Chicago: Private Lake Michigan Sailing from Navy Pier

★★★★★★★★★★ 5.00 (73 reviews) 100% rated it 5 stars

Free cancellationExcellent qualityLikely to sell out

1/7

Duration2h

GroupPrivate

LanguagesEN

Mobile ticketAccepted

Sail Chicago’s lakefront with local stories and city skyline views

You’ll sail from Navy Pier with a Coast Guard licensed captain guiding your private group along Lake Michigan—city skyline ahead, music playing, maybe snacks in hand. Expect local stories about Grant Park or Soldier Field if you ask, plus time to simply watch sunlight shift across Chicago’s architecture. It’s relaxed, flexible, and feels like your own day on the water.

Step-by-step itinerary

Private sailing tour on Lake Michigan

Depart from Navy Pier Marina
Complete safety briefing and secure dock lines
Begin flexible sailing route based on wind
Sail past Navy Pier east end and Grand Ballroom
View Chicago skyline from the water
Pass Adler Planetarium and Doane Observatory
See Soldier Field from the water
Pass historic Queen’s Landing and Buckingham Fountain

The Experience

“You can always tell the wind’s in a mood by how the flags are behaving,” Captain Mark said as we untied from Navy Pier. I think he was half-joking, but he really did check the sky like he was reading an old friend’s face. We shuffled around the deck, figuring out where to sit without looking like total newbies. The city felt close but already quieter than it does on land—just muffled voices from the pier and a bit of that deep lake smell, kind of cold and metallic, if that makes sense.

I’d never seen Chicago’s skyline from this angle before. It’s different when you’re out there—less postcard, more real. Grant Park slid by on our left, all green patches and people walking dogs who seemed to have no idea we were watching them from the water. Our guide pointed out Soldier Field (I always forget how old that place is), and told us about Queen Elizabeth coming ashore at Queen’s Landing—apparently for just 13 hours? That made me laugh for some reason; even royalty can’t escape Chicago traffic, I guess.

We brought snacks (Captain Mark nodded approvingly at our plastic cups) and hooked up someone’s playlist to the Bluetooth speakers. There was this moment near the Adler Planetarium when everyone just went quiet—the sun hit the dome in this weird way, almost pinkish, and you could hear nothing but water slapping the hull. I didn’t expect to feel so relaxed on a private sailing tour in Chicago; it felt like time slowed down for a second or two.

The route changed with the wind—Mark let us pick if we wanted to get closer to certain landmarks or just drift along. He shared little stories when we asked but also left us space to just hang out. I still think about that view back toward Navy Pier as we returned—lights starting to flicker on, city buzzing again as if nothing happened while we were gone.

What’s included

Your day includes departure from Navy Pier Marina with all taxes and facility fees covered, use of Bluetooth speakers for your music, and guidance by a professional US Coast Guard licensed captain throughout your private two-hour sailing experience along Lake Michigan’s shoreline.

Good to know

Easy physical levelPublic transport nearby

Operated by Come Sailing, Inc.