Journey to the Islands of the Caribbean

Funchal, the capital of Portugal's Madeiran archipelago, has a timeless old-world charm. Enhanced by a subtropical climate that fills this 'floating garden' with the year-round colours and perfumes of flowers and fruit, Funchal was a favourite of Sir Winston Churchill. His praise of the city has ensured British visitors always receive a warm welcome from locals.

Backed by rolling hills, the town is famous for its harbour, the 17th century São Tiago Fortress (now the Contemporary Art Museum) and world renowned Madeiran wine cellars. Funchal’s parks and gardens are a delight, and a hike through the Laurel Forest nearby is highly recommended. The ancient Funchal Cathedral mixes Gothic and Romanesque architecture, and is noted for its impressive carved wooden ceiling.

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.

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.

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 its balmy climate, buzzing atmosphere, glorious azure waters and incredible beaches, Bridgetown is a tropical city that epitomises paradise. There is rarely a dull day in the capital and largest city of Barbados. 

This very British Caribbean island is a favourite with tourists; the city’s streets are lined with shops, boutiques, street vendors, bars and places to eat – there is always something to do. Broad Street, the main street of Bridgetown is often packed with welcoming locals. It's easy to see why Barbados is known as Little England given Bridgetown’s Georgian houses, the horse-racing track, Parliament Square, and a statue of Nelson.

The entire downtown area of Bridgetown and the 17th century Garrison were named a UNESCO World Heritage site in 2012 in recognition of their historical significance. Near the central National Heroes Square, which fringes Constitution River, the Nidhe Israel Synagogue and museum explore Barbados' Jewish history. [ReadMoreDesk]

For a change of pace, the shore and the glorious sands offer a haven from the bustling centre. Carlisle Bay is home to six shipwreck dive sites, while a catamaran ride on the Caribbean Sea may offer the chance to swim with the once endangered Hawksbill and Green Turtles. The wonder of the impressive stalactites and stalagmites in Harrison’s Cave is another experience that will linger in the memory.