Monday Night Concert Series - 2026 | Tall Ship Windy
We’re Closed for the Season! 2027 Sailing Is Now Open for Booking

Monday Night Concert Series

The 2026 sailing season has ended. Tall Ship Windy will return to Navy Pier in 2027. Explore our sailing experiences and check back for confirmed schedules and tickets.

Chase Away your Monday Blues with a Symphony of Soul!

Quick Details

Join Us for an Unforgettable Evening of Blues Music on Lake Michigan, off Chicago!

We’ll help you chase your “Monday blues”, aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the unique sounds from guitar driven, Grammy elected, Australian born, Hall of Famer Michael Charles and His Band. Whether you’re a long-time fan or a newcomer to his music, you’re sure to be transported by the talent and passion of this 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. Here is his YouTube channel!, please click and subscribe.

Each concert will bring a unique twist to the genres, showcasing the diversity and versatility of his legendary music form. Is he too bluesy to be called rock? Or is he too rocky to be called blues? You be the one to decide as you listen to MC’s distinctive sound. Here is Michael Charles and his band’s website.

Tall Ship Windy’s Monday Music Concerts are set to become the concert event of the summer! Book your tickets now and experience the magic of Michael Charles’ music against the backdrop of one of the world’s most beautiful skylines.

Optional Items:

These can be added to your reservation while booking

Admiral's Ticket - Includes the following:

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  • Ticket
  • VIP boarding, this is a separate boarding line, which boards first!
  • Trip insurance – see description below
  • Taxes & Fees

Optional Items:

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  • Windy Drink Tickets: $10 value redeemable for drinks only. No cash value. Non-refundable. Only valid on the trip purchased.
  • Trip Insurance: Price varies due to the cost of each ticket. You must purchase for all tickets in your reservation. Recommended, but not required.  This gives you the ability to cancel your reservation and receive a full refund (less the cost of insurance).
  • Examples:
    • You contact us, 24 hours before your tour, we will refund you tickets (less cost of insurance
    • We CANCEL or postpone your tour, we will refund you tickets (less cost of insurance
    • No insurance – if we cancel or postpone, you will be offered a credit, for a reschedule of your sail.
    • NO REFUNDS given without insurance.

Cancelation Policy:

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  • No-shows will be charged the full price. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture. We leave ON-TIME – Be Early!
  • The captain reserves the right to postpone the sail for up to 120 minutes; if the sail is cancelled, tickets may be exchanged for another time. We will text , and email, everyone IF a decision is made. If, weather is challenging, pay close attention to your phone (make sure you have the phone listed on the reservation with you!!)
  • All sales are final.
  • No refunds and no exchanges are available without the purchase of additional Trip Insurance. The Windy sails rain or shine.

2027 pricing will be announced with the new concert schedule.