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Chicago Sailing Trips

Chicago Sailing Charters | Sailing Trips Chicago

Sailing trips Chicago offers many unique aspects to the recreational sailor. The city’s skyline is the first noteworthy point. There is no better view of it than out on the lake. The wave protected “Playpen” area is ideal for a cool dip swimming. The predominant west winds make for great sailing conditions. Navy Pier puts on quite a fireworks show twice a week. And viewing the weekend sailboat races never fails to occupy a day out with entertainment and excitement. All of these things make for sailing trips Chicago excursions that won’t be found anywhere else.


Chciago Sailing trips offer swimming in the protected playpen  Playpen Swimming - jump in! Whether in open waters far out from the city, or 200 yards off shore in the playpen, swimming in Chicago on a hot day is a great option during a sailing trip.


Navy Pier Fireworks Shows are every Wednesday and Saturday night fromMemorial Day through Labor Day.

Full Moon Rises over Lake Michigan

Full moon rises, (and nearly full moon rises) can be spectacular in Chicago since there is 90 miles of lake on the horizon where the moon comes up. Each Full moon rise is different depending on the time the sun sets, and the cloud cover on the horizon.


Sailing as the sun sets behind the skyline and the city lights come up, makes for a great start to your night sail.