@PLAYPENCHICAGO
@PLAYPENCHICAGO
@PLAYPENCHICAGO
@PLAYPENCHICAGO
Playpen Chicago hosts spectacular events with its partners in the boating, culinary and entertainment fields.
How early is too early to start putting boats back in Chicago’s harbors for the 2026 season? 🤔
📸: @ashleysummersphotography
That time @heidiers met the most famous “celebrity” at Chicago’s Playpen…
If you’ve been out there, you know EXACTLY who we’re talking about. 👀
Who’s the most iconic “celeb” you’ve spotted on the water?
Chris Lake navypierchicago // July 10 - 11
There’s the show at Navy Pier.
And then there’s the show from the water.
Watch Chris Lake lakeside aboard a private yacht,
or pregame in style and get a private dockside drop-off just steps away from the show.
An exclusive perspective on one of the city’s biggest nights.
Now booking. Limited availability. DM for more info.
Follow for more bass by the lake concert opportunities. brought to you by benlovesboats
navypiermarina
alwill25
sunkatiee
michaelbarbourr
dr.neenadenne
karissakolorist
asiel_imadeldin
taylorkendra2
#chicago #lakemichigan #chicagoboatrental #playpenchicago #thingstodoinchicago
Love is always in the air at Knock Out Charters. ♥️ A look at a few of the sweetest engagements aboard. Our books are open— schedule your private engagement proposal charter for a date you’ll always remember! #happyvalentinesday #knockoutcharters #chicago #chicagodating
When your love language is tax evasion.
Also - If he can’t dock these you shouldn’t date him.
Happy Valentine’s Day ya’ll.
#chicago #yachtcharter #yacht #dating #playpenchicago
Bet you won’t send this to your crush rn 💋💌😛
Chicago | Meme | Valentines Day | Funny | Holiday | Trend | Smart City Locating
*Take $200 Captain School! Use code BOATSAFE200GRBS during the Grand Rapids Boat Show 2/11 to 2/15.
*Captain school link in bio 🔗 & below ⬇️
*Read the BLOG! Link in bio 🔗
A pre-charter guide - So you can maximize your time on the water.
Arrival Time
Please plan to arrive 15–20 minutes early. Marinas can be a bit of a maze, and there’s always someone who ends up at the “other harbor.” Arriving early gives us time to get you onboard comfortably without cutting into your cruise.
Your charter time begins at the scheduled start time — not when the last guest arrives — so the earlier everyone is there, the more time you’ll have underway.
Provisions & Ice
If you’re bringing drinks, food, or ice, please grab those before arrival. Last-minute stops tend to take longer than expected, and we don’t want a bag of melting ice to be the reason we’re still at the dock.
Passenger Manifest
All guests must be listed and sign the manifest prior to departure. This is required for insurance and safety. We cannot leave the dock until it’s complete.
Guest Count
The vessel is licensed for a specific number of passengers. For safety and compliance reasons, we cannot exceed that number — even by one.
Gratuity
Industry standard gratuity for the captain and crew is typically 15–20%, and is always appreciated if you feel they’ve delivered a great experience. They work hard to make your day seamless.
Weather
If there are unsafe conditions, we will always prioritize safety. Light clouds or typical wind are part of boating — but in the event of severe weather, we’ll discuss options together.
⸻
The goal is simple:
Arrive early.
Board smoothly.
Depart on time.
Maximize your time on the water.
You’re investing in an experience — and my job is to make sure every minute of it feels effortless. - Ben
#chicago #playpenchicago #chicagoboatrental #thingstodoinchicago #lakemichigan
Benito loves boats.
#badbunny #chicago #lakemichigan #thingstodoinchicago #playpenchicago
PlayPen Dreaming from 40 E. Huron 😍
#boatsafechicago #boatersafety #playpenchicago #chicago #chicagoboating
Yacht math.
For the price of an overpriced dinner in West Loop at a restaurant (that’s probably going to close in two weeks) you and 12 friends can be on a yacht on Lake Michigan.
Wanna float it: DM benlovesboats
Wanna fly it: DM p3jets
#chicago #lakemichigan #do312 #westloop #playpenchicago
Enjoy a day out on the water!!
-
🚢= stray kat
🚢 =martini
🚢 =espresso
Gmail: boatmartini@gmail.com
phone number: 708-928-2020
website: chicagopartyyacht.com
-
-
#chicago #boats #playpen #charteryacht #lakemichigan
No one talks about how hard it is to go from lake days & skyline views ➡️ layers & shivering 🥶
We feel your pain! Just 3 months until endless sunshine, lily pads, and warm waters 🌊😎. Mark your calendars for the start of boat season—May 1 🗓️ .
.
.
.
.
.
.
.
.
#ChicagoBoating #BoatRentalChicago #ChicagoSummer #ExploreChicago #lakemichigan
The only ski trip will sign up for.
(And yes you can ski Lake Michigan) DM for more info.
#chicago #playpenchicago #lakemichigan #do312 #yachtlife
Paid actor: alwill25
Boat credit: andy_stone_ski
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.
Copyright © 2022-2025 The Playpen Enterprises LLC – All Rights Reserved
