Top Single Travel Destinations in the Caribbean

Planning a solo trip to the Caribbean or a getaway with a group of single friends? It may not be all about the hookups, but you’ll likely want a destination that offers some great nightlife, planned activities, and some opportunities to interact with other singles. Here’s my picks for the top single-travel destinations in the Caribbean:


San Juan, Puerto Rico

As in New York and some other big cities, the nightlife in San Juan doesn’t get started until later in the evening — a late dinner typically followed with drinks and dancing at a local nightclub pounding out a diverse mix of salsa and Latin music, rock, and the latest trends in club music. Bar hopping is an option in historic Old San Juan, and many of the city’s big hotels have casinos, dance clubs, and trendy bars, as well. Whether you’re interested in meeting locals or fellow tourists, gay or straight, you can find it in the unofficial capital city of the Caribbean.

Turks & Caicos

The Club Med Turkoise resort in Turks & Caicos isn’t strictly a singles resort but is adults-only and does tend to attract a lot of single travelers. Plus, fast-growing Providenciales has a nice selection of beach bars, sports bars, and a BET Soundstage, mostly in the Grace Bay area.

Grand Cayman

Frequent cruise-ship stops help pump up the singles scene on Grand Cayman in the Cayman Islands, which also wins points for being a safe and clean destination. The bars do tend to close a bit early for some tastes, but you can find great dancing and ever-changing entertainment at O Bar or Next Level and a casual beach-bar atmosphere at Calico Jack’s, among others.



Singles will find a good party scene in Montego Bay, and the Margaritaville bar — with its multiple levels and elaborate water-play area — is especially popular. Jamaica also is home to a number of all-inclusive resorts, many of which are adults-only — including the famous Hedonism resorts. Hedonism’s reputation may be a bit raunchier than reality, but this is the one resort in the Caribbean that truly caters to singles, and day-passes allow even those not staying at the resort to join in the fun of nude volleyball, naked twister, and other delights.


The Dominican Republic

The Dominican Republic is home to the world’s greatest concentration of all-inclusive resorts, perfect for an inexpensive singles getaway. Unlimited drinking, dining, activities, and access to nightlife provides plenty of interaction with other singles. Punta Cana is a good choice for a laid-back beach vacation and also is host to the annual Jewish Singles Week.



The LaSource resort in Grenada goes the extra mile for solo travelers. First, the resort refuses to sock solo guests with extra room rates. Plus, the staff hosts nightly cocktail hours where singles can mingle, a hosted singles table each night at the Great House Restaurant or Oscar’s Beach Bar, and organized sports activities. The people of Grenada are friendly and the island is considered a safe destination for solo travelers. You can enjoy great diving and rainforest hikes, as well as daytrips to nearby Carriacou.