All Outdoor Adventures
Boating
Chicago, Illinois
Chicago Architecture River Cruise
Cruise Chicago's harbor lasting 1 hour 15 minutes (approx.) with views of Chicago River from the water.
★ 4.8 (17010 reviews)
From $53.70
Chicago Tours & Activities
Chicago, Illinois
Sailing
Chicago Skyline Sunset Sail Aboard a Tall Ship
Price: From $55.00
4.8 rating • 842 reviews
Duration: 1 hour 30 minutes (approx.)
Meeting point: Meet at the Navy Pier tall-ship boarding gate confirmed on your ticket. Arrive 20 minutes early.
This tour is operated by an independent third-party provider.All Outdoor Adventures is a marketplace that connects travelers with local tour operators.
Overview
Chicago Skyline Sunset Sail Aboard a Tall Ship is a water-based guided outing in Chicago, Illinois centered on Navy Pier, Lake Michigan, and surrounding destination landmarks. The route emphasizes Navy Pier, Lake Michigan, Chicago Harbor, and Grant Park. The experience emphasizes Sunset sail aboard the Windy tall ship from Navy Pier, Traditional schooner experience on Lake Michigan, and Skyline and harbor views at golden hour. Scheduled stops include Navy Pier, Lake Michigan, Chicago Harbor, and Grant Park. Landmarks referenced in the route include Navy Pier and Grant Park. The route combines landscape features and scenic viewpoints and neighborhood landmarks and open views. The outing typically lasts 1 hour 30 minutes (approx.). Travel is organized as sail-powered travel with route pacing matched to the destination.
Highlights
- Skyline and harbor views at golden hour
- 90-minute deck time with photo opportunities
- Traditional schooner experience on Lake Michigan
- Sunset sail aboard the Windy tall ship from Navy Pier
- Crew commentary on sailing and Chicago history
What’s included
- Sunset sail aboard the Windy
- Professional crew
- Safety briefing
Itinerary
Stop
15 minutesNavy Pier
Visit Navy Pier during the 15 minutes stop.
Stop
60 minutesLake Michigan
Visit Lake Michigan during the 60 minutes stop.
Pass by
Chicago Harbor
Pass Chicago Harbor as part of the route.
Pass by
Grant Park
Pass Grant Park as part of the route.
FAQs
How long is the Chicago Skyline Sunset Sail Aboard a Tall Ship?
The planned duration is 1 hour 30 minutes.
Where does the tour depart from in Chicago?
Meet at the Navy Pier tall-ship boarding gate confirmed on your ticket. Arrive 20 minutes early.
Additional info
- Not wheelchair accessible
- Confirmation will be received at time of booking
- Near public transportation
- Most travelers can participate
READY TO BOOK?
Lock in your Chicago adventure today.
Secure your spot, confirm the latest availability, and review final departure details before checkout.
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