Chicago: Private Lake Michigan Sailing from Navy Pier

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.

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.

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Step-by-step itinerary

Day 1 — 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.

Top questions

How long is the private sailing tour from Navy Pier?

The private sailing experience lasts two hours.

How many people can join the private charter?

The boat accommodates up to six guests per charter.

Is there a guide or commentary during the sail?

The captain is happy to share stories or point out sights if you ask but will also give you space if preferred.

Can we bring food and drinks onboard?

Yes, food and beverages are allowed except glass containers (wine bottles are okay if kept secure). Bring plastic cups for drinks.

Where does the tour depart from?

The sailing departs from Navy Pier Marina on Chicago’s lakefront.

Are hotel pickups included?

No hotel pickup is included; guests meet at Navy Pier Marina.

Is swimming allowed during this charter?

No swimming is permitted unless your charter is three hours or longer; this two-hour trip does not include swimming.

Is smoking allowed onboard?

No smoking or tobacco use is permitted during any charter experience.