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 villa — 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. Confirm opening dates and compare current property-specific prices; we have not measured a seasonal rate discount. If you travel then, book insurance that covers weather cancellation and keep the itinerary flexible.
- Confirm staffing and total charges — what does that mean for a trip to The Caribbean?
- Confirm the exact villa’s staff roles, working hours, food charges and provisioning arrangements. Compare complete booking terms, not a presumed regional staffing package.
- Sargassum and the windward side — what does that mean for a trip to The Caribbean?
- Sargassum can affect east- and south-facing beaches on some islands at times. Ask the property directly for its current sargassum status and which side of the island the villa faces before booking, if beach swimming is the point of the trip.
The best time to visit The Caribbean
- When is the best time to visit The Caribbean?
- December to April: Ask the property directly about current conditions and its Christmas and New Year rate and minimum-stay policy before booking. May to June: Ask the property directly for its current rate and confirm which restaurants are open before booking this window. July to August: Check the current hurricane forecast outlook and confirm carnival dates and the property's current rate directly before booking. September to October: Check the current hurricane forecast outlook, and confirm directly with the property and nearby restaurants whether they are open before booking. Take insurance that covers weather cancellation. November: Ask the property directly for its current reopening date, staffing status and rate before booking. Rates on every villa 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?
- Ask the property directly about current conditions and its Christmas and New Year rate and minimum-stay policy before booking.
- What is The Caribbean like in May to June?
- Ask the property directly for its current rate and confirm which restaurants are open before booking this window.
- What is The Caribbean like in July to August?
- Check the current hurricane forecast outlook and confirm carnival dates and the property's current rate directly before booking.
- What is The Caribbean like in September to October?
- Check the current hurricane forecast outlook, and confirm directly with the property and nearby restaurants whether they are open before booking. Take insurance that covers weather cancellation.
- What is The Caribbean like in November?
- Ask the property directly for its current reopening date, staffing status and rate before booking.
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?
- Check whether a service charge is included in the bill and ask your accommodation about any staff-tipping guidance. We have not verified a region-wide percentage.
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 villas of ours here yet. Turks and Caicos — Grace Bay for families and flat water; check current forecasts and flight schedules before booking.
- How do I book a villa in The Caribbean?
- In The Caribbean we currently hold villas in St Barths and Mustique and Canouan and Harbour Island and Barbados. Recorded listings are not guaranteed exact matches on partner sites. Use the Stay22 partner search for your dates and confirm the exact accommodation, total price and terms before booking. For the places in this guide where we do not yet list a villa, treat the guide as planning advice rather than an offer.