caribbean vacation in cayman
Cayman Activities
Kiteboarding at sunset


cayman islands sailing
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 Island 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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Mainstay Sailing
Tel: 345-927-1127
Private sailing charters in style. A superb 45 foot blue water catamaran offering flexible sailing charters from a sunset cruise to a 7 day Cuba sail.
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Red Sail Sports
Tel: 345-623-5965
Fax: 345-945-5808
Red Sail Sports is the only premier operation delivering full-service dive and watersports services island-wide. Dive spectacular walls, reefs and the wreck of the Kittiwake, or choose to sail aboard one of our 65ft catamarans. Trust our 27 years of
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Boating in the Cayman Islands have been heightened to a fine art by CIBR - Cayman Islands Boat Rentals. The sense of freedom from owning your boat in the Cayman Islands can now be achieved by every visitor wanting to explore our azure waters.
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Sail Cayman Ltd.
Private sailing and powerboat charters to Stingray City, Snorkeling, Mini Sandbar, Rumpoint, Kaibo, Starfish Beach. Choose from 2 outfitted sailing yachts, twin outboard power boat or Rigid Inflatable Boat.

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.