Caribbean
Cayman Islands
Grand Cayman
West Bay
Places to visit in West Bay
Mainstay Sailing
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Mainstay Sailing

See all things to do
See all things to do
Mainstay Sailing
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About
Grand Cayman's finest private sailing charter. Beautiful 45' Sailing catamaran and a 47’ power cat with plenty of space. The yachts offer 4 cabins all with en-suite, plus a 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.
West Bay, Cayman Islands
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5.0
112 reviews
Excellent
112
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Drew P
Tallahassee, FL31 contributions
The perfect way to explore Grand Cayman
Jul 2022 • Family
What an absolutely gorgeous boat. The Big Fun more than accommodated the needs of our group of 12 people and we all had a ton of fun. The captain took us around to snorkel spots, showed us the stingrays (and provided some squid for the hungry rays), took us to the an area filled with massive starfish, and brought out some fun water sports toys. We even ended with a breathtaking sunset. It was a perfect day.

The captain and his helper Justin were terrific. They were incredibly responsive and anticipated our needs before we could even think of them. Having a top notch powered catamaran with plenty of sitting areas also made it a breeze and everyone was comfortable and cool.

Grand Cayman is such a beautiful place and if you want to escape for a day and beat the crowds, this is a terrific way to do it. I would highly recommend booking the Big Fun next time you want to explore the water.
Written 22 July 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Cathy M
1 contribution
Fun times on Big Fun
Jul 2022
Big Fun is property named and was a ton of fun. We did Sub Wing, snorkeling, swimming, and fishing and floating around on the Lilly Pad. Jon and his crew were amazing, super nice and encouraging to utilized the onboard water toys.
We did a late afternoon into sunset and the sunset was incredible.
Written 12 July 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Richard Handelsman
4 contributions
A day of fun and excitement
Jul 2022
The entire trip was our favorite part of the trip. We were a party of 12 including 4 children under 9. Captain Jon was spectacular as was first mate Justin. Other than some hiccups at the beginning (did not provide transportation to the boat which would have been great for tourists), the two of them provided an exciting and fun filled day. We went to Sting Ray city and Justin provided some exciting fun with the stingrays. He let everyone hold or kiss (7 years good luck) the stingrays. He even put out a floating raft for the little kids to sit on. There were some storms in the horizon but Jon managed to move his boat away from them as we continued our fun filled day. We did some snorkeling followed by a great lunch near Starfish beach. We then went to Starfish beach where all the kiddies and us held the starfish (photo op). All in all, it was a great 6+ hours of fun and excitement with Jon and Justin making sure we all had a fantastic time. I would highly recommend Jon and his team for a spectacular day. Plus, the two of them are such nice guys. We will definitely be back again!!!
Written 7 July 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Champhang W
Santa Rosa, CA5 contributions
Amazing Charter
Jun 2022 • Family
What an AMAZING experience and wonderful Captain and co-Captain Jon and Justin on Mainstay PowerCat. They went above and beyond to make our experience memorable even with the not so wonderful weather. From the Sting Ray encounter to the Snorkeling…everything was Great. I wish I could give them more then 5 Stars!

Definitely a charter I would recommend!
Written 20 June 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Sarah F
Norwich, UK47 contributions
Fantastic experience.
May 2022
We had a fantastic morning with Jon and Justin visiting Stingray City, snorkelling and then onto the star fish bay. Really interesting to chat to the knowledgeable crew. Great trip - getting to the stingrays before the crowds. Would definitely recommend.
Written 22 May 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Meridian456
Grand Cayman9 contributions
Spectacular
Apr 2022 • Friends
Beautiful boat, amazing crew, Jon and Kai were the best. There were eight of us, space for many more... but what a beautiful evening... the kind of rhing dreams are made of!!
Written 16 April 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Jerry T
2 contributions
The best boating experience ever!!!
Mar 2022 • Friends
This was the best boating experience of my entire life! Jon and the entire crew know how to have fun, extremely knowledgeable and professional! I’d highly recommend them for your Cayman Caribbean boating experience. Thank you for making a Texans dream come true out in the Caribbean!
Written 20 March 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Con
1 contribution
Amazing!
Mar 2022 • Family
Best day on the island. Unbelievable experience on a beautiful boat and great crew with top class service from start to finish.
Written 19 March 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Corona
Grand Cayman18 contributions
Cayman's Best Charter (medium groups)
Feb 2022
This team is just the best. That's why we call our days out with them "The Best Day Ever!" I have been on countless trips to see the stingrays on Jon's boat, and we have done something new EVERY TIME! It is always a blast and a treat if you have any musicians on board! Bring along your instrument!

I have worked with them for family trips, corporate incentives, weddings and events and they are always simply fabulous!
Written 2 March 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
KatieMA0724
Shrewsbury, MA9 contributions
Phenomenal Experience with Mainstay Sailing!
Feb 2022 • Family
I can’t say enough about the experience that me, my family and friends had with Jon and Justin on our private excursion today! From ease and flexibility with booking, to the beautiful catamaran, to the personable, knowledgeable and attentive crew. We couldn’t have asked for a better day exploring Grand Caymans amazing natural treasures - swimming with the stingrays, snorkeling in Rum Point and exploring in Starfish Point. If you are looking to make special memories and have an incredible experience, look no further than Mainstay Sailing. We can’t wait to come back. Thank you, Jon & Justin!
Written 22 February 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Mainstay Sailing (West Bay) - All You Need to Know BEFORE You Go