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Caribbean Sailing Vacations

Get ready to hoist the sails on a Caribbean sailing adventure. Whether you are island hopping or gliding along the coast, with 8 sailing vacation packages lasting from 7 days up to 16 days, we have made finding the right sailboat tour a breeze! Click here to see all sailing trips.

8 Caribbean sailing trips with 21 reviews

Caribbean Sailing Tour Reviews

  • "Yes... we knew we were going to have to buy food for meals but the way in which this..."
    Sailing the British Virgin Islands – Tortola to Tortola
  • "Exceeded my dreams! Happy highlights include hammock relaxing Turtle release, tropical..."
    Sailing Cuba
  • "This was an amazing trip. I loved every minute of it! Lovely balance of beach, sailing..."
    Sailing Cuba - South Coast Explorer