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Chicago Skyline Tall Ship Sightseeing Cruise

4.5 (452)
Chicago, US
4.5 (452)
Chicago, US
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Experience the magic of Chicago's skyline from the water with the Skyline Tour Aboard 148 Ft. Schooner Windy. Leave the hustle and bustle behind as you embark on a leisurely sail around Lake Michigan. This 75-minute journey offers stunning views of the world-famous skyline and allows you to discover the Windy City from a unique perspective. Step aboard the historic Schooner Windy, the Official Ship for the City of Chicago, and enjoy a relaxing sail on this truly remarkable vessel. Choose from various themed sails, including Pirates and Maritime Stories, Skyline/Architectural, and Skyline Sunset. Departing from Navy Pier, one of the city's most popular attractions, this tour is a must-do for any traveler seeking an unforgettable experience in Chicago. Don't miss your chance to be part of this incredible adventure on the water.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • Admission Included
  • 1 hours 15 minutes
  • Suitable for 1-15 Participants
  • Small Group Tour
  • Self Guided Experience
  • Leisurely trip around Lake Michigan
  • Spectacular views of Chicago's skyline
  • Experience the historic Schooner Windy
  • Explore the shores of Chicago
  • Relaxing sail on a unique vessel
  • All fees and taxes
  • Restroom on board
  • Live narration from expert guide
  • Alcoholic, non-alcoholic drinks & snacks (available for purchase)
  • Gratuities
  • Hotel pickup and drop-off

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More about this experience

Introduction:

Experience the beauty of Chicago's skyline like never before with the Skyline Tour Aboard the 148 Ft. Schooner Windy, Chicago's Official Tall Ship. Leave the hustle and bustle behind as you embark on a leisurely trip around Lake Michigan. This tour offers a unique perspective of the Windy City, allowing you to take in the world-famous skyline, enjoy spectacular views, and discover Chicago from the water. The Schooner Windy, at 148 feet long, is a truly historic vessel and the Official Ship for the City of Chicago. With its four masts and rich maritime history, it provides an unforgettable sailing experience.

What to expect:

During the Skyline Tour, you can expect to be captivated by the breathtaking views of Chicago's skyline and architectural wonders. As you sail along Lake Michigan, you'll be surrounded by the stunning beauty of the city's iconic buildings, including the Willis Tower, John Hancock Center, and Navy Pier. This tour offers a unique opportunity to see Chicago's skyline from a different perspective, creating unforgettable memories.

Who is this for:

The Skyline Tour Aboard the 148 Ft. Schooner Windy is perfect for anyone looking to experience the beauty of Chicago in a unique and memorable way. Whether you're a local resident wanting to explore your city from a new angle or a visitor looking for an unforgettable experience, this tour is for you. Families, couples, and friends will all enjoy the leisurely sail and stunning views of the Chicago skyline.

Why book this:

Book the Skyline Tour Aboard the 148 Ft. Schooner Windy and embark on an adventure that will leave you in awe. This tour offers a one-of-a-kind experience to sail on a historic tall ship and witness the beauty of Chicago's skyline from the water. The Schooner Windy is not only a majestic vessel but also the Official Ship for the City of Chicago, adding to the authenticity and charm of the experience. Don't miss the opportunity to create lasting memories as you sail along Lake Michigan and take in the breathtaking views of the Windy City.

Good to know:

Please note that the Skyline Tour is approximately 75 minutes long and departs promptly at the scheduled time. Make sure to allow enough time for parking, as the ship is located on the South dock of Navy Pier. Alcoholic drinks and food are available for purchase onboard, and gratuities are not included. The Schooner Windy is easily accessible from the south side of Navy Pier, in front of the Billy Goat Tavern. Follow the signs and walk along the south dock until you reach the ship. Get ready for a delightful sail and an unforgettable experience.

Reviews:

Customers who have embarked on the Skyline Tour Aboard the 148 Ft. Schooner Windy have raved about their experiences. They describe the tour as breathtaking and highly recommend it to anyone visiting or living in Chicago. Many reviewers mention the stunning views of the skyline and the unique perspective of the city that the tour provides. The historic Schooner Windy and its knowledgeable crew have also received praise for their hospitality and passion for sharing Chicago's maritime history. Overall, the reviews highlight the unforgettable nature of this sailing experience and its ability to create lasting memories.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Is an adult required for the booking?

  • At least one adult or senior required per booking

Your Itinerary

Navy Pier

(Pass by)

Departs from the historic Navy Pier, one of the most popular tourist attractions in the city.

Lake Michigan

Sail on the third-largest of the Great Lakes. Lake Michigan is itself a natural wonder.

Admission Included

Reviews

(452)

4.5 (452)

Sharon_C

The tall ship was cool but the seating for a 2-hour cruise was lacking. It was hard sitting that long on a metal platform with no back support. The crew was great however!

Steven_L

I love being in the water viewing the Chicago skyline without needing a motor. Using only the win to propel us!

Sean

Great sailing experience. Perfect weather and breeze. The boat is fun and well managed. Felt safe with crew engagement at all times. Amazing sunset view of chicago skyline. Navy pier is a fun venue . Enjoyed the unique experince of a tall ship sail.

Daniel_K

Fun being propelled by wind on a large ship. Have skyline interpreted along the way. Affable crew. Fewer passengers than other tours. .

James_S

The crew was fun. The guide/ docent was unfunny, uninteresting and uninterested. The boat was tacky but that's part of the fun. The bar was great and the people there genuinely interested in making a memorable experience

Varden_P

Connor’s storytelling was top notch and kept us interested in the history of Chicago buildings aside from hiding from the rain it was a fun and new experience would do it again!

Flyer48180282809

Had a short girlfriend trip to Chicago and had a wonderful time. We had done the morning activities and our pizza was done quickly so asked to move our 3pm trip to 1:00. They kindly obliged. The staff was very nice and we enjoyed talking to Marlon who was helping raise and lower the sails. Interesting guy. I previously rode a tall ship in the San Fran Bay and it was much rougher waters and much colder. This was super relaxing! Would definitely do it again!

Joshua_M

Was a great tour. was a great good sailing tour. Was a great tour. was a great good sailing tour. Was a great tour. was a great good sailing tour.

virtualJay

We sailed on a Monday evening, so this review only applies to the Sunset Cruise with a Live Blues Band (only on Mondays). It was my first opportunity during my 73 years to sail on a tall ship. It was a bucket list item for me, so I enjoyed it immensely. The blues band made it even more interesting. I do wish the band would have taken song requests, and I wish the ship staff would have at least pointed out a few significant sights - so I knocked off one star.

tishr2024

The best waterfront sightseeing trip. Fun to be on a schooner, see the sails go up and/or help hoist the sails. The crew was friendly, personable and entertaining. The tour guide was terrific and knowledgeable. My 12 year old also had a great time.
Collected by Evendo & our supplier partners
2024-07-03 19:04