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With Captain
Relaxed Chicago waterfront outings with skyline views and easy planning support, popular for milestone celebrations and capturing fun photos together.
Comfortable cruiser suited for Playpen hangs and city cruising, giving groups space to relax, socialize, and enjoy the Chicago skyline on the water.
Guests highlight attentive, prompt communication and thoughtful extras like helping plan details and capturing photos, making celebrations feel effortless.
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AI Overview
Owner's Description
Step aboard our beautiful 30' Sea Ray Sundancer—the perfect way to soak in Chicago’s iconic waterfront. Whether you're cruising past the skyline, relaxing in the Playpen, or spending a laid-back day with friends, this stylish boat is designed to make every moment unforgettable. With comfortable space for up to 10 guests, it's ideal for celebrations, casual outings, or simply enjoying life on the water. We’ve got you covered! Your rental includes fuel, tax, cleaning, cups, plates, and a cooler ready to keep your drinks ice-cold. The boat is BYOB, so feel free to load up with your favorite food and beverages to make the day your own. You’ll need a U.S. Coast Guard-licensed captain to drive the boat. After booking, we’ll send you a list of awesome captains you can choose from To make the most of your day on the water, don’t forget to bring: - Towels - Sunscreen and sun protection - Your favorite food and drinks (yes, alcohol is allowed!) - A music playlist (you can connect via Bluetooth to our premium DJ sound system) **Please note: No boat tie-ups are allowed.** WE DO NOT PARTICIPATE IN SCENE PARTIES AND TIE UP.
Gina
20 total bookings
- Capacity
- 10 guests
- Powerboats, Pontoons, & RIBs
- Bowrider
Reviews
(4 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
4 photos have been added by reviewers who booked this listing.
BR
Brooke
We loved our boat day with Gina! She was very accommodating and professional while still being fun and personable. As a group of all women, we really loved that we had a woman boat captain. She even gave recommendations of places to go around the city after the boat! We had so much fun and highly recommend Gina and her boat!
CP
Carol
We had such a great time, Gina was soo good about making sure she answered all our questions promptly via text. I was soo nervous about things going smoothly and she helped execute our plan flawlessly. She even took pictures and videos of us and sent it to us after. We couldnt have asked for a more perfect experience. Thank you Gina and team for making my husband's 40th birthday so memorable <3
JP
James
MT
Morgan
Gina
20 total bookings
I’ve spent my whole life on Lake Michigan, it’s where I learned to drive a boat, catch the best sunsets, and appreciate the city from a different view. After years on the water, I started sharing that experience through private charters. Whether it’s anchoring in the Playpen with the skyline behind you or cruising along the river, my goal is to create safe, laid-back, and memorable moments for everyone on board. There’s no better way to see Chicago than from the lake. My goal is simple: offer safe, fun, and memorable experiences on the water, with a personal touch that comes from truly knowing this lake.
Features & Details
- Sea Ray
- SUNDANCER 300
- Capacity: 10 people max
Safety Equipment
Life Jackets (10)
Guest Amenities
Cabins (2)
Sun Protection
Toilets (1)
Leisure & Entertainment Equipment
Bluetooth
Sound System
Accessories
Water Mat
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
2601 North Cannon Drive
Chicago, Illinois, 60614
United States
Departure Location
Cancellation Policy
Free cancellation up to 10 days before your trip.
Additional Terms & Information
We only allow USCG Licensed captains to operate our boats. A boating license itself does not qualify. Thank you. WEATHER POLICY: Your safety always comes first. If the vessel owner or captain determines that conditions are unsafe—such as severe storms, strong winds, or dangerous waves—your trip may be rescheduled or canceled. Light rain or cooler temperatures usually won’t stop the fun!
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