The best ways to use our boats
Chicago · Lake MichiganChicago Boat Experiences
Every way to get out on Lake Michigan and the Chicago River — from a private yacht, captain included. Anchor at the Playpen, cruise the Chicago River, take in the skyline from Monroe Harbor, or stay out for Navy Pier fireworks.
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Experience 01
The Chicago Playpen
The iconic Lake Michigan anchorage where boats raft up, music plays, and the whole Chicago skyline sits behind you.
Explore The Chicago Playpen -
Experience 02
Monroe Harbor
Calm water, sweeping lakefront views, and the full Chicago skyline — the most scenic anchorage on the lake.
Explore Monroe Harbor -
Experience 03
Chicago River
Surrounded by the Wrigley Building, Tribune Tower, and Marina City — the city at its most cinematic, from the water.
Explore Chicago River -
Experience 04
Navy Pier Fireworks
Front-row seats to Navy Pier's Wednesday and Saturday night fireworks from a private yacht on Lake Michigan.
Explore Navy Pier Fireworks
Our Fleet
Match the experience to your groupA boat for every experience
Whether you're anchoring at the Playpen with 125 guests on the Amalfi, cruising the river for 49 on the Sophisticated Lady and Montauk, or keeping it intimate with a group of 13 on the Sea Ray Fleet — there's a boat in the fleet for every experience.
- Amalfi
- Up to 125 guests
- Sophisticated Lady and Montauk
- Up to 49 guests
- Sea Ray Fleet
- Up to 13 guests
The Full Day · Do Them All
One boat, one crewOne boat, one crew,
all of it.
It's a full Chicago day — river, lake, harbor, and fireworks — without ever changing boats. Tell us your priorities when you book and your captain plans the route.
Book the full day- Morning
Monroe Harbor
Start easy — calm water and the full skyline before the lake gets busy.
- Noon
Chicago River
Bridges, architecture, the city rising around you.
- Afternoon · Golden hour
The Playpen
Push out, drop anchor, and stay through golden hour.
- After dark
Navy Pier Fireworks
Stay out for the show, Wednesday or Saturday night.