Caribbean island guide: Get back to basics

Do you know your Windwards from your Leewards, your Lesser from your Greater Antilles? Jo Cooke gets back to basics with a beginners’ guide to the Caribbean.

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The islands of the West Indies spread out like stepping stones between North and South America. They gather in groups that have complementary and contrasting characteristics, and with the right know-how, you can create clients a perfect cocktail of flavours. Here’s our guide to the whens, wheres and hows of island-hopping holidays.

The Greater Antilles

Location, location: Cast your eye south of the Florida Keys and you’ll see the Greater Antilles. It’s the island chain that kicks off the Caribbean, and as its name suggests, it includes the four biggest islands in the region.

Which islands? Cuba, Jamaica, Hispaniola (the landmass that Haiti and the Dominican Republic share) and Puerto Rico, plus their smaller neighbours, the Cayman Islands and Turks and Caicos.

“The Caymans’ pristine waters offer some of the best snorkelling and scuba diving in the region.”

What’s the vibe? Size does matter, and as well as incredible beaches, the larger islands offer a variety of terrains, from wetlands to alpine, plus charismatic cities. Cuba, the Dominican Republic and Puerto Rico share a Latin vibe and Spanish is the predominant language, while English is spoken in Jamaica, Turks and Caicos and the Cayman Islands, which have more of an affinity with Britishness. The Caymans’ pristine waters offer some of the best snorkelling and scuba diving in the region, while the multiple islands of Turks and Caicos deliver bucketloads of seaside charm.

Getting out and about: This bunch is mainly a direct flight away from the UK. British Airways serves the Dominican Republic, Jamaica and the Caymans non-stop, Turks and Caicos via Antigua, and Puerto Rico with a pit-stop stateside. For Cuba, Virgin Atlantic flies direct. InterCaribbean Airways, based in Turks, offers flights between its hub and Jamaica, Puerto Rico, the Dominican Republic and Cuba. From Jamaica, the Caymans are less than an hour’s flight with Cayman Airways, and it’ll take just over an hour to reach Cuba with Cubajet.


Leeward Islands and French West Indies

Location, location: Lying east of Puerto Rico, the Leewards begin where the Greater Antilles end. Leeward means sheltered from the wind, and these islands cluster together in the central zone of the West Indies.

Which islands? The British Virgin Islands (BVI), Anguilla, St Kitts and Nevis, and Antigua and Barbuda. This is also where you’ll find the French enclaves of St Barts, Guadeloupe and Martinique, and their Dutch-speaking neighbours, Saba and Eustatius. They share Saint Martin/Sint Maarten, which is French in the north and Dutch in the south.


What’s the vibe? Small is beautiful, chic and glamorous here. Hike through the bewitching scenery of Guadeloupe, Saba and Sint Eustatius, or charter a yacht in the BVI. For ‘paradise-found’ beaches and award-winning restaurants, head to St Barts and Anguilla. Nevis exudes colonial charm and Antigua and St Kitts offer activities and historic sights. The frigatebird colony on Barbuda is a natural wonder not to be missed, but if clients want more bustle, Saint Martin, Martinique and Sint Maarten are known for their nightlife and casinos.

“Hike through the bewitching scenery of Guadeloupe, Saba and Sint Eustatius, or charter a yacht in the BVI.”

Getting out and about: Antigua is a hub of the Leewards with direct UK flights from BA and Virgin. BA serves St Kitts with a brief stop in Antigua. Anguilla can be reached by onward connections courtesy of Trans Anguilla Airways, and Tradewind Aviation connects St Barts with Antigua. Air France flies via Paris to Martinique and Guadeloupe and St Martin if you fancy a French fling. For Saba and Sint Eustatius, Winair flies from Sint Maarten. By ferry it’s a short, regular,
low-cost ride between St Kitts and Nevis, Anguilla and Sint Maarten and Antigua and Barbuda.


The Windward Islands

Location, location: Occupying the eastern reaches of the region, the Windward islands are so-called because they are perfectly positioned to catch the trade winds.

Which islands? Dominica, Saint Lucia, Barbados, Grenada, and St Vincent and the Grenadines.

“Barbados is a coral island and, like the exquisite Grenadines, has fabulous white-sand beaches.”

What’s the vibe? This is the Caribbean’s sweet spot, with jaw-dropping greenery springing from the volcanic soils. Grenada, Saint Lucia and St Vincent are richly fertile with a thicket of rainforest inland, while Dominica is the eco epicentre of the West Indies. Barbados is a coral island and, like the exquisite Grenadines, has fabulous white-sand beaches.

Getting out and about: Both Virgin Atlantic and British Airways fly to Grenada, Barbados and Saint Lucia (although Virgin’s Saint Lucia service is set to end in June 2020, with BA increasing its frequency in response). For Dominica, passengers can pick up flight connections in Antigua, Barbados and Saint Lucia.
For St Vincent, a connection in Barbados is the most common route. Caribbean Airlines also connects Grenada to Trinidad, and Liat flies Grenada to Barbados. From Saint Lucia, ferries are also an option if clients fancy a jaunt to Martinique,
Guadeloupe or Dominica.


The Bahamas

Location, location: Lying in the Atlantic Ocean, due east of the Florida coast, the 700 islands of the Bahamas are scattered across 760 miles and end just shy of Turks and Caicos.

What’s the vibe? Combining Caribbean spirit with US flair, carnival and corporate blend beautifully here. Choose from large-scale resorts such as Atlantis Paradise Island, the three-resort development at Baha Mar, all-inclusive Sandals properties or luxury beach-bum hideaways on the Out Islands. The nation’s capital, Nassau on New Providence island, is the gateway with extensive beaches, historic sites and a lively bar and restaurant scene, plus a multimillion-dollar regeneration of its port area. Meanwhile the Out Islands give clients a sense of remoteness and are a match made in heaven for lazing, lounging, watersports and weddings.

“The nation’s capital is the gateway with extensive beaches, historic sites and a lively bar and restaurant scene.”

Getting out and about: BA flies non-stop to Nassau four times a week, increasing to five from March 31, 2020, and from there, a network of ferries and domestic flights whizz you over to the Out Islands. Hopping between Out Islands, however, often involves heading back to Nassau first. InterCaribbean Airways connects Nassau to destinations region-wide.


The Southern Caribbean

Location, location: Nudging up to the shores of Venezuela, these islands mark the end of the line for the Caribbean region as it gives way to South America.

Which islands? The Dutch Antilles, Aruba, Bonaire and Curacao, and Trinidad and Tobago.

“Tobago is dotted with affordable package-deal beach resorts, plus hiking trails through the Main Ridge Forest Reserve.”

What’s the vibe? White-sand beaches galore and buzzing capitals, which have architecture akin to Amsterdam, can be found on Aruba and Curacao, while Bonaire has windmills and a sleepier atmosphere. Over in Trinidad, it’s less touristy, with birding and the legendary February carnival the main draws. Tobago, on the other hand, is dotted with affordable package-deal beach resorts, plus hiking trails through the Main Ridge Forest Reserve.

Getting out and about: KLM flies to Aruba, Curacao and Bonaire from Amsterdam’s Schiphol airport, with Winair flying between the islands. BA offers a direct service to both Trinidad and Tobago with a passenger ferry connecting the pair.


Ask the experts

“Twin a larger ‘gateway’ island to a smaller island or group of islands for a contrasting experience. A destination specialist tour operator can help you not just work out which hotels and islands best suit your clients, but how long to stay at each to get the most convenient connections with international arrivals and departures, plus give advice on local departure taxes and luggage limits for small-plane island hopping.”
Helen Tabois, Caribbean and cruise senior product and marketing manager, Inspiring Travel Company

“For those who would rather not travel on smaller, inter-island aircraft, Saint Lucia and Grenada are a popular option. BA’s direct flight to and from Saint Lucia also stops in Grenada, making it a convenient way to see both islands.”
Jenny Peart, head of product, Caribtours

“Perhaps the simplest island hop is St Kitts and Nevis, which are just a 15-minute boat ride from each other. But as the BA flight stops in nearby Antigua, it’s also possible, and practical, to do a three-centre.”
Malcolm Davies, product destination manager, Funway Holidays


Book it

Funway Holidays offers six nights in St Kitts and Nevis from £1,659 per person room-only, including three nights at Marriott St Kitts and three at Oualie Beach, inter-island transfers and return flights from London with American Airlines, departing January 11, 2020.

The Inspiring Travel Company offers a nine-night twin-centre in the British Virgin Islands and Antigua from £4,165 per person, including five nights’ at Rosewood Little Dix Bay in an Ocean View Cottage and four at Carlisle Bay in a Garden Suite, both on a bed-and-breakfast basis, plus return economy-class flights, inter-island flights and private transfers based on a July 1, 2020, departure.

Caribtours offers 14 nights in Barbados and St Vincent and the Grenadines, including breakfasts, from £3,369, with a week at Coral Reef Club, Barbados, and a week at Bequia Beach Hotel, Bequia, based on departures in May or June 2020, including flights, private transfers (shared for boat transfers), and access to a UK airport lounge.

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