Chicago Skyline Tall Ship Sightseeing Cruise

Badge of ExcellenceChicago, USA

Small Group Chicago Skyline Sightseeing Cruise

1 hour 15 minutes
Offered in: English

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Overview

What's Included

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

Meeting and Pickup

Meeting point

600 E Grand Ave, Chicago, IL 60611, USA
We are located on the South dock, on the south side of Navy Pier, immediately in front of the Billy Goat Tavern. If walking on the south dock from the entrance, walk where you see restaurants and boats, walk pass the Ferris wheel, walk past the sign for the Shakespeare theater, then on right!

End point

This activity ends back at the meeting point.

What To Expect

Embark on a nautical adventure from the South Dock of Chicago’s Navy Pier aboard the magnificent schooner, Windy, which spans 148 feet (45 meters), ensuring plenty of room for guests.

Rather than spending hours exploring Chicago on foot, this hassle-free tour allows you to explore the beauty of Lake Michigan and Chicago’s magnificent skyline in just over an hour.

Each journey aboard Windy is distinct, defined by the time of day. Choose from the themed pirates and maritime stories tour, appreciate the city's architectural grandeur on a skyline-/architectural-themed tour, or bask in the evening hues during the skyline sunset tour. Whatever excursion you’re on, there are great views, as well as a fantastic atmosphere of being on a vessel steeped in history.

The tour ends after around 75 minutes, right back at the port so you can continue your independent explorations in the city.

Navy Pier (Pass By)

Lake Michigan

1 hour • Admission Ticket Included

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
Service animals allowed
Dress code:should be sensible for the weather
Near public transportation
Not recommended for travelers with back problems

Travelers should have a moderate physical fitness level
Children under 16 years of age, must be accompanied by an adult
Windy is NOT HANDICAP accessible.
Guests must be able to ambulate up and down 6 steps on each side of the 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 140 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

For a full refund, you must cancel at least 24 hours before the experience’s start time.
If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
Any changes made less than 24 hours before the experience’s start time will not be accepted.

Cut-off times are based on the experience’s local time.
This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Traveler Photos

Featured review

Gladys_F

It was a beautiful experience. Lovely huge sailboat. The crew was friendly, experienced and professional. The captain made the sail smooth and very confortable. I would definitely recommend it to my family and friends

Reviews

4.5

434 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews

Reviews by Viator travelers.

We perform checks on reviews

Showing 1-10 of 434 reviews

Wonderful evening.

David_F, Sep 2023

The views were spectacular!! The crew was very knowledgeable and friendly. We are already talking about doing it again next year.

Response from Host, Sep 2023

Thank you for joining us! We're so glad you had fun, and we look forward to SEAing you next season!

Amazing

Suzy_S, Sep 2023

The view was amazing. Such a beautiful night for sailing. Getting a beer was nice too. Liked the music on board

Response from Host, Sep 2023

We are glad you joined us and hope you come back again soon!

Great evening sailing on a Pirate Ship.

kathiej, Sep 2023

This was a great experience. The crew was very friendly and knowledgeable. We sat at the front of the ship, and the guys helped “hoist” the sail. The views were incredible. I appreciated the music, too. It was nice, mellow and appropriate. Sailing on Windy is a must do, and a “must-do again”.

Response from Host, Sep 2023

We are glad you joined us and look forward to seeing you next time!

This is just advice for...

eric_g, Sep 2023

This is just advice for the tour company. I’d save the pirate talk, pirate music, and anything else obnoxious for the pirate cruise that takes palace for the kids during the day. For the sunset cruise, you guys should try your best to keep it classy and romantic for the couples. That cruise at that hour is not for kids. It’s for couples looking for romantic vibes.

Response from Host, Sep 2023

Hi Eric, that for the advice but our 7pm is for everyone. Couples, kids, parents, solo guests, etc. Though we do try to keep the 7pm a relaxed sail. That is why we do not offer any narration on that sail besides safety and docking speeches. We do offer 21 and up only sails if you are looking to completely get away from the kids in the future

Good times, enjoying the Skyline!

Andrea_B, Sep 2023

Views of Chicago skyline were spectacular. My teenage son enjoyed hoisting the sails! We definitely could have stayed on the ship longer!

Response from Host, Sep 2023

I am glad you joined and and hope you do so again soon! If your son enjoyed helping to raise the sails, maybe he has a future as a sailor!

A fun activity for our a anniversary

Julia_V, Sep 2023

Our favorite part of the sunset cruise was the gorgeous lights of the skyline after dark & snuggling with my husband because it was a bit chilly. Quite romantic.

Response from Host, Sep 2023

The sunset is my personal favorite sail as well! I am glad you joined us and hope you joins us again soon!

Do it!

Page_S, Sep 2023

Scenery and beautiful weather. Crew was fun. Glad we did this. Well worth it. Wasn’t crowded as apprised to the smaller boats.

Response from Host, Sep 2023

I am glade you joined us and hope you will sail with again soon!

Best for families with young children

Robbee_K, Sep 2023

The crew was very professional and nice. But I would not recommend this for an adult-only group. The pirate narrative is best for families with young kids; too juvenile for adults. Also thought there was going to be narration about Chicago architecture.

Response from Host, Sep 2023

Hi, It looks like you joined us for our the 1pm sail which is our most kid friendly sail where we have fun as pirates, but we also do offer architecture and history sails at 3pm and 5pm and our 7pm there is no narration just music and sailing which may be more to your liking.

Awesomeness. Will...

Dawn_A, Sep 2023

Awesomeness. Will definitely recommend and will be back. Great for all ages also. Tje crew fro. Beginning to end were great

Response from Host, Sep 2023

We are glad you joined us and had a great time! I will pass your praise on the the crew!

Arrghh!! Hey Mates, do this cruise.

Frank_M, Sep 2023

We took the sunset cruise. The view was phenomenal. Speaking of phenomenal so was the crew mates. I'd do again in a heartbeat.

Response from Host, Sep 2023

I am glad you joined us and I will pass the phenomenal praise on the the crew!

Great family fun activity

Cassidy_L, Sep 2023

Had a great time! It was a hot day, but the breeze on the lake was great. The crew was super nice and gave a an engaging tour with options to participate in raising the sails.

Response from Host, Sep 2023

We are glad you joined us and hope you sail with again soon!

Mediocre

Ann_B, Sep 2023

The weather was beautiful, the sail was just OK. It was a short ride, not a sail. A bit pricey too!!

Response from Host, Sep 2023

I am sorry we didn't live up to your expectations, but as much as we we it would be, the wind is not always in our sails. We do offer longer sail, like our 2 hour blues sail on mondays nights if you are looking for a longer sail.

Beautiful

Artie_H, Sep 2023

Very beautiful, relaxing evening. We got to watch the super moon vine up over the lake. Great memories!

Response from Host, Sep 2023

I am glad you joined us and hope you join us again to make even more memories!

The Crew and the Weather were Fantastic

Matthew_M, Sep 2023

It was an enjoyable hour and a half! Crew was engaging and it was fun ro see their interaction with the younger members of the group. This was a nice ride out into the harbor, though we didn't venture beyond the break. There was an opportunity to learn about piracy on Lake Michigan.. interesting history. Would enjoy it again for the sunset cruise!

Response from Host, Sep 2023

I am glad you enjoyed your time with us! We dont always go past the break water and a lot of factors go into the decision, such as wind direction and wave size. I want to give a comfortable ride to all our guests and sometimes the water outside the break water is not the most friendly

Great sunset cruise from Navy Pier

Paul_B, Aug 2023

Beautiful boat and cruise at sunset was great. Wonderful views of the lake and the city. Crew was friendly and very safety minded.

Response from Host, Sep 2023

I am glad you joined us and I will pass on your praise to the crew!

Great views of skyline

Peter_S, Aug 2023

Very enjoyable excursion. Emcee Matt, was corny but informative as well as entertaining. Some of the staff (Andrew or Andy) engaged the people in our section and posed with people and/or acted as photographer for us. Very nice view of skyline at dusk going out and with city lit up on way back to dock. If you go on night tour bring a sweater shirt or light jacket.

Response from Host, Aug 2023

As the summer turns to fall a light sweater is good advice! We are glad you enjoyed your time with us and even if Matt was bit corny we glad you found him still entertaining!

Informative and Fun

Paula_G, Aug 2023

Excellent time. Although we are from Chicago, we learned a lot. The crew were great and knowledgeable. Thanks.

Response from Host, Aug 2023

We are glad you joined us and I will pass on your praise to the crew!

Interesting and fun

Marj, Aug 2023

We helped put the sail up. Crew was great, friendly and informative. It was a great day for sailing.

Response from Host, Aug 2023

We are glad you joined us and hope you join us again soon!

Enjoyed

Brenda_C, Aug 2023