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    ChicaGo By Boat

    Private sailboat charters offering scenic views and tailored sailing trips.

    In-Person 2h 30m (est.) $150 USD per person (est.)

    How it works

    ChicaGo By Boat offers private sailing experiences on the serene waters of Lake Michigan, departing from Waukegan Harbor and Marina. The company provides an opportunity for groups of up to six people to enjoy a unique sailing adventure aboard the S/V Nightswimming. Guests can customize their outings, with options ranging from two to three-hour trips. Whether watching the sunset over the city's skyline, experiencing the Navy Pier fireworks up close, or simply enjoying a peaceful day on the water, each trip is designed to cater to diverse preferences.

    The company caters to a variety of occasions and interests. Whether planning a corporate outing or marking a special personal moment like a proposal, ChicaGo By Boat facilitates memorable experiences on the water. Seasonal events such as the annual Air and Water Show and other local happenings provide additional excitement for passengers looking for something extra during their sail. With its focus on private charters, this service provides an intimate setting for creating lasting memories while enjoying Chicago's picturesque views from Lake Michigan.

    Location

    Your event takes place at 1559 South Lake Shore Dr, Q Dock, Chicago, IL 60605.

    1559 South Lake Shore Dr, Q Dock, Chicago, IL 60605

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    Activity Attributes

    Where this experience lands next to others — descriptive, not a rating.

    Core Feel

    Energy A comfortable middle gear
    Movement Mostly seated
    Challenge A gentle challenge

    Team Dynamics

    Teamwork Built around working together
    Mingling Great for mixed groups
    Connection Designed for deep bonding
    Celebration Big celebratory vibes

    Engagement

    Problem solving A few light puzzles
    Creativity Room to make it your own
    Learning Mostly fun, a few takeaways
    Based on expert review, AI assist, and community sentiment.

    Operating Hours

    Monday
    9:00 AM 10:00 PM
    Tuesday
    9:00 AM 10:30 PM
    Wednesday
    9:00 AM 10:00 PM
    Thursday
    9:00 AM 10:00 PM
    Friday
    9:00 AM 11:30 PM
    Saturday
    9:00 AM 10:00 PM
    Sunday
    9:00 AM 10:00 PM

    Our Review

    Updated

    Our first impression of ChicaGo By Boat is that it offers a charming and intimate team-building experience, particularly well-suited for small teams looking to foster closer connections. With a maximum capacity of six people, this activity is ideal for tight-knit groups or departments within larger organizations who want to escape the office environment and enjoy a unique bonding opportunity on Lake Michigan. The customizable nature of the sailing trips allows teams to tailor their experience, whether they prefer a serene afternoon sail or an exciting evening watching fireworks from the water.

    One thing to keep in mind is that this experience may not be the best fit for larger groups or teams seeking more structured team-building activities with specific goals in mind. While the scenic backdrop and relaxed atmosphere can certainly facilitate organic conversation and camaraderie, analytical teams or those looking for problem-solving exercises might find the lack of formal structure less engaging. However, creative teams or those in need of a refreshing break from routine will likely appreciate the tranquil setting and potential for inspiration. Overall, ChicaGo By Boat provides a memorable outing that combines leisure with spectacular views, making it an appealing choice for small groups aiming to strengthen personal connections in a unique setting.

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