easy
4 hours
All levels; moderate physical activity involved in swimming.
Set sail on Lake Michigan aboard the luxurious S/V Dragonfly for a four-hour adventure filled with scenic views and refreshing swims. Discover why this high-end charter is a top choice for water lovers in Chicago.
All-Inclusive, 4-Hour Luxury Charter • Up to 7 guests • Perfect for bach parties & birthdays!
Embark on a thrilling 4-hour sail and swim adventure aboard the luxurious S/V Dragonfly, a 37' sailing yacht. Enjoy breathtaking views of Lake Michigan, a complimentary champagne toast, and a fully-equipped onboard experience. With a USCG-certified captain at the helm, create unforgettable memories with friends in a stunning setting.
This Half-Day Charter includes adventurous sailing & summer swimming with friends on Chicago's Lakefront. Entwined with comfortable amenities aboard our 37' luxury sailboat, guests will have the unique chance to experience Lake Michigan from a privately owned, meticulously-maintained sailing yacht.
✅ USCG-Certified Captain trained in First Aid and CPR.
✅ Private use of our fully-permitted, fully-insured sailing yacht.
✅ Complimentary champagne toast, beverages and snacks on board.
✅ Fully-stocked kitchenware, fridge and bathroom.
✅ Stereo surround sound speakers with Bluetooth connection.
✅ Swim platform with ladder, life-jackets, noodles, floaties & towels.
❌ NO Separate Captain Fee
❌ NO Fuel and Docking Fee
❌ NO Damage/Cleaning Deposit
We do our best to have on board everything you might need, some personal items to keep in mind include:
You may bring any food and beverages of your choosing including beer, wine, champagne, or hard seltzers. We have alcohol for purchase on board or ahead of time and can provide catering for an added fee.
If there is current or forecasted lightning or high wind, we make a weather cancellation one hour before your scheduled departure and provide a full refund.
You can see all of our FAQs here on our website
On A Boat Sailing, LLC
info@onaboatsailing.com
312.619.7858
Protect your skin during midday hours while on deck or swimming.
Capture stunning skyline views and memorable moments from the boat.
Weather can change quickly; pack layers for comfort.
Swim and sail days can be dehydrating; keep water handy.
Lake Michigan has been vital to Chicago’s development, with shipping and trade dating back over a century.
The charter operators follow sustainable practices to minimize environmental impact and protect Lake Michigan’s natural beauty.
Protects your skin from sun exposure during the boat trip.
summer specific
Necessary for swimming in Lake Michigan.
summer specific
Provide sun protection while on deck.
summer specific
Warm layers for cooler weather on open water.
spring/fall specific