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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
Fishing Charters
Let a captain do the driving while you do the fishing
$300-$400
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$300-$400
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$375

Brittney
Boston Whaler 24ft Sandbar Hangout Key West
We booked for an 8 hour boat day and it did not disappoint. We were able to adjust times based on weather, which was very nice and appreciated. We made multiple stops at sand bars and sight seeing. We finished at the pier in Key West and watched the sunset. Captain Mike was a blast and fantastic host! He’s very knowledgeable of the area and was able to speak to the wildlife and some of the history. We highly recommend! Thanks for the great experience!

Tiffany
Best Ocean Adventure in Key West – GetMyBoat Superowner and Best of 2025.
David made sure it was a special day for all of us.

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!!
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.
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!
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!
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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October 09, 2023
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November 28, 2022
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May 20, 2021
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December 30, 2019
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December 26, 2019
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