The Chicago Playpen
Drop anchor and swim in Chicago's most famous stretch of water, minutes off the skyline.
Chicago's Finest, Handled Personally
You show up.
I handle everything.
Richard personally arranges every detail of your day on and off the water — the yacht, the car, the watercraft, and everything around them. One point of contact, one booking. You just enjoy it.
Chicago LakefrontScroll ↓41.89° N · 87.61° W
The Collection Concierge
I take care of everything.
From the first message to the last dock line, you deal with me — not a call center, not a rotating cast of vendors. I've spent years building the network in Chicago it takes to pull a day like this together: the captains, the chefs, the florists, the drivers, the photographers, the hotels. You tell me what you want the day to feel like. I quote one all-in price, coordinate every moving part, and hand you a plan that already works.
No vendors to chase. No guesswork. No surprises at the dock. Just show up.
01 — How it works
Three steps. One call.
01
Tell Richard what you're celebrating
One message with the date, guest count, and the vibe. That's the entire brief.
02
He builds the plan and quotes one all-in price
Richard designs the day, coordinates every vendor, and comes back with a single, transparent number.
03
You show up and enjoy it
Everything is set before you arrive. Guests just walk on and have the day.
02 — The Fleet Richard Runs
The fleet, for you.
Three verticals, one standard. Whatever you book, expect the same level of care from the moment you reach us.
— Cruises
Types of cruises.
Pick the shape of your day on the water. Every charter is private, up to 12 guests, and built around your group.
Skyline Cruise
A relaxed run along Lake Michigan with the full downtown skyline as your backdrop.
Sunset Cruise
Golden hour on the water as the city lights come up. The most-requested charter we run.
Chicago River Architecture Cruise
Through the locks and onto the river for a private look at Chicago's iconic architecture.
Subject to lock traffic and timing.
Celebration Charters
Birthdays, proposals, bachelor and bachelorette weekends, and corporate outings — built around your group of up to 12.
Half-Day, Sunset & Overnight
Flexible charter terms to fit the occasion — from a quick sunset to a full overnight on the water.
03 — The Weekend
Make It a Weekend.
The yacht on Saturday. The car to get you there in style. The watercraft to close it out Sunday. Tell Richard what you're celebrating and he'll build the whole weekend around you, one booking.
- FriExotic car delivered to your hotel
- SatHalf-day yacht charter on Chicago's lakefront
- SunSunrise jet ski session, two skis
04 — Guests
A name they remember.
“The way The Richard Collection runs a charter is unlike anything else in Chicago. Effortless from booking to dock.”
Alessandra R.
Hosted a 12-guest birthday on Soulshine
“Pulled up to the harbor in a McLaren, jumped on the yacht, ended on jet skis. Surreal weekend.”
Marcus D.
Did the full Weekend bundle
“Richard knew exactly what I wanted before I did. That's the difference.”
Priya S.
Sunset cruise, July
@therichardcollection
From the lake.
Now Booking
Summer 2026 · Chicago Lakefront
05 — Reserve
One call. Every detail handled.
Tell Richard the date and the vibe. He'll build the day — vessel, watercraft, cars, chef, transport — and hand you a single confirmation.
- Direct line to Richard, 7 days a week
- One booking, zero handoffs
- Every detail arranged before you arrive