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About Chicago Skyline Tall Ship Cruise

Book Direct with the Owner at Chicago Skyline Tall Ship Cruise with Tourism Bookings in Chicago, for all your Attraction and travel needs.

Itinerary
This is a typical itinerary for this product

Pass By: Navy Pier, 600 E Grand Ave, Chicago, IL 60611-3419

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

Stop At: Lake Michigan, Beaches for swimming, IL

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

Duration: 1 hour

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OPERATES
  • See Availability
INCLUSIONS
  • Local taxes
  • Entry/Admission - Lake Michigan
EXCLUSIONS
  • Alcoholic drinks (available to purchase)
  • Food and drinks (available for purchase)
  • Gratuities
  • Hotel pickup and drop-off
ADDITIONAL INFO
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • All Passengers must be present 30 minutes prior to advertised sail time. The Ship leaves on time. Please allow ample time for Chicago traffic, getting lost, and not being able to park close.
  • Minimum drinking age is 21 years
  • Dress code:should be sensible for the weather
  • Service animals allowed
  • Near public transportation
  • Not recommended for travelers with back problems
  • Children under 16 years of age, must be accompanied by an adult
  • Travelers should have a moderate physical fitness level
  • Windy is NOT HANDICAP accessible.
  • Guests must be able to ambulate up and down 6 steps on each side of then boarding ladder.
  • Assistive devices must be left on the dockside storage area and may not be used on the ship while underway.
  • Windy is NOT HANDICAP accessible
  • This tour/activity will have a maximum of 20 travelers
  • Face masks required for travelers in public areas
  • Hand sanitizer available to travelers and staff
  • Regularly sanitized high-traffic areas
  • Gear/equipment sanitized between use
  • Regular temperature checks for staff
  • Advisory: Exposure to COVID-19 is an inherent risk in any public location where people are present. By completing your ticket purchase, you are acknowledging and accepting that risk, with the understanding that absolute social distancing cannot be maintained in an outdoor space with open seating.
DEPARTURE & RETURN
700 E Grand Ave, Chicago, IL 60611, USA
TERMS & CONDITIONS
All sales are final and incur 100% cancellation penalties.

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Overall Ratings

4.0 based on 10 reviews

Reviews
  • Rating
    826jezm 5
    16 Sep 2021

    Went on last sail of the season this weekend, the crew and ship are fantastic and my 3yr old daughter was allowed to steer ship and help with hoisting the sails, we had a great time! Thank you

  • Rating
    312grahamr 5
    14 Sep 2021

    I was looking for something fun to surprise my girlfriend while killing time at Navy Pier on Labor Day, before catching a flight home. Tall Ship Windy was an AWESOME choice! Great crew, beautiful boat, fun atmosphere! I will definitely book for a fireworks tour or the Air Show if I have a chance in the future.

  • Rating
    289jes 5
    13 Sep 2021

    As a Chicago resident I had never taken a skyline cruise from Navy Pier. Thanks to the habibis, we had tickets for the very last cruise of the season. It was very well run, the crew is awesome, friendly, helpful and very entertaining. They deserve big tips for the work (looks hard to me:) I will recommend this cruise to anyone who is interested in boats, ships, lakes, skylines, etc. This one was just 75 minutes long. Maybe next year we'll check out the Jazz cruise.

  • Rating
    summer_summer000 1
    13 Sep 2021

    It’s one thing to have a firm exchange policy it’s another thing to be unethical and to lie to a loyal paying customer. I bought a Groupon deal (2 rides to sail on Lake Michigan) I went the first time, it wasn’t bad, and I was looking forward to my second tour. When I realized I would be late to my 1pm tour, I called two hours ahead to reschedule to 3pm, the last outing for the day and for the season, but I was told I couldn’t do that unless I paid a $7.00 exchange fee. I thought cool, let me at least try to make it on time. Fast forward, I’m in the city by 12:15 but parking is hard to find, I’m a local and I know where to find free parking (or unregulated as the city calls it) so I was hoping to wait it out, get a spot, walk to Navy Pier and enjoy myself with a beverage of my choice for the ride, I didn’t like the drinks they served the first time. So I call back, and the same guy answers, Bruce, so I remind him, “hey it’s Summer, we spoke earlier can I rebook for 3pm?” He then pauses and sighs all within a 5 second interval, then tells me that the 3pm show is sold out after sounding surprised that I called back. At this point, he sounded disingenuous and I tried to finesse my way in thinking “you get more bees with honey than with vinegar.” After exchanging a few remarks to see what he could do. I finally ask him if he can squeeze me into the 3pm tour: my pitch was: “I’m a local, I went before, I already paid, can you make it happen?” He did his best to hear me before he flat out rejected my request. The conversation has been friendly up to this point. I didn’t throw a hissy fit, even though I felt like, “dude just get me in, I know I’m late but put the customer first, so the customer can continue to come back,” but I knew I was at fault, so honestly I cursed myself out and then dropped it. At this point, I ask him about the most affordable and closest parking spot to Navy Pier, and he gives me a few recommendations. So I drive off to make it in time for the 1pm tour, and I PAY for parking at NAVY PIER because I realize I can’t let this ticket go to waste and everything around navy pier is either too far or just as expensive so I end up using Spothero which saved me $10 but whatever, I get there with 5 minutes to kill, and as I approach the ticket booth stand, I notice the line is kinda short, which is weird because the first time the line was super long, and then I look at the ticket booth, and no one is standing there, which is also weird, because it’s usually packed with people trying to purchase the next tour, and then I walk up to the guy in front of the ticket booth and ask to buy a ticket for the 3pm show, I don’t know why I did this, a part of me wanted to feel like I was making it up in my head, and that this guy wasn’t being a lazy jerk, I needed to be sure so I could settle the issue and blame myself and do better next time. Then the sales guy asks, “FOR HOW MANY PEOPLE?” I couldn’t believe my ears. “There are tickets available,” I shot back both validated that my hunch was right and pissed at the same time that he lied to me. I start thinking about what I could have done with that $32.00 dollars. I could have gotten my toes done, I could have bought 6 Starbucks lattes, I could have gone on another water tour. The sales guy then tells me that they have a few tickets left. At this point, my anger has flipped into disappointment because I had planned on signing up for more sessions and partnering with them for sailing stuff, and I wondered, “why would he do this?” There were fewer people sailing on the ship than the first time, they had room and it wouldn’t have inconvenienced him to let me on the 3pm and honor his word. My thoughts then jump to questioning his professionalism and yada yada yada. Now, why don’t I just ask to speak to a supervisor right? Well, Bruce is the boss, and I know that because I was supposed to send him an email about the upcoming workshops I wanted to enroll in which is why I was extra polite when I was talking to him on the phone. With a few minutes left, I approach the ship and one of the lovely ladies, Mads, calls out my name with enthusiasm to hand me my ticket, and the photographer interrupts my thoughts to ask for a picture. Now I didn’t know what to expect the first time, so I wore sneakers like they suggested, which was not cute, but this time I was more picture ready with my summer dress and flip-flops, but I was too bummed out to even pose for a picture. I then went on board, found a seat and did my my best to let it go. After all, what could I do? I tried to enjoy the ride and that was that. I told myself no one is perfect, and stuff happens, but this guy owns the company and calls the shots. It’s one thing to be able to spend money on leisure, it’s another thing when people don’t respect you enough to respect their own word or policy. You expect this from the big corporate people, not the small family owned business, and that’s fine, he can do as he pleases, but I, too, will do as I please. I lost out on $32 and got a whatever experience. He lost out on ten times that and more because of the classes I, and my students, were going to take. P.S. I wouldn’t have expected any sort of accommodation unless I was told by the sales employee, Mads, that “vouchers are good forever even after the season is over.” So my thinking is, why be so generous in accepting old, expired Groupon vouchers but so strict about same day exchanges. Again it’s one thing if they are sold out. It’s another thing when I am told they are sold out but aren’t, and it’s another to refuse to sell me something that is available, that I was offered. Honestly, I’m over this.

  • Rating
    Sarahadam100 1
    12 Sep 2021

    Don’t do it. There weren’t enough seats for everyone. Most people were unmasked including most crew and the captain. Yet an announcement went off about putting masks on when we docked, only a few complied. I went on Labor Day and they sold more tickets than seats available. It was impossible to socially distance. It was hot too hot people were sweating, it was sticky, and people were sitting too close. I could smell the body odor. Music was loud, and very pirate-ish. I had to stand up the whole time. To make it worse, they kept making announcements before and during the trip that it ruined any sort of enjoyment one could gain from being out on the water. Honestly, What’s the point of the trip? Germs everywhere and no comfort for an hour and fifteen which felt like three hours. Don’t get me wrong, the crew members greeted you warmly as you entered and left, but it was a subpar experience at a touristy spot, don’t be fooled by the reviews. If you’re a local stay away, if you’re a tourist, at your own risk.

  • Rating
    Andrew P 5
    12 Sep 2021

    Wow, what a great trip! We got to hoist the foresail too! My son got to hold the wheel with the wonderful captain! Wind filled the sails as we went out onto the lake. It was great. It was idyllic, really. Highly recommend!

  • Rating
    Scott_W 3
    12 Sep 2021

    Disappointed with the lack of seating. Nothing in website information prepared us for this. Crew was nice

  • Rating
    Martyne_P 5
    12 Sep 2021

    Raising the sails and just being on a sail boat. Very fun, crew was very fun and nice. I would do it again.

  • Rating
    AlondraV11111 5
    06 Sep 2021

    I felt like a pirate 🏴‍☠️🦜there was no talking bird but the staff was very chatty and wonderful 🦜

  • Rating
    KATHERINE_S 5
    06 Sep 2021

    Beautiful day, beautiful view! Crew was very friendly. Boat was clean and plenty of seating. Boarding was efficient.

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Chicago Skyline Tall Ship Cruise

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