Tall Ship Windy Skyline Sail

Under Sail From Navy Pier

⏱ About 1.5 to 2 hours👤 All ages$$$

Windy is a classic schooner rather than a modern sightseeing boat, and passengers can often help with sails, depending on the trip. The experience is quieter and more relaxed than a big-deck cruise, with views of the skyline from the lake rather than the river. The ship is based at Navy Pier, so boarding is easy to combine with other pier attractions.

Because it is a sailing vessel, the schedule varies with the season and wind. The booking page do not give a fixed schedule, so check available dates when you book and keep flexibility in case of weather changes. Expect a cooler breeze on the lake than on the shore, even in summer.

The fireworks cruise is the showpiece for many visitors, since a night sail beneath the skyline adds atmosphere. Dress in layers, bring a camera with good low-light capability, and arrive early to board. For families, a sailing trip is a memorable change from conventional tours; for couples, the sunset option is a classic.

Sailing on Windy differs from boarding a motor cruise in several ways. Passengers are on an open deck, so wind and weather matter, and the ship's movement under sail is gentler and quieter than an engine-driven boat. The crew often invites passengers to help raise sails or simply to relax and watch, depending on the sailing. The ship's home at Navy Pier means you can make a half-day of it, with lunch or the pier's attractions before or after the sail. Check the departure dock location and time on your ticket, since Navy Pier is large and the tall ship berth is at the water's edge. Bring a light jacket even on warm days, sunglasses and a hat, and avoid high heels on deck. If you are comparing options, remember that the river architecture cruise is better for building history, while Windy is better for atmosphere and the feel of being under sail.