Explore Chicago’s scenic shores with a relaxing sail around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water. Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tour at 3pm, Sunset and Skyline Sail at 5pm and Late Summer Twilight Sail at 7pm.
Monday Night Blues Summer Concert Series
Chase your Monday BLUES away aboard Tall Ship Windy
- Adults VIP Event
Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this summer. We’ll help you chase your Monday BLUES away aboard the 148 foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the blues. Whether you’re a long-time fan or a newcomer to the blues, you’re sure to be transported by the talent and passion of each amazing artist. With a full bar and a friendly, knowledgeable crew, you’ll be able to relax and enjoy the music in comfort and style.
Each concert will bring a unique twist to the blues genre, showcasing the diversity and versatility of this legendary music form. Dave Weld brought the good time party Rock and Roll energy aboard Windy. Still to grace our decks, enjoy music’s greats, including Grammy-elected Michael Charles and his band and Andrew Diehl throughout the season.
Tall Ship Windy’s Monday Blues is set to become the concert event of the summer! Book your tickets now and experience the magic of blues music against the backdrop of one of the world’s most beautiful skylines.
Mondays August 21 & 28 and September 4 & 11
Andrew Diehl grew up in the mountains of West Virginia, picked up the harmonica when he was nine and spent his teens wearing the grooves out of Little Walter records. After moving north to Chicago at seventeen, Diehl fell in love with the guitar and it hasn’t left his hands since. You can catch him performing all over the Midwest, delivering a heavy hit of electric blues and vintage rock n’ roll.
You can purchase these optional items when you book:
- Trip Insurance: $8.00 per person—gives you the ability to cancel your reservation if needed and receive a full refund. This applies up to 8 hours before your scheduled sail time or if Tall Ship Windy cancels your sail due to weather.