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

Imagine gliding across Lake Michigan on a charming tall ship, with Chicago’s iconic skyline sprawling around you. That’s what this Chicago Skyline Sail offers—a relaxing, scenic cruise on Tall Ship Windy, Chicago’s official Tall Ship ambassador. While we haven’t personally taken this sail, reviews and detailed descriptions paint a picture of a unique way to enjoy the city’s beauty from the water.

What makes this experience appealing? First, the stunning views of the Chicago skyline from the lake are unbeatable—especially at sunset or during bright days. Second, the interactive element—helping raise sails or even driving the boat—adds a hands-on feel rarely found on typical boat tours. Lastly, the ship’s friendly crew and the full bar onboard create a welcoming, laid-back atmosphere.

However, one thing to consider is the price point—$91.23 per person—which may seem steep compared to quick boat rides, but many feel the breathtaking views and unique sailing experience make it worthwhile.

This tour is ideal for those who appreciate scenic, leisurely outings and want a different perspective of Chicago’s famous skyline. Families, couples, or anyone interested in maritime charm and lakefront serenity will find plenty to enjoy here.

Good To Know

• Stunning Lake Views: Get an exceptional vantage point of Chicago’s skyline from the water.
• Interactive Sailing: Opportunity to help raise sails or assist with sailing, making it more engaging than a typical cruise.
• Relaxing Experience: A calm, peaceful sail inside the break wall, perfect for unwinding.
• Family Friendly: Fun for all ages, with a friendly crew and beautiful scenery.
• Value for the Price: Although the cost might seem high, reviews highlight the priceless skyline views and unique sailing vibe.
• Convenient Location: Easily accessible at 600 E Grand Ave near public transit.

In-Depth Look at the Chicago Skyline Sail Experience

The Itinerary and What to Expect

The tour lasts around 1 hour and 15 minutes, making it a perfect quick escape without feeling rushed. Starting at 600 E Grand Ave, the sail takes you onto Lake Michigan, where you’ll enjoy a peaceful, unhurried cruise. The route primarily involves a quiet, scenic sail—there’s no mention of active narration or extensive commentary, which many reviewers find ideal for soaking in the views in peace.

One highlight is the view of Chicago’s skyline from the lake, which provides a different perspective compared to the city streets or river cruises. You’ll see the impressive cityscape, reflecting off the water, with the skyline often described as “priceless,” especially at sunset or during golden-hour moments.

What Makes the Sails Special?

The ship, Tall Ship Windy, is described as nice with a friendly, competent crew. Guests have the chance to help raise sails, which adds a tactile element to the experience that many find memorable. Some reviews mention that you can even drive the boat, adding a fun, interactive aspect that appeals to those wanting more than just sightseeing.

According to reviews, the ship does try to sail whenever possible, though the vessel may sometimes operate under motor due to weather or operational considerations. Reviewers note that the sailing experience is sometimes more about relaxing and enjoying the scenery than intense sailing.

The Views and Photo Opportunities

The main draw is the stunning backdrop of Chicago’s skyline—a photographer’s dream. Whether capturing the city’s silhouette at dusk or the bright reflections on the water, this sail provides prime photo opportunities. Several reviews emphasize that the length of the trip feels just right—not too long to get bored, but enough time to enjoy the scenery and take plenty of photos.

The Ship’s Amenities

Tall Ship Windy has a full bar onboard, making it easy to enjoy a drink while taking in the sights. There’s also a gift shop for souvenirs. Restrooms are available, which is a practical touch for a 1-hour trip. However, alcoholic beverages and snacks are not included in the price, so you’ll want to bring your wallet if you plan to indulge or nibble.

Practical Details and Accessibility

The departure point at 600 E Grand Ave is convenient and near public transportation, easing access for most visitors. The boat accommodates up to 150 travelers, so it’s usually a good-sized group but still intimate enough to feel personal and relaxed.

Guests should have moderate physical fitness, especially if they wish to help with sailing or move around comfortably on deck. Service animals are allowed, making it accessible for travelers with specific needs.

What the Reviews Say

• Amanda_D gave the experience a perfect 5-star rating, praising the beautiful views and friendly crew. She noted that “the skyline views are priceless,” and called the ship itself “nice.”

• Megan_S also enjoyed helping raise the sails and emphasized that if you’re prone to seasickness, Dramamine is advisable. She described it as a “very cool experience” with stunning city views.

• Barbara_L’s review was less positive, citing that the sailing was motorized and that there was no narration—which some might see as a drawback if they prefer more commentary. The response from the provider clarified that they do try to sail, but sometimes operate under motor, especially for those seeking a quiet, non-narrated experience.

• Marylou_D found the timing perfect for capturing skyline shots, highlighting the inside break wall that reduces waves and keeps the experience smooth and comfortable.

Is It Worth the Price?

At just over $90 per person, the cost might seem high for a short cruise. However, reviews underscore the value of the experience—the combination of serene sailing, stunning vistas, and the chance to be involved in the sailing process makes it more than just a typical boat ride. For those looking to see Chicago from a fresh perspective and enjoy a relaxing, interactive experience, many feel it’s well worth the investment.

Who Will Love This Tour?

This sail appeals most to outdoor lovers, photography enthusiasts, and families seeking a unique Chicago outing. It’s perfect for anyone who appreciates a laid-back atmosphere with beautiful scenery and doesn’t mind spending a bit more for a memorable experience. Because the trip is inside the break wall most of the time, even those worried about waves or seasickness tend to find it manageable.

Final Thoughts

The Chicago Skyline Sail on Tall Ship Windy offers a charming, scenic escape from city hustle, with the added thrill of helping to sail a historic vessel. It’s a great way to enjoy Lake Michigan’s beauty while being part of an interactive, peaceful adventure.

While the price might give some pause, the breathtaking skyline views and the authentic sailing vibe make this experience stand out. Whether you’re a first-time visitor or a local looking for a different perspective, this cruise combines relaxation with visual splendor in a way that feels both special and authentic.

For travelers seeking a low-key, scenic, and memorable experience, this sail on Tall Ship Windy is definitely worth considering. Just remember to bring your camera, a jacket, and maybe some Dramamine if you’re prone to seasickness.

FAQs

How long does the Chicago Skyline Sail last?
The tour lasts approximately 1 hour and 15 minutes, providing enough time to enjoy the views and participate in sailing activities without feeling rushed.

Where does the tour depart from?
It departs from 600 E Grand Ave, Chicago, which is conveniently located near public transportation options for easy access.

Is the experience suitable for children?
Yes, the experience is fun for all ages. Kids and families often enjoy helping with sails and taking photos of the skyline.

Are alcoholic beverages available onboard?
A full bar is available, but alcoholic drinks are not included in the ticket price. You can purchase drinks during the sail.

Can I help sail or drive the boat?
Absolutely. Guests have the opportunity to help raise sails or even assist in driving the vessel, making it more engaging than a typical tour.

Is the tour narrated?
There’s no mention of extensive narration; some sails are quiet, allowing you to enjoy the scenery at your own pace. If you prefer a narrated experience, check with the provider beforehand.

What should I bring?
Bring a jacket for the breeze, your camera for photos, and perhaps some cash for drinks or souvenirs. A moderate level of physical fitness is recommended if you want to participate actively.

In the end, this Chicago Skyline Sail on Tall Ship Windy combines scenic beauty, maritime fun, and a relaxed pace—making it a distinctive way to see the city from the water. Whether you’re after Instagram-worthy views, a new sailing experience, or a peaceful break from the city streets, this tour offers a memorable outing that’s well worth exploring.