If you're looking to travel during winter holidays like Christmas or New Year's, book as far ahead as possible (6-10 months in advance) as airlines and accommodations sell out fast. Expect to pay a small fortune.
Confirm Flight
Many smaller island-hopper airlines have erratic service. Confirm your reservations a couple of days in advance--yes, we mean it--and anticipate schedule changes if the airlines don't find enough passengers to justify a previously arranged flight.
Watch your Bag
Arriving at Caribbean airports can be a harrowing experience. Expect encounters with overworked (and sometimes rude) customs officials and beware “porters” who offer to “help” with your bags only to run off with them.
Just in Case
Occasionally, when small planes are booked to capacity, weight requirements force airlines to ship baggage separately. Pack a day's worth of necessities in a carry on just in case, especially for St. Barts, Anguilla, Saba, St. Vincent, and Nevis.
Currency
There are 13 official currencies in the Caribbean so be aware of what currency each island uses before you go – the French islands of Martinique and Guadeloupe, for example, deal in Euros.
Cruises
Eastern Caribbean cruises are better for travelers looking to maximize ocean- and shop-time, while Western cruises are better for diving and snorkeling aficionados. Southern Caribbean cruises tend to be longer and offer a mix of the two.
Jazz Festivals
Barbados is renowned for its annual Jazzfest each January, while the Dominican Republic hosts show-stopping acts in October. St. Lucia hosts a superb jazz festival as well, usually at the beginning of May.
Easily Accessible
The easiest islands to reach via nonstop service include the Bahamas, Puerto Rico, the U.S. Virgin Islands, Jamaica, and the Dominican Republic.
Travel Effort
Islands that are off the beaten track require a connecting flight from one of the main Caribbean gateways like San Juan, St. Maarten, and Montego Bay.
Pack your hiking gear
If the beach gets to be too much, the interiors of many islands offer stellar hiking. Be sure to pack your boots, waterproof gear, and mosquito repellent so that you can take advantage of the action.
Adapt to island time
Caribbean islands have a distinctly slow pace of life that makes business hours a loose term and customer service whimsical. Once you get used to island time (and discard your mainland expectations), you’ll enjoy the local rhythm.
Check in early
However small it may be, arrive to the airport two hours before departure. Occasionally, flights are overbooked and, once planes are full, even passengers with confirmed seats are put on a later flight – around here, may mean days later!
Drive on the left
If renting a car is part of your holiday plan, remember that many Caribbean islands conform to the UK rule of driving on the left. Some of those include Antigua, Bahamas, Barbados, British Virgin Islands, Cayman Islands, and Jamaica.
