We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Mainstay Sailing

Cayman Yacht Club, West Bay, Grand Cayman
+1 345-927-1127
Review Highlights
5+ Stars - Highlight of our trip - Multiple excursions in one - GREAT PEOPLE running this operation - Thank you so much!

We chose the sailing catamaran for a 7 hour tour - Easily the highlight of our trip. 6 adults and... read more

Reviewed 7 August 2017
New Orleans
Best Boating Day Ever!

I can't say enough great things about our trip with Captain Jon. The day was amazing and our kids... read more

Reviewed 28 July 2017
Chicago, Illinois
via mobile
Read all 60 reviews
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
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.
  • Excellent100%
  • Very good0%
  • Average0%
  • Poor0%
  • Terrible0%
Travellers talk about
“captain jon” (9 reviews)
“day sail” (3 reviews)
“great trip” (5 reviews)
Cayman Yacht Club, West Bay, Grand Cayman
+1 345-927-1127
Write a Review
Reviews (60)
Traveller rating
Traveller type
Time of year

1 - 10 of 60 reviews

Reviewed 7 August 2017

We chose the sailing catamaran for a 7 hour tour - Easily the highlight of our trip. 6 adults and 6 kids from 10 to 24 years old (you get the picture). We had a couple kids say 7 hours on a boat would be...More

Thank coecpa
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 8 August 2017

Charles. Big thanks for singing our praises with style. This keeps us afloat and rewards us immensely when we receive feedback like this. We hope to see you again, with some new ideas to ensure everyone is entertained....that's our job.... ...and we love it. Cheers...More

Reviewed 28 July 2017 via mobile

I can't say enough great things about our trip with Captain Jon. The day was amazing and our kids had a blast. The mates were incredible and so helpful and actually super protective of the little ones keeping them safe. Our girls continue to ask...More

1  Thank chicagojacobs
Reviewed 28 July 2017

We had a group of 18 people. 4 children, 14 adults and the afternoon could not have gone any better. Cayman is amazing and Jon and his crew made it even better. If your trying to charter a large boat, look no further, Captain Jon...More

Reviewed 24 July 2017

I found this company on Trip Advisor when looking for a new company to replace the company we had been using for years.(they recently sold their boat) Tilley and JB gave us the best boat trip we have had......just liked they promised. We did the...More

1  Thank kls20
Reviewed 11 July 2017

This trip was just what we were hoping for! I echo the praises for Tilley and JB. Our group loved them and we all had a great day sailing and snorkeling. The sub wing was a lot of fun for the kids as was jumping...More

Thank FlyingK6517
Reviewed 1 July 2017

When you take six teenagers on a cruise, you need a special type of Captain and crew as well as a special kind of boat (shade for those who have passed sun baking age and lots of deck space for laying out for the teens...More

Thank Rocky M
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 21 July 2017

Hi Rocky. What an amazing review. Are you an author/writer ? You managed to paint the scene with detail, humour and imagery so accurately. In fact, so well that people may think you were paid for it ! If you guys are smiling, we love...More

Reviewed 26 June 2017

Capt. Tilley and mate JB provided our family with a great afternoon of memories during our visit to Grand Cayman in early June! Snorkeling, Stingray City, and Starfish Point were a hit with everyone, and we had an added bonus seeing our youngest passenger land...More

Thank gfbiii
Reviewed 19 June 2017

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 18 June 2017 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 20 June 2017

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 13 June 2017

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
Questions & Answers
Get quick answers from Mainstay Sailing staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines