PLAYPEN PARTIES INCLUDED IN THIS BOOKING
Sail & Swim Half-Day Charter
Experience 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.
4 Hour Charter
USCG Captain
Up to 10 Guests
10am-2pm | 2:30pm-6:30pm
Fridays • Saturdays • Sundays
All bookings depart from centrally-located Monroe Harbor in Downtown Chicago.
PRIVATE HALF-DAY SAILING FOR UP TO 10 GUESTS
SAIL, SWIM & FLOAT IN STYLE ON LAKE MICHIGAN!
MEET YOUR SAILING YACHT FOR THE DAY
S/V DRAGONFLY
Guests:
Up to 10
Length:
37'
Bluetooth
Speakers
Private
Bathroom
Refrigerator
Access
Kitchenware
Available
Dragonfly offers comfort & style compared to other sailboats. The bimini umbrella in the cockpit provides shade while the dodger windshield provides a wind break from the cool breezes on the Lake. Lounging space in the sun is available on the foredeck. Down below, the teak interior cabin has two private changing rooms, a bathroom with shower, kitchen and comfortable salon seating area.
We sail out of
Monroe Harbor
in Downtown Chicago
View our Half-Day Charter
dates & times:
CUSTOMERS LOVE SAILING WITH US
7 years of fresh waters, exclusive parties & unforgettable times on Lake Michigan!
Private Bathroom
Be Your Own DJ
Floaties Included
Sun bathe in style on deck, stay shaded in our spacious cockpit or enjoy our comfortable amenities in the cabin below. This 4-hour sailing experience allows guests to split their time between sailing the Lake & anchoring for a swim & float party. The choice is yours!
Pricing from $183pp + 6% booking fee
Flexible Booking Plan
50% Deposit, Fully-Refundable
We recognize that plans change, so we've designed our booking options to be incredibly flexible. This ensures you have the freedom to make adjustments with ease, providing peace of mind for your experience with On A Boat Sailing.
100% Refund up to Two Weeks From Departure
50% Refund up to 48 Hours From Departure
Full Refund for Weather Related Cancellations
Swap Dates With No Fees-Subject to Availability
Start planning your summer sail now!
STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront.