The Best Sailboat Rentals Near West Bay

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!

Sailing Catamaran Grand Cayman Sunset, Stingray City, Starfish Point & Snorkel

James and his staff were beyond hospitable, friendly and extremely professional. Made my wife’s bday trip so special beyond words. Everything was smooth, relaxed and fun. Our friends who boat often also said it was top notch. A big thank you and will return!

Sailing Catamaran Grand Cayman Sunset, Stingray City, Starfish Point & Snorkel

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 Sunset, Stingray City, Starfish Point & Snorkel

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 Sunset, Stingray City, Starfish Point & Snorkel

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!