Leave the bustle of Navy Pier for two hours on a private sailboat and watch Chicago’s skyline redraw itself from the water. This flexible charter—operated by a USCG-licensed captain—lets you choose photos, sunset, or relaxed cruising with local stories on request.
More ways to explore the area's outdoor wonders
You step off Navy Pier and the air smells faintly of lake and oil; the city’s hard edges soften as the boat slips away and the skyline rearranges itself into a horizon of glass and stone.
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for all fitness levels; requires basic mobility for boarding a marina dock and climbing a few steps on deck.
Wildlife
History
Navy Pier opened in 1916 and has served as a military embarkation point, transit hub, and public entertainment venue, shaping Chicago’s lakefront development.
Conservation
Lake Michigan faces runoff and invasive species challenges; follow captain guidance on waste removal and avoid throwing anything overboard to protect water quality.
Reserve your spot on the Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Layer up for wind and spray
Even on warm days the lake breeze can be cool; bring a lightweight windbreaker and a warm mid-layer.
Bring motion-sickness remedies
If you’re prone to seasickness, take medication or use acupressure bands before boarding; remain on deck if you feel ill.
Secure drinks and plastic cups
Glass is prohibited; use plastic or reusable containers and stow bottles to prevent breakage during maneuvers.
Plan photo locations
Ask the captain early which side of the boat gives the best views for the landmarks you want to photograph.
Windbreaker or softshell
Blocks lake breeze and light spray while keeping you agile on deck.
spring
Non-slip deck shoes or sneakers
Provide traction on wet surfaces and make boarding safer.
summer
Sunscreen and sunglasses
Reflective water amplifies UV exposure—protect skin and eyes during midday sails.
summer
Small dry bag
Keeps phone, wallet, and layers dry when spray or sudden rain occurs.
fall