Jamaica is a crowd-pleaser—many families return to the same hotel (and sometimes, the same suite!) religiously during the holidays. That’s why pre-Christmas and New Year’s is the best time to go. The best hotels, including Jamaica Inn and Round Hill , almost always have much more availability in the first few weeks of November than in December and January. No matter where on the island you stay (from the resort-heavy Ocho Rios and Montego Bay to hip Port Antonio), there will be beautiful beaches to enjoy , wonderful live music, and plenty of Red Stripe beer, which unsurprisingly pairs fantastically with conch fritters .