Obtain a passport if you do not have one. You will need to have legal documentation verifying your citizenship before traveling. A visitor's visa might also be needed to travel to some Caribbean countries. Details on tourist visas can be obtained by visiting the official website for the country you intend to visit.
Choose a location based on island size and your preference for vacation style. If you prefer a more commercial approach you should target one of the more popular Islands in the Greater Antilles such as Jamaica. If you prefer a smaller intimate locale, you can visit a few of the more popular islands in the Lesser Antilles, St. Lucia and Antigua are two good places to start.
Choose your particular type of vacation. Opting to take a cruise vacation will allow you to explore more than one island, and sometimes the opportunity to visit South American destinations lying on the Caribbean Sea. You can search for cruise options by visiting www.cruisesonly.com, where you can find specials on 4 night cruises based on which state you live in. If you would prefer the relaxing atmosphere of a resort, then choosing an all-inclusive vacation is the way to go. You can visit www.all-inclusive.com to receive quotes for all-inclusive vacation packages in some parts of the Caribbean and South America. There are only limited locations provided, however you can always select to work with the more traditional vacation planning websites such as www.expedia.com or www.orbitz.com. They might provide more variety in selecting a location.
Narrow down your vacation choice by the size of your group. For the most part cruises are a good choice for singles, couples or families. However, there are a few Caribbean resorts that might be more suitable for singles or couples: in Jamaica those resorts include Hedonism II and III and Royal Plantation by Sandals; in St. Lucia you can visit Ladera Resort and Spa; and in Antigua there is the Beach House of Galley Bay Resort.
Resorts catering exclusively for couples in Jamaica include Sandals Dunn's River Golf and Spa and Sandals Grand Ocho Rios.
Family friendly all-inclusive resorts in Jamaica include Holiday Inn Sunspree Resort Montego Bay and Beaches Negril Resort & Spa; in St. Lucia try Almond Morgan Bay Resort; and in Antigua St. James's Club is a promising choice. See additional resources below to book online and get more details on each of the adults-only, couples and all-inclusive family resorts.
If possible, have a list of available vacation times in order of preference. Great savings can be enjoyed if you are flexible on dates. The peak time for travel to the Caribbean is December to April and vacation packages are generally pricier during this time. Discount packages can be found from June through August.
