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All listings in the Cayman Islands

Awesome tours in Cayman Islands.

Page 1 of 17 listings

Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise
Sailing in West Bay · 12 guests

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

5.0
$400+/hour
40' Motor Yacht Charter - Friendly North Sound Exploration, Swim, Snorkel, Relax
Events in George Town · 10 guests

40' Motor Yacht Charter - Friendly North Sound Exploration, Swim, Snorkel, Relax

5.0
$250/hour
Private Custom Charter - 28ft Grady - Stingrays, snorkeling, Starfish, tubing.
Tours in West Bay · 8 guests

Private Custom Charter - 28ft Grady - Stingrays, snorkeling, Starfish, tubing.

New
$200+/hour
The Ultimate Stingray City Tour
Tours in Rum Point · 15 guests

The Ultimate Stingray City Tour

New
$275+/hour
Your perfect day on our 380 Searay, in the Cayman Islands,
Events in George Town · 8 guests

Your perfect day on our 380 Searay, in the Cayman Islands,

5.0
$375/hour
Private Boat Excursions w/ Captain David in the Cayman Islands
Powerboats in West Bay · 10 guests

Private Boat Excursions w/ Captain David in the Cayman Islands

New
$200/hour
Instant Book
Private Yachting & Adventure Tours in Paradise
Events in West Bay · 25 guests

Private Yachting & Adventure Tours in Paradise

New
Snoozed - Active 17 Oct 2025

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Tours Reviews in Cayman Islands

  1. Ricardo

    Ricardo

    Your perfect day on our 380 Searay, in the Cayman Islands,

    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!

  2. Dennese

    Dennese

    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!!

  3. KM

    Kelley

    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.

  4. CC

    Catie

    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!

  5. SP

    Sydney

    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!

  6. JM

    Jennifer

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

    I cannot recommend James enough for his incredible catamaran trip! From start to finish, he went above and beyond to ensure we had the best experience possible. His knowledge of the local area and marine life was truly impressive, and he shared fascinating insights throughout the journey. The boat itself was luxurious and well-maintained, providing a comfortable and enjoyable ride. James's passion for sailing shone through in his attentive service and expert navigation skills. He took us to some breathtaking spots that we never would have discovered on our own. Overall, this 5-star review is well-deserved, as James surpassed all expectations and provided an unforgettable adventure that left us feeling exhilarated and grateful. I highly recommend booking a trip with him - you won't be disappointed!