Sail Cayman Ltd.
Sail Cayman Ltd.
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About
Sail Cayman provide private sailing trips in a yacht or power boat around Grand Cayman. We specialize in trips to the famous Stingray City to swim with the Stingrays in the Caribbean Sea. Sailcayman now offers Cayman's Newest Sailing catamaran available for Private Charter on Island Tomcat is a 2014 39' Lagoon Catamaran with capability of taking up to 20 guests.
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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
412 reviews
Excellent
408
Very good
3
Average
0
Poor
0
Terrible
1
Megan Y
Gressoney-la-Trinité, Italy1 contribution
Dec 2024 • Family
Private Boating Charter Review
Our family recently had the absolute pleasure of booking a private boating charter with Matt and Hugo, and it was hands-down the best day of our trip! We had a mix of teens and elementary aged kiddos in our group, and they both managed to make it a fun, safe, and unforgettable experience for everyone.
The highlight of the day was visiting Stingray City, where the kids and adults got up close with the stingrays. Matt and Hugo were so knowledgeable and patient, making sure everyone felt comfortable and enjoyed themselves.
Afterward, we went snorkeling in some of the clearest water we’ve ever seen. The teens loved exploring the vibrant underwater world, and even the little ones had their share of fun splashing around and spotting fish.
This experience was the highlight of our vacation, and we’re already looking forward to booking with them again. If you’re looking for a private charter that’s fun for all ages, look no further. Highly recommend!
Our family recently had the absolute pleasure of booking a private boating charter with Matt and Hugo, and it was hands-down the best day of our trip! We had a mix of teens and elementary aged kiddos in our group, and they both managed to make it a fun, safe, and unforgettable experience for everyone.
The highlight of the day was visiting Stingray City, where the kids and adults got up close with the stingrays. Matt and Hugo were so knowledgeable and patient, making sure everyone felt comfortable and enjoyed themselves.
Afterward, we went snorkeling in some of the clearest water we’ve ever seen. The teens loved exploring the vibrant underwater world, and even the little ones had their share of fun splashing around and spotting fish.
This experience was the highlight of our vacation, and we’re already looking forward to booking with them again. If you’re looking for a private charter that’s fun for all ages, look no further. Highly recommend!
Written 31 December 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.
Ms.Mari
Orlando, FL16 contributions
Mar 2024 • Family
Sail Cayman is a must! If you are staying on the island or if you are coming to the island on a cruise (like us). Neil recommended transportation for our group of 14. I contacted the transport company to set up and they were at the port as soon as we got off the boat with a sign with my name on it. We arrived at the marina, after a scenic and informative drive, where we met Neil and his co-captain (I believe his name was Danny).
We stopped at the Sting Ray sandbar first and when I saw how packed the cruise excursions were when they arrived to the sandbar, I was so grateful that we did not book through the cruise excursions! Neil and Danny were amazing at explaining everything and making sure we all got a chance to hold and feed a string ray.
We also did some snorkeling at another location and went to Starfish beach as well which were both lots of fun and we really enjoyed.
Neil and Danny really went above and beyond for us to have a wonderful day! The boat was extremely nice and clean and in great condition.
Our transportation was waiting for us when we arrived back at the marina. We took our 10 minute drive back to the port and made it back with plenty of time to spare. Thank you for making our family vacation a memorable one!
We stopped at the Sting Ray sandbar first and when I saw how packed the cruise excursions were when they arrived to the sandbar, I was so grateful that we did not book through the cruise excursions! Neil and Danny were amazing at explaining everything and making sure we all got a chance to hold and feed a string ray.
We also did some snorkeling at another location and went to Starfish beach as well which were both lots of fun and we really enjoyed.
Neil and Danny really went above and beyond for us to have a wonderful day! The boat was extremely nice and clean and in great condition.
Our transportation was waiting for us when we arrived back at the marina. We took our 10 minute drive back to the port and made it back with plenty of time to spare. Thank you for making our family vacation a memorable one!
Written 2 April 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.
Dan D
8 contributions
Apr 2024 • Friends
We, two couples seeking a tranquil day on the water sans touristy crowds, had the pleasure of sailing with Fin and Matt as our captains. Their intimate knowledge of the island led us to discover hidden gems and breathtaking spots. It was an utterly fantastic day! Unlike other charters that dictate the itinerary, Sail Cayman allowed us to tailor our experience to our preferences. Highly recommended!
Written 22 April 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.
Beth
Cincinnati, OH17 contributions
Jun 2024 • Family
Matt and Hugo made our day on the private charter perfect! They customized every aspect of our trip to ensure it was everything we wanted. Both were knowledgeable about the island and the ocean life. They were great at “reading” our group, to fit right in. We had a family of 14 with teenage kids and older. This was definitely the highlight of our trip, and we would absolutely do it again. Can’t recommend them enough!
Written 29 June 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.
Andbrecal
Roslyn Heights, NY34 contributions
Mar 2024 • Couples
We loved Captain Neil and First Mate Hugo so much that we immediately booked our second excursion before departing the immaculate , modern, comfortable catamaran which had transported us to paradise. They know everything and are a delight to be with. Lifelong friendships have been made and we will return! Do not hesitate! xoxox Eileen, Ken, Doug and Gladys
Written 17 April 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.
Michael C
1 contribution
Mar 2020
My family and I had an absolute blast with Sail Cayman’s Captain Neil providing the perfect afternoon. We were able to design our own tour with the guidance of Neil ultimately deciding to snorkel at the reef and visit stingray city (which is actually a sand bar in the middle of the bay). The experience exceeded expectations. The entire excursion—lead by Neil and his crew—is like going boating with friends (opposed to a paid for excursion with the masses). You board the boat from a yacht club (not a “tourist” in site) and can change your mind on the fly depending on the conditions. For example, we made a decision to go snorkeling first at an exclusive location and saved the stingrays for last (waiting for the crowd to subside). Neil educated us but not in a guide type of way. More like a friend having a casual conversation letting you know what to expect with just enough background and fun facts. A few truths that I didn’t read anywhere but found important: We did have a concern about the wind and what impact that would have on the stingrays. The bay is surrounded by a reef which acts as a natural barrier (the wind is buffered). The best time to sail if it is windy is during low tide (because of surrounding reef). I was skeptical about the stingrays and if they would be as good as described. It was BETTER. I highly recommend Sail Cayman!
Written 11 March 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.
WG2022
2 contributions
Aug 2022 • Couples
Our group of 6 spent 4 hours with our amazing hosts’ Neil & Matt. Neil offered to pick our group up from the North side @Kaibo - which saved us the 40-75m to the west side & gave us more time on the water.
We spent time with the stingrays (really cool), several snorkeling locations that were great, and visiting the starfish.
The catamaran was nice - had Bluetooth, beanbags up front, covered rooftop, 2 bathrooms, etc. Our group brought drinks and food but never spent any time eating and spent most of our time in the water.
10/10 recommend a tour with Neil & Matt, bruh were experts on the ship and in the water, polite & social.
We spent time with the stingrays (really cool), several snorkeling locations that were great, and visiting the starfish.
The catamaran was nice - had Bluetooth, beanbags up front, covered rooftop, 2 bathrooms, etc. Our group brought drinks and food but never spent any time eating and spent most of our time in the water.
10/10 recommend a tour with Neil & Matt, bruh were experts on the ship and in the water, polite & social.
Written 22 August 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.
Margaret M
Middletown, NJ49 contributions
Apr 2023 • Friends
Captain Orneil is the BEST! Incredible 1/2 day sailing the ocean blue waters! So peaceful and fun! Orneil is personable filled with knowledge and stories about the Cayman Islands! Don’t miss this and book it!
Written 19 April 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.
ScubaSteve345
George Town, Grand Cayman10 contributions
Jun 2023 • Family
We did a half day trip with visiting family and a bunch of local friends. This was our third trip with Capt. Nelly in recent years. He and the crew keep everything safe and fun. Our age range was 80years to 4 years. The catamaran hull helps with those who don't like rolly boats. Nice clean bathrooms. He will always go where the crowd is not.
Written 20 June 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.
Mayra C
11 contributions
Aug 2023
Had an amazing day with family with Captain Neil and Hugo. We visited Stingray City, Rum Point, and Starfish Point. There was plenty of room for our family of 6 onboard. First class service during the entire experience. They even provided snorkel gear for us to use. Thank you creating a beautiful memory for our family.
Written 27 August 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.
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