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 Tours at 3pm and 5pm and Sunset and Skyline Sails at 7pm.
Monday Night Blues Summer Concert Series
Chase your Monday BLUES away aboard Tall Ship Windy
- General Admission Boarding
- Adults Ages 13+
- Child Ages 0-12
- VIP Captains Boarding
- Adult Ages 13+
- Child Ages 0-12
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. We’re still planning out what is sure to be an exciting concert series again this season; check back for updates. Every Monday from June 24 to August 12, enjoy the Grammy-elected Michael Charles and his band.
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.
Celebrating his 40th anniversary in 2024, Michael Charles boards Tall Ship Windy from Navy Pier every Monday night from June 24 – August 12. Come sail with us!
Learn More About Michael Charles:
The year was 1984. With a newfound confidence and looking into the future, a young muso from Melbourne Australia decided the time was right to break out on his own and take the solo billing of “Michael Charles”. The next few years were filled with a heavy promotional schedule, writing, recording, touring, honing his style and enjoying the self-expression and the hard work of presenting his own music.
In 1989 a turning point in his life and career materialized in the form of an invitation from Mr. Buddy Guy’s management to appear at Buddy Guy’s Legends in Chicago. Without hesitation, Michael traveled the 12,500 miles and after performing with Mr. Guy, Junior Wells, James Cotton, Eddy “The Chief” Clearwater and many more of the blues greats in Chicago, Charles returned to Australia. But within days he re-boarded the plane with the solid intention of this time staying and growing his career in America. Not too long after landing an opportunity quickly presented itself and MC accepted the honor of joining up with legendary “Fast Fingers”, Jimmy Dawkins and toured the U.S.A. for two years.
Some thirty years later Michael Charles’s roots are in America and his career comprises a catalog of forty releases, his Chicago Blues Hall of Fame induction, 10 Grammy elections and the recognition of remaining one of America’s most driven artists as he continues to record and annually tours non-stop across the U.S.A., Canada, and Australia delivering at each stop a precise, energetic, intense, original, guitar-driven concert of contemporary blues, “MC style”.
All seating on board Tall Ship Windy is first come, first served. Guests with VIP Captains Boarding tickets board first before General Admission ticket holders. A limited number of VIP tickets are available and are likely to sell out. Board first to choose your seat on one of Windy’s three decks: the forward, middle or aft.
All VIP Captains Boarding tickets also include trip insurance. Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.
$8.00 Per Guest | Add to your ticket at checkout
Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. Refunds for cancelled charters are less the $8.00 cost of insurance and 3% booking fees.
General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.
- RAIN OR SHINE EVENT: In the unlikely event that your tour is cancelled, you may exchange your ticket for another day or receive a refund.
- No-shows will not be eligible for rescheduling or refund. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.
- The Captain reserves the right to postpone a sail for up to 15 minutes in the case of passing inclement weather.
- General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.
- Add-on Trip Insurance: Allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time.