Cayman Islands Sailing Charters

Cayman Islands Sailing Charters

Cayman Islands Sailing Charters
5
Scuba & SnorkellingBoat ToursWater SportsPrivate Tours
7:00 AM - 8:00 PM
Monday
7:00 AM - 8:00 PM
Tuesday
7:00 AM - 8:00 PM
Wednesday
7:00 AM - 8:00 PM
Thursday
7:00 AM - 8:00 PM
Friday
7:00 AM - 8:00 PM
Saturday
7:00 AM - 8:00 PM
Sunday
7:00 AM - 8:00 PM
About
Sail around the beautiful Cayman waters with Cayman Islands Sailing Charters. Offering luxury sailing trips aboard our 37' Catamaran. Visit Rum Point, Starfish Point, Stingray City or wherever you desire around Cayman. As our guest, enjoy your very own Captain taking you to wherever you choose. There is so much to take pleasure in and relax on your private sailing boat. Our boat is your boat.
George Town, Cayman Islands
Meets animal welfare guidelines

Awards
Travelers' Choice
2024

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Travelers talk about

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 wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles147 reviews
Excellent
139
Very good
5
Average
0
Poor
1
Terrible
2

Randolph W
Long Branch, NJ58 contributions
5.0 of 5 bubbles
Jan 2020 • Family
Our family enjoyed a wonderful afternoon with Ben aboard Be Happy. Ben picked us up at Kaibo Yacht Club and we set sail to some deserted snorkeling spots that we shared only with the fish and stingrays. Ben fed them and we never lacked for company as we snorkeled the reefs. Our last stop was Stingray City after all the tour boats had left and our girls got to play with the rays by themselves. Our day ended with a lovely sunset sail back to Kaibo. We enjoyed a private day with just our family for only a little more then the cost of a tour boat with 50 other people. Ben and his crew were friendly and very competent and we highly recommend them.
Written January 18, 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.

Kami C
2 contributions
5.0 of 5 bubbles
Jan 2020 • Family
Tonight was the highlight of our trip! We chartered a catamaran for a sunset Cruise then on to the bioluminescent Bay. Swimming in it was the most amazing experience ever! It was like swimming in millions of glowing diamonds. I felt like I was Tinkerbell and spreading magic pixie fairy dust. I wish I could have captured it on video or film. The magic can never be explained unless you do it yourself. Captain Ben and Paul we amazing! They made us feel like the most important people in the island. They were knowledgeable and helped us have a safe and amazing experience. This was something I am so thankful I got to share with my family!!
Written January 27, 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.

Leslie H
9 contributions
5.0 of 5 bubbles
Mar 2023 • Family
Our family of six had a wonderful half day sailing/snorkeling trip with Captain Ben on his catamaran, Be Happy. It was incredibly relaxing taking in the beautiful sights, snorkeling near Rum Point and visiting Stingray City. Captain Ben is very knowledgeable and highly experienced. He easily maneuvered his catamaran into the perfect spot away from some larger groups. We learned about the beautiful stingrays and he showed us how to hold and feed them. He made sure we had a great time and we never felt rushed. I highly recommend this excursion!
Written March 19, 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.

Gina D
10 contributions
5.0 of 5 bubbles
Apr 2024 • Couples
Captain Ben was exceptional! We enjoyed our time on Be Happy, and were thrilled with our fantastic Captain. We opted to add on lunch sandwiches, which were fresh and delicious!! Captain Ben brought us through Booby Cay Island, then to Starfish point, over the “the aquarium” for snorkeling, and then to sing ray city before setting the sails to head back. We did a 1/2 day charter and it was well worth it! We saw so much, and Captain Ben was sure to teach us about the animals we saw and ecosystems along the way. We brought our own snorkel gear, and he had it all laid out for us when we got to the snorkeling spot, and then I had mentioned I’m a newer/nervous snorkeler so he happily laid out a rope line for me to hang onto. At all sights he brought food for the animals where appropriate, and was happy to guide us in the activity whether it be feeding/holding and petting sting rays, holding the starfish, or snorkeling!
Written April 20, 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.

Michelle C
3 contributions
5.0 of 5 bubbles
Jan 2024 • Solo
I don’t even know how to put into words how amazing of an experience we had on our sunset boat tour with Captain Ben! He far surpassed my expectations and I cannot thank him enough! Prior to our tour, I sent him a message and asked if he could possibly hang up a little banner and get a small cake for my boyfriend’s birthday, (for an extra fee of course). I was not really expecting him to say yes, but thought I’d try. Not only did he agree, but he went out of his way to make it even more special by grabbing some fireworks to be able to shoot when we stopped for dinner! When we were on the boat, he was SO accommodating with everything and really just made sure we were having a great time! After we did our dinner stop, he went and set off the fireworks himself so we’d have a special show. He had the “Happy Birthday” sign hung up and had the restaurant come out with a cake and candle, singing the happy birthday song. I am just so WOWed over the entire experience! Thanks, Ben for making this such a special experience for my boyfriend and myself!
Written January 22, 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.

Ben W
Austin, TX30 contributions
5.0 of 5 bubbles
Mar 2024 • Family
We did both a 4 hour daytime sail and an evening Bio Bay sail with Ben during our recent trip. Both were great! He is very responsive to emails so we felt secure knowing our reservation was confirmed. On the 4 hour charter, we did Stingray City (where his assistant Clay had an encyclopedic knowledge of the stingrays!), some snorkeling, a quick trip by Starfish Point, and then time for lunch at Kaibo restaurant near Rum Point. A few days later we returned for the Bioluminescence Bay tour. Sailing out at sunset was calm, peaceful, and gorgeous. The bioluminescence is really interesting to see! Some nights the brightness of the plankton is just better than other nights depending on luck - our night happened to be a less great night but it was still fun. We highly recommend these tours - you'll be in good hands!
Written March 17, 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.
Hi Thank you for coming out for two trips and taking the time to write a review and such a great recommendation. As a small company it's reviews like yours that really help. Look forward to your next visit to Cayman Capt Ben
Written April 13, 2024
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

PamelaBelle
Seven Mile Beach, Grand Cayman17 contributions
5.0 of 5 bubbles
Feb 2024 • Friends
We have chartered with Captain Ben several times. Most recently we started an early afternoon cruise and went to Starfish Point, snorkeled not far from Rum Point, then went to Stingray City before sunset. Because it was later in the afternoon, the stingrays were especially gentle and there wasn’t much boat traffic. We headed to Kaibo for dinner and experienced a beautiful Cayman sunset, a fantastic fireworks display, then headed to Bio Bay for a bioluminescent swim. Just an overwhelmingly magnificent day. Captain Ben does an outstanding job. Always looking forward to our next cruise with Cayman Islands Sailing Charters!
Written April 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.
Hi Pamela, Thank you for taking the time to write such a fantastic review. I'm glad you enjoyed your fullday custom charter with Stingray City, Starfish Beach, Snorkeling, Dinner at Kaibo and our night swim in the glowing waters of Bio Bay. It's always alot of fun adding fireworks to the night and I'm so happy you had a great time.
Written April 13, 2024
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Josh S
Pittsburgh, PA9 contributions
5.0 of 5 bubbles
Jun 2022 • Couples
Captain Ben is amazing! He clearly loves his job and knows the Cayman Islands very well. We had a great day on a private charter. We went snorkeling twice, visited stingray city, star fish point, and explored the entire bay. Would highly recommend.
Written June 9, 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.

vacationer
Chicago, IL4 contributions
5.0 of 5 bubbles
Aug 2022 • Family
Ben (who is the solo owner of the charter company) is an experienced sailor and diver and an upbeat, very friendly personality. You won’t be disappointed! His boat name says it all: Be Happy! You will have a good time, whether you decide to go to Starfish Point, Stingray City, or one of the many snorkeling or dive spots on reefs. The Be Happy catamaran is seasoned and well-kept, comfortable, has been sailed everywhere from Cayman to Cuba. Rates are reasonable and you will get personalized service. Don’t worry, Be Happy!
Written August 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.

CherylJJ
Howell, MI4 contributions
5.0 of 5 bubbles
Feb 2020
This full day sailing excursion was by far our favorite day of our Grand Cayman vacation! Ben was knowledgeable with so many interesting facts about the Islands. I would definitely suggest booking the full day sail so that you have plenty of time to just enjoy being on the water and see the many attractions Ben will sail you to (swim with the rays, starfish, snorkeling and more!) It was so amazing to have only our group of 6 on the boat with Ben. Hands down our favorite excursion and our favorite day!
Written February 26, 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.

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Cayman Islands Sailing Charters - All You Need to Know BEFORE You Go (2024)

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