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Cities for Nightlife Lovers in Caribbean 

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  • 1

    San Juan

    Puerto Rico
    4.5
    103 reviews

    Skip the party at the beach and head into the center of San Juan, which is technically the oldest city under U.S. control, for an incredible spring break. The historic Old San Juan is chock-full of colorful houses, landmark attractions, and stately museums, plus plenty of restaurants serving traditional Puerto Rican Creole cooking. At night, dig into the local music ...

  • 2

    Santiago de Cuba

    Cuba
    4.5
    15 reviews

    Santiago de Cuba is the second-largest city in the country and birthplace of the Cuban Revolution. This where traditional dancing, el Son, got its start and where a big majority of the Afro-Cuban community resides. An evidence of that are the higher numbers of Santeria initiates, all wearing white clothing. Some of Cuba's most famous musicians, including Compay Segundo, Ibrahim ...

  • 3

    Worthing

    Barbados
    4.5
    2 reviews

    Great area to stay in Barbados that's easy to get around from, walking distance to beautiful beaches,shopping, A huge supermarket, beach bars...even a sports bar, low end to high end restaurants and a new little outside shopping area with a place for a good cup of coffee...not easy to find on Barbados...

  • 4

    Shoal Bay Village

    Anguilla
    5
    2 reviews

    I don't know how else to describe AniVillas other than, SPECTACULARLY AMAZING!

  • 5

    Petit St. Vincent

    St. Vincent and the Grenadines
    5
    1 review

    Countless islands to explore while in St. Vincent.

  • 6

    Santa Clara

    Cuba
    4
    6 reviews

    Home to the third-largest university in the country, Santa Clara is full of young people. It's also a bit gritty. Local life revolves around Parque Vidal, where the youth gathers in what becomes a lively Cuban scene. Due to the large number of students, Santa Clara has a vibrant and edgy nightlife. One example is the bohemian terrace bar Peña ...

  • 7

    Negril

    Jamaica
    4.5
    42 reviews

    Nice village on the coast with bars, shops and many hotels near by. All the locals are friendly and appreciate you spending your tourist cash with them.

  • 8

    Kingston

    Jamaica
    4.5
    24 reviews

    link me up......I know where to find the best chill spot in Kingston Jamaica

  • 9

    Castries

    St. Lucia
    3.5
    10 reviews

    A vibrant city with a cute, though touristy market and fun port. The restaurants offer authentic Caribbean food and the people are great.

  • 10

    La Parguera

    Puerto Rico
    5
    9 reviews

    Great place to spend the whole day and night. Experience great clear blue waters great for snorkeling, and at night experience the magical water the lights up at night as you splash it. great fresh sea food and pina coladas as well

  • 11

    Mustique

    St. Vincent and the Grenadines
    5
    2 reviews

    This private island is the choice retreat of the Royal family, most recently Duke and Duchess of Cambridge. The 3 x 1.5 mile island is renowned for its wild 70s hedonism, a legacy continued at world-famous Basil’s Bar. Cotton House, the sole full-service hotel, boasts an impressive guest book of celebrity signatures. 17 suites span 13 acres, neighbouring mansions of ...

  • 12

    Montego Bay

    Jamaica
    4.5
    64 reviews

    Largest city on the island of Jamaica. If you stay in Montego Bay you would only be about 10 minutes from the airport so it is really convenient. The beaches are good and the nightlife is even better! The city has what is called "The Hip Strip" which is all bars and nightclubs that cater to the tourists. It is ...

  • 13

    Gustavia

    St. Barthelemy
    4.5
    8 reviews

    It's gotten more crowded and the number of businesses have doubled over the past few years, but St Jean is as lovely as ever. It's also a great resource if you're staying in a villa in Point Milou or Lorient, because it's much closer than Gustavia and has all of the things you might need.

  • 14

    Red Hook

    US Virgin Islands
    4.5
    7 reviews

    About two minutes from Sea~N~Islands, VRBO #496862. Red Hook is a great collection of shops, restaurants, bars and more. Urgent care, pharmacy, convenience store, gas station and ferry service to St. John and beyond. Free parking available. Enjoy popular spots like Duffy's Love Shack, Fish Tails, Pesce, The Cellar, XO Bistro, Island Time Pub and more!

  • 15

    Cabarete

    Dominican Republic
    4.5
    18 reviews

    Cabarete is a great beach town with five different beaches, good eats, a lively bar scene, and tons of expats and vacationers who flock to the town year-round. There are lots of hotels to choose from, though if you're looking for an all-inclusive the pickings are slim. The main reason people to Cabarete are the windsports--this happens to be one ...

  • 16

    Las Terrenas

    Dominican Republic
    4.5
    7 reviews

    Once a sleepy fishing village, Las Terrenas is now a full-on beach town with tons of French and Italian expats, many of whom run hotels/restaurants/bars. The focus here is on beach-time, eating, and drinking though there are plenty of nearby excursions, like kiteboarding, diving, and horseback riding. All to say--perfect!

  • 17

    Nassau

    The Bahamas
    4.5
    100 reviews

    I'm talking about the beach at Atlantis. It's definitely worth the taxi ride (not boat ride to view it). The beach really is a giant long stretch of paradise with clean soft sand and clean blue water. You can ride jet skis there and the banana boats are super fun. If you go around the front of the Atlantis hotel, ...

  • 18

    Ocho Rios

    Jamaica
    4.5
    46 reviews

    Stopped here from a cruise, but a great place to visit nonetheless even if we were just there for a day. You should definitely have their jerk chicken barbeque. If going in the market, just beware of aggressive vendors. Learn to bargain and say no. hehe

  • 19

    Vieques

    Puerto Rico
    4.5
    11 reviews

    Vieques is small and beautiful, mostly water activities to do, but also shopping and spas. People are friendly enough, and the food is delicious but a little pricey. Great for a family, maybe not the best for backpacking.

  • 20

    Havana

    Cuba
    4.5
    79 reviews

    Me and Ernest Miller Hemingway in El Froridita bar!

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