The Best Sailboat Rentals Near the Cayman Islands

Captained 42' Sailing Catamaran with 3 cabins and all the toys

One of the better charters I've done. Aaron was responsive before the trip, the boat was in excellent shape, and he made the whole day effortless — no stress, no surprises. If you're deciding, book it. Five stars.

Enjoy cruising the Montego Bay coastline In a 46 feet Searay yacht

It was such a pleasure meeting Dedrick in person. Very kind. Shadika and crew were phenomenal!! I reserved this yacht for my 50th birthday celebration,and the crew went above and beyond to ensure that this was an unforgettable experience! From food (wings were BOMB), to drink, fruit, and attentiveness, everything was great! You can’t go wrong with Deidrick and crew!

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!!!

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.

Lagoon 450F Catamaran

Capt. Dean was excellent at communicating with us (even when I messed up the booking times). The crew was very kind, knowledgeable and accommodating. We had such a great time we have already decided to spend next spring break in Grand Cayman. We are looking forward to booking again!

Lagoon 450F Catamaran

Capt Dean and Jasper were nothing less than amazing. The boat itself was beautiful, and had all the amenities my group needed and more. They were accommodating in more than ways than one and which allowed us to have an amazing experience. I was comfortable, and knew I was in good hands with our boating adventures. I thank both of them over and over and will definitely be the only captain/boat I book with when I visit the Cayman Islands.