@PLAYPENCHICAGO
@PLAYPENCHICAGO
@PLAYPENCHICAGO
@PLAYPENCHICAGO
Playpen Chicago hosts spectacular events with its partners in the boating, culinary and entertainment fields.
🚤 Chicago’s Yacht Tax TRIPLE THREAT ⚓
Mayor Brandon Johnson’s 2026 budget aims to triple the city’s 7 % boat-mooring tax—raising it to 23.25 %.
The proposal targets high-end leisure craft to help fill a billion-dollar budget gap, but critics warn it could sink the city’s boating economy.
Would this make Chicago’s harbors less attractive—or is it a fair share for luxury boaters?
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Read the full breakdown in our featured article (link in bio)
#PlaypenChicago #ChicagoBoating #LakeMichiganLife #ChicagoPolitics #YachtTax #ChicagoHarbor #BoatLifeChicago #PlaypenScene #LuxuryLifestyle #WindyCityWaterfront
So, much fun hanging out with playpenchicago at the lake.
We were able to catch one of the last beautiful days out! Popping bottles, eating oysters, charcuterie and feeding ducks.
Thank you to the captains of Persephone for taking care of us all and having me as an add on to the party.
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Just a reminder of how beautiful Chicago is and the fact that I will shuck you oysters ANYWHERE you needem.
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Shoutout to the incredible artist c.k_reed For this incredible piece that will be going on my wall immediately.
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#lakemichiganlove #chicago#boating#oysters#oyster#playpenchicago #oyster#showmeyourhellhole
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Scenes from yesterday on the boat learning about shucking oysters with loganoystersocials playpenchicago heidiers themetropolitanchicago 🦪🍾🥂 WHAT FUN!!
Always a great day on the water with chitownboating 🛥️🍾
Special thanks to el_capitan_jesus ⚓️
We’re celebrating the end of the season on the water today with oysters by @loganoystersocials and bubbly thanks to @themetropolitanchicago!
While boating season may be coming to a close, we’re keeping things rolling all winter long. Keep an eye out for our events on land through next May! ✨
When the city is your Playpen, the seasons become irrelevant—from the lake to downtown, we’re doing it all! ✨
Pasta and Chill: Pasta Making Class with @chefandysuarez
Photography by @caseyalexandramedia
Vibes by @playpenchicago
Boating season is about to end but the fun doesn’t have to! Being a member of The Metropolitan, which has 50+ years of heritage as Chicago’s premier private club, means you get to enjoy all of these perks over the winter and more:
▪️Access Playpen Chicago x The Metropolitan events all year round and rotating 5–8 member-only events per week, from networking socials to themed dinners
▪️Located up above the city in the Willis Tower with panoramic skyline views
▪️Exclusive access to over 250 reciprocal clubs worldwide
▪️Coworking spaces perfect for remote professionals or creative entrepreneurs
▪️Family-friendly programming for when you want to mix business with personal life
Join us in the sky! ☁️
Full vlog on our youtube ~ Link in Bio #playpenchicago #yachtlife #chicago
Summer 2025 stole our hearts! Huge shoutout to @citywineryriverwalk for the vino, @chicagowinesnob for the wine wisdom, @caviardreamofficial and @nautichicago, @lifestyleboatrental for an epic Wine and Caviar bash at @navypierchicago ✨ Special thanks to @rockroseproductions for bringing the visual magic! 🎥
Multitasking at its finest: Who said you can’t be both flexible and fabulous?
But next time, make sure the engine is OFF with keys on the dash before doing your yoga workout on the swim platform ✅
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Video credit 🎥🤩 leahpaskero
#BoatLife #SplitsOnTheGo #HighNoonMoment #BoatSafeChicago #SummerVibes #DangerousAndDelicious #WeekendWarrior #YachtLife #FlexibleFun
We don’t know what tomorrow holds, but we know God is holding us. Live your life today! 80+ degrees in October!!!! 😅🥰 #summertimechi #liveyourlife #fitmodel #playpen #chicago #views #peace #serenity #naturalmodel #blondehair #blackisbeautiful❤️🖤💚
It`s been a great season, but Winter Is Coming!!
#chicago #lakemichigan #imsexyanditowit
10/5/2025 - Beautiful (maybe) last sunday! Seeing good people and spending time on the Pearl
leahpaskero is also out here!
(I`m not purposefully leaving out friends or boat friends names! Its just the top of my head!)
10/4/2025 - still in the 90s in October! I`m excited for this beautiful weekend! And we`re nearing 1000 followers!
Chicago is my Playpen 💫 built by the creators & entrepreneurs who make this city thrive. Know someone who should be at the next playpenchicago event? Tag them or send them my way 💌
👨🏻🍳: chefandysuarez
📸: caseyalexandramedia
Playpen Chicago hosts spectacular events with its partners in the boating, culinary and entertainment fields.
Join Playpen Chicago and find your friend with a boat.
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