Classes & Activities in Chicago

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    Sailing Lessons

    Two Brothers Sailing Chicago
    Is Jack Sparrow your hero? Do you dream of sailing the open seas with nothing but the wind at your back? Whether you're a rookie mariner or a seasoned veteran, this sailing class has it all. Each lesson is custom tailored and taught by a USCG certified sailboat captain, and the hands-on approach to sailing instruction allows you to maximize your potential while increasing your ability to sail safely and confidently. After this sailing lesson, you'll feel Magellan-like confidence and be ready to sail around the world!
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    Nighttime Sail (Weekday)

    Two Brothers Sailing Chicago
    Chicago is home to one of the most beautiful skylines in the world. Stop settling for that postcard on your fridge and come see the view for yourself! This nighttime sailboat cruise around Lake Michigan will give you a perfect view of The Windy City's breathtaking, twinkling skyline. You'll spend a relaxing and entertaining evening on the lake as your USCG certified captain navigates you to all the premier viewing spots. See Chicago the way it was meant to be seen... from the water!
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    Nighttime Sail (Weekend)

    Two Brothers Sailing Chicago
    Chicago is home to one of the most beautiful skylines in the world. Stop settling for that postcard on your fridge and come see the view for yourself! This nighttime sailboat cruise around Lake Michigan will give you a perfect view of The Windy City's breathtaking, twinkling skyline. You'll spend a relaxing and entertaining evening on the lake as your USCG certified captain navigates you to all the premier viewing spots. See Chicago the way it was meant to be seen... from the water!
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    Sunset Sail (Weekend)

    Two Brothers Sailing Chicago
    Sunsets are beautiful. There's a reason they're included in just about every romantic movie. Now you, too, can recreate your own Hollywood moment with this sunset cruise on Lake Michigan. Feel a sense of relaxation and tranquility as you rock gently back and forth on the waves with the Chicago skyline ahead of you. The best part? You'll see the Windy City the way it was meant to be seen... from the water.
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    Sunset Sail (Weekday)

    Two Brothers Sailing Chicago
    Sunsets are beautiful. There's a reason they're included in just about every romantic movie. Now you, too, can recreate your own Hollywood moment with this sunset cruise on Lake Michigan. Feel a sense of relaxation and tranquility as you rock gently back and forth on the waves with the Chicago skyline ahead of you. The best part? You'll see the Windy City the way it was meant to be seen... from the water.
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    2-Hour Sail

    Two Brothers Sailing Chicago
    Looking for a different way to relax? Are the Youtube videos and Netflix movies just not cutting it? Then why not spend a day on the water enjoying the beautiful sights of Chicago on this two-hour sailboat adventure with you and your loved ones? With Two Brothers Sailing Chicago, set sail from Montrose Harbor with a USCG certified sailboat captain and kick-back with the calming waves of Lake Michigan. This is the perfect tour for couples who want to have a romantic time on a private boat with the Chicago skyline as their backdrop. See the Windy City the way it was meant to be seen... from the water!
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    3-Hour Sail

    Two Brothers Sailing Chicago
    Looking for a different way to relax? Are the Youtube videos and memes just not cutting it? Then, why not spend a day on the water enjoying the beautiful sights of Chicago on a three-hour sailboat adventure? On this weekend tour, set sail from Montrose Harbor with a USCG certified sailboat captain and kick-back with the calming waves of Lake Michigan. This is the perfect tour for couples who want to have a romantic time on a private boat with the Chicago skyline as their backdrop. See Chicago the way it was meant to be seen... from the water!
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