Stingray Sailing
Stingray Sailing
5
Scuba & SnorkellingBoat ToursWater SportsEco ToursPrivate Tours
About
Remember when customer satisfaction came first? We do!! At Stingray Sailing, you will get to experience the main attraction in Cayman, swimming with the friendly Southern Stingrays, and you will get to do so with a company who's bottom line isn't a dollar sign. As a proud, family owned and operated business, we focus on getting to know our guests on a personal level, while at the same time, providing life long memories. With limited spaces, only 25 per tour available, you are guaranteed to be treated as a friend, not just a number. We offer relaxing tours done on board a beautiful, 43 foot sailing catamaran, to the world famous Stingray City Sandbar; and whether it is swimming with the stingrays, snorkeling the coral reef, or just enjoying the beautiful Caribbean sun and water, Stingray Sailing is committed to helping you make the best of your time in Grand Cayman. With daily tours scheduled to accommodate both cruise ship and on island guests, booking your tour is just a quick email or phone call away! Join our family, we look forward to having you on board!
Grand Cayman, Cayman Islands
Meets animal welfare guidelines

Awards
Travellers' Choice
2024

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(235 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 bubbles1,032 reviews
Excellent
991
Very good
31
Average
9
Poor
0
Terrible
1

K8ofthewoods
2 contributions
5.0 of 5 bubbles
Dec 2019 • Family
We met Stingray sailing off our cruise ship. They have a convenient meeting space and transportation to their boat inside of the cruise the port fence. There are fancier accommodations but I don’t think you’ll find a more respectful or attentive tour. Capt Matthew took us out to stingray city and proceeded to dazzle us with his love for the rays and their love for him. They seek him out and swarm him and he talks to them by name. Other boats wrestle the rays away and hold them for pics while Matthew’s stay with him and return to him when they escape. We were there during the busiest week of the season (between Christmas and New Years) but he still gave us a great trip and we didn’t feel like we missed out. He finished our excursion with a trip to a reef for some amazing snorkeling in warm, crystal clear water with some of the most gorgeous and varied fish I’ve seen. Again- respectful of the reef. I’m fairly certain that the other excursions see where the black catamaran is and follow because they know it’s the place to be.
Written January 14, 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.

BRBTravelingnow
14 contributions
5.0 of 5 bubbles
Feb 2020 • Friends
We sailed with Captain Chip and Matthew today and were greatly satisfied with the experience. We had a small group tour in comparison to the other boats we saw at Stingray City. Chip and Matthew were so kind in their interactions with the rays, while we watched crew from other ships chase, catch, and lift them out of the water. Several rays came up to Matthew, Chip and our boat and we were able to pet and feed them. It is obvious that Capt. Chip and Matthew care about the stingrays and the reef and we appreciate the positive experience. Highly, highly recommend!
Written February 19, 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.
Thank you for coming out with us; we appreciate customers who research what they are supporting. It is unfortunate that other companies have not caught on to how to properly treat the rays. We hope that through our continued effort to model how to properly handle and treat these wonderful, gentle creatures, other companies will start to follow suit. We thank you again for a wonderful day and hope to see you in the future.
Written February 21, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

RosemaryRowntree
Nova Scotia, Canada54 contributions
5.0 of 5 bubbles
Mar 2020
There were two main reasons we booked with Stingray Sailing: 1. it was on a sailing vessel rather than a crowded motor boat and 2. they avowed care and safety for the stingray.

We had plenty of room on the catamaran - with only Chip and Matthew to guide us and 6 other guests. We saw many stingray tours with boats crammed shoulder to shoulder. Our experience was far better.

We were first told and then shown how to interact with the stingrays. Being in the sea with these huge fish was truly a fabulous experience. They are gentle and very sociable. We fed them little fish (sardines?), stroked them and admired them in their natural habitat. Chip and Matthew were very caring about both the fish and their guests.

After about 45 minutes in the water with the stingrays we moved on to a reef for snorkelling. This too was a wonderful experience.

We would recommend Stingray Sailing in a heartbeat!
Written March 7, 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.
Thank you for your feedback, we are pleased you enjoyed your time with us. We hope to see you again in the future.
Written March 8, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

moonbeam24
Toronto, Canada277 contributions
5.0 of 5 bubbles
Dec 2023 • Family
Third time doing the Stingray City experience with Stingray Sailing. Captain Chip is very impressive with his handling of the rays and respects them to the point that they seem to come to him immediately when he pulls up to the sandbar. When Chip got in the water, the rays were immediately swimming over and hanging around him. This made for a wonderful experience having so many gentle rays swimming around us. Chip made it easy for us to feed and pet the rays. The rays were so friendly and happy to rub up against us. Such a wonderful experience I never tire of.

There were a few guests that were nervous to get in the water and walk among the rays but Chip made everyone feel safe and even had a large floating mat that guests could sit or lay on and still experience seeing the rays so close. My cousin was very nervous to both be in the water and with the rays. Chip held her hand while touching the rays, making the experience an exciting one for her. You really couldn’t ask for more personal attention. While the rays were swimming around us Chip gave us lots of interesting information about them. After we were done with the rays we sailed to a spot close by to snorkel among some beautiful corals. Wonderful day.

For those trying to decide which Stingray tour to take (and there are many) keep in mind that Stingray Sailing keeps his tour at 20 ppl max on a beautiful catamaran with a large tarp out front to lay on and other shaded seating areas. There are also washroom facilities on board. Stairs on back of catamaran make for easy entry and exit from the water. Other boats had very large groups on board which would not provide the same experience. Some employees from the other tour boats came to Chip’s catamaran and would grab the stingrays in their arms and force them over to their group as they rays did not naturally go to them. Chip’s gentle interaction with the rays kept them close by for all of us to enjoy.

If you are on a cruise, I would also recommend that you book directly with Stingray Sailing online rather than take a ship Stingray excursion as the ship’s cost is almost double and you are on a very crowded boat with a hundred other guests. They are quick to respond, easy to reserve and will meet you at the dock when you get off the ship’s tender.

I hope you enjoy your experience as much as I did.

Written December 11, 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.

EvieSuger2014
Alexandria, VA11 contributions
5.0 of 5 bubbles
Jan 2023
We had an absolutely fantastic day with our group. A return tour for us after a great tour with Stingray Sailing 4 or 5 years ago. Captain Chip and Kyla are welcoming and friendly. By being on the first tender off of our ship, we were able to beat the cruise ship tours out to Stingray City and enjoy the stingrays. Captain Chip brings bait and you can pet the stingrays. He treats them with respect and they swarm all around him because of it. He has an awesome yellow lily pad that you can float on if you don't want to be in the water with the rays. My kids had a lot of fun on the lily pad. We then went to Starfish Point. There were less starfish there now as more boats are visiting. We still saw 3 and the beach is pretty and the waters are calm. I cannot recommend doing a private catamaran tour if you have a larger group (we had 10 people). It was the same price or less than the cruise excursions, which were PACKED full of people We had the boat to ourselves, lots of space, bottled water provided. I would take this tour over and over again with Captain Chip when returning to Grand Cayman.
Written February 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.

Monica B
Boulder, CO9 contributions
5.0 of 5 bubbles
Jan 2020 • Family
Our family of 10 (including four children 13, 11, 8, 6) had a great time on our Stingray Sailing tour yesterday. On the beautiful catamaran rides out and back, we lounged on bean bags while the kids stretched out on a huge tarp overlooking the water. We visited the stingrays and snorkeled along the reef, seeing lots of different fish. The stingrays were a real stand-out experience for us. We all enjoyed our time in the shallow turquoise water watching them swim and touching them gently. Being in the water with the stingrays was a natural high for sure! Chip and Matthew, our guides, were extremely knowledgeable, personable, and showed real care for the environment and animals we interacted with. My mom loved this tour for her 71st birthday. We highly recommend this experience to any families wanting to get out on the water and have a unique wildlife encounter.
Written January 4, 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.

C Greenwood
1 contribution
5.0 of 5 bubbles
Jan 2020
This was an outstanding excursion. Captain Chip was extremely knowledgeable and friendly. He clearly explained how to interact with the rays and how not to. When we arrived at the “City” the rays flocked to us. There were 30-50 of them swirling around. They would brush up next to us and circle around. At times they almost seemed like affectionate dogs. This was a unique experience and I highly recommend Stingray Sailing and Captain Chip!
Written January 8, 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.
We are so happy to hear that you enjoyed your time with us. Our stingrays are definitely water kitties or puppies, they just love to be pet and treated with respect. We hope to see you in the future.
Written January 9, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

SummerKim
137 contributions
5.0 of 5 bubbles
Aug 2023 • Couples
My husband and I and our 21-year-old daughter and her boyfriend absolutely loved our stingray trip this month! Captain and his wife were fun informative interacted with the people on the boat and totally were respectful to the stingrays which was awesome! This is not a party boat! there were 4 families and it was great and I highly recommend it! So many other boats were around the stingrays at first so he took us to do snorkeling first! captain totally knew how to handle all the stingrays kept them in the water nobody took them out of the water and left them in their natural habitat! Thanks to Chip and Michelle!
Written August 15, 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.

paulC109OW
Greater London, UK152 contributions
5.0 of 5 bubbles
Jan 2020 • Couples
Captain Chip was the perfect host and treats they Rays with respect and love. It was a super trip and he was ably assisted by Matty. The Rays swarmed around Chip
and it was clear they liked Chip and Matty very much. We fed the Rays and they were very relaxed with us. Highly recommended trip. 100% thank you Chip and co.
Written January 8, 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.
Thank you so much for your feedback. We look forward to having you back on board with us in the future.
Written January 9, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

amcintyre15
Darien, CT72 contributions
5.0 of 5 bubbles
Feb 2020
Chip and his mate were a great way to spend an afternoon in Grand Cayman. We had booked for the morning but they emailed us the evening before and said the morning was full at 24 people and would be want to switch to a quieter afternoon trip with only about 10 people. We did and it was worth it. Got picked up from our hotel by Chip in a bus and driven to the dock at the yacht club. Boat was nice catamaran and we motored out to Sting Ray city. Chip and team are very respectful of the sting rays and we have great interaction with them for about 30 mins. We then went over to a snorkeling spot that was underwhelming but still saw some nice fish. We then sailed back to the dock for a very nice 3.5 hour trip and got driven back to the hotel. Chip was chatty and very friendly and the family enjoyed the afternoon a lot.
Written February 23, 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.
We are happy to hear that you enjoyed your time with us. We are sorry that you were underwhelmed by the snorkel location. It is unfortunate that the majority of companies offering what is considered the most sought after tour in Cayman have taken it to be nothing more than a business opportunity. Their staff members care very little about the treatment of the rays and the reefs, leading their customers standing, breaking, kicking, mistreating, etc the reefs and ruining it for everyone. As I am sure you noticed, our company makes certain that all our customers and staff treat the rays and the reef with the utmost care and consideration. It is rare for us to hear that someone has not enjoyed the snorkeling, but everyone expects different things, I suppose. If you expect to see the reef from Disney's "Finding Nemo" then you will most likely be disappointed with any snorkeling you will find here on Grand Cayman. The reefs here have been over used, abused by thousands of flippers, and human hands, and is simply not going to be as vibrant as Nemo's home. With that said, it is still teaming with beautiful fish and sea life. As I said, it is rare to hear anyone complain. We hope that you enjoyed the rest of your time in Cayman and we hope to see you again in the future.
Written February 24, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

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

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