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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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Traveler Overview
  • Excellent91%
  • Very good5%
  • Average0%
  • Poor1%
  • Terrible3%
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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
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Hours Today: 7:00 AM - 8:00 PM
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George Town KY1-1010, Grand Cayman
+1 345-525-1222
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Reviews (56)
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All reviews captain ben spent plenty of time cayman islands starfish point stingray city private charter camana bay day cruise starfish beach sails seas kaibo blast company waves boat paddle
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1 - 10 of 55 reviews
Reviewed November 21, 2018

So excited about our next trip to the Island, but was a bit nervous because I forgot to make our reservation on the Cayman Island Sailing Charters but Capt Ben was so great and accommodating. He really worked with our schedule to get our day...More

Date of experience: November 2018
Thank Sil K
Reviewed August 5, 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

Date of experience: July 2018
Thank Angie L
Reviewed January 29, 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

Date of experience: January 2018
Thank Jessica H
Reviewed January 26, 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

Date of experience: January 2018
Thank Nancyhewitt
Reviewed January 17, 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

Date of experience: January 2018
Thank Adnan M
Reviewed January 6, 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

Date of experience: December 2017
Thank James D
Reviewed January 2, 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

Date of experience: January 2018
Thank Rachael I
Reviewed December 30, 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

Date of experience: December 2017
Thank Colt I
Reviewed November 24, 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

Date of experience: November 2017
Thank Sil K
Reviewed July 10, 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

Date of experience: July 2017
Thank AmyDNJ
Ben W, Owner at Cayman Islands Sailing Charters, responded to this reviewResponded July 17, 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

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