I Asked Our AI-Travel Planner for a Weekend Adventure in Madison, Wisconsin—Here’s What It Created

In this age of rapidly advancing technology, have you ever considered using AI to plan a trip? I've pondered it occasionally, but I've been curious if it would hit the mark or just give me the top search results. With curiosity piqued, I wondered how on point the Only In Your State’s AI-powered Dashboard trip planner would be for a place I used to call home—Madison, Wisconsin.

With its reputation as a college town, my biggest worry was that a curated itinerary would include a ton of bars. Believe me, I love an old fashioned (especially at The Old Fashioned off Capitol Square), but there's more to my beloved former home than all that. Since my spouse is originally from Madison, I let a couple's weekend getaway inform how the trip planner made our itinerary.

Although I didn't call Madison home for more than a handful of years after college, I learned it well between all my jobs. This former news desk reporter knew many streets backwards and forwards. But can AI really plan a romantic getaway that would impress even a couple of former Madisonians?

Best Things to Do in Madison

Right off the bat, the AI trip planner picked a winning attraction. The Allen Centennial Garden is by far one of the most beautiful gardens in Wisconsin. Located at the University of Wisconsin-Madison, the garden is free to visit every day from dawn until dusk. You can meander among the countless native plants to feel at home with nature, but be sure to check out the Agricultural Dean's House. The home is a stunning Queen Anne that once belonged to the first dean of the school's College of Agriculture. It's only fitting that it remains to keep an eye on the gardens. Plus, what could be more romantic than relaxing among freshly blooming flowers?

Not all Madison-bound romantic rendezvous occur in the warmer months, though. It's important to remember that Wisconsin winters can be brutal, which can put outdoor experiences on the back burner. This is also why I am so fond of Olbrich Botanical Gardens. Although the numerous outdoor gardens are breathtaking, especially the gold-leaf Thai Pavilion, the Bolz Conservatory is always a welcome winter escape. Inside, you're brought to a tropical paradise with birds chirping everywhere. You can sit and relax in the warmth with flourishing plant life in a refuge from the bitter winter. Watch for the pheasants running around on the paths—I have yet to see one.

Where to Eat in Madison

If there is one thing that seems to shock my friends who have never been to Madison, it's the food scene. This capital city is overflowing with food options, so color me surprised that the AI trip planner chose two restaurants I adore as its main foodie recommendations: Graze and the Tipsy Cow. It also isn't lost on me that these two eateries are udderly perfect for one another.

First things first, the views from Graze are like no other. This glass-encased restaurant faces the gorgeous Capitol building as well as Capitol Square. There is nothing like people watching while noshing on farm-to-table goodness courtesy of Chef Tory Miller—a James Beard Award winner. No matter the time of year, the food here is impeccable and locally sourced. Plus, the local producers are listed on the menu, so you might be able to scope them out at the massive Dane County Farmers Market, steps outside of Graze, along Capitol Square on Saturdays during market season.

Only a few doors down from Graze is Tipsy Cow, a cozy cow-themed restaurant. I'm so glad the AI trip planner knows about this place because I love finding excuses to pop in. While the comforting pub fare at this casual spot is excellent, the artisanal craft beer is its signature calling card. As a non-beer-drinking person, though, I must recommend their specialty cocktails. The Bourbon Peach Mule is my go-to if I'm not feeling my typical old-fashioned.

Where to Stay in Madison

Here is where the AI trip planner threw me for a loop by recommending a hotel I haven't stayed in, though I have always wanted to. Why? Because, while there are several hotels in Downtown Madison, only one gets to say it is located on Capitol Square—The Park Hotel. Officially the Best Western Premier Park Hotel, this accommodation could well be the most historic place you ever sleep. Originally opened in 1871, The Park has witnessed so much history as it overlooks the Capitol and all its goings on. You can be a fly on the wall of Wisconsin politics, too, if you stay here, with gorgeous views of the Renaissance-style Capitol Building. Just don't forget to stop into The Post, a nod to the Capitol's architect George Post, for a bite or a drink while you're there.

The AI-Travel Planner Itinerary Results

I was pleasantly surprised by the recommendations from the AI trip planner. These locations, activities, and hotels aren't just the usual run-of-the-mill roundup entries. Not only were these spots I visited while living in Madison, they're ones I miss to this day. Plus, the planner suggested a hotel I've long admired from afar but never stayed in. This means I'll have to plan my next visit to the city and stay there! I have had a hankering for some Graze-style people watching.

Disclaimer: This article was made using our award-winning dashboard planner. You'll definitely want to check it out!