Sweets & Spirits Dessert Walking Tour
Our incredible dessert-and-beverage walking tour is the perfect way to experience everything sweet about Chicago! You’ll learn all about Chicago’s rich dessert history and taste some of the finest flavors that the Windy City has to offer. Our Sweets & Spirits walking tour is the perfect Chicago walking tour for birthday parties, bachelor/bachelorette parties, girls’ weekends, couples, date nights, or any other sweet celebration.
This tour is totally customizable for your enjoyment—add or subtract stops to best fit your party’s needs! Want to focus on chocolate? Put an emphasis on romance? Let us know and we can craft your perfect afternoon!
Grab your sweethearts and book this private Chicago dessert tour for a guaranteed unforgettable time!
Looking for Unique Date Ideas in Chicago?
Then you have come to the right place! What could be more memorable than a night spent walking the city together and exploring the sweetest spots around? You will have time to talk and bond as you go from location to location. Our tour is a treasure that will impress your date. It’s outside the usual “dinner and a movie” that so many couples schedule without even considering their other options.
Our dessert tour of Chicago makes an excellent celebration for a special occasion. Is it your anniversary? Is one of you celebrating a birthday? Or are you thinking of popping the question? The romance of enjoying sweets and drinks across the city will turn your special date into something you will both think of fondly for years to come. Since it’s customizable to your preferences, we can even help you with arranging the logistics of a proposal, if needed.
We take pride in being one of the fun things to do in Chicago for couples. Other benefits of booking with us include:
- Tasty treats: It’s impossible to overemphasize just how amazing the cuisine is on our Chicago dessert tour. You may find yourself thinking about the candies or chocolate days later.
- Off-menu samples: On many of our tours, restaurants or bars will offer specials to our guests that they won’t find on the menu.
- Having fun: It’s worth repeating that our tour is just plain fun! You will have a good time, and so will your date as you interact with your guide and the people at each stop.
This tour is a customizable tasting adventure focused on desserts and drinks in the River North area. Exercise your sweet tooth with candy-infused cocktails, gourmet chocolates, delicate French macarons, wine, and more!
One of our enthusiast and fun-loving tour guides will serve as your ambassador for the afternoon, leading you from sweet to sweet, pointing out iconic landmarks and institutions along the way.
You’ll explore Chicago’s vibrant River North neighborhood, stopping in at some of its most iconic eateries and bars.
The tour will begin with a stroll down the Magnificent Mile, the upscale shopping and dining strip located on Michigan Avenue.
Your party will stop at the world-famous Dylan’s Candy Bar, located in the stunning Tribune Tower. Dylan’s is not only one of the largest candy stores in the city, but also sports an entire bar serving candy-flavored cocktails. You’ll get to sip on one of these sweet and unique creations while learning all about the history of the company and the beautiful building in which it resides.
The tour then heads west for some organic chocolate truffles, known for their rich and exotic flavors.
Your group will get to experience the beautiful architecture of the Tree Studios Building up close and personal on the next leg of the journey. You’ll stop for some delicate and decadent French macarons, which have become a global phenomenon in last decade.
After that, you’ll indulge in a wine tasting with authentic Italian dessert pairing at one of the city’s most beloved Italian restaurants.
The best thing about this signature Chicago dessert tour is our ability to cater it to your specific tastes and group needs. Additional stops can be added for champagne tastings, cheesecake, artisan donuts, or more craft cocktails. The possibilities are endless!
The tour generally runs for about two and a half hours, beginning and ending at locations best suited for your party.
Our team is excited to work with you to craft the perfect sweet adventure for your celebration! There is no better way to see and taste Chicago than with a Bobby’s Bike Hike tour.
What To Expect
River North is Chicago’s most popular restaurant and nightlife district, home to some of our most highly-esteemed eateries and bars.
Dylan’s Candy Bar, located in the historic Tribune Tower, is one of the largest candy stores in the city and boasts a full-service, candy-focused bar.
Candy-infused cocktails are becoming a global phenomenon, combining the flavors of beloved candies with fine spirits.
Chicago is home to some of the finest gourmet chocolates in the United States, and rich with exotic flavors and influences from all over the world.
The historic Tree Studios Building is located in the heart of the River North neighborhood, and was first established as an artists’ colony in 1894.
Quartino Ristorante is one of the most highly-esteemed Italian restaurants in the city, known for their authentic small plates menu and distinctive vintage decor.
Home to a large sommelier community, there’s no better place for an urban wine tasting than Chicago’s River North neighborhood.
The newly redesigned Chicago Riverwalk is a stunning feat of recreational architecture. The rolling promenade features bike paths, shops, eateries, and plenty of space to relax and watch boats float by.
French Macaroons have become a worldwide sensation, known for their delicate elegance and wide variety of flavors. Chicago is home to some of the United States’ finest macaron bakeries.
Italian pastries like tiramisu are a staple of the Chicago dessert scene, and are served best with some of our fine dessert wines.
Book Our Chicago Chocolate and Dessert Tour Today
Turn date night into an occasion. When you book our dessert tour of Chicago, you can tailor our options to your liking so you get an experience suited to your (and your date’s!) tastes. Plus, with all the walking you do on the tour, you’ll burn off at least some of the calories you take in at the city’s most fabulous dessert and drink destinations.
Our tours are ideal for people of any age and any fitness level. The walking portion perfectly complements the indulgent desserts. Other reasons to book with Bobby’s Bike Hike include:
- Award-winning service: We have received an award of distinction from Viator.
- Outstanding value: You can save money when you book in advance on our website.
- Excellent reputation: We have been the top-rated tour company in Chicago for 10 straight years.
Don’t wait a second longer. Do something different and fantastic on your next date night to show your significant other how imaginative you can be. You will make memories to last a lifetime and you’ll enjoy food and drink you will crave for months to come. Contact us today to book this one of a kind Chicago dessert food tour.
What Our Customers Are Saying“Loved this tour and would recommend it to anyone! I booked a private tour for my friend’s bachelorette party this past weekend and we had a blast! The guide entertained us and the dessert/beverage samples were perfect! Such a great way to see the city and be active!!”
– Brittany R. Atlanta, GA
Sweets & Spirits Dessert Walking Tour
(includes Food & Beverage Samples)
Reserve Private Tour