Mainstay Sailing
Mainstay Sailing
5
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

Awards
Travellers' Choice
2023

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(20 reviews)
(5 reviews)
(13 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles119 reviews
Excellent
119
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0
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Christine W
3 contributions
5.0 of 5 bubbles
Jan 2023 • Friends
A magical luxurious experience. Captain Jon and First Mate Alex were the consummate hosts to our snorkeling and Stingray City adventure. The vessel itself was well-stocked and clean with plenty of spots to lounge and enjoy the sights. A highlight of our two-week stay!!! (Photo at Stingray city)
Written 25 January 2023
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.

sandrakatznj
Livingston, NJ14 contributions
5.0 of 5 bubbles
Jan 2023 • Family
Great afternoon with Captains Mark and Alex! They tailored the afternoon perfectly for our family. Two different snorkel locations, stingray city, and starfish. They were in the water with us and taught us how to hold the stingrays. Stingrays were the highlight of our trip! Starfish were disappointing since the starfish population has decreased to very few. The captains provided all snorkel gear, food for the stingrays, water bottles, and fresh fruit. Boat was huge and beautiful!
Written 12 January 2023
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.

Joe P
1 contribution
5.0 of 5 bubbles
Dec 2022
We've been out on Jon's boats a number of times in the last few years. He's got two great boats -- a 48-foot power catamaran and a 39-foot sail catamaran. Hard to pick between them. Each is very impressive and beautiful and each has a ton of space above and below deck. Jon will personalize your trip based on whatever you and your group want, at any time of day. He's taken us on a nighttime trip into the bioluminescent bay; he's taken us snorkeling for conch (which he turns into a great ceviche); he's taken us fishing and kayaking. He's also a fun guy who loves being out on the water and sharing the experience with his guests.
Written 31 December 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.

Chris B
Grand Cayman2 contributions
5.0 of 5 bubbles
Nov 2022 • Couples
Another Great trip with Mainstay Sailing! This is our second time using Mainstay Sailing for our guest. We live here in Cayman and wouldn’t use anyone else for a private, boating trip!

Alex and Justin took us to a great spot for reef fishing and the lounge nets were perfect for sun and fun! Their cats are equipped with everything you need for a fabulous day on the water. On our last trip, they dove for fresh conch, and today, we were able to catch dinner that they fileted for us.
Written 29 November 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.

Becky R
Dallas, TX4 contributions
5.0 of 5 bubbles
Nov 2022 • Couples
Captain Jon and his team are hands down the best on the island! They tailor the trip to your requests and needs and not some set schedule. The staff on the boat goes above and beyond to make the trip a memorable experience you’ll never forget! Their staff jumped in the water with us to show us wildlife and taught us how to properly and safely interact with the marine life. You won’t get this level of service and genuine kindness from any other trip outfitter. I travel the world and have experienced my fair share of outfitters. I booked them for a large group event as well as a private charter for two. They handle big and small like it’s nothing. These guys are by far the best!
Written 15 November 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.
Thank you, Becky. That’s a smashing review. We hope to entertain you and your groups again in the near future. 🥂
Written 15 November 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Kim L
1 contribution
5.0 of 5 bubbles
Nov 2022 • Friends
This was the BEST experience! Alex and Justin were an amazing crew. We snorkeled and had fresh conch. We swam with sting rays and walked among starfish. We would do this again - definitely! Thank you Mainstay Sailing, especially Alex and Justin!
Written 4 November 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.

Alice C
1 contribution
5.0 of 5 bubbles
Oct 2022 • Friends
It was such an unforgettable experience! We had a large group of 30 visiting for a wedding weekend and and Captain Jon with his crew took great care of all of us and just added to the experience! We would do it all again and 100% recommended Captain Jon and his crew to share the same experiences whether it’s your first time to Cayman or regular! Thanks again Captain Jon!
Written 21 October 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.

Drew P
Tallahassee, FL73 contributions
5.0 of 5 bubbles
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
5.0 of 5 bubbles
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
5 contributions
5.0 of 5 bubbles
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.

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Mainstay Sailing - All You Need to Know BEFORE You Go (2024) - Tripadvisor

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