And dolphins make us happy. Find out more about our cookies policy here.
Charter this Jeanneau Sun Odyssey 37 Luxury Sailboat with a fully licensed USCG Master Captain for a memorable sailing experience in downtown Chicago! • Comfortable seating areas for 6+ guests (Parties up to 10 guests please inquire for additional options) • Kitchen and bathroom on board • Stereo surround sound speakers above and below deck with bluetooth connection • Fridge, fully stocked kitchenware • Anchoring in the Playpen or Monroe Harbor for swimming • Swim platform with ladder-noodles, life-jackets and floaties • Complimentary beverages and snacks or BYO food and drinks (alcohol allowed) • Depart and return from Monroe Harbor in downtown Chicago • Skyline views of the Loop, Museum Campus, Navy Pier and Chicago Lighthouse. Navy Pier Fireworks are every Wednesday and Saturday night from Memorial Day to Labor Day • Anchor for concerts at Northerly Island Fully licensed, permitted and insured boat operating at the highest safety standards set and maintained by the US Coast Guard. We have hosted engagements, photoshoots, birthday and bachelorette parties, corporate outings and many more memorable events! If you have any questions, we can answer those through GetMyBoat’s messaging platform before you book. Just hit, “Request to Book” and send us an inquiry for a custom offer. Cheers, 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.
A really pleasant day on a really nice boat with a highly capable captain
This was an amazing way to spend the morning on the water. Greg was obviously a great sailor and able to handle his 37' boat by himself. He was full of knowledge about the area and we loved hearing all the fun facts about the city of Chicago.
Great experience, would highly recommend. Was greated at arrival, Greg was an amazing host. The whole experience was perfect for our group. From departure to arrival I would happily do it again.
Greg is a great boat handler and a very mellow, nice person. Trip was wonderful and recommended 100 percent
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.
You’ll get directions to the departure location when you make a booking.
90% refund up to 2 days prior.
Guests are permitted to cancel for a 90% refund up to 48 hours ahead of departure. Less than 48 hours cancellation without notice is non-refundable. We do out best to reschedule in the event of cancellations. 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.