The Island: Jost Van Dyke, British Virgin Islands
The Bar: Soggy Dollar Bar
This 10-seat, five-hammock joint has seen its share of patrons drop anchor offshore (there's no dock) and splash their way in—giving new meaning to the term "swim-up bar." For those who don't want to make the return trip, the owners rent out four cottages and two rooms at their Sandcastle Hotel.
The Cocktail: Painkiller
An island favorite since it was invented here in the 1970s, the Painkiller is best described as a nutty piña colada on the rocks. It contains the bar's namesake Soggy Dollar dark rum, cream of coconut, pineapple juice, and orange juice, topped with nutmeg. soggydollar.com, $6.
The Island: Nevis
The Bar: Sunshine's Beach Bar & Grill
When Llewellyn Caines, a.k.a. Sunshine, first set up shop in 1987, his spot consisted of a few tree-stump tables and a grill under a palm tree. Five hurricanes later, not much has changed. Colorful flags and photos of visiting celebrities just add to the lovably ramshackle vibe.
The Cocktail: Killer Bee
Sunshine's signature drink, made with Belmont dark rum, fresh passion fruit, lime juice, simple syrup, a dash of bitters, and fresh grated nutmeg—in addition to a few secret ingredients—is like a fiery Hawaiian Punch. sunshinenevis.com, $5.
The Island: Puerto Rico
The Bar: Calypso Cafe & Tropical Bar
This open-air grill has been home base for Rincón's die-hard surf set since 1994. A large wooden patio with expansive views of Maria's Beach nearly doubles the bar's capacity when the lunch crowd clears and sunset-watchers pour in.
The Cocktail: Calypso Punch
Get your wave riding out of the way before toying with this potent, Bacardi 151–fueled recipe. Passion fruit nectar and guava, pineapple, and orange juices make it go down all too easily. home.coqui.net/calypso/bar.htm, $5.50.
The Island: St. John, U.S. Virgin Islands
The Bar: Woody's Seafood Saloon
Beyond being a favorite of Kenny Chesney's—the singer has sometimes performed, unannounced, in the bar—this Cruz Bay fish shack is a go-to option for happy hour deals ($1 drinks!) and some of the best conch fritters in the U.S. Virgin Islands. Be sure to claim one of the coveted sidewalk tables in front.
The Cocktail: Bushwacker
At last, a valid excuse to drink a booze milkshake: Cruzan light rum, Baileys, Kahlúa, amaretto, vodka, and cream of coconut, blended with ice and topped with nutmeg. woodysseafood.com, $6.