Looking for one of the most unique ways to explore the Chicago River? Step aboard one of our colorful Retro Boats at our City Winery location and experience a cruise that blends vintage charm with modern comfort. Whether you’re local or visiting, a Retro Boat ride offers a one-of-a-kind perspective of the city — and it’s Instagram gold.
What Makes Retro Boats So Special?
Originally crafted in the 1950s and 60s, each Retro Boat has been lovingly restored with electric motors for a clean, quiet, and eco-friendly ride. With stylish fins, mid-century details, and vibrant colors, they turn heads on the river while offering a surprisingly peaceful escape.
Perfect for couples, friends, or small groups of up to four, Retro Boats are ideal for:
• Romantic date nights on the river
• Scenic city cruises before or after/before dinner at City Winery
• Celebrating birthdays or special moments
• Capturing content-worthy views of the Chicago skyline
Start and End Your Cruise in Style
Our City Winery dock gives you direct access to award-winning food, drinks, and live music just steps away from your boat. It’s the perfect launchpad for your river adventure and an easy way to turn a simple cruise into an unforgettable night out.
Don’t Just Take Our Word for It
Here are just a few of the moments others have captured from their Retro Boat rides:
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@alanainwanderland
Checked off an item on her summer bucket list.
@rachelmichella
showed us a unique date idea that doesn’t involve drinking.
@lauraxlong
had her Barbie dreams come true.
Ready to Cruise?
Retro Boats are available by reservation only and can be booked directly from our City Winery location page. Whether you’re planning a spontaneous afternoon or a special occasion, your floating time machine awaits.
Experience the retro charm, modern comfort, and unbeatable views — only at Chicago Boat Company’s City Winery dock.
