The Caribbean rarely fails to deliver for tourists in search of some budget, all-inclusive, winter sun and fun, but options can be limited for those who want to maintain a modicum of style while in the tropics. Head to Jamaica, St. Maarten or Saint Vincent, for example, and the buzz is undeniable, but the landscape of tiki torches, 2-for-1 happy hour shots and bare, sunburned torsos working up a sweat on the dance floor will strike a jarring chord with visitors who want to dress up, sample the finer things in life, and plug into the local scene. Luckily, a handful of islands either eschew the package tourism model entirely, or stand out for their cosmopolitan vibe.
Just a short flight from the U.S., Puerto Rico enjoys a deserved reputation as the party capital of the Caribbean. The island that gave the world salsa and merengue serves up a relentless menu of nightlife options, while the pounding rhythms of reggaeton provide the soundtrack for a population that is youthful, cosmopolitan, and never shy about dressing up and hitting the town.
Admittedly, on the days the cruise ships are in port, San Juan disappears beneath a morass of visitors, but after dark the city comes alive. Head to Old San Juan for authentic, stylish bars and taverns in which to sample vintage rum and exquisite local cigar, or try the cocktail bars of the top hotel lobbies for an early evening loosener surrounded by a crowd that could have dropped in straight from New York or Miami. The Art Deco town of Ponce provides an elegant alternative to the capital, while a day trip to the offshore islands of Vieques and Culebra accesses tropical island relaxation at its most effortless. The French island of Guadeloupe is famously shaped like a butterfly, but it stings like a bee. Less self-conscious and expensive than its sister-island St. Barts, Guadeloupe nevertheless nurtures a young, hip population with close ties to metropolitan France. 
Above all, locals like to dress up in the latest fashions and hit the clubs in order to pay homage to the island’s dominant rhythm, Zouk. Visitors can enjoy a lively nightclub scene around the marina in Le Gosier, or along the stunning south coast resorts.The language barrier is arguably the greatest impediment to Guadeloupe’s graduation to a destination on a par with Santo Domingo or Puerto Rico. While the official language is French, true Guadeloupeans speak a distinct Creole instead. Nevertheless, with its fine gourmet restaurants, chic clubs and fiercely protected identity, this is as close as a visitor can get to Parisian finesse without crossing the Atlantic.
Not many tourists make the journey down south as far as Curacao, and those that do tend to opt for the all-inclusive, timeshare-saturated Aruba instead. However, Curacao amply rewards those visitors who trust it with their judgment. Not only is the capital Willemsted one of the prettiest towns in the Caribbean, with the UNESCO World Heritage architecture of Punda a particular delight, but simply hanging out along the dockside Otrabanda district after dark also offers perspective onto one of the most distinct cultures in the Caribbean. Although the island has a large Dutch population, ensuring a consistent exchange of ideas with Europe, Curacao’s predominant culture is Papiamento Creole-speaking, with a tendency to dress up and party hard, and of course, if you have access to a private island in the area, any language will do.
The nightclubs and bars around Willemstad are always lively, but the island reserves its greatest flourish for Sunday night, when locals pour outside to finish the week with a blast, particularly around the cocktail bars along Mambo Beach.
Obviously, part of the appeal of the Caribbean is a typically unpretentious outlook and concept of time that tends towards nostalgia rather than trend-watching. However, visitors who want to kick it back in the trade winds without necessarily sacrificing their pursuit of style can focus on a handful of islands that ooze character.
