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With Captain
Relaxed, scenic cruises on the Chicago River and lakefront with skyline views, easygoing vibes, and a fun, stress-free atmosphere for small celebrations.
Well-kept, comfortable Monterey with a welcoming vibe that guests describe as beautiful and enjoyable for both river touring and lakefront hangs.
Attentive captain known for clear communication, flexibility with timing and weather, and a kind, accommodating approach that keeps trips smooth and memorable.
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AI Overview
Owner's Description
Price for weekends : Min 4 hours booking at $ 200 per hour . See Chicago like never before — from the water! Rent this luxury 25’ Monterey private yacht today! Ideal for summer fun, celebrations, or a relaxing cruise with friends and family. Please ask captain to add additional hour while on the boat for availability The Boat - Comfortably accommodates up to 7 guests - Clean, stylish, and well-maintained - Smooth, safe, and perfect for cruising or anchoring at the Playpen Cruising Experience: - Chicago River – iconic architecture and unbeatable photo opportunities - Chicago Skyline – breathtaking city views from Lake Michigan - The Playpen – anchor, swim, relax, and enjoy the summer vibe - Open-lake cruising (weather permitting) Onboard Entertainment: - Bluetooth sound system – play your favorite music - Spacious seating for lounging and socializing - Swim-friendly setup for Playpen days - Perfect for sunset and skyline photo moments Included Extras: - Cooler (BYOB) - All required safety equipment & life jackets - Floating water mat. - Experienced, friendly licensed captain. Great For - Birthday celebrations - Bachelorette / bachelor outings - Date nights & proposals - Family & friends outings - Tourists and locals alike Please inform on your reservation all ages for safety. Under 18, under 21 or all older 21. please don’t bring any red drink or glass cups for safety , cleaning price may apply for any colored drink stain
Optional Add-ons
These options can be added during checkout.
Extra person
$35 per hour
gratuity
15% of trip Cost
Tamer
27 total bookings
- Capacity
- 7 guests
- Powerboats, Pontoons, & RIBs
- Bowrider
Reviews
(11 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
33 photos have been added by reviewers who booked this listing.
MS
Marisa
Great boat day! Very nice and accommodating host and captain!
Hallie
Tamer was the best!! He was so communicative and the experience was fun and stress free. Would definitely recommend and would book with him again. 10/10 experience!
IH
Ivy
Tamer was great! Super kind and accommodating. Our group had so much fun!
Danni
Tamer was soooo awesome! ‘No’ was never an answer & he had the best communication you can ask for! Me & hubby celebrated our honeymoon & Tamer made every second count!
Albert
Had an amazing time with Tamer! Professional service, great communication, beautiful boat, and a great Captain. Would highly recommend 10/10.
Tamer
27 total bookings
Features & Details
- Monterey
- 25 ft
- Capacity: 7 people max
Safety Equipment
Anchor & Rode
Bilge Pumps
Carbon Monoxide Detectors
Ditch Kit
EPIBRS
Emergency Steering
Fire Extinguishers
First Aid Kit
Flares
Haz-Mat Safety
Kill Switch Lanyard
Life Jackets (9)
Life Rafts
Life-Saving Appliances
Medical Supplies
Navigation Lights
Navigation Equipment
VHF Radio
Operating Equipment
Depth Sounder
Generator
Guest Amenities
BBQ
Cabins (1)
Coffee Maker
Cooler
Fridge
Kitchen Utensils
Microwave
Sink
Stove
Sun Protection
Toilets (1)
Towels
Washrooms Onboard
Wine Fridge
Wi-Fi
Leisure & Entertainment Equipment
Bluetooth
Floats
Sound System
Indoor dinning Area
Indoor Lounge Area
Outdoor Dinning Area
Outdoor Lounge Area
Accessories
Fish Finder
Fish-Fighting Chair (1)
Inflatables (6)
Water Toys
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 5 days before your trip.
Additional Terms & Information
- Weather: Trips may be canceled or rescheduled due to unsafe weather at the captain’s discretion. If canceled for weather, guests may reschedule or receive a refund per GetMyBoat policy. - Late Arrival / No-Show: Rental time starts at the scheduled departure time. Late arrivals do not extend the trip. No-shows are non-refundable. - Guest Limit: Maximum 7 guests onboard at all times. No exceptions. - Safety: Guests must follow all captain instructions. Life jackets are provided and required when instructed, especially for children and non-swimmers. - Alcohol: Alcohol permitted for guests 21+. Unsafe or excessive intoxication may result in early trip termination without refund. - Boat Rules: Shoes may be removed onboard. Please treat the boat with care—guests are responsible for any damages. - Smoking: Smoking or vaping allowed outdoors only , Not inside the cabin,No hookah or open flames. - Food & Drinks: BYOB and food welcome. Red wine and staining foods are discouraged. - Swimming: Swimming allowed only when anchored and with captain approval (Playpen or designated areas). - Gratuity: Captain gratuity is not included and is appreciated for great service. Industry standard is 15–20%, at the guest’s discretion.
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