Milwaukee Guys Weekend – A Destination for Manly Men

Guy getaways tend to follow the same broken record of trips – a bachelor party in Vegas, a golf trip somewhere, or a weekend of debauchery in Mexico. Put on repeat. Over and over again. Men, I’m here to tell you that there are better options than unsuccessfully trying to relive your youth in an oomph-oomph club or spending a frustrating weekend making up excuses about why your golf game is so bad. Here are six cool things to do in Milwaukee for a guys weekend getaway.

Why does Milqaukee make such a good dude's weekend? Beer!(Photo credit: Bryan Richards)
Why does Milwaukee make such a good dude’s weekend? Beer! (Photo credit: Bryan Richards)

Travel Mamas and Grownup Getaways sometimes receive compensation and/or hosted travel and sample products related to blog posts. This story may include affiliate links for which we receive a small commission at no extra cost to consumers. As an Amazon Associate, we earn money from qualifying purchases.

Why Milwaukee for a guys trip?

Why not a Milwaukee guys weekend getaway? Milwaukee, Wisconsin has to be one of the manliest towns out there. Not only is the city’s claim to fame beer and cheese (two very manly things) but it’s also home to Harley Davidson and Usinger Sausage. Yeah, I just added brats and motorcycles to the mix. Plus, there’s professional sports, plenty of golf courses (if you must swing some clubs), and a plethora of water activities on Lake Michigan.

Dreaming of owning a motorcycle at the Harley Davidson Museum (Photo credit: Bryan Richards)
Dreaming of owning a motorcycle at the Harley Davidson Museum (Photo credit: Bryan Richards)

Get your bike fix at Harley Davidson Museum.

Begin your weekend by experiencing some Milwaukee iron between your legs at the Harley Davidson Museum. I suggest opting for the behind-the-scenes tour for an extra special Harley Davidson experience. The tour will take you backstage to see the world’s largest collection of unrestored Harleys.

Even if you don’t own a Harley, it’s still worth checking out. The exhibits delve into both the history and culture surrounding the iconic motorcycle brand. Heed my warning though; once you sit on a display motorcycle at the end of the tour, you just may buy one.

Learn to sail a Great Lakes Schooner at Discovery World (Photo credit: Bryan Richards)
Learn to sail a Great Lakes Schooner at Discovery World (Photo credit: Bryan Richards)

Hit the water on Lake Michigan.

Another unique Milwaukee adventure is the three-masted Great Lakes schooner that sits outside Discovery World. The recreation of the 19th-century sailing vessel offers both day trips and multi-day trips. Book one to get a glimpse of what it was like to be the captain of a sailboat in centuries past.

If a planned outing on a sailboat isn’t your thing, there are plenty of other water activities on Lake Michigan from kayaking to surfing. (Yes, surfing!)

Enjoy a brewery tour at Lakefront Brewery during your Milwaukee guys weekend
Enjoy a brewery tour at Lakefront Brewery (Photo credit: Bryan Richards)

Tour and taste Milwaukee’s beer history and future.

Of course, the main reason why Milwaukee is a manly destination is beer. Milwaukee has a rich beer history; hence its nickname, Brew City. There’s a rapidly growing craft beer scene as brewers build upon their city’s legacy.

Buildings throughout Milwaukee carry reminders of the city’s four original breweries: Miller, Pabst, Blatz, and Schlitz. Today, only Miller remains, but Pabst is mounting a comeback under their new ownership with a new craft brewery. The new Pabst will be located in the former First German Methodist Church – originally built in 1873 – in the Brewery District where the blue ribbon brewery was formerly headquartered.

For a look at the future of beer in Milwaukee, start with Lake Front Brewery. I normally don’t recommend guided brewery tours because once you see the process, it’s the same everywhere. I do, however, recommend the Lake Front Brewing tour. Led by actors and comedians, the tour has been lauded as the most entertaining brewery tour in the country. Be sure to purchase your tickets ahead of time.

For brewery tastings, the Walker’s Point neighborhood is your spot with MobCraft Beer, Brenner Brewing, Urban Harvest Brewing and Milwaukee Brewing. Milwaukee Brewing offers a self-paced, interactive tour with plenty of beer samples, including some from the brewer’s secret stash.

Or, if you prefer to do your tastings at beer bar, Milwaukee is home to four of Draft Magazine 100 Best Beer Bars in the Country: Burnhearts, Palm Tavern, Sugar Maple, and Roman’s Pub.

Hanging out at Urban Harvest Brewing - Milwaukee Guys Weekend
Hanging out at Urban Harvest Brewing (Photo credit: Bryan Richards)

Get your fill of man food.

I ate one of the best steaks of my life at Five O’clock Steakhouse. You should, too. Five O’clock Steakhouse is actually a supper club, a tradition that dates back to Prohibition. The experience is uniquely Wisconsin. Upon arrival, even if you have a reservation (which is recommended), the host will direct you to a seat at the bar for a cocktail and menu perusal. Order a Milwaukee Old Fashioned Sweet; trust me on this one. When you’re ready, give your order to your server who will then prepare your table, and present you with a traditional steakhouse salad. Everything at Five O’clock is made from scratch, and the steaks are Wisconsin-bred and wet-aged for 30 days.

Eat the best steak of your life at Five O'clock Steakhouse ~ Milwuakee Guys Weekend
Eat the best steak of your life at Five O’clock Steakhouse (Photo credit: Bryan Richards)

For traditional Milwaukee fare, check out the Wisconsin Cheese Mart and the Uber Tap Room for all things cheese plus a robust beer list. The Vanguard is where to go for sausages made from scratch and cocktails on draft. There’s something called Milwaukee pizza, too, which is thin like St. Louis style but without the gross processed cheese. I didn’t get to sample any but I wish I did. A foodie friend recommends Alphonso’s the Original.

Scratch made sausage at the Vanguard = man food (Photo credit: Bryan Richards)
Scratch-made sausage at the Vanguard = man food (Photo credit: Bryan Richards)

Stay in a manly hotel

Step aside Las Vegas, because hotel choices don’t get any cooler than Milwaukee. And yes, there is a hotel and casino, too. Potawatomi Hotel and Casino is a favorite not only for gaming, but also for its sleek, newly finished rooms. For beer fans, book your stay at the Brewhouse Inn and Suites, a hotel that used to be a Pabst brewery. Motorcycle fans will enjoy the motorcycle themed Iron Horse Hotel, a AAA Four Diamond Hotel.

Yes, this is the interior of a hotel - the Brewhouse Inn and Suites (Photo credit: Bryan Richards)
Yes, this is the interior of a hotel – the Brewhouse Inn and Suites (Photo credit: Bryan Richards)

I had such a good time exploring Milwaukee with my buddies, I can’t wait to plan a second trip after the new Pabst brewery opens in 2017.

Have I convinced you? Book your Milwaukee guys weekend with TripAdvisor now!

Milwaukee Guys Weekend - A Destination for Manly Men

Do you have any questions or tips for cool things to do in Milwaukee for a guys weekend getaway? Tell us in the comments below.

A Note from The Hungry Daddy: I was hosted by Visit Milwaukee. All opinions are mine, as always. This story includes affiliate links. Your clicks and purchases help to keep a free resource for readers like you.

Sharing is caring!

Leave a Reply

Your email address will not be published. Required fields are marked *

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


  1. Hmm….According to this article I may be a DUDE!!!! ROFLMAO

    Debauchery in Mexico? CHECK – been there done that.
    Brewery Tour Lover? CHECK – YAS and YES!!!!

    Sounds like Milwaukee needs to be added to my travel bucket list pronto, I’m here for all of this! 🙂

  2. My husband can’t wait to get a motorcycle. When he does though, I doubt I’ll see him very much. This looks like an incredible experience, I just hope I can go with him!

  3. How fun for the men. You dont often see many posts for the men so this is really great. My husband would love a weekend out like this!

  4. My husband would love to visit these places, however they are too far from where we live. Maybe if we plan a tour to the North Central United States, we can arrange to spend a day or two in Milwaukee so he can enjoy a guy weekend with a girl – me! LOL.

  5. Mu husband would enjoy all of these attractions and activities. He is long overdue for a guys trip, and since his 40th birthday is coming up, it would be the perfect time to arrange one.