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Home > Vacation Types > The Leeward Islands

The Leeward Islands

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A collection of the Caribbean’s brightest gems, the Leeward Islands feature some blockbuster names alongside lesser-known hideaways, says Minty Clinch


North American winter sunseekers searching for diversity need look no further than the Leeward Islands, the paradise archipelago stretching southwards from the east of Puerto Rico to Dominica. Named for the trade winds blowing in off the Atlantic, the islands are largely volcanic, though there are coral reefs among them. On their eastern shores, calm Caribbean waters create idyllic sandy beaches; on the western ones, breakers crash onto dramatic rockscapes. 

image: getty

image: getty

The Leewards include the French overseas territories of Guadaloupe, St Barthélemy (St Barts in English) and half of St Martin — the other half, St Maarten, is in the Dutch sphere of interest, as is tiny St Eustatius. Antigua & Barbuda and St Kitts & Nevis gained independence from Britain in the 1980s, but retain much of the culture of their colonial past. The Virgin Islands, the most northerly in the chain, are partly American, partly British and partly Puerto Rican, along with the Spanish heritage that implies.

The Leeward Islands form the northern half of the Lesser Antilles, with the Windward Islands, Barbados, Trinidad, St Lucia and Martinique stretching south towards Venezuela. As the name suggests, the Greater Antilles, to the west of Puerto Rico, are substantially larger, with big hitters Jamaica, Cuba, Haiti and the Dominican Republic at the top of the list. And that’s just for starters. With an estimated 7,000 West Indian islands to be categorized, grouping them was never going to be easy.

The Caribbean is at its most magical in high season between December and April. The rains may come any time between May to November, with a risk of hurricanes in August and September, but the winter offers mellow tropical heat and gentle sea breezes, with daytime temperatures of around 80F and sustainable humidity. This is perfect for passive relaxation or more active Caribbean activities.

Traditional visitors tend to seek sunloungers on the beach, with the soothing background of rustling palms and waves rippling on the shore. Independent spirits hire sailing boats, often without a crew, and journey from port to port. The middle path can include scuba diving, kayaking, jet skiing, golf and hiking up volcanic peaks. Most tourists prioritize regional delicacies, dark and stormy rum cocktails, and tuning into the infectious Caribbean sounds far into
the night.

image: getty

image: getty

The core of the Leeward archipelago contains two of its most seductive treasures, St Eustatius (or Statia, to those in the know) and St Kitts & Nevis. Statia, barely six miles long and five miles wide, was a vibrant trading center with a population of 20,000 in its 17th-century heyday, a regular port of call for every ship’s captain and pirate in the West Indies. A century later, it grew so rich on the transatlantic slave trade and arms deals related to the American War of Independence that it was re-named the Golden Rock of  the Caribbean.

That particular historical glitter has long gone, leaving in its wake a charming Dutch colonial backwater with fewer than 4,000 inhabitants. A steady flow of enterprising travellers take the 20-minute hop from St Maarten on one  

image: getty

image: getty

of the five flights a day operated by Windward Island Airways (WINAIR). The official language is Dutch, but everyone speaks English, and while the choice of lodging may be limited, all bases are covered.

Built of old bricks used as ballast in sailing ships, the Old Gin House — think cotton rather than liquor — is a faithful reconstruction of an 18th-century workshop, and its 19 ensuite rooms are set in lavish tropical gardens.

With the St Eustatius Marine Park, established in 1996, encircling the island, the diving among coral reefs, sponges, barracuda and the spectacular flying gurnards, is second to none. Shipwrecks add intrigue — at 328ft, Charles Brown is one of the longest subaquatic discoveries in the Caribbean. On land, the dormant Quill volcano that dominates the capital of Oranjestad is the focus of nine marked hiking trails. Those going up to the 2,000ft summit and down into the crater, with its mahogany trees, orchids, iguanas and exotic birds, are by far the most popular.

From the crater rim, visitors can see St Kitts seven miles to the south. Along with neighbouring Nevis, it forms the smallest nation in the Americas, with a joint population of just 40,000. The islands, discovered by Christopher Columbus in the latter years of the 15th century, are just two miles apart; that geography forced the twin sugar colonies into a shotgun marriage when they gained independence from Britain in 1983.

image: getty

image: getty

By that time, Nevis had closed its last cane processing plant and embraced tourism, while St Kitts continued to cling to its outdated agricultural infrastructure for another quarter of a century. Nevis has always resented the dual statehood, but lacks the fiscal strength to go it alone.

But since it woke up to the brave new world of mass tourism a decade ago, St Kitts has worked hard to turn its tiny assets into big attractions. Sand between the toes is being replaced by sleek developments — notably Port Zante in the capital Basseterre. The new dock is equipped to receive three cruise ships a day, enabling 8,000 international passengers  to pass through into the 25-acre shopping precinct constructed on land reclaimed from the sea.

Another aim is to double the number of beds as soon as possible. The Marriott Resort and Royal Beach Casino is oriented towards American visitors, with hotel rooms and villas overlooking Royal St Kitts golf course just outside town. Belle Mont Farm, a former 400-acre sugar planation on the lower slopes of Kittian Hill to the north of the island, has been reinvented as a luxurious organic hideaway, with 68 of out a planned 84 guesthouses already open for business. The Cane Train, which chugs out of Basseterre on a 20-mile round trip that takes two gloriously leisurely hours, is a cheerful way of exploring the island — even the 7am service has a gospel trio and rum cocktails.

Anguilla, a main island with several satellite reefs to the north of St Martin, is a popular celebrity haven, not  surprisingly, as it has no direct taxation for individuals or corporations. Unlike its volcanic neighbours, it’s a flat coral island characterized by magnificent beaches. The ultra-exclusive Cap Juluca, a member of the Leading Hotels of the World consortium, occupies the lovely sand crescent of Maundays Bay. Couples seeking the ultimate romantic break in its Moorish beachfront villas should realize they’ll never want to leave.

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image: getty

Alternatives include the Viceroy, a 3,500ft waterfront property on Barns and Meads Bay, and the seductive Frangipani where people “arrive as guests and leave as friends” — a relationship usually kick-started by the complimentary rum punch on check in.

Anguilla’s Amerindian heritage dates back to 2500 BC. The Fountain Cavern at Shoal Bay, with its petroglyphs and carved stalagmites is the most complete Arawak ceremonial site in the Eastern Caribbean. Shoal Bay is also home to Ernie’s Beach Bar, an establishment that dates back to the dawn of Anguillan tourism. Elvis’s sailboat-cum-bar at Sandy Ground is similarly iconic, while Johnno’s is a perennial headliner on the local dance scene.

The US (USVI) and British Virgin Islands (BVI), scattered liberally across the sea between Anguilla and Puerto Rico, are ideally spaced for enterprising seafarers to find their way from port to port. There are three main islands in the USVI, of which the most important is Saint Thomas. The capital, Charlotte Amelie, named after the 17th-century Danish queen, is a major cruise stop, with a colorful harbor front and all-embracing shopping center that balances quaint local craft shops with duty free stores.

St John, four miles away by hourly ferry, is worthwhile for the sheer unspoiled beauty of an island formerly owned by the Rockefeller family. When they donated it to the United States National Park Service in 1956, it was given the protected status it retains 60 years later. Trunk Bay is consistently rated in the world’s top ten beaches and Caneel Bay, site of the former Rockefeller home, is also worth a visit. The third main island, St Croix, 36 miles south of St Thomas, is larger but less dependent on tourism, due to its oil refinery and rum distillery founded in 1736.

Guadeloupe, christened Santa Maria de Guadeloupe de Extremadura by Christopher Columbus when he landed there in 1493, is an overseas department of France. The locals are French-speaking, as are the 83% of tourists who visit it. As the euro is the official currency, US dollars are less acceptable in shops than they are in other parts of the Caribbean. The five islands are extensively cultivated, with sugar and bananas as the main cash crops.

Guadeloupe certainly obliges with its sophisticated,French-inspired cuisine. In the West Indies, most hotels overlook calm Caribbean waters, but Auberge de la Vielle Tour on Grand-Terre island has stirring views of the turbulent Atlantic — the best ones are offered from the 32 suites that were added in 1995. The restaurant is one of Guadeloupe’s finest, which can also be said of Basse-Terre’s Le Jardin Malanga, where the chef creates his daily dishes from ingredients he selects from the fishing boats. The 1927 colonial house — its nine rooms with wraparound verandas looking out over lush tropical gardens — is also a great place to stay.   

Even though Antigua and Barbuda form a twin-island country in the north of the Leewards, their characters are quite different. Antigua, another port of call for Christopher Columbus during 1493, was named after the Virgen de la Antigua icon in Seville Cathedral. Admiral Nelson found it equally attractive when he established it as Britain’s most important Caribbean base in 1784. Known as the “land of the 365 beaches” for the variety and beauty of the golden sands that surround it, Antigua has resorts to suit all pockets. Hermitage Bay, Galley Bay Resort and Spa and Halcyon Cove have all-inclusive  packages that appeal to travelers who like to budget.

Barbuda, a sun-seeker’s paradise with coral reefs and isolated lagoons, is a smaller and much quieter version of Antigua. Coco Point Lodge, on a 164-acre peninsula that occupies the island’s southern tip, is the original hotel, with 35 bedrooms in beachfront cottages. Its private plane meets guests at Antigua airport for the 12-minute flight to the hotel’s runway. Think barracuda fishing by day, and lobster and fine wines by night. This is yet another Caribbean gem that’s very hard to leave. 

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