sailing in cayman
Cayman Activities
Kiteboarding at sunset



The Cayman Islands is blessed with a rich sailing heritage. This heritage continues with a strong recreational sailing community. The Cayman Islands Sailing Club is the National Authority for sailing in the Cayman Islands and affiliated to the ISAF and the Olympic movement.

There is a strong commitment to developing the sport in the Cayman Islands, and the Club maintains a strong school and youth training programme. Families are especially welcome, with Saturday sailing classes for children. If you are a really keen sailor, interested in taking up the sport or just want to join our social activities you'll fit in straight away. The CISC is happy to provide lessons or recreational sailing on your Cayman Islands tour.

If you are interested in taking a day sail, sunset sail or a romantic dinner cruise, there are various charter operators in Cayman that can accommodate private charter or scheduled service. There is no better way to experience the dramatic Cayman Sunset than under sail.


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Hints & Tips

  • Sailing is part of Cayman's history and culture - be sure to see a Catboat while you're here.
  • Local watersports companies offer sunset sails on pirate ships or catamarans.
  • Regattas are held throughout the year, check the calendar of events for races.


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Xanax Sailing Cruises
Xanax Cruises gives you the diversity you're looking for in sailing and snorkelling. The closest to nature you'll get in the sunny Caribbean.
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Sail Cayman Ltd.
SailCayman Ltd. is your first choice in sailing, powerboating and snorkeling on Grand Cayman. We offer half-day and full day excursions, a fantastic sunset cruise and private charter service with...
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Mainstay Sailing
Welcome aboard our superb 45 foot bluewater cruising catamaran. An award winning design with 4 cabins and en-suites. Available for private charters from a sunset cruise to a week long Cuba explorer.
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Red Sail Sports
Tel: 345-623-5965
Fax: 345-945-5808
Red Sail Sports is dedicated to helping people have fun. We understand that while you're on vacation, you want to make the most of it.