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Mainstay Sailing

Cayman Yacht Club, West Bay, Grand Cayman
+1 345-927-1127
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Review Highlights
AMAZING! Highly recommend

I had the pleasure of booking two days with Mainstay Sailing. The first day we had the sailing... read more

Reviewed 5 days ago
A5006NFseans
,
Denver, Colorado
Stingray city plus!

This was a fantastic water adventure with Captain Jon Dobbin and Tiller on the powered catamaran... read more

Reviewed 6 days ago
KF44
,
Missouri
via mobile
Read all 53 reviews
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Overview
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Grand Cayman's finest private sailing charter.A beautiful 45' catamaran with plenty of space for up to 20 guests. The yacht offers 4 cabins all with en-suite, large sociable cockpit and deck space.Daysails are our specialty, snorkel the reef, swim with the rays, fishing, tubing, exhausting the kids! While you relax.Our rating speaks for itself.See you in The Cayman Islands.
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Travellers talk about
“captain jon” (6 reviews)
“day sail” (3 reviews)
“great trip” (5 reviews)
LOCATION
Cayman Yacht Club, West Bay, Grand Cayman
CONTACT
Website
+1 345-927-1127
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Reviews (53)
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1 - 10 of 53 reviews

Reviewed 5 days ago

I had the pleasure of booking two days with Mainstay Sailing. The first day we had the sailing catamaran. My family, which includes four kids from 9-14 yrs, had an amazing all day trip on the boat. Great crew, super friendly and knowledgeable. The second...More

Thank A5006NFseans
Reviewed 6 days ago via mobile

This was a fantastic water adventure with Captain Jon Dobbin and Tiller on the powered catamaran (50 ft?). The weather was less than ideal but not a deterrent to a memorable event. In fact, Stingray "deep" and Stingray City became a private viewing. So, do...More

Thank KF44
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 5 days ago

Oh yes, the squally wet day !! I couldn't see land ! Yet, you adventurers still wanted to go out...glad we did though, you guys having fun means we have fun too. Thanks, and you hardy guys are welcome any day. Jon

Reviewed 1 week ago

We enjoyed a memorable day on the Enchantress catamaran during a recent vacation to Grand Cayman. Spending a relaxing day on this comfortable boat is just what the doctor ordered! Capt Tilley and his 1st mate, JB, were knowledgeable and diligent (and some pretty great...More

Thank pmfast99
Reviewed 1 week ago

A very relaxing trip seeing the island in a special way with Capt. Tilley and 1st Mate, JB. Snorkeling, swimming, learning unique things about a little piece of paradise from this knowledgeable crew. The Enchantress is a beautifully maintained catamaran that sails smoothly and comfortably....More

Thank Lisa N
Reviewed 2 weeks ago

Speechless, just because I was too relaxed! I can't say enough about our captain and crew on The Enchantress. Capt Mark Tilley and his crew JB were the most accommodating and knowledgeable. Mark is the epidemy of a waterman and was willing to take everyone...More

Thank Doug O
Reviewed 2 weeks ago

A day sailing around Grand Cayman on the Enchantress with Capt Tilley and 1st Mate J.B. was the BEST idea EVER! Our family of 8 adults and our five yr old grandson had a wonderful time. The crew was so accommodating to us and specially...More

Thank Judy O
Reviewed 19 April 2017

Dear Jon....Tilley and Oscar and the Enchantress provided us with a phenomenal day- we enjoyed every moment that we were out on the boat. They are both excellent guides and you are fortunate to have them representing Mainstay Sailing. Thank you very much and we...More

Thank joeharriman
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 26 April 2017

Hi Joe Thank you for your smashing review ! As a trainee skipper I remember learning the 'seaworthiness ' is a measure of the ability of the boat AND crew. As the boat has already done a trans-Atlantic , she is fine ! Capt. Tilley...More

Reviewed 19 March 2017

Spent a day with Jon and Suzanne on the "new" yacht.....'er, catamaran. WOW! Stingray reef!! Starfish island!! A private stop with Jon's friendly "stingray friends". All-in-all......it was probably the Best Day Ever for the entire family! Can't wait to return for another day on the...More

Thank artnewell2017
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 20 March 2017

Thanks very much for the shining review, Arthur. We will have to dream up some new adventures for the next trip... Keep well and come see us soon. Cheers Y'all ! Jon

Reviewed 18 March 2017

Was referred by close friend to book Mainstay Sailing for a day outing with our children and grandchildren, while in port from our Disney Cruise. It was 100 percent the perfect outing. We adored Tinley the Captain and Oscar , the co captain. They both...More

Thank Lau0529
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 20 March 2017

Hi Laurie It's so good to read kind reviews like yours. I'll pass it on to the guys. Keep cruisin' with a smile :). Salut Jon

Reviewed 14 March 2017

We have been going to the Cayman Islands for a long time. Typically we go out with 4 adults and 4-6 kids. The last 4 visits we have gone out with John and Oscar (and now Tilly) for a day. We typically stay a week...More

Thank Matt D
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 20 March 2017

Matt You guys should be earning "mainstay miles" for all the trips !! Thank you for the complimentary review , and for keeping our track record excellent. See you next year, nature willing ;) Jon

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