Memorial Day Start of Summer Celebration Sail

Difficulty

easy

Duration

2–3 hours

Fitness Level

Suitable for most fitness levels; minimal physical exertion required except for occasional movement on deck.

Overview

Kick off your summer with a refreshing tall ship sail on Chicago’s Lake Michigan. Experience breathtaking city skyline views and the thrill of traditional sailing on this special Memorial Day weekend adventure.

Events

Sailing

Tallship

Chicago, Illinois

Memorial Day Start of Summer Celebration Sail

Select participants and date

Date

Mon, Oct 13

Travelers

2

Adventure Photos

Memorial Day Start of Summer Celebration Sail photo 1

About This Adventure

Kick off your summer with an unforgettable evening aboard the iconic 148' Tall Ship Windy! Celebrate Memorial Day Weekend on Lake Michigan, enjoying breathtaking views of the Chicago skyline during a 1.5-hour sail. Honor our heroes while indulging in a festive atmosphere—don’t miss this unique experience!

You don’t want to miss this once a year event and start the summer with a bang!

Set sail into summer and kick off Tall Ship Windy’s season aboard the famous 148′ Tall Ship Windy. This is the best Memorial Day Weekend celebration on Lake Michigan. You can enjoy the spectacular Chicago skyline as you enjoy a fun, celebratory sail.

Please arrive at least 15 minutes prior to departure. This is a 1.5 hour charter departing promptly at 8:45pm and returns to Navy Pier at 10:15pm. Guests must be 21 years of age to drink and/or purchase alcohol and must have valid identification.

As we remember those who have fallen, we would also like to honor those that have served. 10% off tickets for active duty and retired military. Purchase your tickets today and receive your 10% off discount by showing your valid ID at the Ticket Booth on the day of the sail.

Adventure Tips

Arrive Early for Boarding

Give yourself extra time to find parking and check in before the scheduled departure to ensure a smooth boarding process.

Dress in Layers

Lake Michigan’s breeze can be cool even in late spring, so wear breathable layers to stay comfortable throughout the sail.

Bring Sun Protection

Sunscreen, sunglasses, and a hat are must-haves to protect against reflective UV rays on the water.

Secure Footwear

Wear non-slip, flat shoes to safely navigate the ship’s deck and rigging areas.

Local Insights

Wildlife

Common loons
Herring gulls

History

Chicago’s lakefront was integral to its rise as a shipping hub in the 19th century, with tall ships playing a crucial role in trade across the Great Lakes.

Conservation

Operators follow lake conservation guidelines to minimize pollution and protect aquatic habitats, helping preserve Lake Michigan’s water quality.