Mainstay Sailing

07/09/2025

Mainstay moments in paradise 💙🩵💙

07/09/2025

Enjoy a sunset aqua pad ride with us 🌅🌊

Our giant floating aqua pad is just one of our water toys, and it’s included on any charter trip. Trust us, both kids and adults can’t get enough of it!

Add a little extra fun to your Cayman adventure… because memories are made out at sea ⚓️

31/08/2025

Cheers to Mainstay Sailing!

Did you know both of our boats are BYOB? That means you can stock up on your favorites and fill your boots for the perfect day at sea 🥂

Good vibes, great company, and Cayman’s most beautiful views - that’s what it’s all about ⚓️

24/08/2025

Is swimming with stingrays on your bucket list?

If so, you’re in the right place! Our charters take you straight to the world-famous Stingray City Sandbar, a truly magical spot where crystal-clear blue waters meet some of Cayman’s friendliest residents 🌊

Here, the stingrays glide right up to you in the shallows, and with Kai’s help you can even hold one and give it a kiss for good luck 😄

Are you ready to check this one off the list? ✔️

24/08/2025

Meet Kai, one of the friendly faces you’ll find on board with us 🌊⚓️

👉 He started working part-time with us at just 16 during summer and Christmas breaks, and has been full-time since last December

👉 Kai holds his RYA Yachtmaster Offshore Certificate and even spent a year sailing around the Caribbean with his dad as a kid

👉 When he’s not out on charter, you’ll find him free-diving down to 100 ft and chasing his passion for spearfishing (but not in Cayman waters!)

Kai brings his energy, and love of the ocean to every trip. Be sure to say hi when you’re on board! 🌴⛵️

23/08/2025

Set sail your way with Mainstay Sailing 🌊 🛥️

Choose your adventure aboard the Enchantress, our 45ft Leopard sailing catamaran, or cruise in style on our 47ft Power Cat.

Both boats are available to book by the hour (4 hour minimum) or for a full day (up to 7 hours), giving you the flexibility to create the perfect day at sea 🌴☀️

📩 Enquire today to reserve your spot and make your Cayman adventure one to remember!

18/06/2020

I can see clearly now ...

09/01/2019

Sorry for not utilising this media much but here it is.....2 years later (older) we decided to kite again because it was such an amazing experience for all involved.
Face a thrilling endurance open ocean challenge , experience fantastic teamwork, have fun, while benefiting our local Cancer Society - why not ?

Little Grand Race 2019.

Planned event is February 24 - wind permitting!

10 teams have signed, training is well underway, generosity so far is overwhelming ($88 000), GET ON BOARD .

Please help us smash our goal this time of $200 000 donation to the Cayman Islands Cancer Society with this event.
Donate through the Little Grand Race website (below) or contact us.

Or physically get on board as crew, shore support, medic, Santa’s helper , and feel the buzz.

🙏

See

At stake: The glory of winning the Estera Little Grand Race 2019 and a significant sum raised for the Cayman Islands Cancer Society

19/11/2018

Apologies for not doing the FB thing for ages .

My take is -
If you want something to happen...YOU have to make it happen.

Our band was voted to play at the inaugural KAABOO.
See ya at Cayman KAABOO
(With Duran Duran, Chainsmokers, Bryan Adams, Counting Crows, Blondie, etc )

‘Don’t rock my boat’ springs to mind 😉

😎🎶

19/09/2017

Well said Cowboy. Darn straight sense......🤠