North Shore Nine

For those who don’t know, I travel a lot. Not only does my job take me to a lot of places but my wife and I love exploring new destinations.

I know what you’re thinking. “Jim, who would employ you?” Or maybe it’s, “Jim, who would marry you?” To be honest, I’m as surprised as you are. These things are just proof that miracles sometimes happen.

We aren’t going to discuss every place I went for the year, but let’s highlight my 10 favorite cities that I graced with my presence. All images were taken by yours truly.

10. Kansas City, MO

This was my most visited city in 2023, as I count 6 different trips during the year. With how often I go, I’ve got a pretty decent lay of the land. It’s got a lot of the characteristics of a standard midwest city, but I put it above the likes of Indianapolis, Cincinnati, Columbus, and St. Louis thanks to the BBQ, mostly.

9. Pittsburgh, PA

What can I say? It’s home. The family is here. The Pirates are here. Losses in the rain to a pathetic Pitt Football team are here. Always a treat to visit the Steel City.

8. Philadelphia, PA

The next stop is across the state. Despite how many Pittsburghers feel about its commonwealth counterpart, it’s one of my favorite cities in the country. As a history nerd, it’s got it all. Excellent landmarks, museums, and parks. It’s also super walkable, which always bumps up rankings for me.

7. Nashville, TN

I spend a good amount of time here and quite simply, it’s just a fun town. If you like mixing music with alcohol, there just isn’t a better place out there.

6. Austin, TX

I try to avoid Texas as much as I can (because it sucks), but based on the map you see earlier in the article, it’s just a place I can’t avoid. Austin is the one place in the Lonestar State where I went voluntarily. Great Texas BBQ, wonderful nightlife, great outdoor activities, and being not quite the concrete jungle of Dallas/Fort Worth and Houston make it the most enjoyable place there for me.

5. New Orleans, LA

This is one of my favorite cities to visit and for its size, it has a lot to offer depending on the vibes you’re going for. Bourbon Street is obviously a spectacle and a place that I can’t really compare to anywhere else I’ve been. The cuisine here is outstanding. And if you want to go the nerdy, history route, it’s got that, too.

4. Miami, FL

The beach, the food, and the nightlife always make Miami a great spot to visit. Probably a place I’d go more often if it didn’t cost so much damn money, but it’s really hard to not enjoy yourself here and there are a lot of ways to go about it.

3. Savannah, GA

My favorite city in the South. Huge trees line every street and there are parks and squares practically every block. Great southern cuisine, bars, and a good bit of history are just a cherry on top. I can walk around this city for hours and enjoy every single second of it.

2. Chicago, IL

If you told me, “Hey Jim, Louisville has become uninhabitable and you have to move, so where’s it gonna be?” my answer would be, “Chicago.” It is America’s best city (sorry New York). The walkability, the public transit, the museums, the sports, the parks, there’s just an endless amount of things to do here and it’s so easy to do all of it.

1. San Diego, CA

My wife and I have been talking about coming here forever and we finally got around to it this summer and man, it didn’t disappoint. Balboa Park is absolutely stunning. Coronado has the best Pacific Ocean beach I’ve ever seen. The Gaslamp Quarter kinda gives me New Orleans French Quarter vibes without the smell and debauchery. Oh, and I didn’t even mention the weather. Just a 10/10 perfect city to visit.

That’ll do it. Thanks for following along. Comment with the favorite place you’ve visited this past year, recommendations for 2024 travel, or simply comment telling me how wrong my list is.