Best time of the year: I love getting away from the cold months so I would say anytime from February to April. Just be mindful this may be hurricane season as well.
Food: Everything you can imagine
Activities: Island life is super chilled; beach, food and partying. Island hoping is very cost affected; just take a boat. Most people would make day trips to nearby island. Speak to your hotel concierge and they can give you the run down on island hoping. Enjoy