Getting to know Caribbean

Dozens of islands, each with its own character

The Caribbean is not one destination but dozens, and the differences between them are what make planning fun. Jamaica has reggae, jerk and the Blue Mountains. Aruba is dry, breezy and almost always sunny. St. Lucia has the dramatic twin Pitons and rainforest. Turks & Caicos is all about powdery beaches and calm, clear water. The islands blend African, European, Indigenous and Asian heritage into distinct music, food and festivals.

There are two classic ways to go. A Caribbean cruise shows you several islands in a week, with ships sailing from Baltimore, Florida and other East Coast ports. An all-inclusive resort lets you settle into one beach with meals, drinks and activities included. Many travelers do both over the years — and some combine a cruise with a few resort nights before or after.

The dry season, roughly December through April, brings the most reliable weather and the highest demand. Hurricane season runs June 1 through November 30; late summer and fall offer good value, and the southern islands such as Aruba sit outside the usual storm track. U.S. citizens do not need a passport for the U.S. Virgin Islands or Puerto Rico, but most other islands require one — and we recommend a passport on every Caribbean trip, including cruises.

Planning notes

Choosing the right island

• Cruise or resort? A cruise samples several islands; a resort gives you one beach and no packing. We will help you decide.
• Match the island to the trip. Honeymoon, family reunion, girls' getaway or diving trip — the best island is different for each.
• Hurricane season, handled. Summer and fall bring good value; we will explain your options and suggest Travelex travel insurance.
• Check your passport. Most islands require one valid for your whole stay — some ask for six months beyond it. We confirm the rules for your trip.