Iggies Beach Bar & Grill
St. Thomas, U.S. Virgin Islands
Let the kids play beach volleyball or snorkel in the shallows while you kick back with cocktails at this classic spot at the Bolongo Bay Beach Resort, an all-inclusive near the capital, Charlotte Amalie. Cruise passengers often throng the place during the day, but don’t let that keep you away. There’s live music and a local vibe every night, plus hammocks on the beach and VooDoo Juice (a rum concoction) served in buckets. Go on a Wednesday for Carnival Night: steel drums, West Indian food at the buffet, and fire-walkers performing on a stage in the sand.
7150 Bolongo; iggiesbeachbar.com
Wreck Bar & Grill
The favorite road trip on Grand Cayman must be the drive to Rum Point, a remote spit of beach across the sound from George Town. The name probably came from the rum barrels that washed ashore here during buccaneer times. Today Wreck Bar is the heart of the action, and the thing to drink is the Mudslide—a frozen blend of vodka, Bailey’s Irish Cream and Kahlúa. Sip one while you relax at a colorful picnic table on the sand, or get horizontal in a hammock slung under the casuarina trees. Sunday afternoons bring the biggest crowds, including a flotilla of party boats anchored offshore.
Rum Point Dr.; rumpointclub.com