Quick Details
General Admission Boarding
Adult
Ages 13+
$ 59
Child
Ages 0-12
$ 49
VIP Captains Boarding
Adult
Ages 13+
$ 74
Child
Ages 0-12
$ 64
The famous Tall Ship Windy Sunset Sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings and evenings out, the sunset sail aboard one of the only four-mast Schooners still in operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn toward the Chicago skyline for a view of our spectacular sunset. Sit back and relax, enjoy some soothing music and gently complete your day with this dramatic sunset.
Chicago’s Tall Ship Windy Sunset Cruise departs Navy Pier promptly at 7pm. The sunset cruise tends to sell out so we highly recommend the purchase of VIP tickets to ensure your choice of seating.
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Our sailing schedule changes with the season. Beginning September 3, enjoy a Sunset Skyline sail at 5pm and a Late Summer Twilight Sail at 7pm.
On our Twilight Sail, enjoy the beautiful colors splashed across the post-sunset sky. You’ll enjoy an evening sail on Lake Michigan aboard Tall Ship Windy and take in the world-famous Chicago skyline as day transitions to night.
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All seating on board Tall Ship Windy is first come, first served. Guests with VIP Captains Boarding tickets board first before General Admission ticket holders. A limited number of VIP tickets are available and are likely to sell out. Board first to choose your seat on one of Windy’s three decks: the forward, middle or aft.
All VIP Captains Boarding tickets also include trip insurance. Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.
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$8.00 Per Guest | Add to your ticket at checkout
Trip insurance allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time. Refunds for cancelled charters are less the $8.00 cost of insurance and 3% booking fees.
General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.
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- RAIN OR SHINE EVENT: In the unlikely event that your tour is cancelled, you may exchange your ticket for another day or receive a refund.
- No-shows will not be eligible for rescheduling or refund. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.
- The Captain reserves the right to postpone a sail for up to 15 minutes in the case of passing inclement weather.
- General Admission tickets without trip insurance may only change or cancel a reservation and receive a refund up to 48 hours before their scheduled sail time.
- Add-on Trip Insurance: Allows you to change or cancel your reservation and receive a refund up to 8 hours before your scheduled sail time.