Quick Details
Set sail from Navy Pier and take in the Chicago skyline from the deck of Tall Ship Windy. This public Lake Michigan sail gives guests a unique way to see the city, enjoy fresh lake air, and experience Chicago from aboard a 148-foot, four-masted schooner.
Good to Know Before You Sail
Please arrive early so you have enough time to check in and board before departure. Sailing is an outdoor experience, so guests are encouraged to dress for the weather and bring layers when temperatures are cooler on the lake.
Food and drinks may be available for purchase onboard. Seating is informal, and guests are welcome to move around designated deck areas during the sail.
Tall Ship Windy sails rain or shine when conditions allow. The captain and crew make final decisions about weather and lake conditions for the safety of all guests.
What to Expect on Your Skyline Sail
Your sail begins at Navy Pier, where you will board Tall Ship Windy and get settled on deck before departure. Once the ship leaves the dock, you will head out onto Lake Michigan for open-air views of the Chicago skyline.
During the sail, guests can relax, take photos, enjoy the breeze, and experience the city from the water. Depending on weather, lake conditions, and the day’s route, you may enjoy views of Navy Pier, the downtown skyline, Museum Campus, and other lakefront sights.
This is not a Chicago River architecture tour or a river cruise. Instead, it is a Lake Michigan sailing experience designed around skyline views, fresh air, and the unique setting of Chicago’s Official Tall Ship.
Why Choose a Tall Ship Sail?
There are many boat tours in Chicago, but Tall Ship Windy offers a different kind of experience. Instead of seeing the city from a standard tour boat, guests can step aboard a real tall ship and enjoy the lakefront from an open-air deck.
Guests love the Chicago Skyline Sail because it offers:
- A unique tall ship experience from Navy Pier.
- Beautiful views of the Chicago skyline and Lake Michigan.
- A relaxed alternative to a traditional architecture boat tour.
- Great photo opportunities with the city, water, and ship’s rigging.
- A family-friendly activity that works for both visitors and locals.
- A memorable way to enjoy Chicago during the day, evening, or weekend.
If you are comparing Chicago boat tours near you, this sail is a great choice for anyone who wants something scenic, relaxed, and a little more memorable than the usual sightseeing cruise.
Looking for Fireworks or Special Event Sails?
If you are searching for Navy Pier fireworks, Chicago fireworks, firework shows near you, or special lakefront events, you may be looking for one of our evening or specialty sails instead.
Tall Ship Windy also offers select special-event experiences, including Chicago Fireworks Sails, holiday sails, live music sails, and Chicago Air and Water Show sails. These experiences are separate from the standard Chicago Skyline Sail and may have different departure times, pricing, and availability.
View All Special Sailing Experiences
Sailing with a Group?
This page is for individual public Skyline Sail tickets. If you are planning for 20 or more guests, a school group, company outing, wedding, reunion, or private event, visit our Group Sails page for group discounts, private event options, and planning details.
Sail More Than Once This Season
Planning to join us more than once? Tall Ship Windy memberships are a great option for guests who want to enjoy multiple Skyline Sails throughout the sailing season.
Membership options allow you to return for public Skyline Sails based on your selected membership level, making them a great fit for locals, frequent visitors, and anyone who wants to experience the Chicago skyline from the water again and again.
FAQs
How long is the Chicago Skyline Sail?
The Chicago Skyline Sail is approximately 1 hour and 15 minutes.
Where does Tall Ship Windy depart from?
Tall Ship Windy departs from Navy Pier in Chicago.
Is the Chicago Skyline Sail family-friendly?
Yes. The Skyline Sail is open to all ages and is a great option for families, couples, visitors, and locals.
Is this an architecture tour?
The Chicago Skyline Sail may include views of Chicago’s skyline and lakefront, but it is not the same as a Chicago River architecture tour. This is a Lake Michigan sailing experience aboard Tall Ship Windy.
Can I see Navy Pier fireworks on the Skyline Sail?
The standard Skyline Sail is different from Tall Ship Windy’s Fireworks Sails. If you are looking for Chicago fireworks or Navy Pier fireworks from the water, check the available Fireworks Sail dates and times.
Should I book tickets in advance?
Yes. Advance booking is recommended because sail times and ticket availability can vary by date.
What should I wear?
Dress for the weather and keep in mind that it can feel cooler on Lake Michigan than it does on land. Layers are recommended, especially for evening sails.
What happens if the weather is bad?
Tall Ship Windy sails when conditions allow. The captain and crew make weather-related decisions with guest safety in mind.
Can I book this for a large group?
This page is for public individual tickets. For 20 or more guests, private events, school groups, corporate outings, or celebrations, visit the Group Sails page.
