Summer Special Events

Step aboard the iconic Cap Streeter for an unforgettable evening cruise departing from Navy Pier. Shoreline’s Special Event Series combines curated local beverage tastings, delicious light bites, live music, and breathtaking skyline views into one elevated Chicago experience.

Whether you’re planning a date night, gathering with friends, or simply looking to unwind after work, this 90-minute cruise offers the perfect blend of relaxation, entertainment, and local flavor on the water.

2026 Special Event Lineup

Brew Cruise with Revolution Brewing

Dates: June 11 & July 9
Enjoy craft beer tastings from one of Chicago’s most beloved breweries while cruising along the skyline at sunset.

Wine Tasting with Chicago Winery

Date: June 25
Sip curated wine selections paired with skyline views and an elegant evening atmosphere aboard the Cap Streeter.

Wine Tasting with Lynfred Winery

Date: July 23
Experience award-winning wines from Illinois’ oldest winery during a relaxing evening on Lake Michigan.

Brew Cruise with Haymarket Brewery

Date: August 13
Sample locally crafted brews while enjoying music, light bites, and panoramic city views.

Tiki Luau with Three Dots and a Dash

Date: August 27
Escape to the tropics with tiki-inspired cocktails, island vibes, music, and a festive luau atmosphere on the water.

Cider Cruise with Right Bee Cider

Date: September 10
Celebrate the season with refreshing hard cider tastings from one of Chicago’s favorite local cider makers.

Boarding 7-7:30PM

Cruise 7:30-9:00PM