When asking yourself about something to do near me in Chicago with a group of friends or family, consider
Windy City Sailing, Inc.
Why Windy City Sailing, Inc. is a fun option when searching for things to do near me with friends and family
Windy City Sailing, Inc. offers an exceptional setting for friends and groups looking to enjoy a memorable day or evening on Lake Michigan. Their private yacht charters in Chicago cater to groups from 1 to 10 people, with options for crewed charters for up to six passengers and bareboat charters for up to ten. This flexibility makes it an ideal spot for intimate gatherings, special occasions, or simply a relaxing escape with friends. Guests appreciate the luxury accommodations on board, including yachts equipped with modern amenities and two bathrooms, ensuring comfort throughout the voyage. Departures are conveniently located at Belmont Harbor near Wrigley Field, just a short trip from downtown Chicago, accessible by rideshare, taxi, or bike. Each charter is fully customizable, allowing guests to set their own schedule and bring their own food and beverages, including alcohol, fostering a relaxed and personalized atmosphere. The experienced, US Coast Guard licensed captains and crew provide professional and safe service, adding peace of mind to the elegant sailing experience. The option to extend the charter beyond the minimum three-hour duration enhances the experience for those wishing to linger on the water. Windy City Sailing’s combination of luxury, convenience, and expert care creates an ideal venue for friends to unwind, celebrate, and take in stunning views of the Chicago skyline and lakeshore.
Here's what people think of Windy City Sailing, Inc.
As of recent, Windy City Sailing, Inc. holds a 5-star rating based on 31 reviews.
Customer reviews highlight Windy City Sailing's consistent excellence, reflected in their perfect 5.0-star rating from over 30 reviews. Guests frequently praise the professionalism and friendliness of the crew and captains, noting their safety expertise and helpful guidance during charters. Positive reviews emphasize the calm and relaxing nature of the trips, the beautiful views of Chicago’s skyline, and the ability to customize experiences to fit their schedules and occasions. The luxurious yachts, spacious accommodations, and the convenience of the Belmont Harbor location are also commonly appreciated. Some reviewers mention how accommodating the staff are when handling rescheduling or cancellations, showing strong customer service even under difficult circumstances. Although negative feedback is minimal, a few guests have noted minor improvements such as better announcements or on-board entertainment during sails would enhance the experience further. Overall, the reviews culminate in a glowing endorsement of Windy City Sailing as a top choice for private yacht charters in Chicago. Guests recommend it for anyone seeking a unique, relaxing, and upscale way to experience the city’s waterfront and celebrate special moments with friends or family.
Highlights from reviewers (Most Relevant)
Elizabeth Elkayam
What a fun afternoon sailing with an amazing Captain Josef! Extremely knowledgeable, friendly and AWESOME!!! His sailing professionalism made our experience fun and thrilling! The views of Chicago’s amazing shore and skylines are breathtaking! Thank you Windy City for this amazing Summer afternoon, we can’t wait to be back!!
Olga
Had a great time! Captain and crew were professional, fun, and safety-focused, which was important for me with two kids on board. Boat was beautiful inside and out, great way to see the Chicago skyline. Highly recommend booking them to see the fireworks off Navy Pier - spectacular views!
Raelene Noles
We recently had the pleasure of vacationing in Chicago and made an excellent decision by booking a sailing trip with Windy City Sailing on Nebula. Captain Mike provided exceptional guidance, showcasing the city's stunning sights from Lake Michigan. Notably, our group of five, including four Chicago natives, gained valuable insights from Captain Mike's informative commentary, revealing unfamiliar facts about the city. We highly recommend Windy City Sailing for a fantastic experience exploring Chicago's landmarks from Lake Michigan aboard a luxurious yacht.
janice zassenhaus
My four dear friends and I were fortunate enough to choose Windy City Sailing for our weekend getaway last month and everything was perfect. Placing our reservation was made so easy with Edwina…. She walked me through all of the pertinent information and gave me ideas for food and drinks to bring aboard. The caption couldn’t have been any better, he called out points of interest and made us feel comfortable. My friends and I are already planning next years cruise…… I can’t wait.
Randy Stark
We had multiple great days on the water with Windy City Sailing. Made memories that will last a lifetime! The boat was clean, staff is knowledgeable and helpful and it is hard to come up with things they can improve upon!
How to reach Windy City Sailing, Inc.
None
Website: None
Why Windy City Sailing, Inc. may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out
Why rally at Windy City Sailing, Inc. with your friends?
Gathering with friends for a memorable experience often means finding a venue that combines excitement, relaxation, and a shared sense of adventure. Windy City Sailing, Inc. in Chicago offers exactly that and more, making it an exceptional choice for rallying with your friends. The joy of sailing together on the picturesque waters of Lake Michigan, coupled with panoramic views of Chicago's iconic skyline, already sets the tone for an unforgettable group outing. Beyond the stunning scenery, Windy City Sailing provides a luxurious yet comfortable atmosphere aboard their custom yachts, which accommodate up to 10 guests. This exclusivity means your group can enjoy private moments, good conversation, and uninterrupted fun. Adding to the appeal, the company offers flexible departure times and charters, allowing you to tailor your experience to fit your group’s schedule and preferences. Whether it’s a celebratory occasion, a casual get-together, or just a unique way to unwind, a sailing adventure with Windy City Sailing turns any meetup into a cherished memory. The combination of expert captains, elegant yachts, and the vibrant energy of Chicago makes it a top destination for groups looking to connect and celebrate together.
What activities can you enjoy at Windy City Sailing, and why is it perfect for group meetups?
At Windy City Sailing, the array of activities is not only varied but also customizable, making it an ideal setting for groups to engage in a shared adventure. The primary activity is chartered yacht sailing along the beautiful Chicago lakeshore, offering a serene and scenic alternative to traditional city outings. Whether your group prefers a leisurely cruise, a sunset sail, or a special occasion on the water, the experienced U.S. Coast Guard certified captains ensure a smooth and safe journey. Another highlight is the option to rent a bareboat charter for up to 10 people, perfect for groups who want to captain the yacht themselves or add their own personal touch to the experience. The yachts feature modern amenities, including two bathrooms and comfortable seating areas, ensuring everyone in your group stays comfortable throughout the trip. Additionally, guests are encouraged to bring their own food and beverages, including alcoholic drinks, allowing for customized picnics or celebrations. The ability to extend charter time means you can linger longer to take in the sights or tailor the trip length to your group's desires. All of these features combine to create a private, exclusive, and flexible environment for group bonding and celebration.
How does Windy City Sailing ensure safety and comfort for group gatherings?
Windy City Sailing places a premium on safety, professionalism, and guest comfort, which is essential when hosting groups where everyone’s well-being matters. Their yachts are maintained to the highest standards, ensuring all equipment functions optimally for a worry-free sailing experience. Moreover, each captain employed by Windy City Sailing is a U.S. Coast Guard certified professional with over 20 years of sailing experience, guaranteeing expert navigation and adherence to safety protocols. All captains also undergo rigorous drug screening programs as mandated by the Coast Guard, adding an extra layer of trust and reliability. Onboard comfort is meticulously addressed through the yachts’ well-appointed interiors, featuring modern amenities, climate control, and clean, fully-equipped bathrooms. This combination of safety and comfort means groups can relax fully and enjoy their time without distractions, focusing on socializing, sightseeing, or celebrating special moments. For any group considering a sailing meetup, knowing that both fun and safety are prioritized makes Windy City Sailing a dependable choice.
Where is Windy City Sailing located, and how accessible is it for group events?
Convenience is key when organizing any group event, and Windy City Sailing excels here with its prime location and accessibility. The yachts dock at the North End of Belmont Harbor, which is just east of Chicago’s famed Wrigley Field and only about 15 minutes from downtown Chicago. This proximity to major city landmarks makes the location easy for all group members to find and reach, whether they live locally or are visiting from out of town. The area is well served by transportation options including Uber, Lyft, taxis, and even bicycles, which makes arriving stress-free for any size group. For those who prefer to drive, ample parking is available nearby through the City of Chicago parking systems. This flexibility in getting to the location helps accommodate different preferences and needs among your group members. Moreover, Windy City Sailing offers gift certificates and straightforward reservation policies, making it simple either to pre-arrange a special surprise for friends and family or to handle bookings with ease. This excellent accessibility supports seamless group coordination, removing logistical barriers that might otherwise complicate your meetup plans.
Why is Windy City Sailing the ideal venue for all types of group celebrations and experiences?
Windy City Sailing stands out as the ideal venue for a wide variety of group celebrations due to its blend of customization, luxury, and the unique appeal of sailing on Lake Michigan. Whether you are planning a birthday party, anniversary, corporate retreat, family reunion, or a casual day out with friends, the private charter experience can be tailored to meet the specific tone and requirements of your group. The yachts’ capacity of up to 10 people ensures an intimate yet lively atmosphere perfect for meaningful conversations and group bonding. You can bring along food, drinks, and decorations to personalize the event, turning the yacht into a floating party space with stunning views. The professionally trained crew not only manages the sailing but also ensures guests’ needs are met discreetly, allowing your group to focus on enjoyment without worry. The combination of luxury yachts, picturesque backdrops, and impeccable service elevates any gathering from mundane to extraordinary, leaving your friends or family with memories that last far beyond the final wave.
How do personalized services and flexibility enhance the experience at Windy City Sailing for groups?
Flexibility and personalization are at the heart of the experience at Windy City Sailing, making it especially attractive for groups who want a tailored outing that fits their unique preferences. All charters operate on a schedule that you define, with a minimum of three hours and the option to extend, so your group has control over the timing that works best for everyone. This means you can plan a sunset cruise, a midday adventure, or a special event aligned with your group’s way of celebrating. Clients are encouraged to bring their own refreshments, including alcoholic beverages, which permits the crafting of a completely personalized menu and vibe aboard the yacht. If your group prefers to have a professional crew, you can book with a licensed captain and crew who provide expert service and local knowledge, enhancing your Chicago sightseeing experience from the water. Alternatively, more experienced sailors might opt for a bareboat charter where they take the helm themselves, adding an adventurous and interactive dimension to the meetup. This variety in customization options means Windy City Sailing can appeal to both relaxed and hands-on groups, ensuring every outing is exactly how the group envisions it.
What kind of customer feedback underscores Windy City Sailing’s reputation as a top group venue?
Windy City Sailing boasts a remarkable 5.0 rating based on 31 reviews, reflecting consistent high praise from past guests. Customers frequently highlight the professionalism of the captains, the pristine condition of the yachts, and the overall luxury of the experience. Many reviews mention special occasions such as family outings or celebrations, noting how smoothly everything is coordinated and how relaxed they felt while sailing. Guests appreciate the option to bring their own food and drinks and the beautiful vantage points for viewing Chicago’s skyline and fireworks, which adds to the unique ambiance. Additionally, the flexibility in scheduling and personalized service is a common theme in positive reviews. This praise from diverse groups demonstrates that Windy City Sailing successfully delivers an exceptional experience that meets or exceeds expectations, making it a highly recommended choice for those planning group meetups or special outings on the water.
What amenities make Windy City Sailing comfortable and convenient for group use?
Windy City Sailing’s yachts are meticulously designed to balance luxury and practicality, ensuring group gatherings are comfortable and hassle-free from start to finish. The vessels accommodate between one and ten passengers comfortably, with two modern bathrooms onboard, a crucial convenience for longer trips or family groups. Seating areas are spacious enough to allow guests to socialize freely without feeling cramped, while the yachts’ interiors offer high-quality finishes and climate comfort. Guests can easily bring their own snacks and drinks, which makes planning the event easier and more personalized. Professional crew members handle sailing operations and guest needs, allowing the group to relax rather than worry about logistics. Furthermore, because the company uses licensed and experienced captains, you can trust that your journey will be smooth and safe, regardless of weather or other conditions. This combination of thoughtful amenities adds significant value to your group outing, making Windy City Sailing a superior choice for hosting friends and family on the water.