Highlights

• Select dates include Aug 13th (Haymarket Brewery), Aug 27th (Three Dots and a Dash) or Sept 10th (Lynfred Winery)
• A 90-minute evening cruise aboard the Cap Streeter, offering a perfect blend of relaxation and entertainment.
• Curated beverage tastings from local partners, allowing guests to savor Chicago's unique flavors.
• Delicious light bites and music, enhancing the festive atmosphere and overall experience.
• Breathtaking skyline views of Chicago, creating unforgettable memories and photo opportunities.
• A perfect gift for a date night, gathering with friends, or unwinding after a long day.

What to Expect

Guests are invited to step aboard the iconic Cap Streeter for a memorable 90-minute evening cruise departing from Navy Pier. Shoreline Sightseeing's Special Event Series artfully combines curated local beverage tastings, delicious light bites, and engaging music into one elevated Chicago experience, providing an ideal setting to relax and enjoy.

Whether planning a romantic date night, a lively gathering with friends, or simply seeking to unwind after work, this cruise offers the perfect blend of relaxation, entertainment, and local flavor on the water. Participants will be treated to breathtaking skyline views, creating lasting memories against the stunning backdrop of Chicago.

Plan Your Visit

• Tour Schedule

  Boarding for the special event cruises begins at 7:00 PM and concludes at 7:30 PM. The cruise sails from 7:30 PM to 9:00 PM.

• Duration

  Each special event cruise lasts for 90 minutes, providing ample time to enjoy the experience.

• Departure & Arrival

  Cruises depart from and return to Navy Pier. Specific departure location details are available on the merchant's website.

Important Information — The 2026 Special Event Lineup features themed cruises such as Brew, Cider, Tiki Luau, and Wine Tasting. Guests should check specific dates for each unique experience.

Event Schedule

7:30 PM - 9:00 PM

Brew Cruise with Haymarket Brewery - August 13

Sample locally crafted brews while enjoying music, light bites, and panoramic city views.

7:30 PM - 9:00 PM

Tiki Luau with Three Dots and a Dash - August 27

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

7:30 PM - 9:00 PM

Wine Tasting with Lynfred Winery - September 10

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

How It Works

1. Plan your visit

Select and reserve your preferred date.

2. Grab the Deal

Proceed to checkout to buy & book your Groupon!

3. Redeem your Mobile Ticket

Scan your Groupon upon arrival.

4. Enjoy the Experience!