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

If you’re thinking about a unique way to see Chicago’s famous skyline, a ride on the Tall Ship Windy might just be worth considering. This sail offers a leisurely cruise on Lake Michigan that combines scenic views, a bit of hands-on sailing, and a relaxing atmosphere. While it’s not a high-energy adventure, it’s a lovely way to spend an hour and change soaking in the wind and the skyline.

What we really like about this experience is the chance to enjoy the lake from a different perspective—seeing the city’s iconic architecture from the water is quite special. Plus, the option to help raise the sails or simply sit back and relax caters well to those who want a bit of interactive fun or just a peaceful cruise. One potential downside is the price—at around $91 per person, it’s on the higher side for a short tour, but many felt the views made it worthwhile.

This sail suits travelers who appreciate scenic, laid-back experiences, especially if you’re into boats or want a different angle on Chicago’s skyline. It’s also a decent pick for those who enjoy a bit of nautical history or just looking for a different way to enjoy Lake Michigan. If you’re after a structured narration or a full-on sailing adventure, you might find this isn’t quite what you’re looking for, but for most, it’s a charming water-based outing.

Key Points

• Relaxed, scenic cruise with breathtaking views of Chicago’s skyline from Lake Michigan.
• Options to help raise sails or just sit back, making it suitable for both active and passive participants.
• Includes a full bar and gift shop, adding to the leisurely vibe of the cruise.
• Short duration of about 75 minutes, perfect for a quick escape without a big time commitment.
• Limited inclusion of narration or guided commentary, so it’s more about the scenery than storytelling.
• Price point is somewhat higher but reflects the value of the views and experience.

The Experience of Sailing on Tall Ship Windy

The Tall Ship Windy isn’t just a boat—it’s an ambassador for Chicago’s maritime charm. As the city’s official tall ship, it’s designed to give you a taste of classic sailing, with the added bonus of fantastic city views. Your adventure begins at 600 E Grand Ave, where you’ll meet a friendly crew ready to welcome you aboard.

Once onboard, you can choose to get involved by helping to raise the sails. If you’re eager to participate, you’ll find it satisfying to contribute to the operation of the ship, all while enjoying the fresh lake air. For those who prefer to relax, just taking in the sights from the deck works equally well. The crew is friendly and approachable, making the experience feel welcoming whether you’re a seasoned sailor or a first-timer.

The Itinerary Breakdown

Start Point: The cruise begins at the designated marina at 600 E Grand Ave, a central spot easily accessible by Chicago’s public transport. From here, the ship sets sail on Lake Michigan, heading toward the open water for about 75 minutes.

Sailing on Lake Michigan: The main draw of this tour is the sailing on Lake Michigan, where you get a peaceful yet invigorating ride. The ship stays within the break wall for about half the time, so you won’t encounter serious waves, making it a comfortable experience even for those who might be prone to seasickness. You’ll enjoy stunning views of Chicago’s skyline, which is especially captivating during sunset or clear days.

View of Chicago from the Water: The highlight is definitely the scenery. You’ll see the city’s towering buildings from a unique perspective, with the skyline reflecting on the water—perfect for skyline shots or simply soaking in the beauty of Chicago from the lake.

Return: After drifting back to the starting point, you’ll disembark feeling refreshed, with a new appreciation for the city’s lakeside charm.

What Travelers Say

One thing that comes across clearly in reviews is how much people appreciated the spectacular views. Amanda_D raved, “Nice ship. Nice crew. Great experience. Its a little pricey, but views of skyline are priceless!” That phrase sums up what most find memorable—those panoramic cityscapes.

Another review from Megan_S highlights the interactive aspect: “You can help raise the sails and even drive the boat,” which adds a playful element and makes the trip more engaging. She also mentioned, “If you get seasick, be sure to take Dramamine,” which is worth considering if you’re sensitive to motion.

On the downside, Barbara_L pointed out a possible misconception: “There was no narration and they did not sail. It was motorized not sail powered. This was poorly advertised.” The response clarifies that while they do try to sail when possible, sometimes the vessel runs under motor, especially if they’re keeping some speed or conditions don’t favor sailing. For those expecting a narrated or fully sailing experience, it’s good to keep this in mind.

The Practical Details

The tour lasts roughly 1 hour 15 minutes, giving you plenty of time to relax without feeling rushed. The price of around $91 per person includes the sail, restroom facilities onboard, and access to the gift shop. The cost might seem a bit steep for a short ride, but considering the views and the chance to be on a historic tall ship, many travelers believe it’s fair.

Group size is capped at 150 people, so it’s a comfortably sized group without feeling crowded. The tour is also accessible for those with moderate physical fitness levels, and service animals are allowed—no worries if you’re traveling with a support animal.

Who Will Love This

This tour is ideal for those seeking scenic, peaceful moments on the water, especially if you enjoy city skylines and lake views. It’s also a good pick for anyone who appreciates boats, sailing history, or just wants a different perspective on Chicago’s iconic architecture. Those who enjoy a relaxed pace over a structured narrative will find it appealing, and it’s equally suitable for couples, groups of friends, or solo travelers.

If your priority is a lively, narrated voyage with lots of historical stories, you might find this less satisfying. But if you’re after Instagram-worthy views, fresh air, and a taste of nautical life, you’ll likely walk away happy.

Frequently Asked Questions

Is this tour suitable for children?
While the experience isn’t specifically marketed as family-oriented, it’s generally suitable for all ages, especially if your kids enjoy boats or scenic views. Just keep in mind the moderate physical activity involved if helping to raise sails.

How long does the sail last?
The sail lasts approximately 75 minutes, which is a manageable time for most people and leaves plenty of room for sightseeing without fatigue.

Does the tour include narration?
No, this particular cruise does not feature a narrated commentary. It’s more about enjoying the views and the sailing experience itself.

Can I help raise the sails?
Yes, if you’re interested, you can join the crew in helping to raise one of the sails. It adds a hands-on element that many find enjoyable.

Are drinks available onboard?
Yes, the Tall Ship Windy has a full bar, so you can purchase alcoholic beverages during the cruise. Snacks are not included but might be available for purchase.

What about accessibility?
The tour is designed to accommodate travelers with moderate physical fitness levels, and service animals are permitted.

Where do we meet for the tour?
The meeting point is at 600 E Grand Ave, Chicago, making it easy to reach via public transportation or car.

What if I need to cancel?
The booking is non-refundable, so plan accordingly. Once booked, changes or cancellations won’t result in a refund.

Final Thoughts

Sailing on Tall Ship Windy offers a peaceful, scenic escape with unbeatable views of Chicago’s skyline, especially if you’re looking for a relaxed and visually stunning experience. The chance to be part of the sailing or simply enjoy the breeze and scenery makes it versatile and appealing. While the price might be a consideration, many travelers find the views and atmosphere justify the expense.

This trip is best suited for those who enjoy a gentle cruise, love beautiful cityscapes, and want a memorable lakeside moment. If you’re after an active sailing adventure or detailed narration, you might want to look elsewhere. But for a tranquil, picture-perfect outing, it’s a solid choice.

In summary, the Chicago Skyline Sail on Tall Ship Windy is a charming way to see the city’s famous architecture from a different angle. The relaxed pace, friendly crew, and stunning vistas make it a worthwhile addition to your Chicago itinerary—especially if you’re a fan of boats, lakes, or panoramic city views. Just remember to bring your camera and some patience, and you’ll likely come away with some beautiful photos and memories.