Chicago Tall Ship Sails with Tall Ship Windy
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; mostly standing or seating on deck with some light climbing on and off the ship.
Overview
Step aboard Chicago’s official tall ship for a variety of unique sails that combine hands-on sailing with panoramic city and lake views. Tall Ship Windy invites adventurers to experience Lake Michigan like never before.
Private & Semi Private Stand Up Paddleboarding Lessons
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Adventure Photos
About This Adventure
Join Coastline Adventures for an unforgettable paddleboarding experience! Whether you opt for private lessons or gather friends for a semi-private session, you'll learn essential paddling techniques and water safety in a fun, supportive environment. Perfect for all skill levels, this adventure promises to enhance your skills while enjoying the great outdoors.
The Coastline Adventures team will educate you on proper paddling techniques through demonstrations, drills, and progressive skill building. Choose between private One-on-One lessons or grab two of your friends and learn together! No previous paddleboarding experience necessary! Participants must be able to swim.
Introductory lessons include equipment; land and water instruction; basic water safety and basic rescue techniques; proper body position, and paddling techniques.
Advanced lessons include location and condition assessment; rescue techniques, and fitness training for balance, endurance, and strength and more.
Available most days, by appointment only from Memorial Day to October.
Rates: Private SUP Lesson: 1.5 Hour Lesson, all equipment included. $75 per person
Semi-Private SUP Lesson: 1.5 Hour Lesson, all equipment included. Bring your friends and family and increase the fun factor while saving money! 2 paddlers - $130 ($65 per paddler) 3 paddlers - $165 ($55 per paddler)
Open to ages 9 and up.
Customized Private Group, Wave Riding Lessons, and Racing Technique Clinics are available upon request and by appointment only.
Your safety and enjoyment are very important to us and we reserve the right to cancel and/or change the schedule due to dangerous weather, water, and/or high wind conditions.
Adventure Tips
Arrive Early for Boarding
Give yourself extra time before departure to check in and get familiar with the ship’s layout.
Dress in Layers
Lake Michigan’s weather can shift quickly; bring windbreakers and comfortable shoes with good grip.
Participation Optional but Recommended
Feel free to help raise sails for a hands-on experience, but you can also relax and enjoy the views from deck.
Bring a Camera
There are plentiful photo opportunities of Chicago’s skyline and lake vistas during daylight and special events.
Local Insights
Wildlife
- Seasonal migratory birds such as gulls and terns frequent Lake Michigan shores.
- Occasional sightings of river otters near close shoreline areas.
History
Tall Ship Windy honors Chicago’s rich maritime heritage, sailing a classic vessel reminiscent of the city’s shipbuilding days in the early 20th century.
Conservation
The company promotes Leave No Trace principles on board and supports local lake clean-up initiatives to maintain Lake Michigan’s natural health.
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Frequently Asked Questions
Recommended Gear
Windbreaker Jacket
Protects against lake breezes and changing weather conditions on the water.
spring|summer|fall specific
Comfortable Non-Slip Shoes
Ensures safety and stability while moving around the ship’s decks.
Sunscreen
Helps protect skin from sun exposure during daytime sails.
summer specific
Camera or Smartphone
Captures stunning cityscape and lake views throughout the trip.