Share a peaceful Lake Michigan sail with Chicago skyline views
2 hours
Up to 6 people
Private sail, cooler, bottled water
Sail privately on Lake Michigan with your partner and take in Chicago’s skyline from the water. Settle into an intimate outing suited to date nights, anniversaries, and special occasions.
Cancel or reschedule less than 72 hours before departure for a 10% fee. No refund for cancellations less than 24 hours before departure.
Product ID: UH8YCF
Your private sail may operate in light rain. If high winds or lightning make conditions dangerous, the charter will be canceled and you will be notified about rescheduling or a refund.
Dress in layers, as it can be cooler on the water. Wear soft-soled shoes such as sneakers or boat shoes; high heels and black-soled boots are not permitted on deck.
Yes. Bring your own snacks and beverages. A cooler with ice and bottled water are available on board.
We can’t say enough great things about our sailboat cruise!! Erik and Catherine were incredibly welcoming and friendly. I would recommend booking this to everyone! We will absolutely be back.
Margaret May
July 3, 2026
We can’t say enough great things about our sailboat cruise!! Erik and Catherine were incredibly welcoming and friendly. I would recommend booking this to everyone! We will absolutely be back.
Margaret May
July 3, 2026
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