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We offer a high-end, VIP sailing experience departing from Monroe Harbor in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is the yacht for you! - Starting at $200/hr weekdays - $250/hr weekends/holidays minimum 3 hours - Custom quotes based on group size and day of the week Amenities on board include: - Large open cockpit seating area - Complimentary beverages and snacks or BYO (alcohol allowed) - Stereo surround sound speakers with Bluetooth connection - Fridge with ice, fully stocked kitchenware - Anchoring in the Chicago Playpen or Monroe Harbor for swim and float parties - Swim platform with rinse shower-lily pad, noodles, life-jackets and floaties - Depart and return from Monroe Harbor in downtown Chicago - Skyline views of Downtown Chicago, Navy Pier and the Chicago Lighthouse - Anchoring for concerts at Northerly Island - Kitchen, bathroom and changing room on board Fully licensed, permitted and insured boat operating at the highest safety standards set and maintained by the US Coast Guard. Fuel, complimentary snacks, ice and drinks are included in the quoted cost. Specific requests for provisioning or catering available for additional fee. Captain’s fee is $150-$200/hr. Charter industry gratuity is 10%-20% of the contract cost per level of service and client satisfaction. If you have any questions, we can answer those through GetMyBoat’s messaging platform before booking. Just hit, “Send Booking Inquiry” and send us an inquiry for a custom offer. Cheers!
Starting from
Base Cost
- $300/hr2 hrs min
- $200/hr4 hrs min
- Independent Captain
- Payments go to the captain directly on your behalf.
Cait
- Capacity
- 7 guests
- Sailing
- Cruising Monohull
Check Availability
Reviews
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
AwesomeCommunication
AwesomeValue
AwesomeItinerary & Experience
Awesome
AC
Alicia
When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!
RM
Raymond
Cait was a lifesaver! Another captain canceled on me less than 40 hours from a booking on a Saturday! The horror of potentially having 10 guest in my crew with that time of letdown was so disappointing. Luckily Cait answered my bat signal and things happen for a reason because we got her amazing sailing yacht and awesome husband, captain Greg, to take care of us which was such a great upgrade! Thank you for taking such good care of us! We will be back and recommending you to all our friends!
rb
ryan
Booked this as a last night surprise for my family and friends. On the day, it ended up being super cloudy and rainy but Cait was so great at letting us reschedule. Her communication was excellent throughout. We ended up pushing by a few days and got perfect weather. We had an amazing sunset sail. The boat was clean and comfortable. We sailed and stopped to swim as well. Captain Greg (Cait’s husband) was super friendly and knowledgeable. He was a pleasure to be around. I would highly recommend booking this trip. For us, it was a life changing experience.
MC
Madeline
We had a great time sailing! Boat was nice and clean. Captain was friendly and helpful.
BL
Bryan
Highly recommend! Communicative and made sure group had a great time!
Cait
We are avid, professional sailors and enjoy sharing our passion for sailing with travelers and locals! For us, sailing offers adventure, relaxation, and the discovery of new places and people. Together we have sailed over 7,000 miles cruising the Great American Loop, Bahamas and Caribbean. Chicago is our homeport and there is no better place to combine the thrill of sailing with views of a world class skyline. Greg holds a Master Captain’s license from the US Coast Guard, and Cait is a licensed architect who will accompany your cruise when her schedule allows. Our boat is fully licensed as a commercial passenger vessel and operates under the highest safety standards as monitored by the US Coast Guard. Cheers! Cait & Greg
Features & Details
- Make
- Jeanneau
- Model
- Sun Odyssey
- Length
- 37ft
- Year
- 2003
- Bar
- Bluetooth
- Galley Stove & Oven
- Life jackets/required safety gear
- Wi-Fi
- GPS
- Berth
- Inverter
- Furling Mainsail
- Furling Headsail
- Fuel type: Diesel
- Dodger
- Chart Plotter
- Bimini
- Autopilot
- Inboard Engine
- Head
- Music System
- Paddleboard
- Sailboat
- Charter
- Toilet
- Cabin
- Full Bath
- Radio
Approximate Location
You’ll get directions to the departure location when you make a booking.
Cancellation Policy
Full refund up to 14 days prior.
Additional Terms & Information
Guests are permitted to cancel for a full refund two weeks in advance or 50% refund up to 48 hours ahead of departure. Less than 48 hours cancellation without notice is non-refundable. We do our best to reschedule in the event of cancellations but cannot guarantee future availability. In the event of severe weather, bookings will be cancelled and fully refunded or rescheduled at the guests convenience. Determination of weather related cancellations are made one hour ahead of scheduled departure. Guests must sign a waiver prior to departure. A safety informational speech will be given to all guests.
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