FRI • SAT • SUN 10AM & 2:30PM
Sail & Swim Playpen Charter
4-Hour Private Charter
Up to 7 Guests
Money Back Guarantee
The all-inclusive booking for summer birthdays, bach parties, and incredible photoshoots with your favorites.
Enjoy unrestricted access to our 37' luxury sailing yacht while you spend the day lounging under the umbrella, soaking up the rays on the sun deck, or floating with your crew on Lake Michigan.
500+ 5-star reviews
Friends love celebrating at Chicago's Playpen. We make it effortless.
Luxury meets comfort aboard our 37' sailing yacht, S/V Dragonfly.
Guests:
Up to 7
Length:
37'
Bluetooth
Speakers
Private
Bathroom
Refrigerator
Access
Kitchenware
Available
S/V Dragonfly offers world-class sailing with comfortable amenities, encouraging you & your guests to focus on the unforgettable day ahead.
The bimini umbrella in the cockpit gives ample shade and some light rain protection in our main seating area. Willing guests are welcome to relieve our captain and try their hand at the helm!
Lounging space for sunbathing and lake-gazing is available on the foredeck. This will be a popular locale for photo opportunities on beautiful days! Those camera rolls are no match for these views.
Down below, the teak interior cabin has two private changing rooms, a bathroom with shower, kitchen and comfortable salon seating area. The perfect place to store your bags, keep your drinks cool and prepare the days provisions.
New in 2025, our sailing experiences are all-inclusive! That means fewer coolers to carry, less ice to lug, and more time to focus on making memories with your favorites. Your all-inclusive booking includes a complimentary champagne toast,12-pack of High Noon on ice and unlimited snacks & non-alcoholic drinks.
This half-day, all-inclusive sailing experience allows guests to split their time between sailing the Lake & anchoring for a swim & float party at the Playpen. Sun bathe in style on deck, stay shaded in our spacious cockpit or enjoy our comfortable amenities in the cabin below.
Starting at $1,399 for up to 7 guests
FRI • SAT • SUN
DEPARTING 10AM & 2:30PM
Looking to Sail & Swim with more than 7 guests?
Check out Sailing Chi's Sail & Swim+ for more time on a larger boat with a bigger group of your friends!
No hidden fees. No surprise charges. 100% transparent pricing.
❌ NO hourly captain fees
❌ NO refueling costs
❌ NO docking fees
Golden Sail Money-Back Guarantee
Bad weather? Unexpected issues? We recognize things come up. Our money-back guarantee ensures you have the freedom to make adjustments with ease, providing peace of mind in the weeks and days leading up to your planned outing with us.
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
Three easy steps to pre-book your private boat charter this summer:
STEP 1 - Choose Your Adventure
Browse our all charters & cruises page. We offer something for everyone!
STEP 2 - Recruit Your Crew
Fire up those group chats and start recruiting. Summer weekends will sell out.
STEP 3 - Lock-In Your Big Day
Book with a 50% fully-refundable deposit. Remaining balance to be paid at end of experience.
