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San Juan, Puerto Rico
Explore colorful Old San Juan with its historic forts El Morro and San Cristóbal. Try mofongo and fresh seafood at La Mallorca. Stay near the port in Condado or Old Town for easy embarkation.
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Saint Thomas, U.S. Virgin Islands
Charlotte Amalie is a duty-free shopping haven with stunning harbor views. Take the aerial tram to Paradise Point for panoramic vistas. Magens Bay is one of the most beautiful beaches in the Caribbean.
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Philipsburg, Sint Maarten (Dutch part)
Split between French and Dutch sides, St. Maarten offers two cultures in one island. The Dutch side features casinos, beaches, and lively Front Street shopping. Don't miss the famous plane-spotting beach at Maho Bay.
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Basseterre, Saint Kitts and Nevis
The charming capital of St. Kitts features Georgian architecture and Brimstone Hill Fortress, a UNESCO World Heritage Site. Zip-line through the rainforest or relax on pristine black-sand beaches. Sample local rum punch and fresh conch fritters at the Circus area.
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Saint John's, Antigua and Barbuda
Antigua boasts 365 beaches — one for every day of the year. Visit Nelson's Dockyard, a beautifully restored Georgian-era naval base and UNESCO site. The local market near Heritage Quay is perfect for fresh tropical fruit and handmade crafts.
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Bridgetown, Barbados
Barbados blends British heritage with vibrant Caribbean culture in its UNESCO-listed capital Bridgetown. Explore the rum distilleries, including the famous Mount Gay Rum tour. Oistins Fish Fry on Friday nights is an unmissable local culinary experience.