Saturday, April 20, 2024

Chicago Sails and Tours

sunset cruise chicago

“Tailgating on a tiki boat, it doesn’t get better than that,” he says. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. This 90-minute Sunset Chicago Architecture boat tour cruises down the shimmering waters of the Chicago River during sunset. A fun, relaxing, informative boat tour along Chicago's beautiful waterways is the ultimate way to experience the city and leave a lasting impression on your group. The crew is fantastic and the tour guide is hilarious.

General Boarding Tickets Start At

Savor the views with friends and family as you enjoy a relaxing evening on the water with cocktail in-hand. Docks are home to a surge of drinking vessels designed for every occasion, vibe, and price point. A returning line of retro motor boats are apparently the ticket to getting engaged, with seven proposals out on the water last year. Want to watch dolphins give birth on the Chesapeake this summer?

sunset cruise chicago

City Cruises – Premier Lunch Cruise on Lake Michigan

Experience the city’s most unique floating event venue! City Cruises offers all-inclusive packages, chef-prepared menus, full bar options, and entertainment customized to fit your needs—all... Bike & Roll Chicago allows guests to rent bicycles for a fun experience on the lakefront. Soak up monumental views along the Potomac River, drink in tow, with this running list of bookable boats.

sunset cruise chicago

Explore Chicago Sailing Special Events

Take Shoreline’s award-winning 75-minute Architecture River Tour to discover Chicago’s renowned landmarks as presented by our expert and entertaining guides. Navy Pier Seeks to Defend Title as ‘Best Place to Watch Fireworks’ in USA Today’s 10Best Readers’ Choice Travel Awards!

This tour is regarded as the best tourist attraction in Chicago and promises visitors a fun-filled, romantic evening on the Chicago River. Our sister company, Mercury, offers the popular Canine Cruise on summer weekends. Tall Ship Windy offers the most spectacular Chicago fireworks cruises during the summer. Charter Seadog for an event everyone will enjoy! With the ability to travel both the lake and river,... With the sunshine reflecting off the lakefront, there’s no better place to enjoy an afternoon in Chicago than aboard a lunch cruise.

Our boat tours are both fun and educational, which makes them the perfect way to see Lake Michigan. Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail. Two TVs air “whatever people want to watch,” he says, which has included everything from March Madness to the Bachelorette (bachelorette parties are popular bookings, after all). As are corporate teams, birthdays, Whitlow’s fans, and even 50-year wedding anniversaries. Individual tickets are also available, to “mix and mingle like you would in a normal bar,” he says. Sea Suite caters to Washington Nationals fans with a traffic-free cruise from Georgetown to the Yards Marina, docking just in time to walk over for the first pitch.

City Cruises – Premier Dinner Cruise on Lake Michigan

The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. I’m a life long Chicagoan and I brought my out of town relatives on this cruise and we all loved it! It was a gorgeous summer late afternoon and the city was just sparkling. I thought the price was great for the experience.

We highly recommend this tour for architecture enthusiasts and history buffs! You will learn about Art-deco, Gothic, and Neoclassical architecture styles. You are accompanied by a well-informed tour guide who provides detailed information on the architectural history of Chicago and its famous architects. Chicago's Leading Lady, Chicago’s Classic Lady, and Chicago's Emerald Lady are wheelchair-accessible. These vessels cruise at the 9am, 10am, 11am, 12pm, 1pm, 2pm, 3pm and 5pm departure times.

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Knapp also mans other Wharf vessels for parties of six or more, partnering with Nautiste to offer dining excursions with his catering company Curated. You can get all your questions answered by the friendly guides on board. After this brief session, you can explore the cruise freely and enjoy the dazzling skyline view.

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Book your group aboard one of Odyssey's regularly scheduled lunch or dinner cruises, or have an event... A two-hour Lake Michigan lunch cruise is the perfect way to enjoy time with family or the company of great friends. Lake Michigan dinner cruises are the perfect setting for celebrating with friends, connecting with colleagues, or a romantic evening. Chef and sommelier Troy Knapp makes Michelin-level menus on his luxury sailboat Cru Classé.

There is something special about sailing in Chicago combined by kicking off your week and joining us for a 2-hour concert sail. This Navy Pier boat tour sails from 7pm-9pm every Monday this summer. Most architecture boat tours last for around 1.5 hours. The most baller option of the bunch by far, the Wharf’s luxe Pendry hotel offers guests a captain-chartered Aviara cruise that’s available to the public for the first time. Bar selections, beer or wine, and appetizers can be customized, depending on the parties’ preference.

Highly recommend the 7pm sail to watch the sunset between the buildings. Fun and knowledgeable crew made the Windy the highlight of our Chicago visit. For the best Chicago sunset, visitors and residents alike, join us aboard the 148′ Tall Ship Windy – the official ambassador for the City of Chicago.

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