Chicago Skyline Sail

Experience Chicago from a breathtaking perspective aboard the Chicago Skyline Sail with Tall Ship Windy. This private boat tour offers a unique opportunity to glide across Lake Michigan while taking in iconic cityscapes and architecture. Whether you’re a photography enthusiast, celebrating a special occasion, or simply seeking an adventurous escape, this sail provides a blend of tranquility and stunning vistas. As you cruise along, you’ll see the stunning skyline perfectly framed by shimmering waters, with the Chicago Loop, Navy Pier, and John Hancock Center creating a spectacular backdrop. The calm waters and favorable weather often make this trip an ideal highlight for visitors and locals alike. Personalized service and flexible scheduling ensure a memorable experience tailored to your interests. Whether you're catching the sunset or admiring the city lights at dusk, this adventure promises unforgettable views and quality time on the water. The captain and crew are passionate about sharing Chicago’s maritime history and guiding you through an indulgent outdoor experience that combines nature, architecture, and celebration. Perfect for small groups seeking exclusivity, this private sail transforms a regular day into an extraordinary adventure on Lake Michigan. It’s an excellent choice for creating lasting memories, enjoying scenic photo opportunities, and exploring Chicago from a fresh angle. Book your exclusive Chicago Skyline Sail today and see the city from the water’s edge like never before.