Mainstay Sailing
Mainstay Sailing
5
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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.
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Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
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5.0
120 reviews
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Drew P
Tallahassee, FL73 contributions
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.
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 July 22, 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.
MrsGlor
7 contributions
Jul 2024 • Family
Our family stayed in Grand Cayman for a week in July and we chartered Big Sun for a day - it was definitely the highlight of our vacation! Captain John and first Mate Kai did so much to ensure we had a fun day - we went snorkeling, we swam with and fed stingrays, we saw the Starfish, we ate lunch at Kaibo on Rum Point, our kids got to do Tow Snorkeling and we capped it off with a beautiful sunset cruise back home! The boat was really beautiful and the crew was great! Highly recommend Mainstay for your stay in cayman!
Written July 8, 2024
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.
Terry M
Naples, Florida4 contributions
Dec 2023 • Family
The half day trip was wonderful for both children and adults. The crew not only took care of the boat but went snorkeling with us, caught and prepared conch, and helped the kids at Stingray City to hold and feed the stingrays. Crew was capable and very friendly and we would recommend the trip to anyone interested.
Written January 2, 2024
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.
SV S
24 contributions
Jul 2023 • Couples
Husband and I were in Grand Cayman celebrating our 25th anniversary and chartered the sailing catamaran for 4 hours. We had worked with Jon prior to our arrival to book the sail and he was great about staying in contact and answering questions.
On the day of our sail, Alex and Jeremy were our crew and we had a great time! They were both personable and whether coincidence or not, Jon knew I was hoping to see sea turtles and Jeremy is the "turtle spotter" - and boy did he! We saw 3 turtles in the wild and one was pretty close - it was amazing!
Places Visited: Sting Ray City, Reef, and went to Starfish Point.
On the day of our sail, Alex and Jeremy were our crew and we had a great time! They were both personable and whether coincidence or not, Jon knew I was hoping to see sea turtles and Jeremy is the "turtle spotter" - and boy did he! We saw 3 turtles in the wild and one was pretty close - it was amazing!
Places Visited: Sting Ray City, Reef, and went to Starfish Point.
Written August 21, 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.
Pamela P
Barrie, Canada5 contributions
Nov 2023 • Friends
We had the most amazing day of our vacation going out on Mainstay Sailing for the day. We went to Stingray City and had so much fun swimming with the stingrays. I was very apprehensive, at first but seeing how Jon handled them made us feel far more comfortable to get in and swim among them. We later went to Starfish Point where the water is so warm and beautiful and plenty of starfish to handle under water! It definitely was the highlight of our trip.
Written December 6, 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.
Richard Handelsman
5 contributions
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 July 7, 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.
Sharon M
5 contributions
Feb 2020
I do not write reviews, but Mainstay Sailing deserves one. We were 4 families with kids ranging from 9 to 17. The Power Cat is beautiful and well appointed. We went to Stingray City, Starfish Point and snorkeling in 2 incredible reefs. Big thanks to Captain Al and Justin who made our half day excursion super fun for everyone! We will be back next year and look forward to another incredible day on the Power Cat!
Written February 29, 2020
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.
Family Vacation
2 contributions
May 2023
We had an excellent time with Jon and Cathy. They did a great job of making this sailing experience memorable and enjoyable. Our kids loved it and we as adults got to relax. The stingrays and snorkeling were awesome. I highly recommend this company. We will use them again when on Cayman Island.
Written May 23, 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.
Becky R
Dallas, TX4 contributions
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 November 15, 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 November 15, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Cathy M
1 contribution
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.
We did a late afternoon into sunset and the sunset was incredible.
Written July 12, 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.
You can book a private sail for 2 people - we booked a half day sail for just us. I hesitate to give pricing as it may change with the season or it may have changed in general since we've been there. They are very responsive though - if you email them they will respond and answer all of your questions!
Written February 3, 2024
I've been looking into sailing possibilities inGrand Cayman. I was wondering if they did sail most of the time
Written December 23, 2019
We usually sail home with the breeze. Going upwind we motor to save time on a short half day.
Tropical regards,
Jon.
Written January 8, 2020
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