Mainstay Sailing

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

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.

39 five star tripadvisor reviews. Our repeat booking rate says it all!

CALL 345 927 1127 OR EMAIL US TODAY!

Call or email bookings@mainstaysailing.com early to ensure you have that amazing sail with Mainstay Sailing in the Cayman Islands.

Mainstay Sailing Charters

Don't Just Take Our Word For It, Read our tripadvisor reviews.

trip1

Family_Day

"My family group (7 adults and 2 teenagers) had a fabulous day with Jon and Oscar on our last trip to Cayman. It was so good, we are going again in May 2016. We've already...."

- CarolAnn1955
Denver, Colorado

trip1

OLYMPUS DIGITAL CAMERA

"We had the most amazing day out on the water with Jon and Oscar! So many fantastic qualities, I could go on and on. We were three generations, and they were just...."

Princeton Junction

trip1

Exterior_C1

"Capt John, Oscar, and Wes all did a great job our excursion! Our whole group had an great day! I would absolutely recommend Mainstay Sailing to all my friends We will...."

- Julie G
Saint Louis, Missouri

trip1

DSC8740-1024x685

"John and his mates Wes and Oscar were great! Just great friendly people. We swam with the stingrays, snorkeling on the reef and went to starfish beach. Coolers available...."

Springfield, Missouri

CALL 345 927 1127 OR EMAIL US TODAY!

Call or email bookings@mainstaysailing.com early to ensure you have that amazing sail with Mainstay Sailing in the Cayman Islands.

Two Awesome Boats

One awesome company.

DSC_0140-1024x680

Enchantress

cat

Power Cat

CALL 345 927 1127 OR EMAIL US TODAY!

Call or email bookings@mainstaysailing.com early to ensure you have that amazing sail with Mainstay Sailing in the Cayman Islands.

See Us In Action

Just another day out with Mainstay Sailing in the Cayman Islands.