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The Caribbean includes more than 5,000 islands, reefs and cays. Among the most popular are Aruba, Jamaica, the Bahamas, Cayman Islands, Barbados and the U.S. Virgin Islands. The average temperatures in this climate zone fluctuate, with lows in the low 70s°F in winter and daytime highs in the mid-to-upper 80s in summer. The best time and weather to travel to the Caribbean largely depends on the traveler's preference for weather and travel conditions. Sailing yacht charters in the Caribbean involves the rental or hiring of a boat that may or may not be accompanied with a captain.

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