This lively bar on Jamaica's western tip is a nonstop show—from locals performing aerial acrobatic dives from even higher cliffs, to tourists psyching up to take their own leaps from one of five rocky platforms descending from the bar's clifftop aerie (ignoring red warning signs detailing the risks). Consider bringing some extra cash for offering the local divers a tip. And don't forget to watch for that glorious sunset.
Signature Drink: Grab a local beer, because is there anything better on a hot Jamaican day than a cold bottle of Red Stripe? Rum drinkers go for Rick's Famous Planter's Punch, a sweet, classic blend of rum and fruit juices that is, as the bar menu reminds, "a way of life here, mon."
Stay: Just down the coast, the mood goes from party to romance at The Caves, where 12 thatched-roof cottages dot the limestone cliffs. All-inclusive rates start at $470; 876/957-0270. —Tracey Minkin