Tall Ship Windy: Skyline Sail and Skyline Sail with Tales of Real Pirates of the Inland Seas

Tall Ship Windy offers two different versions of their popular Skyline Sail tour, with both excursions lasting over an hour and departing from Chicago’s beloved Navy Pier. The Skyline Sail tour runs several times a day during the summer months, and provides passengers with the opportunity to behold Chicago’s breathtaking skyline from the lovely waters of scenic Lake Michigan. Tall Ship Windy also regularly runs a special version of the Skyline Sail that features a series of stories and performances highlighting the history and adventures of the pirates that once roamed Lake Michigan.

Money Saving Tip! This tour is included in the Go Chicago Card as well as the Chicago Explorer Pass. Both Chicago Tourist Passes can save you a lot of money if you are going to multiple Chicago attractions.

Tall Ship Windy Skyline Sail Tour Details

The Skyline Sail and Skyline Sail with Tales of Real Pirates of the Inland Seas tours are two fascinating ways to experience the fabulous city of Chicago and its world-renowned lakefront and skyline. The Skyline Sail tour lasts approximately 75 minutes and presents guests with all sorts of opportunities to soak in the scenery from a truly unique perspective. Tickets usually run around $40 for adults and $15 for children under the age of 12—though more expensive VIP tickets are available as well. During the heart of summer, the Skyline Sail tour usually runs several times daily. The Skyline Sail with Tales of Real Pirates of the Inland Seas tour supplies you with the same assortment of outstanding views as the Skyline Sail tour, but it also comes with a series of live performances during which crewmembers tell and act out stories of pirate adventures that are reported to have once taken place on Lake Michigan. This kid-friendly tour runs twice daily during the summer, with tickets costing about the same amount of money as tickets for the standard Skyline Sail tour.

Skyline Sail Major Highlights

Navy Pier: Both Skyline Sail outings on the Tall Ship Windy leave from lively Navy Pier, where in addition to this tour you’ll find a nice assortment of shops, restaurants, and bars. Notable attractions here include the Centennial Wheel, the Chicago Shakespeare Theater, and the Chicago Children’s Museum.

Chicago Skyline: The Skyline Sail tours give guests an unforgettable vantagepoint on Chicago’s iconic skyline. Whether you’ve lived in Chicago for years or are brand new to the Windy City, you’ll be amazed what it’s like to witness this beautiful city from the waters of Lake Michigan.

Tall Ship Windy: As busy as you’ll be snapping photographs of the Chicago skyline, you’ll also need to make some time to explore this wonderful schooner, too. Checking in at 148-feet-long, the Tall Ship Windy resembles a classic sailing ship, but also features such modern amenities as internal pressurized plumbing, a 300-horsepower diesel engine, a small gift shop, and a full-service bar well-stocked with a variety of snacks.

Live Pirate Performance: If you choose the Skyline Sail with Tales of Real Pirates of the Inland Seas tour, one of the major highlights will be the series of interactive pirate performances and storytelling sessions you’ll get to watch unfold live—with Lake Michigan as a spectacular backdrop.

Is the Tall Ship Windy Skyline Sail for You?

If you’re visiting Chicago as part of a group or family traveling with small children, then you’ll definitely want to consider choosing the Tall Ship Windy Skyline Sail with Tales of Real Pirates of the Inland Seas tour.  The kids will likely love the cast of swashbuckling characters acting out stories and adventures of yesteryear right there in front of them on a real, live historical sailing vessel. Meanwhile, the adults will enjoy the fresh air and stunning scenery. If pirates and playacting isn’t quite your cup of tea, the regular version of the Skyline Sail is a good option. You won’t get as detailed a narrative as you would with, say, Tall Ship Windy’s Lakeside Architecture Tour, but still the Skyline Sail has all the makings of a peaceful, enjoyable afternoon out.

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