The Best Sailboat Rentals in the Cayman Islands

Private Yacht Charters, Enjoy The Beautiful Cayman Waters in Comfort.

We had a beautiful private tour of the island, filled with various adventures. Our guide was very helpful and knowledgeable about the area. My fiancé and I loved the experience and definitely recommend it!

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!

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!

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

We truly could not have asked for a more perfect sailing experience with Captain James!! Our time on the water was so fun thanks to his warmth, hospitality, knowledge, and love for sailing. Our group (including a toddler) loved experiencing the DC area all the way to Mount Vernon. We surprised our friend for her birthday and it was the most fun. I highly recommend this for any and every group looking for a different experience around DC!