By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$250-$500
Sailboats
Set sail with these traditional wind-powered boats
$375-$500
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$250-$375
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$300
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$375
Cassadee
Key West Luxury Charters
We had the BEST day out on the water with Captain TJ and Carlos from Reel Paradise Charters! From start to finish, they made the entire experience so fun, smooth, and unforgettable. TJ was absolutely amazing — so knowledgeable, personable, and clearly passionate about what he does. He went above and beyond to make sure everyone was having a great time, and we couldn’t have asked for a better captain. Carlos was equally awesome, super friendly and attentive, and made sure everything ran perfectly. The boat was beautiful, the views were stunning, and the energy the whole day was unmatched. If you’re thinking about booking a boating adventure, I HIGHLY recommend Reel Paradise Charters — you’ll be in the best hands with TJ and Carlos!
JD
Jepera
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
This was an amazing experience. Mr. Israel was awesome and made us feel very comfortable. His hospitality was great. I will definitely be back. The boat was perfect for my birthday.
elizabeth
Enjoy Cancun in 32ft Wellcraft for 6 people!
Edgar estuvo atento desde el día uno de la reserva, ofrece toda la actitud y disposición para un viaje súper divertido. Sus amenidades están increíbles. Nos encantó y definitivamente reservaríamos siempre con él.
LQ
Laura
MainSqueeze-Private Boat Charters🏝️🇯🇲Rum Punch, snorkeling,Music included.
We had an absolute blast! Would recommend to anyone! Darren and Israel were so much fun they celebrated our birthday event with us and even decorated the boat for us. They let us play our music and bring food. We snorkeled and they took amazing pictures for us. Book now!
Michelle
31ft Chaparral Yacht Charter from Cayman
We had an incredible time visiting Stingray City and snorkeling! From start to finish, the experience was seamless, professional, and full of unforgettable moments. The crew was friendly, knowledgeable, and clearly passionate about what they do. They made us feel safe and welcome right away, and their enthusiasm was contagious. They provided great instructions and fun facts about the stingrays, which made interacting with these amazing creatures even more special. Stingray City was everything we hoped for – surreal, thrilling, and beautiful. Getting to stand in crystal-clear water surrounded by gentle stingrays was a once-in-a-lifetime moment. Afterward, the snorkeling stop was just as amazing. The water was so clear, and we saw tons of colorful fish and coral. The guides even pointed out hidden sea life we would have missed on our own. The boat was clean, spacious, and well-equipped with everything we needed. It felt like a private, VIP experience. Whether you’re a first-timer or a seasoned snorkeler, this tour is a must-do in Grand Cayman. Highly recommend – they delivered an experience we’ll never forget!
KE
Kristyn
31ft Chaparral Yacht Charter from Cayman
This was the best day of our entire vacation!! Nick and his crew went above and beyond to accommodate any and every request we had. The experience was priceless, and I couldn’t recommend them enough!! If you’re traveling to the Cayman Islands this is the way to go!!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!