We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

Cayman Islands Sailing Charters

Features Animals
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Get directions
Address: George Town KY1-1010, Grand Cayman
Phone Number:
+1 345-525-1222
Website
Today
07:00 - 20:00
Open now
See all hours
Hours:
Sun - Sat 07:00 - 20:00
Description:

Sail around the beautiful Cayman waters with Cayman Islands Sailing...

Sail around the beautiful Cayman waters with Cayman Islands Sailing Charters. Offering luxury sailing trips aboard our 36' trimaran. 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.

read more

TripAdvisor Reviewer Highlights

Read all 42 reviews
Visitor rating
  • 36
    Excellent
  • 3
    Very good
  • 0
    Average
  • 1
    Poor
  • 2
    Terrible
Incredible Experience!!! Highly Recommended!!!

We decided to book a full-day charter with this company because the prices were so reasonable compared to other companies. The price for our group was the same price that we would... read more

Reviewed 5 December 2016
whaletail16

Similar Things to Do in George Town

Add Photo Write a Review

42 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
Showing 42: English reviews
Level Contributor
3 reviews
Reviewed 5 December 2016

We decided to book a full-day charter with this company because the prices were so reasonable compared to other companies. The price for our group was the same price that we would have paid for all of us to do one of the mainstream stingray city trips that are much shorter and include less. When we got on board, the... More 

Helpful?
Thank whaletail16
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hey guys, Thanks for taking the time to write a review. I'm really happy to hear your family had such a great time out on the water. I always try and make sure everyone in the group has fun and gets involved in the sailing if they want to. I hope on your next family vacation to Grand Cayman you... More 

1 review
Reviewed 27 November 2016

We were a group of 5 people and booked super last minute (the day before) but Ben was super flexible and made one of the best days happen for us! We started out sailing for about an hour and Ben took us through a channel, explaining the surroundings. He then surprised us with a stop at star fish point which... More 

Helpful?
Thank Cor N
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hey guys! Thanks so much for taking time to leave a review. Feedback is always appreciated. The first hour of sailing is what I think really sets up a great trip. i feel like it's a sailboat let sail as much as possible. Going into the mangrove channels is one of my favorite spots to visit. In the channel you... More 

Edinburg, Virginia
Level Contributor
11 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
Reviewed 16 September 2016

We booked with Captain Ben on a whim and it was the best experience for a day out on the water! We really didn't have an agenda other than being on the water and checking out Sting Ray City. Which was awesome. He kept us entertained all day and took very good care of us. I highly recommend booking your... More 

Helpful?
2 Thank Lv2skibryce
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hey guys , Thanks so much for taking the time to write a review . It's always nice to get five stars and hear good things. I'm so glad you guys enjoyed your trip to stingray city going , snorkeling , and spending time at Sailing around Grand Cayman's water. I hope you get the chance to come to the... More 

1 review
common_n_attraction_reviews_1bd8 4 helpful votes
Reviewed 7 August 2016 via mobile

Do NOT book with this company. We searched and searched and decided on Captain Ben to take our party of 9 (ages ranging from 3yr old - 60s) to take us out in Grand Cayman on his catamaran to Stingray City, Starfish Point and a reef. The day of our reservation we arrived at the meeting place as directed by... More 

Helpful?
4 Thank Christa R
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hello Christa, My apologies for any inconvenience. I did try contacting you to let you know I had to cancel. The night before a bad storm had hit and I was unable to run the tour. I am glad you were able to find a alternative company to take you boating. I would of loved to take your family sailing... More 

The Woodlands, Texas
Level Contributor
121 reviews
35 attraction reviews
common_n_attraction_reviews_1bd8 38 helpful votes
Reviewed 7 August 2016

My family had a wonderful day with Captain Ben sailing around North Sound and visiting with the Stingrays during our private charter. When we received an email that the boat we were originally scheduled to sail with the next morning (with another company) had mechanical problems, we contacted Cayman Islands Sailing Charters and left a message to see if they... More 

Helpful?
Thank GSRDPM
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hey guys thanks so much for writing a review. I'm glad I was able to help you guys out on such short notice and I had the ability to take you guys out sailing. Leave starting the tour at the Kaibo boat dock is always a lot of fun because it is so close to stingray city. I hope next... More 

washington, dc
Level Contributor
4 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 3 August 2016

My 80 year old mother, myself, and my 8th grader went on a half day sail with Captain Ben. It was really fun, and we felt completely safe and relaxed throughout. We went to a great snorkeling spot. Ben could not have been more accommodating. This was definitely a highlight of our trip!

Helpful?
Thank stcc
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hi guys thank you so much for taking the time to write a review . I'm glad I was able to take care of your elderly mom and your younger kids. It's always awesome to hear I was the highlight of a trip and I hope next time you visit Grand Cayman you get the chance to go sailing again. More 

Princeton, New Jersey
2 reviews
Reviewed 27 July 2016

We had an awesome day with Captain Ben and Cayman Islands Sailing Charters. He was incredibly conscientious, knowledgeable, helpful, and passionate about his business. We went on a full day private tour. We were two couples. This was probably our fifth private catamaran charter we have taken in the Caribbean, including a 7-day charter in the BVI. It is one... More 

Helpful?
Thank D P
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hey guys , Thanks for taking the time to write a review .getting feedback is always appreciated and it's awesome to hear that I rank so well amongst other Sailing trips you've had in the past. I hope all you guys are doing well. Hope to see you on your next trip to Grand Cayman . Captain Ben More 

Aix-en-Provence, France
Level Contributor
10 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 12 July 2016

We were only 3 persons with ben, he took us snorkelling to the reef ! We saw wonderful fishes, and had the opportunity to snorkell on several spots, all interesting . Sailling on the catamaran was an unbelievable and very pleasant experience. No noise and you run over the sea with the waves music. Nice music and rhumpunch are also... More 

Helpful?
1 Thank pascal13410
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hello Pascal, I'm glad you guys had a good time and thank you so much for the great review. It was awesome to hear your stories from France and I hope you enjoyed visiting the stingrays. I hope you get a chance to visit grand Cayman again. Thank you once again for the great review and I hope you guys... More 

1 review
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 5 July 2016 via mobile

Me and my boyfriend booked captain Ben through some friends at eco divers and were really happy with everything! We were lucky enough to be the only ones on the boat that day and it was fantastic. Ben gave us a few options for stops and we did Stingray city, starfish beach, and the reef. Ben was knowledgeable about the... More 

Helpful?
1 Thank Krista D
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hi Krista thanks so much for the great review . It's always great to take out couples . Grand Cayman and such a beautiful island and visiting the stingrays with just you and your boyfriend was such a great time. I hope you guys are doing great and I hope to see you soon. happy sailing ! More 

Level Contributor
2 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 30 June 2016 via mobile

This was our first time on a Trimaran and it was a fantastic trip. Captain Ben picked us up at our hotel and after a short trip to the marina, we started our private cruise. He was very knowledgeable about the boat, island, and stingray city/reef. He made our trip memorable and can't wait to go back sail with him... More 

Helpful?
1 Thank James H
Ben W, Manager at Cayman Islands Sailing Charters, responded to this review

Hey James thanks so much for writing the great review. I'm glad your group had such a great time going out sailing. it was a awesome day on the water. I hope you guys come back to Grand Cayman soon and we get a chance to go sailing once again. More 

Travellers who viewed Cayman Islands Sailing Charters also viewed

George Town, Grand Cayman
Seven Mile Beach, Grand Cayman
 

Been to Cayman Islands Sailing Charters? Share your experiences!

Write a Review Add Photos & Videos

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Questions & Answers

Questions? Get answers from Cayman Islands Sailing Charters staff and past visitors.
Posting guidelines
Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?