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With Captain
Relaxed, social cruises from Navy Pier with skyline views, attentive crew, and fun touches like surprise jet ski rides that make the outing feel special.
Clean, stylish flybridge layout with plenty of room to spread out, easy flow between spaces, and a setup guests say feels open, comfortable, and well kept.
Guests consistently describe the captain and crew as professional, kind, and attentive, making the whole outing smooth, easy, and genuinely welcoming.
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AI Overview
Owner's Description
Step aboard this 50’ Azimut Flybridge and settle into a relaxed day on the water with Chicago’s skyline all around you. The layout is social and easy to move through, with comfortable spaces upstairs and below deck for groups who want to spend time together without feeling crowded. This yacht works especially well for lake days that mix conversation, music, food, and time in the sun. The setup feels polished without being formal, and everything is arranged so guests can arrive and enjoy the day without extra coordination or last-minute stops. Onboard Features: - Flybridge seating area - Open social layout - Sun pads - Swim platform - Premium sound system - Air conditioning and heating - Wi-Fi onboard - Wine fridge - Microwave and stove - Shower and washrooms - Towels and pillows provided Water Activities: - Floating island - Electric surfboard rides included - Paddleboards - Water mat - Inflatables - Water toys - Swim access from platform Good to Know: - Capacity for up to 13 guests - Captain optional - Suitable for birthdays and group gatherings - Comfortable setup for sunset cruises - Ice included - Wireless phone charging - Complimentary keepsake photos - Seasickness patches available - Saturday and holiday bookings limited to set 4-hour blocks
Optional Add-ons
These options can be added during checkout.
Amazing Tequila Package
$225 per unit
VIP Shuttle Service
$149 per trip
Douglas
63 total bookings
- Capacity
- 13 guests
- Luxury, Events & Large groups
- Motor Yacht
Reviews
(9 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
1 photo has been added by reviewers who booked this listing.
ME
Marcos
The boat was as described! I would recommend captain Douglas for anyone looking to book a boat in the future!
HO
Heather
Our boat was incredible, Captain John and Jen were amazing. Highly recommend this company and this crew.
MC
Michelle
We had a great experience, the crew was very nice and offered to get drinks and water for us. The boat was excellent, exactly what I wanted, enough space for people to spread out and not feel cramped. We even got surprise jet ski rides which was an added bonus. If I need a boat, I would book it again!
CS
Cornelius
Captain Doug was very professional and super nice and helpful would highly recommend him!
AK
Ashutosh
Doug's boat rental was awesome. The boat was clean, looked great, and my family had an amazing time out on the water. The location at Navy Pier made everything super convenient—we were able to get on the river quickly without wasting time, which was a big plus. The captain and his assistant were fantastic too. They were really attentive and made sure we were taken care of the entire trip. Highly recommend Doug if you’re looking for an easy and enjoyable boat rental experience in Chicago.
Douglas
63 total bookings
Why Book Me I love what I do with a passion that shows I have a knack for reading a group and adjusting for the vibe. I offer free sea sick patches that often save the day. I take a keepsake photo & print one out for everyone on charter for free - always a hit. I bring my own Insta360 for some great photo videos for your group for free! Just learning to fly my drone - happy to capture some unique videos. I bring plenty of portable phone batteries - so you are never untethered! I am arguably the most 5 star reviewed captain in Chicago - read the reviews. When I'm not driving, I'll juggle, clean up around you and refresh your drinks. I bring my own awesome floating saddles for fun in the water. I know the best fireworks locations in the harbor. I navigate the Chicago locks to get you in and out of the river.
Features & Details
- Azimut
- 46 Fly
- Capacity: 13 people max
Safety Equipment
Anchor & Rode
Bilge Pumps
Carbon Monoxide Detectors
Fire Extinguishers
First Aid Kit
Flares
Life Jackets (15)
Medical Supplies
Navigation Lights
Navigation Equipment
Oil Pollution Prevention
PFDs (2)
Radar Reflectors
Tool Kit
VHF Radio
Operating Equipment
Autopilot
Bow Thruster
GPS ChartPlotter
Salon Helm
Generator
Guest Amenities
Air Conditioning, Climate Control
Berths (2)
Cabins (2)
Cooler
Fridge
Heating
Kitchen Utensils
Microwave
Oven
Pillows & Blankets
Shower
Sink
Stove
Sun Protection
Toilets (2)
Towels
Washrooms Onboard
Wine Fridge
Wi-Fi
Leisure & Entertainment Equipment
Bar
Bluetooth
Floats
Sound System
Indoor dinning Area
Indoor Lounge Area
Outdoor Dinning Area
Outdoor Lounge Area
Outdoor Sun Bed
Accessories
Inflatables (2)
Water Mat
Water Toys
Paddleboards
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
797 East Grand Avenue
Chicago, Illinois, 60611
United States
Departure Location
Cancellation Policy
Free cancellation up to 5 days before your trip.
Additional Terms & Information
Weather Policy: If it is unsafe to operate on the day of your charter due to weather, then we will give you a full refund or reschedule at a discounted rate on a date/time the boat is available. On the day of your charter, we have the authority to deem whether weather conditions are considered safe or unsafe. Uncharterable weather conditions are typically the result of (but are not limited to) heavy storms, waves forecasted over 4+ feet, small craft advisory warnings, gale storms, and strong winds. Light rain and passing storms are typically considered safe. In the case that conditions are considered unsafe, our team will work with the guests to temporarily postpone or reschedule your charter to a future date. Rental Agreement: A boat rental agreement will be sent by email, following the booking confirmation, for your review and siganture. 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. Please note - hourly pricing varies between weekdays, weekends and holidays. Pricing noted is for regular weekend rates.
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