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With Captain
Groups rave about lively, memorable outings with friendly captains, easy logistics, and a fun, relaxed vibe that works well for parties and celebrations.
Guests describe a beautiful, spacious, clean, and well‑maintained cruiser that comfortably hosts social groups and keeps everyone enjoying the ride.
Renters note smooth communication and simple directions, with sociable, engaging captains who keep trips running comfortably and on schedule.
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AI Overview
Owner's Description
This yacht is a 42ft Regal with all you need for a day out on the water. Soak up the sun on the sun pads on the bow or at the swim platform. You can get some shade in the comfortable cockpit seating on in the inside lounge areas. It has a brand new sound system with lighting. Bring your own food & drinks. Why should you book with us? - We are the most experienced boat rental company in Chicago - Check out our Superowner profile to see that we have done over 1400 rentals through the GetMyBoat platform alone! - Our boats are professionally cleaned between all rentals (this service is included in the rate) - All boats are highly equipped for rental - multi-zone bluetooth sounds system, sun pads, swim platform, high-capacity coolers, full bathroom Captain: The captain rate included in the offer pricing is intended as an indication of the typical captain pricing expected. The actual captain fee will be negotiated between the Charterer and the charterers hired captain. If necessary, an adjustment to the captain rate can be done through GetMyBoat as GetMyBoat will pay the Captain fee portion of the booking rate directly to the captain after the booking is completed. The owner will not be paid the Captain fee. We provide a pre-approved Captain contact list but you have your choice of who to hire. You may hire a different qualified captain through our owner-approval process. Fuel: Fuel to the playpen is included. A river cruise must be coordinated in advance with owner and will require a fuel fee. Water Toys: We have a large inflatable raft available for rent for $90.
Chris
1436 total bookings
Superowner
Best of 2026
- Capacity
- 13 guests
- Powerboats, Pontoons, & RIBs
- Cuddy Cabin/Walk Around
Reviews
(37 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
6 photos have been added by reviewers who booked this listing.
PC
Paige
Our party of 12 had an amazing time with Captain Dan Leslie on the 'Big Daddy' boat. From start to finish, the experience was absolutely fantastic. Our captain was not only well-informed but also incredibly fun, making the journey enjoyable and engaging. The boat itself was exactly as advertised, clean and well-maintained, which added to the overall experience. Whether you're looking for a relaxing day at sea or an adventure with friends, this boat trip delivers on all fronts. I can't wait to do it again!
MF
Maggie
Can't say a negative thing! Directions were simple to follow, very easy to contact a captain for our trip. The captain was great! Very sociable and friendly. Thank you for everything!
mm
molly
Chris was very communicative and the experience was amazing! I enjoyed a great day for my birthday with several friends. Highly recommend using Chris and his boat!
KC
Kendall
Our boat ride to the playpen was great! The boat was clean and the photos really don't do it justice. Would highly recommend renting the raft (similar to a lily pad).
ML
Maddie
We had an amazing experience working with Chris and Captain Kelly was awesome! They were super responsive and helpful throughout the booking to the actual experience. Will definitely use again!
Chris
1436 total bookings
Superowner
Best of 2026
We have been renting boats since 2013. We pride ourselves on providing a safe and professional experience for clients. Our boats are well equipped, squeaky clean, and ready for your special outing! We love working with all groups including families, corporate outings, bachelorbachelorette parties and just groups of friends who want to get off shore for a few hours! Come see the difference it makes to work with a professional boat rental company.
Features & Details
- Regal
- 402 Commodore
- Capacity: 13 people max
Safety Equipment
Life Jackets (12)
Operating Equipment
Autopilot
Guest Amenities
Cabins (2)
Sun Protection
Toilets (1)
Leisure & Entertainment Equipment
Sound System
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
3155 South DuSable Lake Shore Drive
Chicago, Illinois, 60653
United States
Departure Location
41.8345926,-87.6043971
Chicago, Illinois, 60616
United States
Cancellation Policy
Free cancellation up to 14 days before your trip.
Additional Terms & Information
Location: We are docked at 31st street harbor which is about a 10 minute taxi from downtown. There is paid parking available nearby. Rental Agreement: A boat rental agreement will be sent by email, following the booking confirmation, for your review and signature. This agreement must be signed for the rental to proceed. Waivers: Our insurance company requires that all passengers sign a liability waiver. This waiver must be signed by all passengers prior to the boat's departure from the dock.
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