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Take a Daytime Sailing and Swimming Trip in the Windy City

If you’re looking for a unique way to explore Chicago and the Windy City, consider taking a daytime sailing and swimming trip with Windy City Sailing. From the comfort of a beautiful sailboat, you’ll experience the city from the water while taking in the sights and sounds of this amazing city. Plus, you’ll get the chance to take a dip in the lake, which is a great way to cool off on a hot summer day. Whether you’re a sailing enthusiast or just looking for a fun way to enjoy the city, a Windy City Sailing trip will surely be an unforgettable experience.


The best time to go

For the best beach weather and sailing experience in Chicago, visit Lake Michigan during May, June, July, August, and September. During these months, the predominant southwest and west winds make for an unforgettable experience, with breathtaking views of the Chicago skyline while on a boat charter. Enjoy the sun while sailing and swimming in one of the most spectacular sailing venues in the world.


Where to go

Your boat charter will set a course based on your preferences and the day’s conditions. Whether sailing along the shoreline towards Navy Pier or heading straight away from shore, you’ll get to take in some amazing sights as you enjoy the wind, sun, and lakefront skyline. With the experienced staff at Windy City Sailing, you can rest assured that your charter is tailored to your needs.


Not only do you get to experience sailing on Lake Michigan, but you also get to take in some of the most remarkable sights Chicago offers. From downtown Chicago to the city’s various beaches, there is plenty to explore while on the lake. With the help of experienced captains and crew, you can be confident that you are in safe hands while sailing.


What to expect

If you’re looking for a unique way to explore the beautiful lakefront of Chicago, a sailboat charter is an excellent option. With a bareboat charter, you’ll have up to 10 people on board, including a licensed United States Coast Guard Captain and one crew member. And you can bring your beverages for a celebratory bubbly on the sail. You can drop sails away from the shore or inside the breakwater-protected playpen, depending on conditions. Whether you want to explore the coastline or spend time on the lake, a boat charter in Chicago will give you an unforgettable day sailing experience.


Swimming in Lake Michigan is an ‘at your own risk’ activity, so be aware of the potential risks of swimming in open water.

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