The Caribbean: how to choose the right island

Why choosing the right Caribbean island matters

The Caribbean is often spoken of as if it were one destination, but its islands have very different characters. The volcanic islands of the Windwards are green and mountainous: St Lucia's Pitons, two forested volcanic spires of 770 and 743 metres rising straight from the sea, were inscribed as a UNESCO World Heritage Site in 2004. Anguilla, by contrast, is a flat, low-lying limestone island whose highest point is around 65 metres; it has little in the way of scenery but is known for its beaches. Some islands, such as Barbados, have a long tradition of tourism, a wide choice of restaurants and a social atmosphere; others, such as Nevis and the smaller Grenadines, are quiet by design. History differs too, with British, French and creole influences shaping architecture, food and language. Two holidays of the same length and budget can feel entirely different depending on the island, so the choice deserves more thought than it usually receives.

Start with the journey: direct flights and connections

For UK travellers, the journey narrows the choice more than anything else. British Airways flies non-stop from London to Barbados, Antigua and St Lucia in around eight and a half to nine hours, and Virgin Atlantic also serves several islands directly. Grenada and St Kitts can also be reached from London, though with fewer flights. The smaller islands require a connection: Nevis is reached via St Kitts or Antigua, Anguilla via Antigua or by a short ferry from St Martin, and the Grenadines by a shared charter flight and boat from a larger island such as Barbados. These connections are usually straightforward and often worth making, since the seclusion is the point, but they add time at each end and another link that weather or schedules can disrupt. For a first visit, or a short stay of a week, an island with direct flights generally makes more sense; for a longer holiday, the extra step is easier to justify.

Matching the island to the holiday you want

Each island has a clear strength. Barbados offers the widest choice of hotels and restaurants, calm Caribbean water on its west coast and a wilder Atlantic shore to the east, and suits those who like a social atmosphere. Antigua is known for the number and variety of its beaches and has direct flights, making it a practical choice for beach-focused holidays and families. St Lucia is the island for scenery, rainforest walks and dramatic views, though the terrain means some hotels sit on hillsides rather than on long beaches. Grenada, the Spice Island, known for its nutmeg, cinnamon and cloves, is relaxed and green, with a less developed feel. Nevis suits those who want peace, historic plantation inns and very little else. Anguilla combines beaches with a well-regarded restaurant scene but has little to explore inland. The Grenadines offer sailing waters and private-island seclusion. Few islands offer everything equally well, which is why the order of your priorities matters.

How to choose well, and how most people choose

Most people choose an island by name recognition or price, then book a large resort for two weeks and rarely leave it. It is an easy formula, but it misses much of what makes the Caribbean rewarding. A better approach works in stages: first decide what the holiday is for, then choose the island that suits it, then the coast, and only then the hotel. The coast matters more than people expect, since the sheltered Caribbean side of most islands has calmer water and less seaweed than the Atlantic side. Smaller hotels with a strong sense of place often give a truer impression of an island than large resorts, and a hotel chosen for its setting will shape the holiday more than any list of facilities. For stays of ten nights or more, a two-centre holiday is often the best answer: pairing a familiar island with an unfamiliar one, or a lively base with a secluded one, shows two sides of the region for little extra travelling.

An honest verdict: which islands suit whom

Families generally do best on islands with direct flights and hotels designed for children, such as Barbados and Antigua; the smaller islands can suit older children but offer fewer facilities. Couples looking for scenery and romance tend to favour St Lucia or the Grenadines. Those who value food and a choice of restaurants will be happiest on Barbados or Anguilla. Travellers who dislike connections should stay with the directly served islands. It is also worth being frank about cost: the smaller, more secluded islands and private-island resorts are expensive, and peak-season prices everywhere are high. All-inclusive terms offer simplicity and suit some holidays well, but they can discourage exploring and eating out, which on islands with good local restaurants is a loss. Finally, anyone who wants a great deal of culture or sightseeing may find a Caribbean holiday limiting; its pleasures are principally the sea, the landscape, the hotels and a slower pace.

How Expressions Holidays helps you choose and organise a Caribbean holiday

Every Expressions holiday to the Caribbean is tailor-made. We include flights, private transfers and any inter-island flights or boat transfers, with accommodation in personally selected 4- and 5-star hotels and a choice of bed and breakfast, half board, full board or all-inclusive. Combining islands is where our knowledge counts most, and our suggested two-centre holidays show the kind of pairings that work well: Barbados and St Lucia, staying at The Sandpiper and Anse Chastanet; Grenada and St Lucia, at the Calabash and East Winds Inn; Nevis and Antigua, at Montpelier Plantation and Blue Waters. Each is ten nights and can be adjusted. We will advise on which island and which coast suit you, and on timing. Your holiday is handled throughout by one consultant, and comes with our handcrafted notes and ATOL protection.

Planning a Caribbean holiday with Expressions Holidays
Expressions Holidays has been organising luxury, tailor-made holidays since 1989, and the Caribbean has long been one of our core destinations. We design each itinerary around your interests, pace and preferred style of accommodation, and talk the quotation through with you day by day before you decide. If you are unsure which island, or which combination of islands, would suit you best, we would be pleased to help you choose.
Call us on 01392 441245
Monday to Friday 9.00am to 5.30pm; Saturday 10.00am to 2.00pm
Email info@expressionsholidays.co.uk