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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$250-$1,000
Sailboats
Set sail with these traditional wind-powered boats
$425-$500
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$300
Fishing Charters
Let a captain do the driving while you do the fishing
$300
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Alok
31 Foot SeaRay from Cayman
I was fortunate to book a ride with Yarick. We did a short cruise on the north side of the Cayman Islands. He is very thoughtful and the places that he took me. Overall, it was a great experience and I highly recommend him.
MB
Maria
Experience Luxury in Key West on Your Own Terms - Key West's Premier Charter
The communication was excellent, and Captain Brian and the boat owner were personable.
JG
Joe
Experience Luxury in Key West on Your Own Terms - Key West's Premier Charter
We had an amazing experience with this boat rental. The boat was perfect and large enough for our family. The communication and all the details were a breeze. We would definitely rent this boat again and will share with friends. Thank you!
Cedric
31 Foot SeaRay from Cayman
**5 Stars** We had an incredible experience yesterday on Yarick’s captained 31 ft Chaparral yacht while cruising the North Bay in Grand Cayman. Our family of five visited two reefs for snorkeling, Stingray City, and Starfish Point. The yacht, although older, was well-maintained, spacious, and perfect for a leisurely tour. The interior was roomy, the bathroom was convenient, and the bow sunpad provided a fantastic spot for soaking up the sun. However, the true highlight of our day was Yarick himself. His warm and genuine attitude made us feel right at home, especially our younger children (7, 11, and 13). Yarick was incredibly patient and helpful with their snorkeling gear, and he had plenty of extra gear on hand if needed. His guidance at Stingray City was top-notch—our kids went from being nervous to not wanting to leave in a matter of minutes, all thanks to Yarick’s encouragement and expertise. If you’re looking for an unforgettable day on the water with a captain who truly cares about his guests, I’d recommend Yarick in a heartbeat!
LD
Laura
Private Custom Charter, Stingray City, Coral Reef Snorkeling, Starfish 34ft
We had a wonderful day aboard Escape Hatch with Captain Jason! Boat is a bit older, but the ability to beat the crowds and adjust the schedule was totally worth it. Additionally, Jason knew all the local secrets so we had all the string rays in our private area even though a few other boats were nearby. Cheers!
Jason
BackCountry Sandbars Key West
We had an absolute fantastic day. Anthony knows the spots to find that moment you are looking for in a special trip to the Keys. My wife and I had a magical trip, visiting a remote island and sharing a romantic sunset together. He even took pictures for us along with being a fantastic host. Next time we are in the Keys, we will be giving Anthony a call again as our Captain. Thank you from A and J for taking us to the Edge of Heaven!
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!
August 01, 2023
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December 30, 2019
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December 26, 2019
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