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Cities for Backpackers in Caribbean 

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  • 1

    Gros Islet

    4.5
    5 reviews

    Don't be fooled by the machete. This guy was really cool.

  • 2

    Castara

    5
    1 review

    Castara is a laid-back fishing village with a few guesthouses and cafes. The beach is set under a a rainforest-clad mountain. The town is a real fishing village which would subsist without tourism. The snorkeling is OK, but the beach is quite nice.

  • 3

    Petit St. Vincent

    5
    1 review

    Countless islands to explore while in St. Vincent.

  • 4

    Vinales

    4.5
    3 reviews

    Amazing valley with mogotes (interesting caves with water inside) & tobacco fields... I enjoyed spending 2 days 1 night here... Hotel los Jasminas is a very unique location to enjoy the nature...

  • 5

    Ocho Rios

    4.5
    45 reviews

    Ocho Rios is beautiful and the people are wonderful! The drive there from the airport was a little scary with the way our driver weaved in and out of oncoming traffic but once there it was wonderful!

  • 6

    Guanica

    4.5
    5 reviews

    This the town where the American invasion to the island started in 1898. This invasion led to Puerto Rico being acquired by the United States. Guánica is about 100 miles (160 km) from San Juan, the capital of Puerto Rico, and about 20 miles (30 km) west of Ponce, the second largest city of the island. Guánica is characterized by ...

  • 7

    Santo Domingo

    4.5
    32 reviews

    Awesome! Totally crazy huge city, about 8 million people live with in the city limits, great shopping and bargains on unique and local products, "El Duarte" is full if hidden shops and street venders. You could get a 3 piece suit custom made for about 30-50 US. Great food: the "chimi" sandwich is so good.. (Take all your shots before ...

  • 8

    Jayuya

    5
    16 reviews

    How can you not love "La Isla del encanto!" My homeland!!!

  • 9

    Las Galeras

    5
    2 reviews

    Las Galeras is a small, laid back beach town with a number of expat-run businesses--hotels and restaurants, mostly. It's also a great spot to explore gorgeous beaches, go hiking/diving/horseback riding, or do nothing at all but chill out in a hammock. I spent a week here and, honestly, never felt restless. If anything, I just wished I could have extended ...

  • 10

    La Vega

    5
    3 reviews
  • 11

    Montego Bay

    4.5
    64 reviews

    Beautiful resorts with friendly people...keep an eye on the sky at dusk when the weather comes over the mountains to the south.

  • 12

    Bridgetown

    4
    16 reviews

    The main shopping area cave shepherd top spot to shop while in bridgetown,this is where mainly tourist meet up for duty free shopping etc

  • 13

    Havana

    4.5
    79 reviews

    Havana, Cuba, isn't exactly the place our parents warned us about anymore. The people are extremely friendly and always willing to help. Havana is a magical place where you can easily find yourself getting lost in the music and a good few mojitos! If you ever get the chance to go, jump on it! I won my trip to Cuba ...

  • 14

    Cienfuegos

    4
    7 reviews

    A nice place to stop if you are driving to Trinidad, but it did not seen like a destination in itself. Some very impressive buildings here.

  • 15

    Mayaguez

    3.5
    3 reviews

    Not a great city, but a good jumping off place for lots of activities. Far enough west that it makes Rincon, Guanica, and other costal cities very accessible. There are great hikes and trips around Mayaguez - there is amazing jungle and rainforest there! Music and activities in the city center around Christmas time, but otherwise not much going on.

  • 16

    Matanzas

    3.5
    7 reviews

    It was a nice town. Bigger than most towns with alot of resort workers living there. Had nice streets and cool looking buildings in it.

  • 17

    Nassau

    4.5
    100 reviews

    Nassa is a great launching spot to see the islands. The waters are turquoise and so beautiful!

  • 18

    Vieques

    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.

  • 19

    Vieques Island

    4.5
    13 reviews

    This island is UNIQUE. small island. NOt very commercial. On a saturday night, people party on the road.Enjoyed it. Must do.

  • 20

    Punta Cana

    4.5
    76 reviews

    Excellent option to relax and enjoy the Caribbean Sea.

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