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Cayman Islands Sailing Charters

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George Town, Grand Cayman
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About Cayman Islands Sailing Charters
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.
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Hours Today: 7:00 AM - 8:00 PM
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Cayman Islands Sailing Charters
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Reviews (61)
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All reviews captain ben spent plenty of time cayman islands stingray city day cruise starfish beach great trip boat mate shore
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1 - 10 of 59 reviews
Reviewed 2 days ago via mobile

Had an amazing time with Captain Ben and Rose. They were very accommodating (especially to our sea sick passenger!) and found all the great snorkeling sites for us to explore! Packed in 8 hours of fun that seemed to go by way too quickly. Thank...More

Date of experience: November 2019
Thank F8967ADlorim
Ben W, Owner at Cayman Islands Sailing Charters, responded to this reviewResponded today

Hi Guys! Thank you for leaving this lovely review, it is always great to know our guests have enjoyed themselves. It was our absolute pleasure to host your group and we really enjoyed our day with you, the Eagle Rays in the mangroves are certainly...More

Reviewed 1 week ago

We had a wonderful day with captain Ben and Rose. Knowledgeable about the sting Ray's, made the starfish even more fun. Beautiful day on the water!More

Date of experience: October 2019
Thank Mcamurph
Ben W, Owner at Cayman Islands Sailing Charters, responded to this reviewResponded 1 week ago

Hey there, Thank you so much for taking the time to write a review for us, we love hearing your feedback! We are so glad that your group had a great time out on the water with us. We also hope you will be back...More

Reviewed 4 weeks ago

Great trip so good we used them again another day for a sunset cruise and dinner. Highly recommended. Great boat and knowledgeable staff. Great to see all the major sites and with all the equipment need to snorkel and enjoy the waters in Cayman. The...More

Date of experience: October 2019
Thank 371NickB
Ben W, Manager at Cayman Islands Sailing Charters, responded to this reviewResponded 4 weeks ago

Hi Nick, It was wonderful to spend not one, but two trips out on the water with your group. The best part of our job is interacting with our guests onboard and both Rose and I really enjoyed your group's company. Thank you so much...More

Reviewed June 14, 2019

Had my wife and two kids on Captain Bens boat and we had a great time! Ben and his mate Stephanie were very attentive to my kids and very knowledgeable about the island and its history. Highly recommend!!More

Date of experience: June 2019
Thank Ric S
Ben W, Manager at Cayman Islands Sailing Charters, responded to this reviewResponded 4 weeks ago

Hi Ric, Thank you so much for taking the time to write this lovely review, I am glad to hear that your family enjoyed their trip out with us. We hope to see you back in Grand Cayman soon for another excursion out with Cayman...More

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
Ben W, Manager at Cayman Islands Sailing Charters, responded to this reviewResponded 4 weeks ago

Hey, Thank you for such a warm and honest review, we pride ourselves on being relaxed, personable and approachable. We are glad you found your experience with us to be a pleasant and easy one! Making sure you enjoy yourself is our main priority and...More

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
Ben W, Manager at Cayman Islands Sailing Charters, responded to this reviewResponded 4 weeks ago

Hi Angie, I am so happy you and your family had a great day out with us on 'Be Happy' here in Grand Cayman. Thank you for writing such a pleasant review, it is always lovely to hear that you enjoyed your stopover on the...More

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
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