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Captain Optional
Relaxed, social outings with an easygoing vibe, where groups enjoy hanging out on the water, using floaties, and making a day of it in Chicago’s playpen.
Well‑maintained, clean cruiser with plenty of comfortable seating inside and out, plus a cooler and floaties that guests consistently appreciate.
Guests describe the captain and owner as respectful, easy to work with, and highly responsive before and during trips, creating a smooth, low‑stress experience.
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AI Overview
Owner's Description
ABOUT THE TRIP Set sail on the beautiful waters of Lake Michigan and turn your day into an unforgettable experience. Whether you're celebrating something special or just escaping the city, this private yacht charter is the perfect mix of relaxation and fun. Cruise the shoreline, anchor at the Playpen, enjoy your favorite music, and soak up the sun with your crew. Want more time on the water? You can easily extend your trip if availability allows—just ask! ABOUT THE BOAT Step aboard our stunning Sea Ray Sundancer 340, designed for both comfort and entertainment. This well-maintained yacht features a spacious layout, plush seating, and a removable canopy so you can choose between sun or shade. Enjoy a premium sound system with Bluetooth, subwoofer, and tower speakers—perfect for setting the vibe. There’s also a clean onboard restroom for your convenience, so you can relax all day without worry. WHAT’S INCLUDED - Yacht rental - Fuel - Premium sound system (Bluetooth) - Coolers (just bring ice!) - Captain & crew coordination WHAT’S NOT INCLUDED - Gratuity for captain and crew (20% standar) - Ice (please bring your own) - Lily pad $75 (Pay at dock) - Flooting Raft $100 (pay at dock) No hidden fees — what you see is what you pay. CAPTAIN INFORMATION - A licensed captain is required and not included in the base price - You’ll receive a list of pre-approved captains to choose from - The captain's payment is made directly at the dock IMPORTANT DETAILS - Maximum capacity: 13 passengers (strict U.S. Coast Guard regulation) - BYOB: Bring your own food and drinks - We provide coolers for your convenience PERFECT FOR Birthday parties Bachelorette & bachelor parties Corporate outings Sunset cruises Playpen party days
Peter
93 total bookings
- Capacity
- 13 guests
- Luxury, Events & Large groups
- Motor Yacht
Reviews
(41 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
14 photos have been added by reviewers who booked this listing.
CW
Claire
Great boat rental! Very affordable, and captain provided a cooler and lots of floaties to use in the playpen. Captain and owner were both super responsive leading up to the booking. Boat was well maintained, clean and lots of sitting space both inside and outside. Will definitely be booking again!
Peter
Highly recommend booking with Capt Pete. Such an awesome time for our group. Communication with us was great ahead of time, and had an awesome time on the water. Thanks Pete!
Carina
Had a great 1st experience chartering this boat. Owner Peter was communicative and helpful through the process. Everything was thought of for our trip and we appreciated the amenities provided! It was smooth sailing for us and we will definitely book again.
Bria
Our group of 11 had an amazing time out on the lake with captain pete! He communicated well and had all of the amenities needed- coolers, Lilly pad, blue tooth, refrigerator space for food, etc. the boat was clean and had lots of space, accurate to listing. We would definitely book with Captian Pete again!
AI
ANTHONY
Peter is the best. Communication 100, patience- 100 out of 100. He is the best among the rest. I will recommend Peter 100 x out of 100. Look no more, you gat the best among the rest.... thank you Capitano ...
Peter
93 total bookings
Private Luxury Charter in Chicago 🚤✨ Hi, being on the water isn’t just what we do, it’s how we live. Every charter we host is designed to deliver a seamless, high-end experience from the moment you step on board. I specialize in private luxury charters in Chicago, curated for guests who value comfort, style, and attention to detail. Whether you’re celebrating a birthday, hosting clients, planning a romantic escape, or just enjoying a day with friends, I make sure your experience feels effortless and unforgettable. Our priority is simple: your safety, your comfort, and your experience. The boat is always meticulously maintained, and every trip is run with professionalism and care—so all you have to do is relax and enjoy the moment. Expect great energy, stunning skyline views, and a premium atmosphere that transforms a regular day on the water into something truly special. Let’s make your next boat day one to remember !!
Features & Details
- Sea Ray
- Sundancer 360
- Capacity: 13 people max
Safety Equipment
Fire Extinguishers
Life Jackets (1)
Operating Equipment
Generator
Guest Amenities
Cabins (1)
Cooler
Toilets (1)
Washrooms Onboard
Wi-Fi
Leisure & Entertainment Equipment
Bluetooth
Sound System
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
3100 South DuSable Lake Shore Drive
Chicago, Illinois, 60614
United States
Departure Location
Cancellation Policy
Free cancellation up to 7 days before your trip.
Additional Terms & Information
⚓ Weather Policy Charters run rain or shine. In the case of severe weather (captain’s discretion—lightning, high winds, unsafe conditions), your trip may be rescheduled at no cost. Refunds are not guaranteed unless rescheduling is not possible. ⏰ Late / No-Show Policy Please arrive 15–20 minutes early. - Late arrivals will not extend charter time. - No-shows or arrivals over 30 minutes late may result in cancellation without refund. 💳 Cancellation Policy - Cancellations made 7+ days in advance: Full refund (minus processing fees if applicable) - Within 7 days: Non-refundable, but we’ll try to reschedule when possible - Same-day cancellations: No refund 🛟 Safety Rules - The captain has full authority during the charter - Life jackets are available and required in certain situations - No swimming unless approved by the captain - Follow all safety instructions at all times 🍾 Boat Rules - BYOB allowed (no red wine or staining items preferred) - No drugs or illegal substances - No glass containers if specified by the captain - Guests must respect the boat, crew, and other passengers - Excessive intoxication may result in early termination of the trip 👥 Capacity & Responsibility - Maximum of 13 guests per charter (per Coast Guard regulations) - The booking guest is responsible for the behavior of their group and any damages 💵 Gratuity A standard 20% gratuity for captain/crew is not included and is greatly appreciated.
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