The Caribbean destination guide FAQ
Your The Caribbean questions, answered.
The same ground the The Caribbean destination guide covers — travel tips, the best months, local culture and where to go — set out as the questions people actually ask us before they book.
Planning a trip to The Caribbean
- Choose the island before the house — what does that mean for a trip to The Caribbean?
- 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 — what does that mean for a trip to The Caribbean?
- 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 — what does that mean for a trip to The Caribbean?
- 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 — what does that mean for a trip to The Caribbean?
- 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 — what does that mean for a trip to The Caribbean?
- 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 time to visit The Caribbean
- When is the best time to visit The Caribbean?
- 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. Rates on every house move with these seasons, and the live partner panels on each listing show what a given week actually costs.
- What is The Caribbean like in 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.
- What is The Caribbean like in 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.
- What is The Caribbean like in 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.
- What is The Caribbean like in 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.
- What is The Caribbean like in 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 in The Caribbean
- Greet before you ask — what is expected of visitors?
- 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 — what is expected of visitors?
- 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 — what is expected of visitors?
- 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 — what is expected of visitors?
- 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.
Where to go in The Caribbean
- Which places in The Caribbean should I build a trip around?
- 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.
- How do I book a house in The Caribbean?
- In The Caribbean we currently hold houses in St Barths and Mustique and Canouan and Harbour Island and Barbados. Each listing shows live partner rates for your dates, and the booking completes with our partner — Booking.com, Expedia or Hotels.com — at the partner's own price. For the places in this guide where we do not yet list a house, treat the guide as planning advice rather than an offer.