top of page

STARTING AT $1,399 - NOW INCLUDES 10 GUESTS!

Sail & Swim Playpen Charter

4 Hour Cruise

USCG Captain 

 Up to 10 Guests

Summer is your time to let loose & meet up with friends. That's why On A Boat Sailing offers weekend trips to the playpen all summer long. So no matter when you & your crew can make it happen, we'll be here to host the celebration.

FRI • SAT • SUN
DEPARTING 10AM & 2:30PM

airbnb-logo
getmyboat-logo
bucketlisters-logo
playpenchicago-logo

OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018

YOUR VIP SAILING EXPERIENCE AWAITS YOU.

Guests:

Up to 10

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 adventurous day ahead.

dragonfly-cockpit

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.

dragonfly-cabin
onaboat-8501.jpg

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.

CUSTOMERS LOVE SAILING WITH US

7 years of fresh waters, exclusive parties & unforgettable times on Lake Michigan!

SAIL, SWIM, SIP & FLOAT ON THE LAKE.
PRICE NOW INCLUDES UP TO 10 GUESTS!

Private Bathroom

Bluetooth

Floaties Included

This 4-hour sailing experience allows our 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 10 guest

FRI • SAT • SUN
DEPARTING 10AM & 2:30PM

IMG_4688.jpeg

Flexible Booking Features
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

IMG_2451_edited.jpg

OUR PRIVATE SAILING ADVENTURES ARE LIMITED!

bottom of page