North America,  Travel

A (Failed) Surprise Weekend Trip to Milwaukee

It is a widely known fact within my circle of friends to not trust me with any secrets.

I have made it known in previous blog posts that my patience-o’-meter is minimal. This extends to all areas of my life: from as small as waiting for a waffle in the toaster oven, all the way to ticking back my departure time for road trips. It also includes telling people about all of the birthday or holiday presents I am planning on gifting them.

I just can’t wait.

So when I planned out a surprise weekend to Milwaukee for David’s 24th birthday, the “surprise” aspect was already predestined to fail. For weeks I managed to hold it in while simultaneously and persistently badgering him for guesses. He never did guess it, I just not-so-subconsciously blurted it out two days before while packing because I am a moron. Oh well. I am astounded it stayed a secret as long as it did.

“Why go to Milwaukee?” was the question I, at first, asked myself, and then had echoed back to me by friends and family alike (whom I told to try and quench my need to tell David about it).

Milwaukee was the perfect brief birthday getaway for David for two reasons:

  1. David wants to visit every state before he dies, and neither of us had yet explored any of Wisconsin.
  2. David loves beer and cheese, which are two aspects that Milwaukee is quite known for!

We took off in my trusty, red 2004 Hyundai Santa Fe (affectionately named Paul) for the 5 1/2 hour drive that promptly turned into 6 due to the relentless and evil tolls. Usually Google warns me about tolls, but failed me on this journey. Thankfully, I have a car-full of loose change that we were able to dig for until we found a gas station that would break a $10.


Upon arrival, we stayed at the nicest basement Airbnb in a suburb called Bayview. David accurately described the small apartment as feeling like a hotel, aside from the steps-on-hardwood we could hear from above us. I didn’t do much detective work about Bayview and just assumed it was a normal suburban spot, but we were both surprised to find that the neighborhood was a bit on the ritzy side. The house right across the street from us must have been worth over half a million dollars! Despite the fancy first-impression, the Airbnb itself was a bargain, so I was pleasantly surprised and would definitely recommend the area.


Within walking distance of our temporary home was Humboldt Park – not to be confused with Chicago’s. The park hosts 73 acres of gorgeous trees and hidden within is even a beer garden, which we took full advantage of.

Speaking of beer – we drank a lot of it. Gallons, perhaps. That’s likely an exaggeration but let’s just go with it. We visited several delicious breweries, as well as restaurants and festivals, which I will detail in another post!


After filling our bellies with loads of food and booze, we did what we do best and walked miles around town. As we strolled along the Riverwalk, we (well, maybe just me) got as excited as a child every time a drawbridge rose and waved at the tiny boats carrying tons of bachelorette parties. We appreciated the architecture of the old buildings and the glimmer of the lake as the sun set. And when we got tired and were too cheap to pay out for a surcharged Uber, we hopped on the local bus and took it back home.


On our last day, we walked along Lake Michigan’s beaches. We had intended to maybe take a dip, but chickened out and proclaimed it as freezing. Instead, we smooshed our feet in the sand and cringed as we watched a guy jump off some rocks and cannonball in. These Wisconsin folk have to know how to handle the cold, I suppose.


All in all, we enjoyed our stay in this boozy city and would be happy to return and indulge ourselves once again!


Questions? Ideas? Concerns? Let me know in the comments section!


Getting there: My 2004 Hyundai Santa Fe. Milwaukee is on the Amtrak line and has an airport, as well.
Staying there: I chose to stay in an Airbnb in Bayview, just a 10 minute drive from the city center.
Wearing there: My gray dress is from the ever trusty Piper & Scoot. Stylish, comfy, and versatile – perfect for the colder weather up north.
Shooting there: Images are all captured with either my Nikon D750 with a 35mm lens, or were shot on my iPhone 6. Check out these neat lenses I bought for the occasion, including a fun fish eye!
Etc., etc.: Milwaukee is known for their abundant summer festivals. If visiting during this season, be sure to google what festivals might be in store for you!

Note: Nothing in this blog post was sponsored and all thoughts are my own. Post may contain affiliate links. 

No Comments

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.