Events, Fireworks Cruises, Wine Tastings

Make Memories With Us

Chicago Sailing offers a number of special events that can be designed as romantic outings, bachelor/bachelorette parties, or even just a fun night out with friends!  With options ranging from weekly fireworks cruises, monthly wine tastings, even dockside bashes with libations and live music we have you covered!

Don’t see exactly what you are looking for?  Give us a call and let us work our magic!

Featured Event: Wind & Wine

Wind & Wine is Chicago’s exclusive sailing and wine-tasting event.  Join the fun as we showcase wines from around the world while cruising Chicago’s world class lakefront.  There is no more elegant way to meet new friends than toasting a fabulous golden sunset from the water.  We begin with a 6:30pm dockside reception, where you will sample hors d’oeuvres and exciting new wine pairings.  Then the wine tasting continues as guests board our luxury sailing vessels and enjoy an evening of sailing with a captain on board to show you the ropes.

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