Consider who will be taking the trip. Different places cater to different demographics. If looking for a romantic getaway or honeymoon, Aruba is considered one of the most romantic. If this is a family vacation involving children, try Paradise Island in the Bahamas. If partying with friends on spring break, try Jamaica or Nassau, Bahamas which have exciting nightlife.
Choose between rest and relaxation, excitement or something in between. For a vacation full of sports and adventure, consider Anse Chastanet Resort on St. Lucia which has some of the best snorkeling in the world. For surfing, try Barbados. Visit Cocobay in Antigua for lazy days full of dozing in a hammock.
Consider personal interests. Music buffs may visit Jamaica to see Bob Marley's grave. Others may be interested in colonial architecture. If gambling is a personal hobby, then stay at the Atlantis Resort on Paradise Island in the Bahamas.
Determine what level of escapism is ideal. If spending a week at a spa with friends, consider the Malliouhana Hotel & Spa in Anguilla. For a week long trip without seeing another soul, consider renting an entire island if your budget allows for such an extravagance.
