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Here at Mainstay Sailing, we make it our mission to ensure you have the best day of your vacation.

We will build a tailor made charter that’s flexible to your group’s needs while still holding our Mainstay personal touch. We ensure, every time, no matter what age, that everyone onboard has the maximum amount of fun

We accommodate families with ease…we keep the kids entertained with a plethora of water toys at their disposal including a kneeboard, tube, fishing gear, lobster snares (when in season) even a splash pool for the toddlers in the cockpit!

We have entertained  weddings, renewing of the vows, engagements, corporate groups, disabled groups, kids birthdays, staff parties, hen nights (we even installed a dance pole for that one -mainly for our entertainment!). Just let us offer a few options to make your day and we will deliver what you expect…and so much more

100% 5 star reviews and tripadvisor certificate of excellence

DAY sail suggestions 9:30am – 4:30pm
With up to 20 people aboard our 45′ catamaran. Explore the north sound and snorkel the seven mile long barrier reef that extands from West Bay to Rum Point. Swim at the famous Stingray City and snorkel the other excellent underwater sites which, even on windy days, are sheltered from the outside sea.

Select your catering menu from one of our catering partners or go ashore to Rum Point or Kaibo Restaurant on the eastern side of north sound. Or simply choose a self provisioning system which gives you the flexibility of bringing whatever you like. After lunch we set sail again through the tranquil Booby Cay and then to find some more snorkeling sites on the reef. For the more adventurous we could sail outside of the reef and try some fishing.

If the conditions are right we could sail offshore and around the point of West Bay to Seven Mile Beach (approximately 2 and a half hours), to explore some more superb reef stops such as Devil’s Grotto or Cheeseburger Reef, near George Town. We have a towable for the thrill-seekers and can arrange kayaks, wave runners amd other water toys at the usual market rates. When on the west side, at the end of the day we can drop you off by dinghy anywhere along Seven Mile Beach. It is your day out so we make the suggestions and you make the choices.

New for day-sail guests… Dolphin and stingray safari. What a day !

HALF DAY sail 9:00am – 12:30pm or 2pm – 5.30pm (flexible)
With up to 20 people aboard our 45′ catamaran. The expansive North Sound is five minutes away from our dock at the Yacht Club and offers a sheltered playground for many water sports activities, including reef snorkeling, swimming with the stingrays or just relaxing aboard your own 45′ yacht. Imagine the photo opportunities. If you like, we will have enough time to head out offshore for a sample of deep blue sailing.

OVERNIGHT Charter 10:00am – 10:00am
6 persons max. A real adventure and plenty of time to do it all. Sail offshore to SMB, with some snorkeling along the way. A sunset sail or an evening sail with a bright moon is one of those magical experiences that you will not soon forget. Dinner can be aboard or ashore as we can anchor close to your choice of beachfront restaurant and take the dinghy ashore.

North Sound restaurants can include Kaibo, Rum Point, Calypso Grill, Morgans Harbour and restaurants at the impressive Camana Bay.

On Seven Mile Beach; Yoshi Sushi, Hemmingways, The Reef Grill, The Lobster Pot and Harveys.

“Cayman’s finest charter catamaran” -Jan Lederman (thanks!)

The Caribbean is one of the world’s most popular charter destinations and understandably so. The images readily pop into your mind’s eye, of warm blue seas, gleaming coral-sand beaches, gentle trade winds and you, lying on the deck of your own private yacht. Mainstay Sailing can take you there

To find us you need to get to a jewel of an island that needs little introduction – Grand Cayman.

Create Your Own Adventures

We provide a flexible private charter service with a personal touch. Whether you require a day sail or a two night Cayman Explorer, we will do our best to shape an itinerary to suit you.

Small groups are our specialty, maintaining guest numbers at around twenty for day sails and up to six for live aboard charters. We offer the suggestions and you make the choices. After all, the time is yours, so we can make it as active or relaxing as you like.

‘Enchantress’ is a kid-friendly zone and we know how to entertain them all. We have them too!

Our captains are certified RYA Yachtmasters so your safety is well assured.

Onboard snorkel gear, some light fishing equipment, kayak, dinghy and inflatable are all available for your use.

Your time aboard will be ‘the highlight of your vacation’, as we often hear.

Recommended by the Holidaysplease Cayman Islands holidays guide
Also see comments on Trip Advisor for Mainstay Sailing, Stingray City.
Listed on the Cayman Department of Tourism site.