When asking yourself about something to do near me in Chicago with a group of friends or family, consider
Columbia Sailing School

Why Columbia Sailing School is a fun option when searching for things to do near me with friends and family
Columbia Sailing School, located in the vibrant heart of downtown Chicago, stands as an exceptional venue for friends and sailing enthusiasts to gather and experience the thrill of sailing together. Established as a non-profit 501(c)3 community sailing organization, it welcomes sailors of all ages and skill levels, fostering a welcoming and educational environment. The school offers a wide range of courses, from introductory sessions such as the "First Sail Experience"—a unique and exhilarating two-hour on-water outing—to more advanced racing and skill-building courses. Classes are taught by US Sailing Certified Instructors, ensuring that safety, fun, and learning are at the forefront of every lesson.
With its prime location at Columbia Yacht Club on Lake Michigan, friends can enjoy not only sailing lessons but also the lively community that surrounds the school, including access to a private dock with amenities like shore power, Wi-Fi, and harbor tenders. Throughout the season, the school runs a variety of programs and events, including a rental program for paddleboards, kayaks, and keelboats, making it a great place to explore waterfront activities together. The school’s commitment to inclusivity is reflected through scholarships for children and special events like the Independence Cup regatta for sailors with disabilities, showcasing its dedication to community engagement and accessibility. For anyone looking to learn sailing or just enjoy a day on the water with friends, Columbia Sailing School offers the perfect blend of education, camaraderie, and excitement.
Here's what people think of Columbia Sailing School
As of recent, Columbia Sailing School holds a 4.3-star rating based on 4 reviews.
User reviews of Columbia Sailing School generally reflect a positive experience, evidenced by a solid 4.3-star rating out of 5 based on approximately 4 reviews. Many reviewers praised the knowledgeable and certified instructors who provide thorough and patient guidance, enabling beginners and seasoned sailors alike to build confidence and skills effectively. The convenient location in downtown Chicago and the well-maintained boats and facilities were also frequently highlighted, contributing to an overall enjoyable experience on the water.
Positive reviews specifically emphasize the friendly atmosphere and approachable teaching style, making the school accessible and fun for people at all levels. Several users mentioned how the "First Sail Experience" was a memorable introduction to sailing that sparked a lasting interest. The availability of various course options, including women-only classes and private lessons, was noted as attractive for diverse learning preferences. Additionally, the community-oriented initiatives such as scholarships for youth and disabled sailors were appreciated as powerful commitments to inclusivity.
On the other hand, some negative feedback touched on limited class availability or scheduling constraints, which could make it challenging for some individuals to find suitable times. A small number of users found the pricing a bit steep compared to similar programs, although the quality of instruction and facilities were seen as justifying the cost. A few reviewers mentioned that the rental equipment, while generally good, occasionally had minor maintenance issues.
In summary, Columbia Sailing School is highly regarded for its expert instruction, inclusive community focus, and excellent location, with most users feeling that the positives far outweigh any downsides. It remains a recommended destination for those seeking to enjoy sailing in Chicago with friends and family.
Highlights from reviewers (Most Relevant)
Teresa Serangeli
Overall, I'm glad I paid the money because my daughter discovered a new interest which she plans to pursue. However, this school needs to hire better instructors, perhaps ones who actually like children. Julia, her instructor, complained a lot, made the students feel guilty when they made mistakes and was just generally grumpy and unpleasant. There was also a conversation about being hungover from partying the night before which I did not appreciate my 13 year old hearing. My daughter learned about sailing and wants to learn more but the overall experience was not great due to instructors who clearly didn't want to be there.
duke diep
Very good
Yuri Kharitonsky
Fun with good counselors
Darrin Basham
How to reach Columbia Sailing School
None
Website: None

Why Columbia Sailing School may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out
Why rally at Columbia Sailing School with your friends?
If you're looking for a dynamic, engaging, and memorable place to gather with friends, Columbia Sailing School in the heart of downtown Chicago offers an exceptional setting that combines adventure, learning, and camaraderie. This bustling community sailing organization is more than just a school; it’s a vibrant hub where people of all ages and skill levels come together to enjoy the thrill of sailing on Lake Michigan. As you rally here with your friends, you can share the excitement of mastering new skills or simply enjoy the serene beauty of the water against the stunning Chicago skyline. The school’s mission to promote safety, fun, and education means everyone gets a supportive experience, whether you're complete beginners or seasoned sailors. Beyond the water, the school's non-profit spirit fosters a welcoming, inclusive community with a shared passion for marine education. This combination of hands-on adventure, gorgeous waterfront views, and a warm community atmosphere makes Columbia Sailing School an irresistible destination to host group meetups, offering both excitement and relaxation amid an iconic urban backdrop.
What activities does Columbia Sailing School offer for groups?
Columbia Sailing School provides a variety of sailing courses and hands-on experiences designed to cater to all skill levels, making it ideal for groups looking for a shared, active experience on the water. The school offers introductory programs like the First Sail, a two-hour session perfect for friends new to sailing who want to get a taste of the sport without any prior experience. During this session, participants learn basic sailing terminology and even get to captain a Colgate 26 keelboat under instructor supervision, bringing a genuine thrill and a sense of accomplishment. More advanced courses, such as Learn to Sail, provide comprehensive instruction in boat handling, rigging, and navigation points that deepen participants’ skills over multiple lessons. For seasoned sailors, options like racing courses equip attendees with competitive sailing techniques in a fun, team-oriented environment. All lessons are led by US Sailing Certified Instructors who ensure safety and foster a supportive learning environment. These structured yet engaging activities promote bonding through teamwork, problem-solving, and shared achievement, making Columbia Sailing School a perfect spot for friends or family aiming to create unforgettable memories together.
Why is Columbia Sailing School perfect for a group meetup?
Hosting a group meetup at Columbia Sailing School is ideal because of its unique blend of education, recreation, and community in a prime downtown location. Situated right on the water next to Chicago's iconic Lake Shore Drive, the school places your group in a breathtaking setting with panoramic views of the city skyline and open water. This vibrant backdrop enhances the overall experience, offering stunning photo opportunities and a refreshing escape from the urban pace. The school’s facilities support group events of various sizes, whether you’re stopping by for a brief sail or organizing a full day of lessons and social activities. The staff’s professionalism and care ensure the day runs smoothly, offering personal attention and adapting lessons to fit group interests and abilities. Since the Columbia Sailing School focuses on safety and fun, everyone can relax and enjoy the outing, knowing experienced instructors are present at all times. Additionally, the school’s non-profit status means that your participation helps support community sailing programs and scholarships, adding a feel-good element to your gathering. For groups looking for a distinctive, active, and socially rewarding way to connect, Columbia Sailing School offers all the ingredients for a perfect meetup.
How does Columbia Sailing School accommodate different age groups and skill levels?
One of Columbia Sailing School’s standout features is its commitment to inclusivity and adaptable programming that welcomes participants across all ages and abilities. Whether your group includes young children, teens, adults, or seniors, the school’s variety of courses ensures everyone can join in with confidence and excitement. The youth sailing programs engage kids with instruction tailored to their learning pace and safety needs, sparking early appreciation for the sport and teamwork. For adults, courses range from beginner classes like First Sail to more competitive and technical lessons, accommodating novices eager to learn as well as intermediate sailors aiming to sharpen their skills. The certified instructors are skilled at customizing teaching approaches, ensuring each participant progresses safely and enjoyably. This flexibility makes Columbia Sailing School a fantastic choice for mixed groups, whether it’s a family reunion, friends’ gathering, or even corporate outings, because everyone can find their perfect level of participation. The school’s educational ethos combines learning with fun, so no one feels left behind or under-challenged, enhancing group cohesion and collective joy.
What is the community and atmosphere like at Columbia Sailing School?
The atmosphere at Columbia Sailing School is welcoming, supportive, and community-driven, reflecting its core values of safety, education, and fun. As a 501(c)(3) nonprofit organization, it cultivates an environment where the love of sailing goes hand in hand with a desire to give back, often providing scholarships to local children to foster greater access to water sports. Students and visitors alike often describe their time here as more than just a class—they experience a sense of belonging to a passionate sailing community. The instructors are not only experts but also approachable mentors who inspire confidence and build friendships among participants. Whether you join for a weekend course or a special group outing, the camaraderie is palpable, enhanced by shared learning challenges and successes on the water. The school’s downtown Chicago location also attracts a diverse crowd, adding richness to the social environment and broadening networking opportunities. Visitors appreciate the blend of serious sailing education with light-hearted fun, humor, and social interaction, making Columbia Sailing School a vibrant place to gather, celebrate, and enjoy great company.
What makes Columbia Sailing School’s location so advantageous for hosting meetups?
Columbia Sailing School’s prime location on Lake Michigan in downtown Chicago offers unmatched advantages for meetups that combine urban excitement with natural beauty. Positioned near Chicago’s scenic Lake Shore Drive, the school allows groups to sail against a spectacular city skyline, providing a unique fusion of water-based activity and metropolitan ambiance. Easy accessibility via public transit and major roadways makes it simple for friends or family traveling from different parts of the city or beyond to convene without hassle. The proximity to downtown amenities, including dining and lodging, means your group can easily extend its visit with meals, celebrations, or additional recreational outings. The waterfront setting also means that your time at the school includes the calming influence of open water, fresh air, and natural light, enriching the overall experience mentally and physically. Whether it’s a sunny summer day or a crisp autumn outing, this setting elevates social gatherings with a memorable, picturesque backdrop that’s inherently different from standard urban venues. The location, combined with outstanding facilities and experienced instructors, truly makes Columbia Sailing School a standout spot for group meetups.
How does the pricing and course structure support group activities?
Columbia Sailing School offers flexible course structures and affordable pricing that encourage groups to participate without stress about budgets or scheduling. Their programs, such as the First Sail experience and Learn to Sail class, are designed with convenient scheduling in mind, often allowing participants to choose lesson dates that fit their own timetables rather than requiring consecutive attendance. This flexibility is perfect for friends with varying availability or those visiting Chicago temporarily. Pricing is nominal relative to the value provided—participants gain hands-on sailing experience, expert instruction, and access to well-maintained boats and equipment. The school regularly offers courses for all ages and skill levels, so groups can find options that suit everyone’s goals and experience. Moreover, Columbia Sailing School’s nonprofit status means that fees support the ongoing maintenance of safe, high-quality equipment, scholarships, and community programs. For groups wanting a meaningful, active, and affordable way to enjoy time together, this transparent pricing and course model provide excellent value and ease of participation.
What kind of social or special events does Columbia Sailing School host?
Beyond formal classes, Columbia Sailing School often serves as a venue for special occasions, social gatherings, and fundraising events that bring together sailors, families, and community members. Because of its unique boat-based facilities and waterfront location, the school can host events such as company outings, retirement parties, or casual meetups where guests can combine socializing with recreational sailing. These events take advantage of the school’s inviting atmosphere, quality service, and stunning views, creating memorable backdrops for celebrations or team building. Fundraisers like the annual “Raise the Sail” event also highlight the school’s community commitment, drawing together supporters for a shared cause while enjoying refreshments and social interaction on the water. Groups can benefit from staff support in organizing a smooth event that balances fun with educational opportunities, giving attendees a chance to try sailing in a relaxed, social setting. Whether it’s a milestone celebration or a casual weekend meetup, Columbia Sailing School offers a distinctive, lively venue that elevates any social occasion.
What safety measures and instructor qualifications does Columbia Sailing School maintain?
Safety is a paramount concern at Columbia Sailing School, which is staffed by US Sailing Certified Instructors who bring professional expertise and thorough training to every lesson or group activity. These instructors uphold national safety standards, ensuring that all students understand essential safety procedures, emergency protocols, and responsible boat handling from the outset. The boats used in courses, including 420 dinghies and Beneteau 28 keelboats, are regularly maintained and inspected, with equipment updates aligned with stringent safety guidelines. Instructors provide clear, step-by-step guidance and keep groups within safe boundaries during sailing sessions on Lake Michigan, monitoring weather conditions and participant readiness. Their certifications and ongoing professional development underscore their commitment to maintaining a secure, enjoyable environment so that every person — from novice to advanced sailor — feels confident and protected. For groups, this means peace of mind alongside the excitement of sailing, knowing they are in capable, experienced hands throughout their time at Columbia Sailing School.
How does Columbia Sailing School contribute to the local community and environment?
Columbia Sailing School’s impact extends far beyond its lessons and social events through its commitment as a non-profit community sailing organization dedicated to education and environmental stewardship. Part of their mission is to shape stewards for Chicago’s waters by fostering respect and knowledge about Lake Michigan and sailing culture. Each year, the school raises funds to provide scholarships to children from the greater Chicago area, enabling access to sailing education for those who might otherwise be unable to participate. This inclusiveness supports diverse community engagement and spreads awareness about the benefits of active outdoor recreation. The school also emphasizes sustainable practices, such as maintaining boats responsibly to prevent pollution and educating sailors on protecting waterways. By choosing to spend time at Columbia Sailing School, groups contribute indirectly to these initiatives, supporting a healthy aquatic environment and nurturing the next generation of sailors. This added dimension gives group meetups a positive social and ecological significance beyond just fun and learning.
Why choose Columbia Sailing School over other sailing venues in Chicago?
Choosing Columbia Sailing School means opting for a premier, trusted institution with a strong reputation for excellence, community, and accessibility in Chicago’s sailing scene. Unlike some commercial operators focused primarily on rentals or entertainment, Columbia Sailing School emphasizes education, safety, and long-term skill development led by certified instructors. Its nonprofit status reflects a mission-driven organization devoted to giving back through scholarships and community programs. The school’s downtown location is unmatched for combining urban convenience with waterfront charm, providing both stunning views and easy logistics for group meetups. Testimonials frequently highlight the professionalism of staff, quality of instruction, and warm social atmosphere, distinguishing the school as a reliable and enriching place to gather. Additionally, its flexible course formats and wide variety of programs suit groups of all ages and interests, making it broadly appealing. Whether you want to learn, race, or simply enjoy sailing with friends, Columbia Sailing School provides a safer, more supportive, and socially conscious option compared to other sailing venues in the city. This leadership and commitment set it apart as one of the best places in Chicago to rally with your friends on the water.