Private Sailing on Lake Michigan: Navy Pier, Chicago
The captain takes direction from you, not the other way around.
A private two-hour sailing charter on Lake Michigan departing from Navy Pier in Chicago, with a US Coast Guard licensed captain who customizes the route, music and pace to your group's preference. You choose whether the captain narrates the landmarks or stays quiet. You decide if you want to sail past Grant Park and Soldier Field or ask for a different course. The boat holds up to six people, and alcohol is permitted in non-glass containers.
Step-by-step itinerary
Private two-hour sailing on Lake Michigan
- Depart from Navy Pier Marina
- Complete safety briefing and prepare dock lines
- Sail along Chicago lakefront with flexible route
- Pass Navy Pier and view Grand Ballroom
- Enjoy views of Chicago skyline from water
- See Adler Planetarium dome from lakeside
- View Soldier Field colonnades from water
- Pass Buckingham Fountain and historic Queen’s Landing
What’s included
- Use of Bluetooth speakers for your own music.
- Navy Pier facility fee.
- professional US Coast Guard licensed captain.
- all taxes.
Next departure: 29 May 2027
Information
Sail Lake Michigan from Navy Pier with a US Coast Guard licensed captain for up to six people. Choose your route, your music, your pace.
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The experience
You depart from Navy Pier Marina on the north side of the pier after a safety briefing. The route depends mostly on wind direction, but since this is a private charter, the itinerary stays flexible. If you want to see a particular landmark or sail a specific direction, the captain will oblige. If you'd rather leave it to them, they'll take you out for an enjoyable sail during which you'll pass some or all of the major sights along the lakefront. Bluetooth speakers are on board, so you can set the mood with your own music.
Navy Pier itself comes into view as you sail past the east end, where the Grand Ballroom is a standout for photos. The pier opened in 1916 and has hosted everything from wartime operations to today's tourist crowds. From the water, you'll see the Adler Planetarium's iconic dome on Northerly Island: built in 1930 and rarely viewed from the lakeside angle where the Doane Observatory sits. Soldier Field, home of the Chicago Bears since 1924, shows its original colonnades from your vantage point. Grant Park reveals Buckingham Fountain, one of the world's largest, which Kate Buckingham donated in 1927 in memory of her brother. The fountain was the centerpiece of a dedication ceremony where John Philip Sousa himself conducted before 50,000 people.
The captain is a professional licensed by the US Coast Guard and happy to share anecdotes and historical details about what you're seeing, or to stay quiet if you'd rather just visit with your group. This isn't a guided tour in the traditional sense. It's your private experience on the water. All taxes and the Navy Pier facility fee are included. The charter is non-smoking, and you can bring food and beverages (no glass containers, but wine and champagne bottles are fine if they stay in a protective case). Three departure times are offered daily.
Top questions
What happens if it rains?
It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.
Can I bring my own music and drinks on the private sailing charter?
Yes. Bluetooth speakers are included, so you can play your own music. You can bring and consume alcoholic beverages within Illinois State law, but they must be in non-glass containers: wine and champagne bottles are permitted if they stay secure in a protective case. Bring plastic cups for drinking.
What landmarks will I see on the Lake Michigan sail?
The sail passes Navy Pier, the Adler Planetarium, Soldier Field, Grant Park and Buckingham Fountain, depending on wind direction and your preference. Since the charter is private, you can ask the captain to sail toward a specific landmark or skip others entirely.
Is the captain going to narrate the whole time, or can we just relax?
The captain is happy to point out interesting sights with historical anecdotes if you ask, but this isn't a guided tour. You set the tone. If you prefer to visit with friends and loved ones without commentary, the captain will stay in their role as captain and let you enjoy the experience your way.
How many people can fit on the private sailing charter?
The boat accommodates up to six people, making it suitable for small groups, families or friends.
Where does the charter depart from, and how do I get there?
The charter departs from Navy Pier Marina on the north side of Navy Pier in Chicago. Public transportation options are available nearby, so you don't need a car to reach the departure point.
What's included in the price of the private sailing charter?
The charter includes use of Bluetooth speakers, the Navy Pier facility fee, a professional US Coast Guard licensed captain, and all taxes. You bring your own food and beverages (non-glass containers only).
Operated by Come Sailing, Inc.. Explorevia does not run this tour: we compare it with similar options, and you book it with our booking partner.
Prices and times updated yesterday
Private Sailing on Lake Michigan: Navy Pier, Chicago
2h · EN
from US$ 507.96 per group
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