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Skyline Sails Membership

Four membership options to choose from!

Quick Details

Sail Any Day of the Week
Admirals Membership Skyline Sails Monday - Sunday
Admirals + VIP Boarding Skyline Sails Monday - Sunday, plus priority boarding
Sail Monday - Friday
Captains Weekday Membership Skyline Sails Monday - Friday
Captains Weekday + VIP Skyline Sails Monday - Friday, plus priority boarding

Join the Tall Ship Windy Family!

Enjoy the beautiful Chicago lakefront and skyline from your favorite tall ship throughout our sailing season. Once you purchase your membership, join us during our Skyline Sails throughout the sailing season for no additional cost. Plus, when friends and family sail with you they enjoy 10% off their ticket price.

Choose from these membership options:

  • Admirals Membership: Join us every day of the week during a Skyline Sail
    • Admirals Membership + VIP Boarding: Also enjoy priority boarding before General Admission guests
  • Captains Weekday Membership: Join us Monday-Friday during a Skyline Sail
    • Captains Weekday Membership + VIP: Also enjoy priority boarding before General Admission guests

Membership exclusions: 

  • Membership tickets to sail are as available. Tall Ship Windy Windy is USCG inspected to carry a capacity of 150 total guests
  • Limit to one membership per guest, membership only redeemable for the guest who purchased it
  • Non-refundable and non-transferable, must show ID prior to boarding to verify membership
  • Blackout Dates: Memorial Day Weekend, July Fourth Weekend and Labor Day Weekend (Saturday, Sunday, Monday)
  • Valid for Skyline Sails only. Not redeemable on Monday Night Blues, Fireworks, Dead Theater Reckoning Co. Sails or any Special Event Sails