Monday Night Concert Series Sail in Chicago 2025
Difficulty
easy
Duration
2 hours
Fitness Level
No special fitness level required; easy for most ages and abilities as the tour is seated and relaxed.
Overview
Enjoy live blues music aboard the Tall Ship Windy on a 2-hour Monday night concert sail. Discover stunning Chicago skyline views in a lively, relaxed setting.
Details
Set sail on an unforgettable 2-hour boat tour every Monday this summer aboard the Tall Ship Windy, right in the heart of Chicago, Illinois. The Monday Night Concert Series - 2025 offers a unique blend of live blues music and breathtaking views of Chicago’s iconic skyline. As the ship glides along Lake Michigan, you'll enjoy the soulful sounds of talented artists paired with a full bar and a relaxed atmosphere. Whether you're looking to unwind after a long day or enjoy a lively evening out, this private boat tour creates an exceptional experience that turns your Monday into a highlight of the week. The historic tall ship adds charm to the event, inviting both locals and visitors to celebrate Chicago’s vibrant music scene while soaking in the summer breeze. With limited spots available, this concert sail is perfect for friends, couples, and music lovers eager to experience the city from a refreshing new perspective. Don’t miss this chance to combine an outdoor adventure with a cultural outing on the water.
Adventure Tips
Arrive Early for Best Seating
Getting to the dock at least 15 minutes before departure ensures you grab a prime spot with great views and easy access to the bar.
Dress in Layers
Even summer evenings on Lake Michigan can get cool, so bring a light jacket or sweater to stay comfortable.
Bring Cash or Card for the Bar
A full bar is available onboard with drinks and snacks; be prepared with your preferred payment method.
Check Weather Before You Go
Lake conditions impact sailings; strong winds or storms may cause cancellations, so monitor weather updates closely.
Local Insights
Hidden Gems
- Explore the lesser-known 12th Street Beach after your sail
- Visit the Chicago Maritime Museum nearby for rich local history
Wildlife
- Seagulls soaring above the lake
- Occasional sightings of river otters near the shoreline
History
Tall Ship Windy reflects Chicago’s maritime heritage, preserving traditional sailing vessels on Lake Michigan.
Conservation
The company practices eco-friendly operations to minimize fuel use and protect lake water quality.
Frequently Asked Questions
Photography Tips
Best Times
Best Viewpoints
- From the upper deck looking east toward the skyline
- Near the ship’s bow capturing reflections on the water
- Along the shoreline while approaching the pier
What to Photograph
Recommended Gear
Light Jacket or Sweater
Protects against evening chills and lake breezes.
summer specific
Comfortable Shoes
Non-slip shoes help with safe boarding and walking on deck.
Sunscreen
Useful for early evening sun exposure on the water.
spring specific
Camera or Smartphone
Capture stunning views of Chicago’s skyline at sunset.