Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Book early, as these tend to sellout! you are free to move about the ship, while the music plays, everywhere.... More

A private sailing charter on Lake Michigan offers a serene escape with stunning skyline views of Chicago. Departing from Montrose Harbor, enjoy a relaxed atmosphere ideal for families, couples, or casual groups looking for a break... More

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is th... More

Enjoy a serene evening on Lake Michigan with a private sunset sailing charter, where the stunning Chicago skyline transforms as the sun sets. Departing from Montrose Harbor, this exclusive experience offers a cozy atmosphere for d... More

Set sail on a private fireworks cruise along the Chicago Lakefront aboard a meticulously maintained sailing yacht. Enjoy complimentary drinks or BYO. Perfect for summer birthdays, romantic proposals, anniversaries, and any reason ... More