Sailing Charters

Sailing Charters in Grand Cayman

Discover the incredible turquoise water, barrier reef and North Sound on an unforgettable sailing tour. Snorkel the reefs, visit Stingray City and more!

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Last updated 16 January, 2024
Sailing trip on the North Sound with Cayman Islands Sailing Charters

Of course, one of Cayman's biggest attractions is its proximity to the ocean. To cater to visitors' and locals' hunger to get out on the waves, there are many sailing charters operating on Grand Cayman. Depending on what type of experience you're looking for – family-friendly, luxury or adventurous – the below charters would be happy to cater to your needs.

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.

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Cayman Islands Sailing Charters

Full Day Sailing Charter

Recommended for all ages

Up to 8 hours
From US$1250
Free Video
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Cayman Islands Sailing Charters

Half Day Sailing Charter

Recommended for all ages

Up to 4 hours
From US$750

Cayman Luxury Charters has three beautiful boat options to choose from, for groups of 12, 13 or 15. Whilst on board, you can go snorkelling, reef fishing and jet skiing! You can also help yourself to complimentary waters and sodas.

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.

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.

Y-Knot Private Charters has 30 years experience chartering locals and visitors alike around Grand Cayman. Their three boats, for 8, 10 or 15 people, mean you can get the perfect boat for your sized group. Don't forget, you can also include seaside dining stops as part of your adventure.

Blue Sky Sailing offers private charters aboard their 47′ sailing yacht. Choose from full-day, half-day, or sunset sails.


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