Caribbean Travel Guides

The Atlantic hurricane season runs from June 1 to November 30, and the risk is concentrated in the middle of it, from roughly mid-August to late October. Plenty of people travel through it and have a fine trip, because a named storm affects a small part of the region at any one time. If you go during those months, book accommodation with a flexible cancellation policy and buy travel insurance that actually covers weather disruption, then check the National Hurricane Center forecast in the week before you fly.

The shoulder months, May to June and October to November. Peak season is December to April, when the weather is at its most reliable and so are the prices. Shoulder season trades a higher chance of rain for meaningfully cheaper flights and rooms, and far fewer people at the same beaches. The last two weeks of April and the first two of December are the sweet spot if you want peak weather at close to shoulder prices.

It depends on where you are from and which island you pick, because the Caribbean is dozens of separate jurisdictions rather than one. US citizens traveling to Puerto Rico or the US Virgin Islands are traveling domestically and do not need a passport, though they do need government-issued photo ID. Almost everywhere else in the region does require one. Check your own government's travel advice for the specific island, and confirm your passport has enough validity left, since several islands ask for six months beyond your return date.

Puerto Rico and the US Virgin Islands use it because they are US territories. The British Virgin Islands, the Turks and Caicos Islands, and the Dutch islands of Bonaire, Sint Eustatius and Saba also use it as their official currency. Elsewhere you will find the Eastern Caribbean dollar, the Jamaican dollar, the Dominican peso, the Cuban peso and others. Many tourist businesses accept US dollars anyway, but the exchange rate they give you is rarely the one you would get from a bank.

One, for a first trip of a week or less. Island hopping looks easy on a map and is slow in practice: most islands are connected to each other by a single daily flight or a ferry that only runs within its own island group, and each hop costs you a travel day plus a new set of arrival formalities. Two islands works over two weeks if they are neighbors with a short ferry between them.

It depends on what you want the trip to be. All-inclusive genuinely does control costs on the expensive islands, where a restaurant meal and a couple of drinks can run higher than you expect, and it removes daily decisions. The trade is that you will see very little of the island and eat almost none of its food. A middle path that works well is an all-inclusive for part of the stay and a few nights in a guesthouse in a town.

On a small island where you are staying near the beach and the town, no, and parking is often the harder problem. On the larger islands, Puerto Rico and the Dominican Republic among them, a car is what turns the trip from one resort strip into the whole place. Note that several islands drive on the left, including Jamaica, Barbados and Saint Lucia, and that some require you to buy a temporary local driving permit at the rental desk.

It varies island by island and sometimes within one island, so it is not a question with a single regional answer. Some islands treat their supply to a standard you can drink straight from the tap, others rely on desalination or rainwater catchment where quality is less consistent. Ask at your accommodation rather than guessing, and check your government's travel health advice for the specific island before you go.

English, Spanish, French and Dutch are the official languages across the region, depending on which colonial power held the island, and most places also speak a Creole alongside the official language. English is widely used in tourism almost everywhere. A few words of the local language still changes how the day goes, particularly in the Spanish-speaking islands where English drops away quickly once you leave the resort areas.

Broadly yes, and the honest answer is that safety varies far more between islands, and between neighborhoods on one island, than any regional summary can capture. The realistic risk for most visitors is opportunistic theft rather than anything worse, and it concentrates in busy tourist areas and on quiet beaches after dark. Read your own government's advice for the specific island, since those pages are updated and a blog post is not.

Usually yes, and often twice if you are not paying attention. Many hotels and restaurants add a service charge of around ten to fifteen percent to the bill automatically, so read it before adding more. Where nothing has been added, ten to fifteen percent is normal in restaurants. Small amounts for housekeeping, drivers and guides are customary and genuinely appreciated on islands where tourism wages are low.

For a first trip the practical answers are Puerto Rico, the Dominican Republic, Jamaica or Barbados, because they have the most direct flights, the widest range of places to stay at every budget, and enough going on beyond the beach to fill a week. Puerto Rico is the easiest of all for US travelers, since there is no passport requirement, no currency change and no roaming charge. The smaller Eastern Caribbean islands are wonderful and better saved for a second trip.