Great Escape: a guide to the Caribbean's Leeward Islands

Known for their pristine beaches and volcanic landscapes, the Leeward Islands are nestled among the Lesser Antilles in the northeastern part of the Caribbean Sea. 

Stretching south of Puerto Rico, the Leeward Islands were named by sailors due to their sheltered position relative to the trade winds that blow across the Caribbean. Their sun-drenched climate leaves approximately 85 per cent of their mountainous land covered in rainforest: the perfect habitat for biodiversity. 

Thanks to the islands’ rich cultural heritage, deep-rooted traditions and slow pace of life, a typical day here will see you kicking back in a beach bar, listening to stories and folklore over potent rum cocktails and local cuisine. 

Each season brings a new celebration. In spring, you can join one of the Caribbean’s biggest seafood festivals on Anguilla, or celebrate Antigua’s emancipation from its colonial past at its annual carnival in summer. 

Every island offers its own unique blend of indigenous culture and colonial history – but while these have left their mark in the form of different languages, architectural styles and currencies, the islands’ shared African heritage is the thread that binds them together.

The Virgin Islands

Divided between the United States Virgin Islands (USVI) and British Virgin Islands (BVI), the Virgin Islands offer an irresistible blend of new and old world culture, scattered across the western reaches of the Leewards like precious jewels. 

Blessed with year-round sunshine, the archipelago is famed for its miles of sandy coastline. Known as the gateway to the Caribbean, the isles are also steeped in maritime lore, with legends of pirate treasure and shipwrecks adding an air of mystery. 

Arawaks and Caribs inhabited the islands before the arrival of Dutch, Danish, Spanish, British and French colonists in the 15th century. Their legacy can still be found at sites such as the bright red Fort Christian, the oldest Danish fortification, which dates back to 1672 and is now run as a museum of indigenous artefacts. 

The three main US islands of St Thomas, St John and St Croix offer high-end shopping, dining and the best excursions in the Leewards. St Thomas has more than 40 major beaches and is a hotspot for scuba diving. St John’s unspoiled beauty and Virgin Islands National Park offer a tranquil escape for nature enthusiasts. St Croix showcases a unique blend of Danish colonial history and Afro-Caribbean culture. 

The BVI, meanwhile, are a sailor’s dream, dotted with secluded coves and vibrant coral reefs for snorkelling. They’re also home to more than 648 plant species, including the endemic pokemeboy, which resembles a yellow pom-pom, and Pitcairnia jareckii, which looks like a red-hot poker.

Anguilla

Tiny yet extraordinary, Anguilla promises an unparalleled escape. Unlike its neighbour Saint Martin and St Maarten, the island is not a popular tourist destination, meaning you can enjoy its serene atmosphere without crowds. 

British settlers arrived in 1650 from St Kitts and Nevis, leaving a unique mix of British and Caribbean traditions. Measuring just 26km long and five kilometres wide, this British Overseas Territory is renowned for its 33 pristine beaches, which are ranked among the best in the world. Powdery white sands such as Shoal Bay and Meads Bay meet pure waters in shades of turquoise and aquamarine, creating a postcard-perfect setting. Beyond its idyllic coastline, Anguilla boasts a fascinating history, from its Arawak roots – evident in ancient petroglyphs at Big Spring Cave – to its colonial past as a British stronghold. 

Known for its hospitality and slower pace of life – even by Caribbean standards – Anguilla offers a bespoke blend of music, cuisine and annual events. As well as the seafood festival – the biggest of its kind in the region – it’s also famous for Anguilla Summer Festival, which showcases the island’s national sport of traditional boat racing. With year-round sunshine and a commitment to sustainable tourism, Anguilla remains one of the Caribbean’s best kept secrets, offering a slice of paradise for those prepared to venture that little bit further off the beaten path.

Saint Martin & Sint Maarten

Tucked away six kilometres south of Anguilla, Saint Martin and Sint Maarten are two nations that share a single tiny landmass. The 96sq km rock – which is roughly the size of the UK’s Forest of Dean – is divided between the northern French side, Saint Martin, and the southern Dutch side, Sint Maarten. Each has its own character, offering a captivating blend of contrasting European cultures. 

Legend has it that 350 years ago, the Dutch and French raced across the northern and southern coasts to determine how much land each nation should have. Both sides chose to fortify themselves with their national drink, with the French opting for wine and the Dutch swigging gin – which explains why French Saint Martin now covers two thirds of the island. 

The Dutch side, Sint Maarten, is famous for its nightlife, duty-free shopping and bustling capital, Philipsburg, where you can stroll along its seafront promenade and Boardwalk, as well as visit historic Fort Amsterdam. Meanwhile, the French side exudes a more tranquil charm, with gourmet restaurants, boutiques and beaches such as Orient Bay and Anse Marcel. The island is home to 37 beaches and there’s one to match every mood – from the secluded serenity of Happy Bay to the lively Maho, where planes land dramatically close to the shore. 

Foodies will delight in the island’s reputation as the culinary capital of the Caribbean, thanks to its array of flavours influenced by French, Dutch and Creole traditions. On the French side of the isle, Doyle Guides author Lexi Fisher recommends trying the signature cocktail Ti’Punch. “It’s made with French Agricole rum, which gives it more of an earthy flavour than regular white rum,” she explains. “It’s essentially a shot of rum, cane sugar and a squeeze of lemon. You drink it just like that, no ice or anything. This is the traditional French Caribbean cocktail.”

St Kitts & Nevis

St Kitts and Nevis is the land of my ancestors and the smallest sovereign nation in the western hemisphere. This twin island paradise is bursting with history, natural beauty and charm, but each island offers a different experience. St Kitts, the largest of the two, is known for its lush mountains, golden beaches and energy. Home to Mount Liamuiga, a majestic dormant volcano that rises 1,156m above sea level, it’s heaven for adventure lovers, who can follow hiking trails through the rainforest to the volcano’s peak. Colonised by the English and French in the 16th century, the island was once dominated by sugar plantations. Their legacy is still evident in the historic St Kitts Scenic Railway, a narrow-gauge train that once transported sugar and now offers breathtaking island views. 

Affectionately called the Queen of the Caribbean, Nevis offers a more tranquil escape, with Nevis Peak, charming boutique hotels and pristine sands such as Pinney’s Beach. Celebrate the islands’ 44 types of mango at a summer mango festival, or dive along coral reefs and finish the day relaxing at a hot spring. 

The island is also deeply religious, with a diverse mix of Anglicans, Catholics and Rastafarians. Nevis Tourism Authority chair Pamela Martin says, “There are over 60 churches within the 36 square miles of Nevis, which means there is one church for every 217 people. Nevis also houses Cottle Church – the first in the Caribbean to have black and white people worshipping together. Religion plays a big part in Nevis island life.”

Antigua & Barbuda

The serene twin islands of Antigua and Barbuda combine to form one of the Caribbean’s most prosperous nations. United by history and proximity, they offer incredible coastlines, tranquil beaches and an old-world charm. From bustling markets and annual festivals to historic landmarks, the nation is steeped in stories that will pique the interest of enthusiastic explorers. 

The land was inhabited by indigenous Arawak and Carib tribes before being spotted in 1493 by Christopher Columbus, who renamed it Antigua after a church in Seville, Spain. In the early 17th century, the island was colonised by the British and became a centre for the sugar trade. 

Antigua honours its indigenous roots through its cuisine. For instance, the indigenous name of the island, Wadadli, is also the name of the local beer, and its famous delicacy, black pineapple, can be traced back to the Arawaks, who introduced agriculture. Shawn Weathered from Antigua VIP Tours describes the fruit, which you can only find in Antigua. “In its early stages of growth it looks black,” he says. “The shape is different, the texture is different and the taste is different. It’s actually golden in colour, darker at the root, and considered to be one of the world’s sweetest pineapples as it has a higher sugar content and lower acidity compared to other varieties.” 

Between them, Antigua and Barbuda offer 365 beaches – one for every day of the year, say the locals. Popular spots include Dickenson Bay, which is ideal for sunbathing, and Half Moon Bay, a more secluded retreat perfect for snorkelling. For history buffs, the Unesco world heritage site of Nelson’s Dockyard offers a glimpse into the island’s past as a British naval base. Explore the dockyard, filled with quaint shops and restaurants serving fungee – a delicacy of the early colonial period made from cornmeal and okra – and ducana, a traditional sweet dish of grated sweet potato and coconut. 

With extensive wetlands, coral reef ecosystems and abundant forests, the islands are home to rare fauna such as the largest frigate bird colony in the western hemisphere.

Montserrat

With its rolling green hills and Irish-influenced heritage, this British Overseas Territory is dubbed the Emerald Isle of the Caribbean. Despite its small size – little more than a quarter of the UK’s Isle of Wight – Montserrat offers rainforests, black sand beaches and volcanoes. Unfortunately the latter proved the island’s undoing, with a series of catastrophic eruptions in the 1990s destroying the capital, Plymouth, displacing two thirds of the population and devastating large tracts of landscape. Even today, half the island is an exclusion zone, closed to visitors, although  the remains of Plymouth – a modern-day Pompeii – can be visited with a certified guide. 

Today, Montserrat is a testament to survival and renewal. Its northern region, untouched by volcanic activity, is home to villages, luxury villas and hiking trails where visitors can spot the island’s national bird, the oriole. 

Less visited than other Caribbean islands, Montserrat offers an authentic experience, as well as untouched coral reefs, ripe for diving. You can also join in festivals such as St Patrick’s Week in March – a memorable celebration of the island’s Irish and Caribbean traditions. 

With each island blessed with a wealth of beautiful landscapes, beaches, biodiversity and architecture influenced by diverse cultures, the Leewards will be sure to offer you an unforgettable experience.

Have you cruised around the Leeward Islands? Share your memories with us by emailing [email protected]