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All listings in Grand Cayman

Incredible sailboat rentals in Grand Cayman, Cayman Islands.

Page 1 of 13 listings

Sailing Catamaran Grand Cayman Sunset, Stingray City, Starfish Point & Snorkel
Sailing in West Bay · 20 guests

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

5.0
$400/hour
Lagoon 450F Catamaran
Sailing in George Town · 30 guests

Lagoon 450F Catamaran

5.0
$500/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

Sailing Reviews in Grand Cayman

  1. LL

    Laura

    Lagoon 450F Catamaran

    5 stars all around! Boat is beautiful and clean! We had a wonderful time with Capt Dean and Dulian. Will 100% book this experience with them next time we are in GC.

  2. DL

    Deshawn

    Lagoon 450F Catamaran

    Great communication and with an excellent crew/staff. Will definitely book again

  3. AM

    Alex

    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!

  4. MM

    McKenzie

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

    James and Nino did an incredible job! Our group of 13 had a blast! Communication was great and very helpful and fun along the way! We will definitely book again in our next trip!

  5. Dennese

    Dennese

    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!!

  6. KM

    Kelley

    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.