Skip to content
ILUXURYTRAVELS

The Caribbean destination guide

The Caribbean destination guide.

The Caribbean is the most villa-led region we cover: on St Barths, Mustique, Harbour Island and Barbados's west coast, a staffed house is the normal way to stay rather than the expensive alternative to a hotel. The decisions that matter are the island, the month and the connecting flight — and this guide works through all three before it talks about houses.

Travel tips

Choose the island before the house

St Barths is French, polished and social; Mustique is private and almost entirely villa-only; Harbour Island is barefoot and small; Barbados has the broadest range of restaurants, flights and beaches. They are four different holidays, and the right one is decided by the kind of week you want rather than by the photographs.

Land in the gateway before mid-afternoon

Almost every island is reached by a connection: St Barths from St Maarten, Mustique and Canouan from Barbados or St Lucia, Harbour Island from Nassau. Those small-aircraft and ferry legs stop at dusk, so an early transatlantic arrival saves an unplanned night in the gateway.

Hurricane season is a real planning input

The Atlantic season runs June to November, with the concentrated risk from mid-August to mid-October. Rates fall by half, and many restaurants and some hotels close entirely. If you travel then, book insurance that covers weather cancellation and keep the itinerary flexible.

Villas here come staffed, and the rate reflects it

A cook, a housekeeper and often a gardener or caretaker are usually included. Groceries, drinks and the chef's menu are billed separately, and a provisioning list sent a week ahead is normal practice. Compare rates on what they include, not on the headline number.

Sargassum and the windward side

Between roughly April and August seaweed can affect east- and south-facing beaches on several islands, while leeward west coasts stay clear. If beach swimming is the point of the trip, ask which side of the island the house faces before booking those months.

The best months to go

December to April
High season: driest air, calmest water and the busiest weeks of the year. Christmas and New Year book close to a year ahead at double rates, with minimum stays of ten to fourteen nights on the private islands.
May to June
The best value in the calendar. The sea is warm, the islands are quiet, most restaurants are still open and rates drop sharply once the February and Easter weeks pass.
July to August
Hot, humid and lively — carnival season on several islands, and popular with families. Hurricane risk is rising but still moderate, and rates are well below winter.
September to October
Peak hurricane risk and the quietest weeks of the year. Many villas, restaurants and hotels close outright. Lowest rates, but only worth it with flexible plans and proper insurance.
November
The season reopens: the weather has usually settled, staff are back and rates sit below December while the islands are still uncrowded.

Local culture and etiquette

Greet before you ask

A good morning or good afternoon comes before any question, in shops, taxis and offices alike. Skipping it reads as rude across the region in a way visitors often miss.

Swimwear stays at the beach

Covering up in town is expected everywhere, and topless sunbathing that passes on St Barths does not on Barbados or in the Bahamas. Dinner in Gustavia or on Barbados's west coast is smart-casual and people do dress for it.

Island time is a pace, not a slight

Things happen when they happen on Mustique, Harbour Island and much of the Grenadines. Build slack into transfer days and restaurant bookings rather than pushing.

Tipping and service charges

A ten per cent service charge is often added to restaurant bills; another five to ten per cent in cash is normal if the service was good. Villa staff are usually tipped at the end of the stay, and the agency or house manager will suggest a range.

Must-visit places

  • St Barths

    The most concentrated villa market in the Caribbean — Pointe Milou for sunsets, Flamands and Gouverneur for beachfront.

  • Mustique

    A private-island community of staffed estates; almost nothing here is bookable any other way.

  • Canouan

    Quiet Grenadine island with a marina, golf and very few visitors; reached by connection from Barbados or St Lucia.

  • Harbour Island

    Pink-sand beach, golf carts and a handful of tables worth booking ahead; reached via Nassau.

  • Barbados

    The west coast for calm water and restaurants, the east for surf and space; the easiest island to reach direct.

  • Anguilla

    Long empty beaches and a serious restaurant scene, a short ferry from St Martin. No houses of ours here yet.

  • Turks and Caicos

    Grace Bay for families and flat water; December to April is driest, and direct US flights are frequent.

Keep reading