Sailing Charters in Grand Cayman

Blue Sky Sailing offers private charters aboard their 47′ vessel 'Splendour in the Wind', which is a fully equipped, ocean-going sailing yacht. Choose from full-day, half-day, Bio Bay or sunset sails. Trips include snorkel stops at Stingray City and other reefs and can be fully customised to suit your schedule, budget and preferences.

Cayman Islands Sailing Charters will ferry you to all of Cayman's most famous attractions, along with all of its hidden gems! Experience their 37' catamaran and try your hand at snorkelling, paddleboarding and fishing. Head out for the day with a group of up to 20 for anything from 2 to 8 hours.

Mainstay Sailing offers tailor made private charters that are flexible and will fit your group's needs. Families are accommodated with ease, regardless of your age, and there are a plethora of water toys at your disposal, even a splash pool for toddlers in the cockpit! With 100% 5 star reviews on Tripadvisor, you will see why they have earned their Certificate of Excellence.

Paradise Pontoons offers a unique experience with an on-board water slide! Conveniently, Paradise Pontoons picks up and drops off along Seven Mile Beach, meaning they're well located near all the beachfront hotels. Groups of 8, if all are adults, or 10, if there are children, can fit on their boat, and all will appreciate the towels and water, along with the on-board WiFi.

Ray Dayz is the perfect option when you want a completely customisable day on the water. Choose from a 23' or 32' boat, depending on the size of your party, and choose to visit Stingray City or Starfish Point, get snorkelling or watch sunrises and sunsets, experience bioluminescence or even deep-sea fishing.

Helpfully, White Sand Water Sports depart from both Camana Bay and Kaibo, making it very easy for those staying in North Side to visit Stingray City. They also have a party boat equipped with a water slide.