Cayman Islands Sailing

Enjoy Cayman Islands sailing with a Grand Cayman sailing tour / sailboat charter. Great Caribbean sailing on half/full day sail, sunset cruise or learn to sail

Sail the Blue Seas of the Cayman Islands – Tours and Charters

Enjoy Cayman Islands sailing with a Grand Cayman sailing tour / sailboat charter. Great Caribbean sailing on half/full day sail, sunset cruise or learn to sail


Caribbean Sailing provides travelers with the unique opportunity to experience the islands from a different perspective. See Grand Cayman’s Rum Point and North Sound from sea and you’ll better appreciate it’s gorgeous aqua blue waters – and then there are the sunsets. Sit back, relax and enjoy the sun’s rays and Caribbean breeze while sailing to Stingray City, Starfish Point or around the island. Of course, you’ll always have clear warm waters at your back door to enjoy swimming, snorkeling and water sports. Enjoy Grand Cayman sailing with local tour / sailboat operators who know the waters – The best Cayman Islands sailing can be found with the operators below.

Enjoy Cayman Islands sailing with a Grand Cayman sailing tour / sailboat charter. Great Caribbean sailing on half/full day sail, sunset cruise or learn to sail




To sail the Cayman Islands, these local Tour/Sailboat Operators will take good care of you (Click on a Tour Operator name below for more details):

Mainstay Sailing (aboard the Enchantress – A Leopard 45ft sailing catamaran):

  • Half Day Sail – With 2-3 stops
  • Full Day Sail
  • Sunset Cruise
  • Live Aboard Sailing (From 1 night to 1 week)

Blue Sky Sailing (aboard Splendour in the Wind – A 47′ Beneteau Oceanis 473 Sailing Boat):

  • Half Day Private Charter (Morning or Afternoon) – Stingray City plus Snorkel stop
    • Optional – Kids Pirate Cruise Add-On
  • Full Day Private Charter – Stingray City plus Snorkel stop, lunch stop and Starfish Point
    • Optional – Kids Pirate Cruise Add-On
  • Sunset Charter
  • Full Moon Charter
  • Custom Sailing Charters also Available

Red Sail Sports (aboard the Ppalu, Poseidon, Cayman or Calypso catamarans):

  • Stingray City Snorkel Sail (Stingray City plus Snorkel stop)
  • Sunset Sail
  • Happy Hour Cruise (From Morrit’s Resort)

Sail With Friends Cayman (aboard a 38 foot Lagoon Catamaran):

  • Half Day Charter with 3 stops
  • Full Day Charter with 4-5 stops
  • Cruise Ship Special
  • Sunset Cruise

Surfside Charters

  • Sailing aboard Bamboozle (52 foot Sailing Catamaran):
    • Private Custom Sailing Charters could include Snorkeling, Paddle Boarding, Fishing, Stingray City, Starfish Point, Sunset Champagne Cruises and more

Enjoy Cayman Islands sailing with a Grand Cayman sailing tour / sailboat charter. Great Caribbean sailing on half/full day sail, sunset cruise or learn to sail


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