"Our family agreed, this was our favorite day in Cayman" - The Brookhouse Family

Fun Day For All Ages (10 yr -50 yr) Aboard" - Jacque G, Missouri

"Wow, what a fabulous day with Captain Jon and Oscar.... we give these guys and the Mainstay an A++" - Michael & Family, North Carolina

“Best Sailboat in Grand Cayman!"- The Rowinski Family, NY

Phone:  +1 345 927 1127

E Mail: bookings@mainstaysailing.com


Here at Mainstay Sailing, we make it our mission to ensure you have the best day of your vacation. Together, 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, wakeboard, fishing gear, lobster snares (when in season) even a splash pool for the toddlers in the cockpit!

We have performed 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.

Our repeat booking rate says it all !