Caribbean
Where to Go in the Caribbean This Winter: Pick by Trip Type
Start from the trip you want — a US hop, a family week, a honeymoon, calm water, a food city, or a lower budget — then open the island page.
Read the guideInformation only · no bookings
Decision guides for the trip you are actually taking: which Caribbean island fits the winter week you want, which Hawaiian island to open first (Maui is on that list), whether to choose Bora Bora, Moorea, or both, whether the Indian Ocean week is the Maldives, Seychelles, Mauritius, or Zanzibar, and whether the Southeast Asia week is Bali, Koh Samui, or Palawan. This is not a travel agency. You book directly on Hotels.com or Viator. If you book after clicking, the site owner may earn a commission. It does not change the price you pay.
Caribbean
Start from the trip you want — a US hop, a family week, a honeymoon, calm water, a food city, or a lower budget — then open the island page.
Read the guideHawaii
Start from the week you want — resort beaches, a city, cliffs, a volcano, or a quiet island — then open the island page. Maui is the usual first page.
Read the guideFrench Polynesia
Who should pick which island, how to shape 3, 5, or 7 nights, and when an overwater bungalow is the point of the stay.
Read the guideIndian Ocean
The Maldives is a resort island you stay on. Seychelles is beaches you can leave the hotel for. Mauritius is a country with lagoons. Zanzibar is the modest page.
Read the guideSoutheast Asia
Bali is temples and a coast you choose. Koh Samui is a beach island you can fly onto. Palawan is lagoons after a second flight.
Read the guideNewsletter
A monthly letter with new guides and the tradeoffs that change by season. Airports, winter weeks, and which trip fits the one you actually want.