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Tall Ship Windy

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Why Tall Ship Windy is a fun option when searching for things to do near me with friends and family

Tall Ship Windy offers a unique and memorable way to meet up with friends by sailing aboard a traditional tall ship on the protected waters of Lake Michigan. The 148-foot four-masted gaff topsail schooner sails from Navy Pier and provides guests with spectacular views of Chicago’s iconic skyline, including landmarks such as Willis Tower, John Hancock Center, and the Navy Pier Ferris Wheel. Whether you enjoy history, architecture, or just want to share a special experience, Tall Ship Windy creates an atmosphere perfect for all ages and interests.

The ship combines the charm of the Age of Sail with modern amenities, ensuring a comfortable and safe outing. Guests can choose from a variety of sailing experiences including educational tours, pirate-themed adventures, sunset sails, fireworks cruises, and even live music events like Monday Night Blues. The crew is passionate about sharing maritime knowledge and fostering ecological awareness, making the outing not just entertaining but also enriching.

With opportunities for romantic sails, group fun, and private charters for weddings or corporate events, Tall Ship Windy is an exceptional venue for connecting with friends while exploring the beauty of Chicago from a fresh perspective on the water. The friendly, knowledgeable staff and the scenic backdrop make it a standout choice for outdoor social gatherings.

Here's what people think of Tall Ship Windy

As of recent, Tall Ship Windy holds a 4.5-star rating based on 543 reviews.

Reviews of Tall Ship Windy highlight it as a delightful sailing adventure with a high average rating of 4.5 out of 5 based on hundreds of reviews. Visitors often praise the spectacular views of Chicago’s skyline and the unique experience of being aboard a beautifully maintained, authentic tall ship. Many commend the professionalism and friendliness of the crew, the engaging nature of the tours, and the overall atmosphere that blends relaxation with excitement.

Positive reviews frequently mention the excellent organization of the sails, the educational and entertaining commentary provided by the crew, and the ship’s cleanliness and comfort. Guests appreciate the variety of themed cruises available, such as fireworks and pirate sails, which add a special touch to their visit. The onboard bar and opportunities for live music enhance the social vibe, making it a great place to enjoy a day or evening on the water.

Negative feedback is relatively limited but often centers on weather-related cancellations or crowding during peak times, which can affect the intimacy of the experience. Some reviewers note that prices are slightly higher compared to other tours, and a few wished for longer sail durations. However, these criticisms are generally outweighed by the positive aspects noted.

Overall, the review consensus portrays Tall Ship Windy as an exceptional venue for sightseeing, learning, and socializing on Chicago’s lakefront. Its combination of historic charm, engaging activities, and scenic beauty makes it a consistently recommended choice for locals and tourists alike.

Highlights from reviewers (Most Relevant)

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Pepper Fee

We had a fabulous time out on The Windy this past weekend. My wife and I were staying at a hotel out on Navy Pier and made the spontaneous decision to go out and we're so glad we did. It was a beautiful day, and super relaxing with incredible city views. Passengers even get to participate hoisting and lowering the sails which was educational and a lot of fun. All of the crew was great too. Big shout out to Joanna for the lovely chat and giving us the history of this beautiful vessel. Highly recommended!

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Bryan Wilson

Excellent trip on the water with the family thanks to the crew of the Windy. Clearly knowledgeable with an eye toward giving folks a taste of sailing, they did a good job of involving some passengers in learning how to raise a sail. Nice and close look at the Chicago Harbor Lighthouse. Andy (the Kid), the pirate docent, did well to describe quite a bit of Chicago history and architecture on the 75 minute trip. Solid value, especially with the Tuesday special, and my whole family enjoyed themselves.

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Zach Taylor

I had the wonderful opportunity to sail on Tall Ship Wendy 3 times! Each sail was a different experience but all 3 where magical thanks to the crew and the view! The vibes on the ship are toasty and everyone is genuine. I even had the opportunity to raise the sails and it was awesome I felt like a sailor! Definitely an experience I won’t forget thanks to Christian who made it an amazing experience sharing sea tells and showing us how to raise the sails!

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Byron

We had a very memorable evening sailing Lake Michigan. Everyone should experience this. The sunset was wonderful even though we had a cloudy sky. Our kids 5-12 thought this was a highlight of our weekend stay in Chicago. I thought this was much better than the motor boat architectural cruise we took last year.

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Persephone Lundolos

OMG this experience is second to none in Chicago - especially if you have kids. Captain Ralph and his entire crew (shout out to Lucas and Carol and Alex) really go the extra mile to make it a core memory. It's unbearably beautiful out there on this schooner and when they cut the engines and just sail, it's breathtaking. It's not too crowded so you can talk to the knowledgeable crew, who are more than inviting, as they encourage your kids to help hoist the masts. It's absolutely a MUST for families.

How to reach Tall Ship Windy

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Why Tall Ship Windy may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out

Why rally at Tall Ship Windy with your friends?

Tall Ship Windy offers an exceptional gathering spot for friends looking to share a memorable experience on the waters of Lake Michigan. The ship, a majestic 148-foot, four-masted schooner, combines the allure of historic tall ship sails with the comforts of modern amenities, setting a uniquely elegant yet relaxed atmosphere perfect for groups. Whether you seek a casual night out, a scenic adventure, or a lively celebration, this vessel invites you and your friends aboard to create lasting memories. The ship’s large decks accommodate up to 150 guests, ensuring ample space for everyone to mingle, relax, and enjoy panoramic views of the Chicago skyline. Accompanied by live music, stunning sunsets, or special events such as fireworks cruises, Tall Ship Windy provides a dynamic backdrop that elevates any meetup. Reasonably priced drinks, attentive staff, and the thrill of sailing all contribute to making it a top choice to rally your friends together for an outing that's both thrilling and intimate.

What activities can you enjoy aboard Tall Ship Windy?

Tall Ship Windy offers a diverse range of activities designed to entertain and engage groups of all interests. One of the highlights is the daily sailing tours on Lake Michigan, which allow guests to experience Chicago’s famed skyline from a breathtaking vantage point. These cruises often feature commentary on the city’s architecture, history, and maritime lore, adding educational value to the scenic voyage. The ship also hosts special event cruises like the Monday Night Blues music sails, where guests enjoy live performances alongside the glittering cityscape and sunset views. Fireworks cruises are another popular option, perfectly timed to coincide with city celebrations, providing an extraordinary visual and social experience. For those interested in immersive storytelling, pirate-themed educational sails bring a sense of adventure and whimsy to the journey, appealing to families and history buffs alike. Additionally, Tall Ship Windy offers private charters ideal for personal celebrations or corporate gatherings, making it a versatile venue for creating customized experiences on the water.

Why is Tall Ship Windy perfect for a group meetup?

Tall Ship Windy’s design and offerings make it an ideal venue for group meetups, combining space, ambiance, and experience in a way few other places can. The ship comfortably accommodates up to 150 guests on its spacious three decks, giving groups generous room to socialize without feeling crowded. The atmosphere strikes a balance between cozy and luxurious, encouraging both relaxation and celebration. The beauty of the Chicago skyline and the lake provides a stunning natural and urban backdrop, perfect for taking group photos or simply soaking in the scenery. The availability of varied themed cruises, such as music nights or educational tours, allows groups to select a vibe that suits the occasion and diverse interests. Moreover, the friendly and professional staff enhance the experience with excellent service, ensuring smooth sailing and attentive care throughout the event. These features make it easy for group members to connect, explore, and unwind together, making Tall Ship Windy much more than just a venue—it becomes part of the shared experience itself.

What special events and features make Tall Ship Windy stand out?

Tall Ship Windy distinguishes itself through its array of special events and unique features. The historical charm of being the first certified four-masted schooner built in the United States since 1921 adds authenticity and character, appealing to those interested in maritime heritage. Its designation as the official flagship of Chicago elevates it as a symbol of the city’s sailing tradition and pride. The ship’s operations include themed sails such as jazz music nights, blues concerts, and festivities timed to align with Chicago’s fireworks displays, creating extraordinary atmospheres that draw guests back season after season. Another notable feature is the educational component, where engaging narratives about the city’s architecture and maritime history are shared, enriching the experience beyond sightseeing. The option to book private charters or host events like wedding ceremonies and receptions onboard provides exclusive and memorable settings for celebrations. Finally, the ship’s scenic sunset cruises offer unparalleled views, blending natural beauty with the thrill of sailing, leaving guests with enchanting memories that extend beyond the voyage.

How accessible and accommodating is Tall Ship Windy for groups?

Tall Ship Windy is thoughtfully designed to accommodate a wide variety of guests and ensure a comfortable experience for groups. With capacity for up to 150 people during public tours and the ability to host up to 36 overnight guests in cabins during private charters, it caters well to large and smaller groups alike. While the ship is built with historical accuracy and charm, it incorporates modern amenities and safety features to provide guest comfort and confidence. The crew is known for their professionalism, friendliness, and helpfulness, enhancing the welcoming environment. However, due to the nature of the vessel’s design—particularly the steep ladders to the upper decks—those with limited mobility are advised to remain on the main deck for safety. Service animals are allowed, ensuring accessibility for guests who require assistance. The ship’s dock location at Navy Pier is convenient, with ample parking and clear directions, simplifying logistics for group arrivals and departures. These accommodations highlight Tall Ship Windy’s commitment to making the sailing experience enjoyable and hassle-free for everyone.

What makes the food and beverage service enjoyable aboard Tall Ship Windy?

While Tall Ship Windy is primarily a sailing and sightseeing vessel, its onboard food and beverage offerings add to the overall enjoyment of the experience. The ship features a full-service bar that accepts credit cards, offering a selection of reasonably priced alcoholic beverages that pair perfectly with the relaxing ambiance and stunning views. Guests often praise the drink service as responsive and orderly, contributing to their comfort during the cruise. While some tours focus purely on the sailing and entertainment aspects, private charters can include customized food and beverage services tailored to the group's preferences, whether that means catered meals, snacks, or cocktail receptions. This flexibility allows groups to complement their visit with culinary delights, making the event feel more complete and festive. The opportunity to enjoy a drink while watching the sunset or during a scenic nighttime sail enhances the social atmosphere, encouraging conversation and camaraderie among friends and family aboard the ship.

How does the location of Tall Ship Windy enhance the experience?

Situated at Navy Pier in Chicago, Tall Ship Windy benefits immensely from its prime location on the shores of Lake Michigan. Navy Pier is a vibrant, easily accessible hub known for entertainment and cultural activities, making the ship’s embarkation point a lively and convenient gathering spot. Departing from the pier allows guests to quickly leave the noise and bustle of the city behind as the ship sails onto the expansive, serene waters of the lake. The position also grants unobstructed views of Chicago’s architectural gems from a unique perspective unavailable by land, offering a constantly changing and impressive city skyline panorama during the cruise. This lakeside setting provides a refreshing outdoor experience regardless of whether the cruise is during the day, sunset, or nighttime, adding a natural element to group outings. Moreover, the proximity to other Navy Pier amenities means groups can easily extend their meetup before or after sailing, creating seamless day or evening plans around their Tall Ship Windy adventure.

What is the safety and professionalism level of the crew and staff?

A highlight frequently mentioned by visitors to Tall Ship Windy is the professionalism and friendliness of the crew and staff. The captain’s skill in commanding the vessel amidst sometimes busy waters—including navigating around smaller boats during events—is widely admired, providing passengers with a secure and smooth sailing experience. Crew members engage guests with informative and entertaining narration, such as riveting maritime stories and interpretive talks about Chicago’s skyline, which enrich the journey far beyond the simple sail. Staff are also described as attentive and helpful, making sure guests’ needs are met promptly and that everyone feels welcome aboard. Safety measures are clearly communicated and strictly enforced, and the team responds capably to varying weather or mobility considerations. This combination of expert seamanship, hospitality, and guest engagement creates an atmosphere of comfort and trust, encouraging guests to relax and fully enjoy their time on the water without concern.

How does Tall Ship Windy cater to different group sizes and occasions?

Tall Ship Windy is versatile in accommodating various group sizes and occasions, making it a desirable choice for diverse gatherings. Public tours provide ample space for up to 150 guests, ideal for large groups or mixed meetups where friends, families, or even organizational outings want to mingle. For more private or specialized events, the vessel offers charter options that can host smaller groups in an intimate setting or larger ones with customized itineraries. It's popular for celebrations such as birthdays, wedding ceremonies, receptions, and showers, blending the charm of a historical sailing ship with elegant event space on the water. The versatility in catering options and tour themes allows groups to tailor their experience based on the occasion’s tone—be it festive, educational, relaxing, or romantic. This adaptability ensures that whether for casual get-togethers or milestone celebrations, Tall Ship Windy presents a fitting and memorable venue for groups in search of something truly special.

Why is the sunset sailing experience aboard Tall Ship Windy so highly recommended?

The sunset sails on Tall Ship Windy are among the most lauded experiences offered by the vessel, often hailed as the perfect setting to gather with friends. As the sun dips beneath the horizon, it transforms the sky into a canvas of vivid colors that reflect beautifully off the waters of Lake Michigan, creating a breathtaking vista all around. This natural spectacle is enhanced by the peaceful sway of the ship and unobstructed views of Chicago’s illuminated skyline emerging in twilight. The ambiance during these sails is both romantic and vibrant, making it an ideal time for groups to relax together, share conversations, and capture stunning photographs. Combined with live music events or simply the gentle sounds of the city and water, the sunset sail turns an ordinary meetup into a magical experience that guests remember long after the voyage. The blend of nature’s artistry and urban grandeur makes this experience uniquely alluring for anyone looking to celebrate friendship and the joy of being outdoors.

What do reviews say about guest experiences on Tall Ship Windy?

Guest reviews consistently highlight Tall Ship Windy as a standout venue for both the quality of the sailing experience and the overall atmosphere. Many visitors praise the knowledgeable and friendly staff, noting the crew’s professionalism and engaging storytelling that bring an added layer to the trip. The beauty of Chicago’s skyline and lake views is a frequent favorite, often described as breathtaking and ideal for photo opportunities. Special events like music cruises and fireworks sails receive high marks for their entertainment value and seamless execution. Reviewers appreciate the combination of historic charm with modern comfort, reporting that evenings spent aboard feel both luxurious and cozy. Several comments specifically mention how the ship’s environment fosters a sense of camaraderie and fun, making it a memorable place to reconnect with friends or celebrate milestones. The consistently high rating of 4.5 stars from hundreds of reviews attests to Tall Ship Windy's reputation as a reliable and enchanting venue for group outings.

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