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Tall Ship Adventures of Chicago

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Tall Ship Adventures of Chicago Information


11 am- 9:15 pm

Varies depending on tour.

When to Go:
Spring, Summer, Fall

Tour Highlights:
Exhilarating sightseeing tours on one of Chicago's finest sailboats.

Age Restriction:

Quick Facts

  • These Chicago Cruises come in a variety of exciting options, like an Arrchitecture Cruise, Real Pirates tour, Rum Runners cruise and more!
  • Tall Ship Adventures of Chicago are perfect for travelers of all ages - so make sure you get tickets for the little ones when you bring them along.
  • These tours are perfect for family outings or a fun Chicago adventure. They also host special events like weddings, parties, corporate functions, tour groups and more. A tall ship can be chartered for up to 150 guests.

600 East Grand Avenue
Chicago, IL 60611
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Tall Ship Adventures of Chicago

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A great variety of fun and fascinating cruises that focus on Windy City history and lore.

Located in


Navy Pier

Ticket Pricing

Prices Range From: $10 - $30


Features: For years now, Tall Ship Adventures of Chicago have been providing exciting boat tours from the Navy Pier and Lake Michigan area. These Chicago cruises are a great way to try sailing in Chicago for the first time, to have fun on a pirate-themed tour, swing into the roaring 30's in Chicago with a rum runners cruise or experience the life of a Tall Ship Sailors.

Why We Go: Sailing down Lake Michigan can be one of the most fun things to do in Chicago on a vacation with the whole family, and these Chicago cruises are great because they combine a relaxing sailing experience with a fascinating tour packed with history and excitement.

  • Real Pirates of the Inland Seas Tour: Who isn't intrigued by pirates? Usually people don't associate piracy with Chicago, but this adventurous tour will share true stories about the pirates who used to sail the Great Lakes.
  • Arrrchitecture Cruise: The Windy City skyline is famous the world over, so going on one of the Chicago Cruises that highlights the fantastic architecture of the city is a perfect way to spend an afternoon.
  • Rum Runners Tour: Chicago is notorious for having a rich history of the prohibition days of the 1920's, and this tour offered by Tall Ship Adventures of Chicago separates fact from fiction about the smugglers who dominated the Windy City during that era.

Inside Knowledge: Chicago's Navy Pier is known for having one of the best firework shows in the city, so why not enjoy the view from the ultimate vantage point of tallship schooner? Tall Ship Adventure of Chicago offer specific tours for the fireworks shows during the summer.

Do's and Don'ts:

Do bring the kids: Children will love setting sail on a cool boat like this tall ship, and will especially enjoy learning about pirates and some of Chicago's other colorful characters.
Do order tickets online: Reserve a ticket for your tour of choice ahead of time by visiting the Tall Ship Adventures of Chicago website once the tours start being offered again in May.

Don't forget a jacket: Even if it's a warm day in the Windy City, Sailing in Chicago can get chilly with the breeze factored in, so don't forget to bring additional layers to keep warm.
Don't forget about private charters: If you have an upcoming wedding, birthday or special event, guests can rent out a private charter through Tall Ship Adventures of Chicago for a fabulous day on the water.