Cookies!

We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.

All listings in the Cayman Islands

Awesome sailboat rentals in Cayman Islands.

Page 1 of 13 listings

New addition! Lagoon 450 Catamaran
Sailing in George Town · 30 guests

New addition! Lagoon 450 Catamaran

5.0
$500/hour
Beneteau Oceanis 473 Luxury Sailing Charter in Grand Cayman, Cayman Islands
Sailing in West Bay · 15 guests

Beneteau Oceanis 473 Luxury Sailing Charter in Grand Cayman, Cayman Islands

5.0
$300/hour
Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
Sailing in George Town · 20 guests

Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

5.0
$425/hour

Top Destinations Nearby

Sailing Reviews in Cayman Islands

  1. mariano

    mariano

    Beneteau Oceanis 473 Luxury Sailing Charter in Grand Cayman, Cayman Islands

    We had an amazing experience with captain Oneil (hope I am spelling is right) and Nino. The boat was amazing and comfortable and both of them cater to our needs and requests to ensure we had a very amazing and customized experience. Karen who helped us book was also super communicative and kind to help us through the booking process!

  2. BB

    Brandi

    New addition! Lagoon 450 Catamaran

    Absolutely beautiful boat and top notch service. Anton was endlessly entertaining and Spencer was a very professional captain. Loved every minute!!

  3. MS

    Mark

    New addition! Lagoon 450 Catamaran

    Capt. Dean was the best. He has excellent navigation skills and was very knowledgeable about the Island. Both he and his first mate Tash, were extremely nice, fun and energenetic with our group. Swimming with the stingrays and hanging out with the starfish were the highlights of the boatride. There was lots of laughter and fun times. It felt like Capt Dean and Tash were part of our group, like we've known them forever!! Thanks Capt. Dean, I would definitely book with you again!!

  4. SZ

    Sheryl

    New addition! Lagoon 450 Catamaran

    Perfect choice for our group of 12. With a 4- and 6-year-old that never swam with stingrays let alone in the open water, we wanted the opportunity to stay at locations on our own schedule. Yes, the trip was pricier than the scheduled tours; but, all agreed it was the perfect afternoon boat trip and wished we booked for the entire day. The catamaran is beautiful and spacious; and, the captain and first mate professional, funny and accommodating. We brought our own food and drinks; but, know, that they supply some nonalcoholic refreshments, ice, some fruit, chips and salsa type refreshments after one of the stops. Also, the first mate had a more in-depth understanding of stingrays than many on other scheduled trips.

  5. Sam

    Sam

    Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

    Don’t miss this chance to have the time of your life with Captain Dean! From greeting to finish, he was very attentive to all of us. We had kids 3,6 and 9. He was able to accommodate all of them plus the Adults. His Crew Art was amazing!!! He was so knowledgeable around the region and helped us threw out the whole tour! The best part of the trip was going to Stingrays and Star fish point without all the crazy crowds in the privacy of your own sail boat. So if you are in town, please don’t miss your chance with captain Dean! Thanks Capt! We look forward to seeing you again soon!!!

  6. ss

    susan

    Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

    The sailboat was immaculate and Capt. Dean was gracious and entertaining. We had a group of 7 with 3 seniors. Capt. Dean was accommodating to help and made it an easy and entertaining day. This is my 7th trip to the island, the weather wasn't great but they made it an amazing experience. Will definitely book with him in the future.