The Best Sailboat Rentals in the Cayman Islands

New addition! Lagoon 450 Catamaran

We were on a cruise and took a taxi to the boat. It was super easy the captain arranged drinks and sandwiches for our day. Again super easy. They crew made our day perfect.

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!!

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.

Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise

Sailing with Captain James was a dream!! You will not regret this experience! Not only is he hospitable, he is full of life and passion which only made our trip better. We enjoyed every part of our trip the only sad part was that we didn’t book longer. 100/10 would book with Captain James again!!

Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise

If you’re looking for a unique and fun way to celebrate a special occasion, or just want to take advantage of the beautiful weather and get out on the water, this is it! I booked a Sunday afternoon trip with friends to celebrate my 36th birthday and it absolutely exceeded my expectations. Captain James was communicative and professional leading up to the trip; he’s a skilled captain and a joy to be around. His catamaran is clean and safe, and equipped with everything you could need, including a sound system and bumpin’ playlist! I will absolutely be booking with him again.

Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise

Our experience with James was nothing short of incredible! We booked a short rental for our engagement pictures session, and James’ boat was beautiful, immaculate, and incredibly picturesque. James was quick and incredibly safe as well as a very skilled captain who accommodated multiple pick ups/drop offs for our shoot and did everything in his power to get the pictures we wanted. We would recommend him for photography or a nice sailing day - we will definitely be back!