And dolphins make us happy. Find out more about our cookies policy here.
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. Two hour minimum for all charters and up to six hours max. Custom pricing based on group size, see below for rates: $250/hr for up to six guests $300/hr for up to eight guests $350/hr for up ten guests 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.
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!
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😍
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.
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.
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!
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.
You’ll get directions to the departure location when you make a booking.
Full refund up to 7 days prior.
Guests are permitted to cancel for a full refund one week 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.