Chicago Skyline Sail | Tall Ship Windy Chicago

Quick Details

Duration: 75 minutes
Ages: All ages welcome
Availability: Daily

The famous Tall Ship Windy sunset sail is truly famous. Used in many world-reknown photos, backdrops for special events, weddings, or just an evening 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.

Standard Boarding

Adult Ages 13+: $39

Child Ages 0-12: $29

VIP Captains Boarding

Adult Ages 13+: $49

Child Ages 0-12: $39

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.

The Tall Ship Windy sailing toward the Chicago skyline at sunset

Tall Ship Windy sailing Lake Michigan with Chicago in background

a close up of a boat next to a body of water

Sunset view during the Twilight Pub Sail on Tall Ship Windy

Tall Ship Windy sailing in front of Chicago skyline

Wedding part aboard the Tall Ship Windy in Chicago, IL

Private Charters

Please visit our private charters page for more info or download our charters fact sheet here.

Includes:
- Ticket
- VIP boarding
- Trip insurance
- Taxes
You can purchase these optional items when you book:
- Trip Insurance: $8.00 per person—gives you the ability to cancel your reservation if needed and receive a full refund. This applies up to 8 hours before your scheduled sail time or if Tall Ship Windy cancels your sail due to weather.
- No-shows will be charged the full price. Guests must arrive at least 15 minutes before the scheduled departure time or risk forfeiture.
- The captain reserves the right to postpone the sail for up to 30 minutes; if the sail is cancelled, tickets may be exchanged for another time.
- No refunds and no exchanges are available without the purchase of additional Trip Insurance. The Windy sails rain or shine. In the unlikely event that your tour is cancelled due to rain, we will provide you and exchange or refund.

View FAQ

Chicago Skyline Sunset Sail

Private Charters

Fireworks Cruise! Departs Every Wed 8:45p and Saturday 9:15p

Educational Sail: Tall Ship Discovery Sail

Chicago Skyline Sunset Sail

Private Charters

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Fireworks Cruise! Departs Every Wed 8:45p and Saturday 9:15p

Educational Sail: Tall Ship Discovery Sail