Sail on Tall Ship Windy, join us for our “Chicago Skyline Sail”

If you’re looking for a relaxing way to see Chicago from a fresh perspective, the Chicago Skyline Sail on Tall Ship Windy might just be your ideal outing. This trip offers a peaceful cruise on Lake Michigan, where you can enjoy unobstructed views of the city’s iconic skyline. It’s a chance to escape the busy streets and see the city’s architecture from a truly different angle — on the water, with a gentle breeze and stunning vistas.

Two things we particularly appreciate about this experience are the opportunity to help raise the sails — giving a hands-on touch to your sightseeing — and the spectacular views of Chicago’s skyline that are hard to beat from Lake Michigan. That said, one thing to consider is the lack of narration or guided commentary, which may leave some wanting more context about the sights.

This sail is well-suited for families, couples, or solo travelers who enjoy scenic views and a relaxed pace. It’s perfect for those wanting a peaceful, photo-friendly outing, or anyone curious about what it’s like to be on a tall ship.

Key Points

• Stunning skyline views from Lake Michigan offer an alternative perspective of Chicago.
• The activity is flexible — you can join the crew to help with sails or simply relax.
• The duration is about 1 hour 15 minutes, making it a manageable outing that fits into most schedules.
• Affordable pricing at just over $91 per person, with a focus on value for memorable scenery.
• The boat features a full bar, gift shop, and restroom, enhancing comfort and convenience.
• The experience is non-narrated, appealing to those seeking tranquility without commentary.

An Authentic Chicago Sailing Experience

The Chicago Skyline Sail offers an experience that emphasizes the beauty of Lake Michigan and the city’s architecture. We loved the way the Tall Ship Windy, with its classic lines and welcoming crew, creates a charming maritime atmosphere right in the heart of Chicago. The ship, acknowledged as the city’s Official Tall Ship Ambassador, provides an authentic sailing environment, even if some trips are motorized — a point that some reviewers noted.

This tour departs from 600 E Grand Ave, a convenient spot near public transportation, making it easy to reach without hassle. After check-in, you’ll board the Windy, a vessel where the crew encourages participation in raising the sails. If you’re interested in hands-on sailing, you’ll enjoy the chance to contribute — it adds an authentic touch most other boat tours can’t provide. If you prefer to sit back and soak in the scenery, you’re welcome to relax and let others do the work.

The Itinerary: What to Expect

The tour is straightforward but packed with visual appeal. Your main highlight is the quiet sail along Lake Michigan with panoramic views of Chicago’s skyline. The route takes you inside the break wall for about half the time, which means calmer waters and fewer waves — making it accessible for a wider range of travelers, including those who might be prone to seasickness (reviewers recommend Dramamine for sensitive stomachs).

You’ll start and end at the same spot, with the boat gently gliding past landmark structures. The sail offers excellent opportunities for photos of the city’s famous skyscrapers from an angle that many visitors overlook. Think of it as a chance to see the city’s gleaming towers from a peaceful vantage point, framed by the open sky and water.

Onboard Comforts and Amenities

The Tall Ship Windy features a full bar for those who want to unwind with a drink — though alcoholic beverages are not included in the ticket price. There’s also a gift shop, perfect for picking up souvenirs or mementos of your Chicago visit. The vessel is equipped with a restroom, so you won’t need to hold it during your 75-minute cruise.

Since the ship can hold up to 150 travelers, the group feels lively but not crowded, striking a good balance between social atmosphere and personal space. The experience is suitable for moderate physical activity, mainly walking around and possibly helping with sails, which adds an interactive element.

Pricing and Value

At $91.23 per person, the price might seem on the higher side for a short cruise. However, considering the unique views of Chicago’s skyline, the opportunity to help with sails, and the overall ambiance, many find it worth the cost. The experience offers a distinctive perspective on the city that you simply can’t get from land, making it a memorable addition to your Chicago itinerary.

Some reviews mention the price as being slightly steep, but they also noted that the views were priceless. For travelers who value scenic photography or a peaceful boat ride, this could very well be a worthwhile splurge.

Authenticity and Customer Experience

Feedback from guests is generally positive, with a 4.7-star rating based on 17 reviews. Many travelers appreciated the friendly crew and the beautiful city views. One reviewer called it a “great experience” with “nice ship and nice crew,” emphasizing that the views of the skyline are truly priceless.

However, one guest expressed disappointment over the lack of narration and the fact that the boat was motorized rather than sail-powered. The organizers responded that they do try to sail every trip but sometimes need to use the motor to maintain a certain speed, especially if winds are light. They also offer quiet sailing options for those seeking a more tranquil, non-narrated experience.

Who Will Love This Tour?

If you enjoy scenic landscapes, peaceful waters, and the charm of classic tall ships, you’re likely to find this experience quite rewarding. It’s especially suited for photographers wanting striking skyline pictures, families seeking an engaging but relaxing outing, and adventure-seekers interested in helping with sails — even if just for a few moments.

Those who prefer guided commentary or want a more narrated history of Chicago’s architecture might find this tour lacking in that regard. Still, for a quiet, scenic escape with excellent photo ops, it delivers on its promise.

The Sum Up

The Tall Ship Windy’s Chicago Skyline Sail is a charming, scenic cruise that offers a peaceful alternative to bustling land-based sightseeing. Its highlight is the breathtaking views of Chicago’s iconic skyline from Lake Michigan, which makes it a memorable experience, especially for photographers or anyone wanting a quiet moment on the water.

While the price may seem steep for a 75-minute sail, the quality of the scenery and the hands-on sailing opportunity add significant value. The vessel’s amenities, such as the bar and gift shop, ensure comfort, and the friendly crew makes the trip welcoming.

This experience caters well to those seeking a relaxing, scenic, and authentic maritime adventure in Chicago, with enough flexibility to help out or simply relax as you take in the sights. It’s a great way to see the city from a different angle without being overwhelmed, making it a worthwhile addition to your Chicago itinerary.

FAQ

Is there a restroom onboard?
Yes, the Tall Ship Windy is equipped with a restroom for passengers’ convenience.

Are alcoholic beverages available during the tour?
The tour includes a full bar, but alcoholic drinks are not included in the ticket price and are available for purchase.

How long does the cruise last?
The sail lasts approximately 1 hour and 15 minutes, making it a manageable and relaxed outing.

Can I help with sailing?
Absolutely. If you’re interested, you can join the crew in raising sails and even help drive the boat — a fun and interactive aspect of the tour.

Is the sailing narrated or guided?
No, this tour is non-narrated, offering a peaceful, quiet experience with panoramic views of Chicago.

What is the meeting point?
The tour starts and ends at 600 E Grand Ave, Chicago — a location accessible by public transportation.

Is this experience suitable for children?
Yes, it’s fun for all ages, and the relaxed pace makes it suitable for families.

Are there any physical requirements?
Participants should have moderate physical fitness as there might be some walking or movement around the boat.

What if I get seasick?
If you’re prone to seasickness, consider taking Dramamine or similar medication, as the waters are typically calm inside the break wall.

Can I cancel or reschedule?
This experience is non-refundable and cannot be changed once booked, so plan accordingly.

Experience a different side of Chicago with a scenic sail that combines relaxation, stunning views, and a touch of maritime adventure — a true highlight for any trip to the Windy City.