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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$85-$1,125
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$60-$990
Sailboats
Set sail with these traditional wind-powered boats
$75-$1,100
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$40-$710
Kayaks
Who says you need a motor to have fun on the water?
$45-$845
Fishing Charters
Let a captain do the driving while you do the fishing
$60-$1,260
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$75-$500
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$60-$1,300
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$60-$3,125
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$100-$400
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$50-$425
Diving
Explore the ocean depths with trained boat operators
$500
Kieron
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Bailey's luxury catamaran was gorgeous and the sunset cruise we took for my husband's 40th birthday with family was a very special experience. Captain Dave and Emma were so nice and accommodating for our group of 12. They provided us with ice and beverages as well as utensils and napkins for the catered platters we brought. We were also able to connect to the sound system to play our music for the entire trip. We had perfect weather and got to see dolphins frolicking prior to heading out into the Gulf for a gorgeous sail and stunning sunset!
DS
Domenic
50ft Catamaran Charter with Water Toys -Boca Raton, FL
This was a great experience. We were 2 families on spring break with 5 teenagers and everyone had a large time. Fantastic Catamaran and exceptional captain (Jamie) and first mate (Kristen). We had so much fun we extended our trip. Well worth the price.
MG
Matt
38ft Leopard Catamaran in Cape Canaveral
Thank you for a great day on the water. We weren't sure what to expect, but the up and down of the the xalm waters of the canal and river provided a relaxing and pleasant experience.
SD
Shaunak
Chicago's Largest Chartered Catamaran!
Captain Brian and Russell were A W E S O M E!!! From the beginning, Brian was great ... very responsive to inquiries and follow up questions. During the cruise, that's when our experience went from GREAT to AWESOME! Brian and Russell were great, on-time, professional and courteous. They took good care of us and just let us relax. Thank you for making our UChicago graduation celebration weekend a fun and memorable experience! HIGHLY RECOMMEND cruising the lakefront and swimming in the Play Pen!!
Veronica
Chicago's Largest Chartered Catamaran!
My friends and I rented the catamaran boat from Jim for the 4th of July and had such an amazing time. The boat was even better in person and comfortably fit me and 12 of my friends. Captains Russell and Brian were also amazing. They were so much fun and so accommodating. They set everything up for us (the cooler with all of our drinks, bowls of chips we had brought, etc). We rented the boat for 3 hours but were having such a good time that we asked if we could pay to extend our use for another hour. Luckily they had no other immediate obligations and they were able to make it happen. As a nice bonus, they even had those fun water noodles for us to use. So much fun and my friends and I can't wait for our next boat outing with these guys!
NS
Nitya
Beautiful Trimaran for 10 People in Toronto
Chris and Rob are simply amazing ! They showed us the best time on the boat. They had all services available on board to heat food and store our stuff. The boat was clean, spacious and both, Chris and Rob, were very attentive to make sure we had everything we needed to enjoy our experience. I'm coming back to these guys each time i want a sailing experience ! Highly recommend these guys
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!
April 17, 2024
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April 17, 2024
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December 30, 2019
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December 17, 2019
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October 09, 2023
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August 24, 2023
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