Travel like a local.

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Riding Harleys and Fear the Deer in Milwaukee, Wisconsin with Jenna Kashou

Best things to do in Milwaukee Wisconsin Jenna Kashou with book

Jenna with her book

I’m really excited to interview Jenna Kashou about Milwaukee, Wisconsin. Jenna’s tips for the best things to do in Milwaukee are awesome because she was born and raised in Milwaukee. She literally wrote the book on Milwaukee (“100 Things to Do in Milwaukee Before You Die“), so you know that she’s an awesome guest.

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Milwaukee, Wisconsin

Milwaukee has all of the cultural attractions of a major city, but everything is affordable and the people are incredibly friendly. There is rarely any traffic and it is easy to get around town. The city is famous for its unpredictable weather. Sometimes, they have all four seasons in a single month. September is Jenna’s favorite month to visit if you’re looking for good weather. If you’re looking for music and festivals, then you need to visit during late June and July. Summerfest is the world’s largest music festival with over 800 bands and 900,000 fans over 11 days on 11 different stages.

We share a lot of resources and local suggestions in today’s podcast, but you should also check out Visit Milwaukee, the local convention and visitor’s bureau. They are a wealth of information and can help you plan an itinerary based on your time, budget, and interests. They even offer a free guide that you can request.

I worked with Visit Milwaukee when Scarlett and I took our first Daddy-Daughter trip in January 2017 for the opening of the Kimpton Journeyman Hotel. We had to much fun and found so many fun things to do in Milwaukee for kids (and parents).

If you’d like to learn how to travel for free using airline miles and hotel points, check out my free 7-day email course.

Best things to do in Milwaukee Wisconsin Jenna Kashou with the Fonz

Jenna Kashou with the Fonz statue

Getting around Milwaukee

The local airport is General Mitchell International Airport (MKE), which is about 9 miles from downtown.

Jenna says that, if you’re staying downtown, there’s no need to rent a car. Uber and Lyft are excellent ways to get around. Milwaukee also has a bus system, a streetcar system nicknamed The Hop, and bike shares known as Bublr.

If you need to rent a car, click here for the best offers from Avis, Budget, or Hertz.

If you only need a car for a couple of hours, you can rent by the hour with Zipcar. Join now to get $25 loaded into your account.

Best things to do in Milwaukee Wisconsin the Hop Streetcar

The Hop Streetcar

Places we talked about on the podcast

Here is a map of all of the places we talked about on the podcast episode with Jenna Kashou about Milwaukee, Wisconsin. You can zoom into the map and click on each dot to explore the city.

  • Red dots = best places to eat in Milwaukee, Wisconsin
  • Green dots = best things to do in Milwaukee, Wisconsin
  • Yellow dots = best places to stay in Milwaukee, Wisconsin

Who is Jenna Kashou?

Jenna Kashou is Milwaukee native, who has lived in several countries, including Greece, Portugal, and Spain. She has always had an enormous amount of pride for her hometown of Milwaukee, which inspired her to write her book. Although we covered a few of her tips from “100 Things to Do in Milwaukee Before You Die” in our interview, we just scratched the surface. If you’re looking for the best local tips for Milwaukee, you should definitely buy her book.

Her writing has also appeared in Milwaukee Magazine, MKE Lifestyle Magazine, The Business Journal, Edible Milwaukee, and more. Jenna was also chosen as a “writer in residence” at the historic Pfister Hotel in Milwaukee. She wrote about and photographed guests and events to capture the culture and experiences of the hotel.

Best things to do in Milwaukee Wisconsin Jenna Kashou with book

Jenna with the second edition of her book

Here are a few articles that she’s written:

You can connect with Jenna at her website and on Facebook, Instagram, and LinkedIn.

Best things to do in Milwaukee Wisconsin City Lights Brewing

A flight of beers from City Lights Brewing

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Best things to do in Milwaukee Wisconsin Black Cat Alley

Black Cat Alley

Stay tuned for our next episode

Best things to do in New York City New York Leslie Tayne Hamilton Play at Richard Rodgers Theatre

Leslie Tayne watching Hamilton

Listen to the next episode when Leslie Tayne of and I talk about the proper way to eat pizza and bagels, the best ways to explore New York City, and the best rooftop bars in New York City, New York. We hope you’ll join us when We Travel There.

What’s your favorite part of Milwaukee, Wisconsin? Send us a Tweet, let us know in the comment section below, or continue the discussion in our Facebook group!

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To see which cities we’ve interviewed and scheduled, please visit If you’d like to be a guest on the show, please submit an application at

Related episodes

To learn more about the Midwest, listen to our other episodes from this area of the U.S.: