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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,000
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$710
Sailboats
Set sail with these traditional wind-powered boats
$120-$370
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$600-$800
Kayaks
Who says you need a motor to have fun on the water?
$50-$280
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$150-$180
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65
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Alexa
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Had an amazing day on the water during the Air and Boat Show with Captain Bob as our guide. He's helpful in giving instructions to the dock, helps set up music and ensures a comfortable and safe experience. Due to his background in the CFD, he knew exactly where to anchor the boat so we could see great views of the air show. It was a worthwhile and memorable experience to share with friends and family!
TT
Tyler
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
I can’t understate how incredible Captain Bob is at what he does. He’s not only Incredibly knowledgeable but strives to make memorable moments during his trips. We booked a 2 hour boat ride, 1 hour speed boat and another hour sunset tour. Captain Bob set us up for multiple mini photo shoots with the perfect backdrops and took the pictures himself. An incredible value for the cost. He made my birthday extremely special. Thank you Captain Bob!!
CG
Clare
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Captain Bob is the GOAT! We love him! He was so accommodating and so much fun. He took us out on the lake and gave us a sight seeing tour. My guests from out of town had so much fun being on lake. He took us to see the Chicago lighthouse, Navy Pier, Planetarium, and Play Pen. Would definitely recommend!!
VH
Valerie
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
We had a brilliant time with Captain Bob - even though the boat is a speed demon (in a good way), he's got a background doing water rescues as a firefighter so we always felt like we were in safe hands. He's also got an encyclopaedic knowledge of Chicago history and some interesting stories about the city. He's also great at stopping at the scenic spots for the most memorable photos. Loved our trip - can't wait to go again some time.
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Shelby
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Highly recommend going out with Captain Bob. He was personable and knowledgeable and took us to a great spot for a photo and video but that was just the cherry on top of a great trip We had to reschedule due to some weather issues and he made it as easy as possible to work with him and the app and made sure we had a great time on our trip. Added note: My friends and I have been on and around water all our lives, but he made sure and made good judgment calls to ensure we were safe and could have a great time even if it meant not being able to go out the day it was originally scheduled and it caused more work for him.
DG
Daniel
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
My dad, a Navy Veteran, was finally laid to rest upon the majestic waters of Lake Michigan. Capt. Bob made this solemn experience a once in a lifetime event. He took us out on his perfectly clean boat to the cribs with a perfect view of the Chicago skyline so I would have a beautiful spot to scatter my beloved dad's ashes. He made this event better than I could have ever imagined. Thanks, Capt. Bob, for an event to be cherished forever. Rest in Glory, Mitchell Glaser! You will be missed...
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!
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