We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

37' Luxury Sailboat with Captain in Chicago, Illinois37' Luxury Sailboat with Captain in Chicago, Illinois37' Luxury Sailboat with Captain in Chicago, Illinois37' Luxury Sailboat with Captain in Chicago, Illinois

37' Luxury Sailboat with Captain in Chicago, Illinois

5.0(97 reviews)
·
155 bookings
·

Charter this Jeanneau Sun Odyssey 37 Luxury Sailboat with a licensed USCG Captain for a memorable sailing experience in downtown Chicago! We have hosted engagements, photoshoots, birthday and bachelorette parties, corporate outings and many more memorable events. Custom pricing based on group size and day of the week. See below for rates: Starting at $299/hr weekdays for up to six guests-additional $50 per hour per guest for groups larger than six up to ten max $325/hr weekends and holiday rate, minimum 3 hours for Saturdays What to expect on board: 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 ladder-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 and captain operating at the highest safety standards set and maintained by the US Coast Guard. Fuel, Captain and complimentary snacks and drinks are included in the quoted cost. Specific requests for provisioning or catering available for additional fee. Gratuity not included and paid in person. 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 you pay. Just hit, “Send Booking Inquiry” and send us an inquiry for a custom offer.

Starting from

$299/hour
  • Hourly
    6 hrs max
  • $299/hr
    2 hrs min
Greg and Cait

Greg and Cait

155 total bookings
Superowner
Captain Provided in Price
Professional Captain provided and included in the price.
Capacity
10 guests
Sailing
Cruising Monohull

Check Availability

Reviews

5.0 (97 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. 37' Luxury Sailboat with Captain in Chicago, Illinois
  2. 37' Luxury Sailboat with Captain in Chicago, Illinois
  3. 37' Luxury Sailboat with Captain in Chicago, Illinois
  4. 37' Luxury Sailboat with Captain in Chicago, Illinois
  5. 37' Luxury Sailboat with Captain in Chicago, Illinois
  6. 37' Luxury Sailboat with Captain in Chicago, Illinois
  7. 37' Luxury Sailboat with Captain in Chicago, Illinois
  8. 37' Luxury Sailboat with Captain in Chicago, Illinois
  9. 37' Luxury Sailboat with Captain in Chicago, Illinois
  10. 37' Luxury Sailboat with Captain in Chicago, Illinois
  11. 37' Luxury Sailboat with Captain in Chicago, Illinois
  12. 37' Luxury Sailboat with Captain in Chicago, Illinois
44 photos have been added by reviewers who booked this listing.
  1. MC

    Megan

    Greg was an amazing captain - he sent a very helpful document that outlined all the details about the boat ahead of time, he was on time and willing to be flexible in wherever we wanted to go. We had an amazing time and I would definitely hire him again!

  2. Sara
    Sara

    My fiancé and I planned a engagement photoshoot, however, due to weather conditions not cooperating, Greg was so flexible at rescheduling with us. He made us feel very comfortable and gave tips on how to take the most beautiful photoshoot out of the beautiful scenery of the city. Would totally recommend him! By the way, the boat was spotless, so clean and so so beautiful😍

  3. GM

    Gerald

    We had an awesome experience on Dragonfly. Greg arrived on time to pick us up and we immediately headed out onto the lake. Greg listened to what we needed as a new sailing couple and really delivered. Greg is extremely knowledgeable and a good teacher. We had a lot of fun, highly recommend Greg and Cait. We will be back aboard the next time we're in Chicago.

  4. Bailey
    Bailey

    We had such a good time taking our engagement photos on the boat. Greg was so accommodating to us with taking the photos and positioning the boat where we needed it. Would 100% recommend to anyone looking to take some amazing photos and have a great time on the lake.

  5. Dyna
    Dyna

    I rented the boat to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner! The boat is very spacious! We had 6 people and Greg was our captain but still had so much space to move around the boat! Greg is very laid back and easy to talk to. We brought food, alcohol and birthday cupcakes on board the boat. There’s a mini fridge to keep stuff cold. There was an aux cable so I was able to play music. There’s also a bathroom on the boat. Overall, I’d definitely recommend Greg and Cait!

Greg and Cait

Greg and Cait

155 total bookings
Superowner

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.

Features & Details

Make
Jeanneau
Model
Sun Odyssey
Length
37ft
Year
2003
  • 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
  • Paddleboard
  • Sailboat
  • Charter
  • Toilet
  • Cabin
  • Radio

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

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.

Similar Listings

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
Best of 2023
$220hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
$200hour
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

4.8
$115-$120hour
Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois
Sailing in Chicago · 6 guests

Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois

5.0
$225hour
Set Sail with 36' Sailing Boat in Downtown, Chicago
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0
Superowner
$225hour

Top Destinations Nearby