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

Why Come Sailing, Inc. is a fun option when searching for things to do near me with friends and family
Come Sailing, Inc. is Chicago’s premier private sailing charter company offering unforgettable sailing adventures on Lake Michigan. With a perfect 5.0 rating from numerous satisfied guests, this business is an exceptional choice for meeting up with friends and enjoying the scenic beauty of Chicago’s lakefront from a unique vantage point. Whether you are planning a relaxed day sail, a captivating sunset cruise, or a special occasion like a fireworks viewing or celebration, Come Sailing provides personalized and intimate experiences designed for groups of up to four people. The company operates out of Navy Pier Marina, conveniently located in downtown Chicago, making it easily accessible for both locals and visitors looking for an extraordinary outing. The owner, Captain Mike, brings a lifelong passion and expertise in sailing, ensuring safe, knowledgeable, and enjoyable trips on the water. Guests appreciate the charming and comfortable sailboats escorted directly from the marina gate, creating a seamless and welcoming experience. Highlighted by the calm waters of Lake Michigan and stunning views of the Chicago skyline, Come Sailing offers an ideal setting to unwind and connect with friends amid fresh air and gentle breezes. Its reputation for professionalism and personalized attention makes it stand out as a must-try aquatic adventure in Chicago.
Here's what people think of Come Sailing, Inc.
As of recent, Come Sailing, Inc. holds a 5-star rating based on 24 reviews.
Guest reviews for Come Sailing, Inc. consistently praise the company’s exceptional service, knowledgeable captain, and the overall quality of the sailing experience. Many users highlight how relaxing and peaceful the time on the water is, complimenting the beauty of the Chicago skyline from the unique perspective of the lake. Several reviewers mention the seamless coordination with the staff from meeting at Navy Pier Marina to embarking on the sailboat, emphasizing the welcoming and professional demeanor of Captain Mike and the crew. Positive feedback often cites the private nature of the charters, which allows for intimate and personalized trips with friends or family, making it a memorable way to celebrate special occasions or simply enjoy a day out. The stunning views during sunset sails and fireworks cruises are frequently mentioned as unforgettable highlights. On the other hand, negative reviews are minimal but occasionally point to limited capacity, as the charters accommodate up to four guests, which might not suit larger groups. A few comments suggest that booking can require advance planning due to high demand. Overall, the reviews conclude that Come Sailing, Inc. offers a premium, highly rated sailing experience that combines expert sailing, beautiful scenery, and personal attention, making it an outstanding option for anyone looking to enjoy Lake Michigan’s waters and Chicago's iconic waterfront in a private and luxurious setting.
Highlights from reviewers (Most Relevant)
Robert Dial
The Sat evening sailboat ride on the Bernard was absolutely amazing. Captain Mike did an awesome job navigating the sail boat to give our group an amazing view of the Chicago skyline and position it for the fireworks display. We recommend it to anyone wanting a truly special experience!! Bob
Sam Rauch
I can’t recommend enough that you head out on a charter with Come Sailing; it’ll be the best part of your Chicago weekend! Captain Mike is excellent, he made sure everyone felt safe and happy as we enjoyed our charter, and he’s got a wealth of cool information about sailing the Great Lakes if you ask him. The Bernard is a beautiful boat, with plenty of places to sit for a gorgeous view of downtown Chicago. Our whole group had an excellent time!
Bavani Rajah
Captain Mike was wonderful and our group enjoyed the daytime private charter! Recommend booking directly from their website instead of a third party like Viator, we had an issue with scheduling but Mike was really understanding and communicated well.
Lohitheshwara M
We had no idea what to expect on our first sailing trip, but it turned out to be one of the most magical experiences we've ever had. The absolute highlight was the sunset. Watching the sky transform into a canvas of vibrant colors while floating on the calm water was something we’ll never forget. Captain Mike was knowledgeable, and clearly passionate about what he does. He made sure we felt comfortable from start to finish. If you're thinking about trying sailing, don’t hesitate—this was an unforgettable escape and we’re so glad we did it.
Pavel Oganyan
Look no further. If you want to get out on Lake MI, I 10/10 recommend booking with come sailing inc.! The boat was extremely comfortable, beautiful and the views from it couldn’t have been any better. Also, Captain Mike could not have been more awesome. Extremely professional and very accommodating to make sure we had a great time!
How to reach Come Sailing, Inc.
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Why Come Sailing, Inc. may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out
Why rally at Come Sailing, Inc. with your friends?
Gathering at Come Sailing, Inc. offers an exceptional opportunity to connect and create lasting memories with your friends or family in a remarkable setting. Located on the pristine waters of Lake Michigan, this premier private sailing charter ensures an intimate, exclusive experience tailored for groups up to six. Imagine stepping away from the mundane urban hustle and immersing yourself in the tranquility of the open lake, framed by breathtaking views of the Chicago skyline. Whether you're celebrating a special occasion or simply seeking an unforgettable outing, this venue balances relaxation and adventure perfectly. The professional captains onboard handle all the sailing intricacies, so you can focus entirely on enjoyment and camaraderie. Their impeccable 5-star rating with over two dozen reviews reflects consistent satisfaction, highlighting an atmosphere that fosters both excitement and comfort. Here, the blend of natural beauty, expert care, and the unique charm of sailing creates an ideal space to rekindle friendships, induce laughter, and savor quality time together. Rallying here guarantees not only an escape but a shared experience that deepens bonds amidst one of America’s most iconic waterfronts.
What types of sailing activities are offered for group meetups?
Come Sailing, Inc. offers a diverse range of sailing experiences designed to accommodate small groups of up to six guests, making it perfect for intimate group gatherings. The core activities include Day Sails, Sunset Sails, Fireworks Cruises, and specially customized private charters. Day Sails provide a leisurely afternoon adventure allowing guests to enjoy the refreshing breeze and picturesque views of Chicago’s architectural marvels. Sunset Sails are particularly popular, offering a magical ambiance as the city skyline glows in the warm twilight—ideal for romantic gatherings or friends celebrating a significant moment. Fireworks Cruises add an extra spark to your outing, typically scheduled to coincide with Chicago’s iconic firework events on Wednesdays and special occasions. With customized private charters, groups gain flexibility to tailor their sail based on preferences, be it a casual outing or a celebratory event, all led by experienced professional captains ensuring safety and enjoyment. This variety of options ensures that any group can find the perfect sailing experience to suit their mood or occasion, creating unique shared memories on the water.
Why is Come Sailing, Inc. a perfect venue for group meetups?
The venue’s appeal for group meetups stems from its balance of exclusivity, scenic beauty, and personalized service. Because Come Sailing, Inc. limits each private charter to just six passengers, it fosters an intimate environment perfect for meaningful conversations and shared experiences without the distractions or crowding common in larger group events. The location at Navy Pier Marina, right along Chicago’s waterfront, adds a stunning visual dimension, giving guests panoramic views that include iconic landmarks such as the Willis Tower, John Hancock Center, and the Museum Campus skyline. The professional crew caters to each group's needs, allowing participants to fully relax or even try their hand at steering, making the experience interactive and engaging. Moreover, the scheduling flexibility—multiple departures daily during the sailing season—enables groups to plan meetups around their availability, whether for a weekend afternoon sail or an evening fireworks cruise. The combination of a breathtaking backdrop, attentive service, and adaptable scheduling makes Come Sailing, Inc. a near-perfect venue to gather friends and family in a lively yet serene setting.
How does Come Sailing, Inc. enhance safety and comfort for groups?
Safety and comfort are paramount at Come Sailing, Inc., which directly contributes to its exceptional reputation and perfect suitability for group outings. Every sailing experience is accompanied by a professional captain who is highly trained in marine safety and navigation, ensuring smooth operations and peace of mind for all passengers. Since guests can be novices or seasoned sailors, the captain’s expertise allows everyone to feel secure while also helping those interested to learn basic sailing skills in a supportive environment. Comfort is achieved through modern, well-maintained sailboats that can accommodate up to six people, providing ample room without crowding. The vessels are equipped to handle various weather conditions, guaranteeing a pleasant journey regardless of mild changes in the elements. Additionally, the crew’s attention to guest needs—from timely boarding at Navy Pier Marina’s Gate D to clear communication on arrival—helps groups focus solely on their enjoyment. These combined factors build trust and a relaxed atmosphere, making it easier for friends and families to fully savor their time on Lake Michigan.
What makes the location of Come Sailing, Inc. ideal for social gatherings?
Situated at Navy Pier Marina in Chicago, Come Sailing, Inc. benefits from a prime location that enhances every sailing adventure with cultural, urban, and natural dimensions. Navy Pier is itself a lively destination, accessible and rich with dining, entertainment, and scenic walking areas, which means groups can easily combine sailing with other activities before or after their charter. The marina’s proximity to downtown Chicago allows guests immediate access to spectacular city views from the water, giving the outing a dramatic and unforgettable visual appeal. The contrast of gliding over the vast waters of Lake Michigan while surrounded by one of the nation’s most iconic skylines creates an unmatched ambiance for meaningful socialization. Moreover, the marina’s well-organized setup and clear pickup point simplify logistics, reducing the stress often involved with group outings. Whether your meetup is casual, celebratory, or something in between, the synergy between an urban hotspot and serene lake environment sets the stage for social experiences that feel both special and effortlessly stylish.
How do seasonal offerings at Come Sailing, Inc. cater to diverse group interests?
Come Sailing, Inc. operates primarily from the Memorial Day weekend through Indigenous Peoples’ Day, coinciding with the prime sailing season on Lake Michigan. This schedule allows the company to offer a range of activities tailored to the changing moods throughout the warmer months. Early summer sails are perfect for groups who want to enjoy mild weather and the launching of various boating events around the city. As the season advances, sunset sails and fireworks cruises become increasingly popular, coinciding with Chicago’s vibrant seasonal events and outdoor festivals. This means any group visiting during these times experiences added excitement and visual spectacle, making their gathering extra memorable. Additionally, for guests seeking more flexibility, Come Sailing, Inc. operates during the off-season Monday through Friday to accommodate private or corporate bookings. By offering various options aligned with seasonal highlights, this business ensures that groups with different preferences and calendars find appealing activities year-round, reinforcing its status as a top choice for social meetups.
What kind of group can best enjoy a sailing experience at Come Sailing, Inc.?
Come Sailing, Inc. caters especially well to small groups of friends, families, or colleagues—maximum six passengers per charter—making it ideal for intimate celebrations or casual get-togethers. This size limitation encourages a closer connection among guests, turning the sail into a shared adventure rather than just a sightseeing excursion. Families can enjoy a safe and educational outing where kids and adults alike can experience the joy of sailing under expert supervision. Groups of friends find the setting perfect for an exclusive party or reunion, sharing laughs while cruising against the backdrop of Chicago’s stunning waterscape. Corporate teams looking to break away from the typical office environment can use this setting for informal bonding or team-building exercises in a relaxed atmosphere. Regardless of the group’s makeup, Come Sailing’s experienced crew and flexible offerings ensure the outing is memorable, comfortable, and engaging for everyone on board.
Why is the customer service at Come Sailing, Inc. highly rated?
Customer service at Come Sailing, Inc. stands out due to its personalized approach and attentiveness to guest needs, contributing significantly to its perfect 5-star rating. From the initial booking to the end of the sailing experience, staff are known to be responsive, professional, and accommodating, responding promptly to inquiries and special requests. Communication is clear and thorough, educating guests about what to expect, what to bring, and how to locate the meeting point outside Navy Pier Marina’s Gate D. On the water, the captains and crew consistently demonstrate warmth, patience, and expertise, enhancing guests’ comfort and confidence. Many reviews highlight the friendliness of crew members and their willingness to make every sail tailored to the mood and interest of each group. The availability of gift certificates adds another layer of service, offering a convenient option for gifting unique and exciting experiences. This commitment to exceptional customer care underpins a seamless and joyful visit, inspiring guests to choose Come Sailing repeatedly for their special outings.
How accessible and convenient is Come Sailing, Inc. for groups planning meetups?
Come Sailing, Inc. ensures accessibility and convenience for its guests with a straightforward location and flexible scheduling that simplifies group planning. The marina’s central spot at Navy Pier in Chicago means it is reachable by public transport, private car, or rideshare, facilitating hassle-free arrivals for groups. Directions are precise, with clear instructions to gather outside Gate D, followed by courteous escorting onto the sailboats, minimizing confusion or delays. Multiple departure times throughout the sailing season enable groups to find a slot that fits their schedules, whether they prefer morning, afternoon, or evening sails. The company’s openness to phone or text communication at 708-824-7245 ensures that last-minute questions or changes can be easily accommodated. This ease of access, combined with the intimate size of each charter, means groups can focus more on their experience and less on logistical planning, making it an attractive choice for a wide variety of social gatherings.
What can guests expect in terms of pricing and booking at Come Sailing, Inc.?
Booking a private sailing charter at Come Sailing, Inc. is designed to be straightforward and provides great value for the exclusive experience offered. Prices start from approximately $508 per group for a typical two-hour sailing excursion, making it an affordable luxury for groups wanting a private adventure on Lake Michigan. This rate includes the expertise of a professional captain and access to a well-equipped sailboat, ensuring comfort and safety throughout the trip. The company offers free cancellation up to 24 hours before the scheduled sail, giving groups peace of mind and flexibility in planning. Reservations can be made easily online or by contacting the provider directly, with options for personalized or customized charters also available upon request. This transparent pricing structure and flexible booking process combined with the high level of service ensure guests know exactly what to expect, encouraging a stress-free decision when rallying friends or family for a remarkable sailing meetup.