2019 proved to be a wonderful weekend for water, wind, Tall Ships® food, and entertainment. Thank you to the ships, volunteers, vendors and partners who helped make this event possible.

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Day & Sunset Sails

Festival Sail Excursions

Day Sail

  • $60 & includes festival ticket (approx. 90 minute excursion)
  • Saturday is sold out. Sunday excursions still available at the gate

Sunset Sail

  • $85 & includes festival ticket (approx. 90 minute excursion)
  • Sunset Sails are sold out


When & If

A 63 foot Alden schooner commissioned by General George S. Patton and built by Pendleton in Wiscasset, Maine.  Even though it never happened, Patton said he would sail the ship around the world “when the war is over and if I live through it.”  When And If was perhaps the strongest vessel Alden built incorporating improvements for comfort and safety on the high seas which half a lifetime of sailing experience had taught him. When And If remained in the Patton family until 1972 when the General’s nephew, Neal Ayer, made a gift of the vessel to the Landmark school in Prides Crossing, MA where she was the centerpiece of a sail training program for dyslexic children.


The Tall Ship Windy, is a 148 foot traditional four masted gaff topsail schooner. She offers fireworks cruises, pirate cruises, and a variety of other public and private cruises in Chicago. She is built of modern materials, however, like old trading
schooners and sail training ships, the WINDY has all the character and charm of the great Age of Sail.

Appledore IV

The schooner Appledore IV is owned and operated an organization based in Bay City, Michigan. Tall ship adventures aboard
Appledore IV further BaySail’s mission to foster environmental stewardship of the Saginaw Bay watershed and the Great Lakes ecosystem and to provide personal development opportunities for learners of all ages through shipboard and land-based educational experiences.

Pride of Baltimore II (Sunset Sails Only)

Sponsored by Oneida Nation OneidaLogo_RGB

The Pride of Baltimore is a reconstruction of a Baltimore Clipper, a class of sailing vessels that were the most successful American privateers in the War of 1812. These privately owned ships were chartered by the American government to prey on English merchant shipping, and their success was one of the factors influencing the British to sign the Treaty of Ghent ending the war.

Things to Know:

  • Day and Sunset Sail Excursion ticket holders must be 5 years old (exception is Tall Ship Windy where all ages are allowed, but under 5 not recommended)
  • Tripping hazards are unavoidable aboard sailing vessels and the highest degree of care and watchfulness is expected of all visitors
  • Proper footwear will be worn by all visitors boarding a ship (rubber sole shoes, sneaker, or boat shoes). Leather sole shoes are slippery and dangerous on deck. Absolutely no spike heels are permitted aboard a ship
  • Visitors will not sit on the caprail, taffrail, or bulwarks enclosing the deck
  • Smoking is not permitted aboard the vessel
  • Alcoholic beverages are not permitted to be consumed aboard, during the open hours of the event
  • No food (including chewing gum) or beverages of any kind will be brought aboard by visitors
  • Handrails will be used by guests when boarding and departing the vessel Visitors will not run, jump, or bounce on the gangways or deck
  • Visitors will not be permitted to climb aloft
  • WILL CALL tickets will be available at the main festival gate on the day of the event.  The person who ordered the tickets must present a photo ID. If someone other than the person ordering the ticket is picking them up, Ticket Star will need to be called IN ADVANCE OF AUGUST 5  (800.895.0071)  to change the name on the WILL CALL tickets