When asking yourself about something to do near me in Chicago with a group of friends or family, consider
SailingChi
Why SailingChi is a fun option when searching for things to do near me with friends and family
SailingChi offers a premier sailing experience on the stunning waters of Lake Michigan, making it an excellent destination for friends, families, and sailing enthusiasts to gather and enjoy a memorable outing. As a volunteer-run, not-for-profit community sailing program, SailingChi stands out for its friendly and knowledgeable team who are passionate about sharing their love of sailing and Chicago's iconic skyline. With a focus on safety and enjoyment, SailingChi caters to both beginners and seasoned sailors, providing detailed guidance and access to a fleet of well-maintained vessels for rentals and lessons. The company creates a warm, inclusive atmosphere where guests can connect, learn, and enjoy the thrill of being on the water. Whether you're looking for a relaxing day soaking in the views or aiming to sharpen your sailing skills, SailingChi delivers a welcoming environment and an unforgettable maritime experience that makes it a fantastic meeting place for friends to bond and celebrate.
Here's what people think of SailingChi
As of recent, SailingChi holds a 5-star rating based on 101 reviews.
Customer reviews of SailingChi consistently highlight the professionalism, knowledge, and friendliness of the staff, which foster a comforting and confident atmosphere for visitors sailing on Lake Michigan. Positive feedback frequently praises how the team creates an enjoyable and safe experience by offering thorough instructions, accommodating changing group needs, and presenting a well-cared-for fleet of sailboats. Reviewers also appreciate the picturesque views of Chicago's skyline and the enjoyable, community-oriented vibe that SailingChi promotes. However, some negative reviews from a different sailing company in the region mention concerns about boat condition and customer service, but these complaints do not appear to be directly linked to SailingChi itself. Overall, the majority of users rate SailingChi highly (5.0 out of 5 from over 100 reviews), emphasizing reliability, expert guidance, and memorable sailing adventures. This strong positive consensus affirms SailingChi as a trustworthy and delightful choice for anyone seeking a quality sailing experience in Chicago.
Highlights from reviewers (Most Relevant)
Mike Hutton
We had an amazing time celebrating our engagement sailing aboard the Guppy. I did not know what to expect but Captain Charles was super communicative before, during, and even after the ride. We got to experience a sailboat race and see the fireworks off of Navy Pier which is beyond amazing. You can not go wrong chartering with SailingChi.
Ashley Kim
Had such a great experience with sailingchi! Charles and the crew were amazing and we had so much fun. The sailboat was very well kept and clean. I would HIGHLY recommend booking a charter with them. Me and my girlfriends had such a blast and felt like the crew really cared about making it special for us. We’d do it again in a heartbeat.
Kelly Gabouer
We had the perfect night sailing with Captain Charles on our beautiful lake! The water was so calm, played some fun music and got to really relax and take it all in with my husband, kids and grandbaby. Highly recommend!
Renee Koontz
We went out for a sunset cruise and had a wonderful time! We definitely want to book with Charles again for a warmer day when we can go swimming in the playpen. It’s the perfect way to spend a Chicago summer night!
Ericka Campos
EPIC boating experience! We took full advantage of having the boat to ourselves. We packed snacks, refreshments & our pup! Captain Charles was a great host and set us up for a awesome day on the water.
How to reach SailingChi
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Why SailingChi may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out
Why rally at SailingChi with your friends?
If you are looking for an extraordinary spot to gather your friends or family and create unforgettable memories, SailingChi is an exceptional choice. Located right in the heart of downtown Chicago on Lake Michigan, SailingChi offers more than just a boat ride—it provides a vibrant, luxurious escape from the city’s hustle and bustle. Imagine setting sail from the iconic DuSable Harbor, with the Chicago skyline fading behind you, and the sparkling lake all around. The atmosphere is inclusive and lively; SailingChi’s experienced and warm staff ensure everyone feels welcome and taken care of. With a perfect blend of relaxation and adventure, your group can enjoy everything from sun-drenched decks to lively music pumped through a state-of-the-art stereo system developed by audio engineers. Refreshments like fresh fruit, sandwiches, and an impressive selection of drinks including high-end spirits are readily available to keep the energy high and the spirits lifted. The vibe is all about freedom—you decide when to pull anchor, generally sailing from noon to sunset, allowing your group to soak in the sunset views over the water together. This makes SailingChi an ideal place to rally your friends for an intimate yet exhilarating day or evening out on the lake.
What activities can you enjoy at SailingChi?
SailingChi offers a variety of activities carefully designed to suit groups looking for fun, connection, and excitement on the water. The core experience is, of course, the sailing itself, where you cruise the beautiful Chicago waterfront aboard elegant, well-maintained yachts. The fleet is stationed at multiple marina locations such as DuSable, Monroe, Belmont, and Montrose, providing flexibility on where your adventure starts. Once on board, there’s no shortage of things to do: guests can lounge on the expansive decks, engage in lively conversation, or soak up sunbathing on comfortable floats and water toys provided. For the more energized crowd, SailingChi hosts frequent open sailing events where community members come together, and there is even an opportunity to participate in Wednesday night racing programs designed to add a friendly competitive edge. Additionally, SailingChi’s premium stereo system enhances the ambiance with curated playlists or your personal music choices, setting the right mood for celebrations or casual gatherings. For groups who enjoy socializing while cruising, a new “Social Member” package launched in 2024 permits individuals or couples to join regular sailing events, including a memorable event aboard the Guppy, perfect for friends and family to mingle on the water. Whether your group prefers peaceful sails, active racing, or vibrant parties, SailingChi offers the mix to suit every preference.
Why is SailingChi perfect for group meetups and celebrations?
SailingChi is tailor-made for group meetups thanks to its unique combination of scenic views, luxurious amenities, and a convivial community spirit. One of SailingChi’s standout features is the exceptional, inclusive service that strives to meet all guests' desires, making everyone—from seasoned sailors to novices—feel entirely at ease. The boats feature spacious arrangements that comfortably accommodate groups, with ample seating and areas for socializing both in the shade and out under the sun. The food and drink options are another key highlight. The crew ensures a generous spread that includes fresh fruits and gourmet sandwiches; plus, the bar is stocked with premium beverages like Modelo, High Noon, tequila, and rum, allowing groups to customize their refreshment experience. This level of personalization enhances the feeling that the event is truly your own. Moreover, the ability to control the schedule—pulling anchor and heading back whenever the group is ready—gives a rare sense of freedom and control over your outing. The location itself is extremely convenient, situated centrally within Chicago and close to parks and other attractions, making it easy to combine your sailing day with other city experiences. For anyone looking to host birthdays, anniversaries, team building, or casual get-togethers, SailingChi offers a sophisticated yet relaxed setting designed to foster connection and joy on the water.
How does SailingChi support community and membership options?
SailingChi isn’t just a boat rental—it’s a vibrant sailing community that fosters lasting friendships and shared experiences. For those who want more than just occasional sails, SailingChi provides a membership system that opens the door to regular events and sailing opportunities. Approved operators and aspiring skippers can captain yachts from different marina locations, gaining hands-on experience and a deeper connection to the lake and sailing culture. If you are not inclined to skipper but still want to be part of the community, the newly introduced Social Member package is ideal. It allows individuals or couples to attend recurring group sails and social events, ensuring there’s always an opportunity to get out on the water with friends or make new ones within the SailingChi network. The community also hosts open sailing days, which are perfect for those who want to try sailing in a friendly, no-pressure environment or for groups seeking new social experiences. Frequent participants rave about the camaraderie, the quality of the boats, and the organized events that cater to all skill levels. This community aspect makes SailingChi more than just a business—it’s a hub for sharing great times and developing sailing skills alongside like-minded enthusiasts.
What makes SailingChi stand out compared to other sailing experiences in Chicago?
Several factors distinguish SailingChi from other sailing and boat rental companies in Chicago. First is their impeccable 5.0-star rating based on over 100 reviews, reflecting consistent and outstanding customer satisfaction. Their commitment to quality is evident in every aspect—from the high-end fleet of yachts kept in excellent condition to the thoughtfully curated amenities on board, such as premium water toys and a top-tier stereo system. The inclusive approach to service ensures that groups feel special, with flexibility about timing and personalized offerings. Unlike many other services that operate on rigid schedules, SailingChi puts the power of when to start and stop sailing in your hands, making the experience genuinely tailored. Their multi-location fleet access across central Chicago marinas allows guests more options and convenience depending on where they are staying or coming from. Additionally, their community-building efforts, including ongoing events, races, and membership options, create a richer, ongoing relationship with clients. This combination of luxury, community, and flexibility places SailingChi at the forefront of Chicago’s sailing experiences, ideal for groups seeking a high-end yet welcoming environment to connect and celebrate.
What practical benefits does SailingChi offer for event organizers and groups?
For anyone organizing a meetup or event, SailingChi simplifies many logistics that can be challenging to manage elsewhere. Their experienced crew takes care of all boat operations, allowing groups to focus on enjoying the day without worries. The on-board provision of food, drinks, and entertainment means fewer worries about external catering, and the generous selection of drinks caters to varied tastes, accommodating even the most discerning guests. SailingChi also provides access to multiple marina departure points across the city, easing transportation planning and parking concerns. The boats’ spacious deck layouts are conducive to conversations, games, and group activities, making it perfect for anything from casual hangouts to more structured celebrations such as birthdays or corporate gatherings. Event organizers can also rely on the expertise of SailingChi’s team to customize the sailing experience to their needs, whether that’s a relaxed afternoon sail or a high-energy race event. By handling the technical sailing components and providing comprehensive onboard amenities, SailingChi delivers peace of mind and a seamless experience for anyone looking to host memorable events on the water.
Why should families choose SailingChi for their next outing?
Families searching for an exceptional way to spend time together with children or elders will find SailingChi to be welcoming and well-equipped for all ages. The staff’s inclusive approach ensures the safety and comfort of every passenger, making it easy for families to relax and enjoy the day. The boats provide a stable, secure environment ideal for families who want to combine education and fun, perhaps introducing younger members to sailing in a friendly setting. The provision of water toys and floats adds playful opportunities, while the spacious decks give room to move and explore safely. The fresh fruit, tasty sandwiches, and beverage selections cater to a variety of palates and dietary needs, satisfying all family members. Moreover, the flexible scheduling means families can choose times that suit everyone, whether it’s a sunny afternoon sail or a sunset cruise. SailingChi’s welcoming environment helps families build lasting memories, enjoy shared adventures, and discover Chicago’s beautiful waterway together in style and comfort.
In summary, SailingChi offers an unbeatable setting for anyone looking to rally their friends or family for a memorable gathering on Lake Michigan. With its top-tier boats, excellent service, lively social scene, and flexibility to tailor experiences, it is a premier destination for group meetups, celebrations, and sailing enthusiasts alike. Whether you are a casual cruiser or an avid sailor, this business delivers a unique and engaging way to celebrate friendship, family, and the joy of sailing.