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Best History & Culture Vacations - Caribbean

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1San Juan, Puerto Rico
The capital city of Puerto Rico and by some measures the oldest city in the United States, San Juan was established nearly five centuries ago by Spanish settlers. Old San Juan continues the tradition of the colonial town, where the historic fort of El Morro and mansion of La Fortaleza still stand.
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    • Adventure
      San Juan
      Aquatic thrills abound in Puerto Rico, from world-class surfing at Rincon where the swells reach 35 feet to relaxed scuba diving, particularly around Mona Island, Desecheo Island and Vieques. On terra firma, the tropical terrain yields prime hiking, horseback riding and rock climbing opportunities.
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2Dominican Republic
The New World starts here: The first cathedral, university and hospital in the Americas opened in Santo Domingo, on the Dominican Republic's south-central coast. Numerous city sights pay tribute to the isle's rich history, including the Castle of Columbus and the museums of the Cultural Plaza.
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    • Family Fun
      Dominican Republic
      Experience the Caribbean and get back to nature in the Dominican Republic. Families can swim with sea lions, dolphins--or sharks for the truly adventurous--at Ocean World, or go into the tropical island jungle on a Jeep safari.
    • Beaches & Sun
      Dominican Republic
      Distinguished by long stretches of glowing white sand and gorgeous blue water, Dominican beaches rank among the best in the world. From Puerto Plata to Punta Cana to Barahona, these beaches cater to bar lovers, sunbathers, jet skiers and scuba divers.
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3Jamaica
Island heritage overflows in Jamaica, from the former seaside banana capital of Port Antonio to reggae legend Bob Marley's former Kingston home. Even natural attractions come with cool history: The age of stalagmite-filled Green Grotto Cave at Runaway Bay is estimated at 500,000 years.
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    • Family Fun
      Jamaica
      Whether petting crocodiles, feeding hummingbirds or bobbing down the Rio Grande on a bamboo raft as calypso bands play bankside, families can have a wonderfully wild time in laid-back Jamaica. Adventurous souls can hike by waterfalls and coffee plantations, clamber up Dunn's River Falls, or splash and sun on glistening beaches.
    • Romance
      Jamaica
      Looking for a destination where the two of you can tempt each other without the distractions of tours, tourist traps and too many other travelers? Couples can enjoy long stretches of beautiful beaches and waterfalls, joyous rhythms of reggae and the natural beauty of a tropical island.
    • Beaches & Sun
      Jamaica
      Blessed with miles of stunning natural coastline, Jamaica is a paradise for beach-lovers. Among the island's best offerings are Negril's Seven Mile Beach--rife with great snorkeling and diving, Treasure Beach on the South Coast and Doctor's Cave Beach in Montego Bay, which has sand that looks like sugar.
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4Barbados
Jacobean and Georgian buildings built from pink and white coral, Gothic churches and pirate castles with ornate ceilings dot the Barbados landscape. Two of the must-see buildings are stately St. Nicholas Abbey in St. Peter and the sugar plantation Drax Hall in St. George, both dating to the 1650s.
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    • Beaches & Sun
      Barbados
      Turquoise waters, fine and soft sands and picturesque rows of palm trees make the beaches of Barbados a true pleasure. Stick to the south and southwest coasts for calm waters and good swimming; for a surfing thrill, don't miss the massive, competition-caliber waves off the south and east coasts.
    • Romance
      Barbados
      Romance is in the air on this lush West Indian island in the Caribbean. Your getaway to Barbados can include a lazy day on the beach, afternoon tea-British style, listening to the pulsating sounds of reggae or calypso, sipping rum and chilling out under a star-studded Bajan sky.
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5Antigua, Antigua and Barbuda
In the capital, St. John's, the baroque towers of an 1845 cathedral dominate the skyline; an 18th-century courthouse holds a museum of island artifacts. Antigua's historical district unfolds around English Harbour, the world's only Georgian dockyard, and Shirley Heights, a colonial observation post.
  • Also recommended for:
    • Romance
      Antigua
      Behind a nearly unbroken coral reef, Antigua basks in balmy Caribbean breezes. With 365 beaches, one for every day of the year, secluded romantic strolls under the palm fronds are guaranteed. Shirley Heights offers breathtaking views out over English Harbour.
    • Beaches & Sun
      Antigua
      With as many beaches as there are days in the year, Antigua and Barbuda make quite a splash. The northwest coast jostles with beach resorts, while harder to find, secluded spots dot the south and southwest coasts. Amazing pink and white sand beaches confetti the family-popular southeast coast.
    • Family Fun
      Antigua
      From the world-famous beaches of St. John's to the megaliths of Greencastle Hill, Antigua offers families both adventure and relaxation. Swim in clear waters, build sand castles and explore ancient geological formations, petroglyphs, nature trails and plantation ruins.
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