If you’re tired of the usual Chicago tourist routine—another museum, another deep-dish pizza place—here’s something worth checking out:
The Wendella Wine & Cheese Cruise.
It’s a two-hour boat tour that actually delivers on the promise of combining good wine with spectacular views.
How It Works
You’ll board at the Wendella Dock, located at 400 N Michigan Avenue on the Chicago Riverwalk, right next to the Wrigley Building.
Once you’re on the boat, the city noise fades and you’re cruising down the Chicago River with a wine glass in hand.
The ticket price covers everything: a curated selection of local wines, artisanal cheeses paired to match, and a spread of hors d’oeuvres.
If wine isn’t your thing or you want something different, there’s a full-service bar selling cocktails, beer, and other drinks.
The Route
The cruise follows a smart two-part route.
First, you navigate the main branch of the Chicago River, passing through the heart of downtown.
You’ll glide past Wolf Point, the massive Merchandise Mart, and a mix of historic and modern skyscrapers that define Chicago’s architectural personality.
The views from water level give you a completely different perspective than street-level walking tours.
Then comes the best part: the boat passes through the historic Chicago Harbor Lock and opens up onto Lake Michigan.
That’s where the full Chicago skyline hits you all at once—the kind of panoramic view that makes you understand why people love this city. It’s genuinely impressive, even if you’ve seen the skyline a hundred times before.
❤️ Recommended Articles
The Atmosphere
This is an adults-only experience (21+), which makes a real difference.
The vibe is sophisticated without being pretentious—people are there to enjoy themselves, have some wine, chat, and take in the scenery.
There’s background music that sets the mood without drowning out conversation.
It’s the kind of setup where you can strike up a conversation with other passengers or just relax with your group. Either way works.
Where to Sit
You’ve got two main options.
The open-air upper deck gives you unobstructed 360-degree views and feels more adventurous.
If you time it right and go during golden hour, the sunset light hitting the buildings is spectacular—easily the best photo ops of the trip.
The climate-controlled lower lounge is the move if it’s chilly, windy, or you just prefer being comfortable indoors. You still get great views through the large windows, plus cushioned seating and protection from the elements.
Who This Is For
Wine lovers will appreciate the thoughtful pairings and local selections.
Architecture fans get a unique angle on Chicago’s famous buildings. Couples looking for a romantic evening that’s not a generic dinner reservation will find this hits the mark.
And honestly, anyone who enjoys doing something a bit different while visiting or living in Chicago should give it a shot.
It’s equally good whether you’re a first-time visitor trying to see the city or a longtime resident who wants to experience Chicago from a fresh perspective.
Practical Details
The entire cruise lasts two hours and returns to the Riverwalk dock around sunset—perfect timing if you want to grab dinner afterward or just walk along the river as the city lights come on.
Here’s the catch: these cruises are popular and sell out quickly, especially during the summer months and on weekends.
Don’t wait until the last minute. Book your tickets in advance at www.wendellaboats.com.
Bottom Line
The Wendella Wine & Cheese Cruise isn’t trying to be everything to everyone. It’s simply a well-executed concept: good wine, good food, and Chicago’s best architectural views, all from the comfort of a boat. No gimmicks, no overselling—just a solid two hours on the water that’s worth your time and money.
If you’re planning a Chicago trip or looking for something different to do in your own city, put this on the list. It’s one of those experiences that’s better than it sounds on paper.
Chicago’s Wine & Cheese Cruise: Architecture Meets Wine Tasting on the Water
If you’re tired of the usual Chicago tourist routine—another museum, another deep-dish pizza place—here’s something worth checking out: the Wendella Wine & Cheese Cruise. It’s a two-hour boat tour that actually delivers on the promise of combining good wine with spectacular views.
How It Works
You’ll board at the Wendella Dock, located at 400 N Michigan Avenue on the Chicago Riverwalk, right next to the Wrigley Building. Once you’re on the boat, the city noise fades and you’re cruising down the Chicago River with a wine glass in hand.
The ticket price covers everything: a curated selection of local wines, artisanal cheeses paired to match, and a spread of hors d’oeuvres. If wine isn’t your thing or you want something different, there’s a full-service bar selling cocktails, beer, and other drinks.
The Route
The cruise follows a smart two-part route. First, you navigate the main branch of the Chicago River, passing through the heart of downtown. You’ll glide past Wolf Point, the massive Merchandise Mart, and a mix of historic and modern skyscrapers that define Chicago’s architectural personality. The views from water level give you a completely different perspective than street-level walking tours.
Then comes the best part: the boat passes through the historic Chicago Harbor Lock and opens up onto Lake Michigan. That’s where the full Chicago skyline hits you all at once—the kind of panoramic view that makes you understand why people love this city. It’s genuinely impressive, even if you’ve seen the skyline a hundred times before.
The Atmosphere
This is an adults-only experience (21+), which makes a real difference. The vibe is sophisticated without being pretentious—people are there to enjoy themselves, have some wine, chat, and take in the scenery. There’s background music that sets the mood without drowning out conversation.
It’s the kind of setup where you can strike up a conversation with other passengers or just relax with your group. Either way works.
Where to Sit
You’ve got two main options. The open-air upper deck gives you unobstructed 360-degree views and feels more adventurous.
If you time it right and go during golden hour, the sunset light hitting the buildings is spectacular—easily the best photo ops of the trip.
The climate-controlled lower lounge is the move if it’s chilly, windy, or you just prefer being comfortable indoors. You still get great views through the large windows, plus cushioned seating and protection from the elements.
Who This Is For
Wine lovers will appreciate the thoughtful pairings and local selections. Architecture fans get a unique angle on Chicago’s famous buildings. Couples looking for a romantic evening that’s not a generic dinner reservation will find this hits the mark. And honestly, anyone who enjoys doing something a bit different while visiting or living in Chicago should give it a shot.
It’s equally good whether you’re a first-time visitor trying to see the city or a longtime resident who wants to experience Chicago from a fresh perspective.
Practical Details
The entire cruise lasts two hours and returns to the Riverwalk dock around sunset—perfect timing if you want to grab dinner afterward or just walk along the river as the city lights come on.
Here’s the catch: these cruises are popular and sell out quickly, especially during the summer months and on weekends. Don’t wait until the last minute. Book your tickets in advance at www.wendellaboats.com.
Bottom Line
The Wendella Wine & Cheese Cruise isn’t trying to be everything to everyone. It’s simply a well-executed concept: good wine, good food, and Chicago’s best architectural views, all from the comfort of a boat. No gimmicks, no overselling—just a solid two hours on the water that’s worth your time and money.
If you’re planning a Chicago trip or looking for something different to do in your own city, put this on the list. It’s one of those experiences that’s better than it sounds on paper.
