Private Sailing Experience on Lake Michigan in Chicago
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Set sail on a private two-hour adventure on Lake Michigan, starting from Navy Pier in Chicago. This experience is perfect for up to six guests who want to enjoy stunning views of the Chicago skyline in a relaxed, personalized setting.
With a US Coast Guard licensed captain at the helm, you can kick back, soak in the sights, and even customize your route or playlist. Whether you’re celebrating a special occasion or just looking for a memorable outing, this private sailing trip offers flexibility and fun in equal measure.
While it’s not a guided tour, your captain is happy to share stories, history, and interesting facts about Chicago’s landmarks along the way. Want to catch a sunset or see the Navy Pier fireworks? Check out our other experiences designed for those spectacular moments.
Frequently asked questions
How long is the private sailing experience?
The trip lasts for 2 hours, giving you plenty of time to relax and enjoy the scenery.
What is included in the price?
Your booking includes use of Bluetooth speakers, the Navy Pier facility fee, all taxes, and a professional US Coast Guard licensed captain.
Can I customize the route or playlist?
Absolutely. Since this is a private charter, you can choose to see specific landmarks, set your sailing route, or select your favorite music.
Is the experience suitable for children or people with mobility issues?
Yes. The experience is suitable for all physical fitness levels and ages from 0 to 99.
Are food and drinks provided?
No, food and drinks are not included. You are welcome to bring your own if you'd like.
What should I do in case of bad weather?
Charters may be canceled for bad weather, and you'll receive a full refund if that happens.
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 2 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Use of Bluetooth speakers
- Navy Pier Facility Fee
- All taxes
- Professional US Coast Guard licensed captain
Not included
- Gratuities
- Food and drinks
- Parking
Itinerary
A flexible, private sailing trip starting from Navy Pier Marina, tailored to your preferences. The captain can adjust the route based on wind and your interests, passing iconic Chicago landmarks along Lake Michigan.
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Departure from Navy Pier Marina
Meet outside Gate D at Navy Pier Marina. After a safety briefing, the captain will start the sail, with the route depending on wind direction and your preferences. Feel free to ask for specific sights or leave the decisions to your captain for a relaxed, scenic cruise.
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Navy Pier
Sailing past Navy Pier, you'll get a great view of the Grand Ballroom and the historic pier itself, which has played many roles since opening in 1916, including during WWII. It's a perfect photo stop and a Chicago icon.
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Chicago Skyline
Enjoy breathtaking views of Chicago’s famous skyline, architecture, and engineering marvels. Your captain can share stories or keep it a quiet, scenic experience—your choice.
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Adler Planetarium
Sitting on Northerly Island, the dome of the Adler Planetarium is a striking sight from the water. Built in 1930, it’s a favorite for wedding photos and offers a lakeside view of the Doane Observatory with its large telescope.
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Soldier Field
See the home of the Chicago Bears and a historic sports venue. The original colonnades are still visible from the water, offering a glimpse into the stadium’s rich past.
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Buckingham Fountain
Passing by this iconic fountain, built in 1927, you’ll get a perfect photo opportunity. It’s one of the largest fountains in the world and a symbol of Grant Park, with a fascinating history separate from the Royal Family.
Meeting point & pickup
Meet at Navy Pier Marina, outside Gate D.
Our boat departs from the new Navy Pier Marina on the north side of Navy Pier. Please gather outside Gate D, then text or call us to let us know you're here. We’ll welcome you aboard and escort you to the sailboat.
Open in Google MapsCancellation & confirmation
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund.
- 100% refund if canceled at least 1 day in advance
- No refund if canceled within 24 hours
- Charters may be canceled due to bad weather
Instant confirmation
Your booking is confirmed immediately after checkout.
From $507.96 per person
- Free cancellation
- Secure checkout with our booking partner
