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Cayman Islands Sailing Charters

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Open Now: 7:00 am - 8:00 pm
Open today: 7:00 am - 8:00 pm

Cayman Islands Sailing Charters
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Traveller Overview
  • Excellent91%
  • Very good5%
  • Average0%
  • Poor1%
  • Terrible3%
Travellers talk about
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...more
Open Now
Hours Today: 7:00 am - 8:00 pm
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George Town KY1-1010, Grand Cayman
+1 345-525-1222
Most Helpful Positive Review
Reviewed 2 January 2016

Day 1 - a beautiful full day cruise sailing around the clear blue waters encapsulated by the Grand Cayman. Mr. Ben Wilson was not only an extraordinary captain but also very knowledgable on what sites to see at the right times. The boat was very...More

3  Thank Joe M
Ben W, Manager at Cayman Islands Sailing Charters, responded to this reviewResponded 30 January 2016

Hey Joe! Thanks so much for the review, and the awesome time we had sailing while you were here. We really lucked out with some epic weather for sailing last month, with sunny skies and trade winds to keep us cool, it really doesn't get...More

Most Helpful Critical Review
Reviewed 8 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...More

5  Thank Christa R
Ben W, Manager at Cayman Islands Sailing Charters, responded to this reviewResponded 24 November 2016

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...More

Reviews (55)
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All reviews captain ben spent plenty of time cayman islands starfish point personal attention stingray city private charter grand cayman great snorkeling starfish beach sea life catherine skiing sails seas mangroves kaibo
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1 - 10 of 54 reviews
Reviewed 6 August 2018

We spent a day with Captain Ben on Be Happy last week. We were on a Princess Cruise and this was our first excursion: the day started with a trip to Starfish Beach where we swam, paddleboarded and hung out with the starfish. Then we...More

Thank Angie L
Reviewed 29 January 2018

My friends and I had a GREAT time out on the water with Captain Ben this past weekend. We went to all the great spots, (starfish, kaibo,stingray) and he was very informative, engaged, and inviting. He also had a paddle board on the boat that...More

Thank Jessica H
Reviewed 26 January 2018 via mobile

Captain Ben and Catherine were great leaders for our day long trip. We enjoyed a visit to Starfish Point, Stingray City and Kaibo Beach Bar. We were served mimosas, Rum punch and waters to enjoy. The boat was roomy enough for 7 girls to be...More

Thank Nancy H
Reviewed 18 January 2018

Had a private charter with some friends on the 'Be Happy' with Captain Ben. Just a great time overall. Ben was very accommodating and tailored the trip to what we wanted to do. We hit up Stingray City, stopped to do some snorkeling by the...More

Thank Adnan M
Reviewed 7 January 2018

I took my wife, 5 teenage children, two grandmas (72 and 85),and my sister and brother in law out to sea with Captain Ben and his first mate Paul during a cruise stopover after Christmas. We did a 4 hour sail. I could not have...More

Thank James D
Reviewed 2 January 2018 via mobile

Went out with Captain Ben with a group of girlfriends and had a blast! Starfish Point, Sting Ray City, sun and surf! It was the perfect day! The “Be Happy” is the perfect size for a fun day out and Ben took great care of...More

Thank Rachael I
Reviewed 31 December 2017

It was AWESOME! We had so much FUN!! You could touch the STINGRAYS!!! The STARFISH TOO!!!! Then sailing while drinking my favorite beers and enjoying the WAVES!!!!! It is amazing to go SCUBA DIVING TOO!!!! We dove off the north Walls and saw some amazing...More

Thank Colt I
Reviewed 25 November 2017

We called several other charters, we were looking for a last minute trip for our friends who had two kids 5 and 3. Captain Ben was so great accommodating us, he didn't try to charge us extra because we were making a last minute reservation...More

Thank Sil K
Reviewed 11 July 2017

We chartered the "Be Happy" for a day of sailing and snorkeling on Grand Cayman. My family (my parents, my kids, me and my husband) had the best day with Captain Ben and Darrell! It was pouring rain when we met Ben near our cruise...More

Thank Amy D
Ben W, Owner at Cayman Islands Sailing Charters, responded to this reviewResponded 18 July 2017

Hey Guys! Captain Ben here thanks for the great review! I will pass on your regards to Daryl. Im so happy your Parents and your whole family enjoyed the time on board " Be Happy". Next time you come to Grand Cayman i hope we...More

Reviewed 28 June 2017 via mobile

Capt Ben and 1st mate Richy are Awesome! Couldn't ask for more personal sight seeing than what they provided. Took us to the best spots to see reefs without the crowds. These guys are top notch, highly recommend if you are wanting that personal attention.More

Thank aappss66
Ben W, Owner at Cayman Islands Sailing Charters, responded to this reviewResponded 18 July 2017

Hey, Captain Ben Here! Thank you for taking the time to write this review. Its always a highlight to our work week when these come in and ill make sure to pass on your regards to Richi. I hope everything is going great for you...More

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