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

If you’re looking for a different way to take in Chicago’s stunning skyline, a sail on Tall Ship Windy offers just that. This 1-hour 15-minute cruise highlights the city’s famous architecture from the calm waters of Lake Michigan, blending scenic views with a touch of maritime adventure. While it’s an experience that’s accessible for most, it does have nuances that might influence your decision—like the price and the non-narrated nature of the sail.

We’re drawn to how this tour balances relaxation with interactive fun—whether you want to lend a hand raising the sails or simply lean back with a drink in hand. The crew’s friendly attitude and the ship’s historic charm make for a memorable outing. However, if you’re expecting a narrated history or a long, active adventure, this might not be the perfect fit. Still, it’s an excellent choice for anyone craving a unique perspective of Chicago’s skyline, especially those who appreciate the beauty of the open water and fresh air.

This experience suits travelers who value spectacular city views, enjoy being outdoors, or want something a bit different from urban architecture tours. Families, couples, and small groups seeking a peaceful, scenic outing will find this sail both accessible and impressive.

Key Points

• Stunning skyline views from Lake Michigan are the main highlight.
• You can participate actively by helping raise the sails or simply relax onboard.
• The trip is short but sweet—perfect for a quick scenic break.
• Friendly crew and a historic tall ship make for an authentic maritime atmosphere.
• Non-narrated sailing offers peace and quiet, ideal for photography or unwinding.
• The tour costs around $91.23 per person, which, while somewhat premium, reflects the unique experience and the stunning vistas.

What to Expect from the Chicago Skyline Sail

This sail aboard Tall Ship Windy is less about detailed narration and more about the experience of being on a historic vessel in one of the world’s most iconic skylines. As seasoned sailors and history enthusiasts, we find that the appeal of this cruise lies in the visual spectacle—Chicago’s architecture rising from the horizon and the vast Lake Michigan stretching in all directions.

The Itinerary Breakdown

The sail begins at 600 E Grand Ave, a centrally located point that’s easy to reach via public transportation or car. After boarding, the boat gently departs into Lake Michigan, leaving the hustle behind. Your first impression will be the panoramic views of Chicago’s skyline, with modern skyscrapers like the Willis Tower and John Hancock building framing the scene.

The cruise is designed as a quiet, scenic glide—you won’t get a detailed commentary or historical narration. Instead, the focus is on visual appreciation and tranquility. The ship’s captain tries to keep some speed on the vessel whenever possible, making it feel more like a true sail rather than a motorized cruise with faux sails. For those seeking engagement, the crew offers the chance to assist with raising the sails or even drive the boat—a fun feature appreciated by many reviews.

The Sights and Views

Our favorite part? The absolutely breathtaking views of Chicago’s skyline from the water. Whether it’s the shimmering glass facades at sunset or the daytime hustle, the city looks completely different from the lake. Reviewers have consistently praised how perfect this trip is for skyline photography and capturing that quintessential Chicago shot.

Since the sail is inside the break wall for about half the time, the waters tend to be calmer, with no serious waves. This makes it suitable for families, seniors, or anyone wary of rough seas. You’ll see other boats, the coastlines, and, depending on the time of day, possibly a sunset or sunrise that adds to the experience.

The Crew and Ship

Tall Ship Windy has a friendly, approachable crew that welcomes questions and participation. Amanda D. highlighted her experience, noting the “nice ship and crew” and calling the experience “priceless” despite the price. The ship itself offers a charming, historic feel, adding to the authenticity of the trip.

The Practical Aspects

The duration—just over an hour—is ideal for fitting into a busy sightseeing day. The price of about $91 per person is higher than many urban boat tours, but you’re paying for the experience of sailing on a traditional tall ship with immersive views. The boat has restrooms onboard, which is a helpful feature given the short duration.

You should be moderately physically fit—helping with sails or moving around the deck might be necessary, and access to the boat is close to public transportation. The number of travelers is capped at 150, ensuring a well-paced, intimate environment, though it can get crowded during busy periods.

Authenticity and Reviews

While some travelers, like Barbara L., were surprised that the ship was motorized and lacked narration, the tour’s primary appeal is the quiet, scenic sail. The tour explicitly states that non-narrated sails are available, catering to those seeking a peaceful, contemplative experience. Megan S. enjoyed helping raise the sails and noted how the views of Chicago were “beautiful,” emphasizing the visual nature of this cruise.

Who Will Love This Experience?

If you’re someone who treasures stunning cityscapes, or if you want a peaceful, scenic break from busy sightseeing, this sail is a great pick. It’s particularly well-suited for families, couples, or groups of friends who want to enjoy Chicago from a different vantage point. The option to participate actively makes it engaging for those interested in sailing or maritime history, even if only lightly.

However, if you’re seeking an educational narration or a longer, more in-depth tour, you might find this experience somewhat limited. The price point might also give pause—consider this a premium, scenic outing rather than a budget-friendly activity.

The Sum Up

A sail on Tall Ship Windy is a charming and scenic way to see Chicago’s skyline from the water, offering a unique blend of quiet beauty and maritime history. The stunning views are the clear star, making it ideal for photography enthusiasts and those who want to relax outdoors while taking in the city. The friendly crew and authentic vessel create an inviting atmosphere, whether you’re helping raise sails or simply soaking in the scenery.

While it’s not a narrated or active sailing adventure for everyone, it offers a peaceful, picturesque experience that’s well worth the price for many visitors. It’s especially suitable for those who appreciate authentic maritime charm and spectacular city views from Lake Michigan.

If you’re craving a memorable, scenic outing that combines the best of Chicago’s skyline with a touch of nautical adventure, this cruise offers a worthwhile, authentic experience—perfect for a short, scenic escape in the Windy City.

FAQs

How long does the cruise last?
The tour is approximately 1 hour and 15 minutes, making it a perfect short break within a busy sightseeing day.

Where does the tour start and end?
It begins and ends at 600 E Grand Ave, Chicago, a location that’s easy to reach via public transit or car.

What is included in the tour?
The cruise includes the use of restroom facilities onboard. You can also help raise sails or relax and enjoy the views.

Are alcoholic beverages available?
No, alcoholic beverages are not included in the tour price, though the ship has a full bar available for purchase.

Is the boat motorized or sail-powered?
The vessel may be running on motor at times, but efforts are made to sail every trip. Some reviews mention the boat is motorized, and the cruise is available as a non-narrated, quiet sail.

Can I participate actively in sailing?
Yes, helping raise the sails or driving the boat are options, adding an interactive element to your scenic experience.

Is this tour suitable for children or people with limited mobility?
While generally accessible, travelers should have moderate physical fitness. Kids who enjoy boats and open water will likely have fun, but mobility considerations depend on individual needs.

What should I bring?
Bring sunscreen, sunglasses, and a camera—the views are fantastic. Dress appropriately for the weather, as much of the time is spent outdoors on the deck.

A sail on Tall Ship Windy offers an authentic, scenic, and memorable way to see Chicago from a new perspective. Whether you’re capturing skyline shots or simply savoring the fresh air, it’s a cruise worth considering for your Windy City itinerary.