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Sleek 29ft Sport Cruiser | Playpen, Skyline, Sunset | Capt, Fuel Incl.
,
29 ft
Boat length
Up to 6
Passengers
Captained
This boat is rented with a captain
83%
Owner’s response rate
The boat
There is no better view of Chicago than from the water. We offer fully private experiences on Lake Michigan aboard a Cruisers 298SS South Beach Edition - a premium 29-foot sport cruiser built exactly for this. Your group of up to 6 has the entire boat. Just your crew, the skyline, and Lake Michigan.
We depart from Belmont Harbor on Chicago's North Side - convenient for Lincoln Park, Lakeview, Wrigleyville, Bucktown, and Andersonville. No fighting downtown traffic. Pull up, board, and you're on the water in minutes.
We run three time slots daily:
Morning - 10:00 AM to 1:00 PM
Afternoon - 1:30 PM to 4:30 PM (most popular)
Evening - 5:00 PM to 8:00 PM
Nighttime Fireworks Cruise - Wednesdays & Saturdays
Wednesday - 7:30 PM to 10:30 PM
Saturday - 8:30 PM to 11:30 PM
Holidays & Special Events:
Premium dates including the 4th of July weekend book fast and are priced accordingly. Reach out early to secure your date.
Extra hours available upon request, subject to availability.
Our most popular experiences:
- The Playpen: Anchor at Chicago's legendary summer boating scene. Swim, sun, socialize, watch the skyline. The quintessential Chicago lake day.
- Sunset cruise: Watch the city go gold from the water as Chicago lights up for the evening. The most photogenic 3 hours in Chicago, period.
- Navy Pier Fireworks: Wednesday and Saturday nights all summer — the best fireworks view in the city is not on the pier, it's from the water. Limited slots available.
- Celebrations: Bachelorettes, birthdays, anniversaries, proposals, date nights, corporate outings. Private boat, your group, your music, your pace.
The Boat:
The 2017 Cruisers 298SS South Beach Edition is a premium 29-foot sport cruiser powered by a 380-horsepower MerCruiser 8.2L engine. Built for open water, it handles Lake Michigan conditions with confidence and covers ground quickly when you want to move.
Spacious bow seating area - perfect for sunning and photos
Wraparound rear-facing lounge seating
Swim platform with ladder for easy water access
Bluetooth audio - connect your own playlist
Cooler with ice - bring whatever you want to drink (no red wine, no glass)
USCG-required safety equipment throughout
What's Included --
Licensed USCG captain for the full charter
Fuel - we cover it, you don't
All USCG-required safety equipment
Bluetooth audio - bring your playlist
Cooler
Spacious platform
You bring: Food, drinks (BYOB - alcohol welcome, 21+, no red wine & no glass), sunscreen, towels, whatever makes your time on the water yours.
Perfect For:
Bachelorette and bachelor parties
Birthdays and milestone celebrations
Anniversary and date nights
Proposals
Corporate team outings and client entertainment
Friends and family lake days
Navy Pier fireworks from the water
Summer visitors who want the real Chicago experience
About Your Captain
The company is operated by a USCG-licensed captain. Your captain handles all navigation, safety, and local knowledge so you can focus on enjoying the experience. We know where to anchor at the Playpen, when to position for the best fireworks view, and how to make your 3 hours on the water feel longer than they are.
How To Book
Select your date and time slot and book directly. We confirm within a few hours and send everything you need to know - exact dock location at Belmont Harbor, parking details, what to bring, and contact info for your captain.
The Details
Departure: Belmont Harbor, Chicago North Side
Capacity: Up to 6 passengers (private — your group only)
Duration: 3-hour minimum, additional hours available
BYOB: Yes - alcohol welcome for guests 21+
Swimming: At captain's discretion based on conditions
Captain fee and fuel: Included in all pricing
Read more
Owned by
James
Amenities
Bathroom
Stereo
Bluetooth audio
Cooler / Ice chest
Swim ladder
Shower
Deck shower
Anchor
Specifications
Year
2017
Length
29 ft.
Make
Cruisers Sport Series
Model
298SS South Beach Edition
Capacity
6
See all
/ (excl. fees)
Terms
- Fuel is included.
- Security deposit: $0.
- Cancellation policy:
- Charter type: Bareboat
Ratings & reviews
Boat location
Exact location information is provided after a booking is confirmed.
Your crew
Things to know
Allowed on boat
swimming
alcohol
kids under 12
shoes
Cancellation policy flexible
- Free cancellations until 24 hours before the booking start time.
- Cancellations within 24 hours of the booking start time are non-refundable.
Commercial owner
This boat belongs to a Commercial Owner, an independent boat rental company. A Commercial Owner is an independent, Boatsetter-approved boat rental company who provides their own insurance to their guests.
Security deposit
A security deposit hold (not a charge) will be placed on your credit card 48 hours before your booking starts to cover any incidental damage that may occur during your rental. This hold is released 48 hours after the booking is complete, if no claims are made. The security deposit amount for the boat you are booking will be outlined during the check-out process.
Learn more about security depositsCaptain info
If requested, the owner can provide a list of available captains for bareboat charter or the renter can use their own qualified captain. If the boat is being time chartered, the owner will provide the Captain.