accessible through the Museo Nacional de Bellas Artes, the Fusterlandia public art project and the Fábrica de Arte Cubano, which champions the movement of Havana's more contemporary art scene. The city is awash with experimentation, exemplified by the explosion of uber cool cafes and Bohemian bars.

Columbus believed this was the most beautiful land he'd ever seen, and it’s hard not to agree given Cuba's 2,000 miles of tropical coastline, lush mountains and some 300 beaches that melt into azure seas.