Here’s Our Top 10 Cities We Visited In 2018

During the first year of our 5 year, 50 state road trip, we visited 10 states and stayed in more than 50 different cities.

We’ve had a great time, but we enjoyed some of those cities more than others. We therefore thought it’d be fun to look back on the past year and pick each of our top 10 cities.

After leaving each state, we publish a post listing our best and worst things of each state. Since visiting Wisconsin mid-year, those posts have also ranked each city we visited in that state from favorite to least favorite.

That made it a little easier putting together this list, but it was still harder to compile than I thought it’d be. That’s because it’s hard knowing how to compare them. Each city has something unique to offer, so how should they be compared?

Also, how should ‘favorite’ be assessed? Let’s take South Carolina for example. My favorite city for visiting was Charleston, but if we were to settle in South Carolina I think I’d rather live in Greenville as I preferred its general vibe.

Similarly, in Alabama I enjoyed myself most in Enterprise, but that was largely due to the new friends we made there. There are fun things to do there, but there are other cities in Alabama that are better for vacations.

For the purpose of this list, I decided to go with what my favorite cities were if I had to recommend places for someone to go on vacation.

Shae and I have created our own lists as they were so different. Without further ado, here are our top 10 cities of 2018.

Stephen’s List

1) Chicago, Illinois

The #1 spot on my list wasn’t too hard to decide. Chicago is one of my favorite cities I’ve visited anywhere in the world. It has interesting architecture, great restaurants, lots to do, has a river running through it and has beaches on Lake Michigan.

2) Savannah, Georgia

We ended up making a good choice with our accommodation in Savannah. There were some hotels we could’ve booked using points on the outskirts of Savannah, but we ended up booking an Airbnb near Forsyth Park which was much more central.

The Airbnb wasn’t the best one we’ve ever stayed in, but the location was perfect and meant we were within walking distance of everything. The city of Savannah is beautiful, it’s home to Byrd’s Cookies, we had great fun going on our first tandem bike ride and it’s somewhere I’d love to revisit.

3) Tulsa, Oklahoma

If you’d told me at the beginning of 2018 that Tulsa would be one of my favorite cities, I’d have laughed in your face. I didn’t hold out high hopes for Oklahoma at all, but we found it surprisingly enjoyable, Tulsa particularly.

It was helped by the fact that we stayed downtown for nine days and so had plenty of time to explore the city by foot. We stayed at a couple of great hotels (the Hyatt Regency and Aloft), ate at some great restaurants, enjoyed Welltown Brewing, went to our first state fair, loved the newly opened park called Gathering Place and so much more.

Tulsa is a hidden gem with plenty to keep you entertained for a weekend away, if not longer.

4) Milwaukee, Wisconsin

I didn’t know much about Milwaukee before visiting, other than the fact that they had a not-very-successful-in-recent-years baseball team.

That baseball team is the Milwaukee Brewers and the city has a ton of breweries. We went on a tour of Lakefront Brewery and I had a great time (Shae doesn’t care for beer, so it wasn’t quite as fun for her!) There were some amazing dog parks and it was nice being on Lake Michigan.

We stayed at the Hyatt Place Milwaukee Airport as it was great value using points. If we were to return though, I think I’d prefer to stay downtown so it’d be easier to explore more.

5) Charleston, South Carolina

Charleston is, quite simply, a beautiful city. There are historical buildings, it’s by the water and it’s home to Rodney Scott’s BBQ – some excellent whole hog BBQ.

6) Terlingua, Texas

One of the last cities we visited in 2018 was Terlingua. The city itself isn’t up to much, but you don’t visit Terlingua if you want a bustling metropolis.

Quite the opposite in fact. The reason you visit Terlingua is to get away from it all and take advantage of the lack of light pollution. The night sky is so dark there that you can see the Milky Way. It’s also close to both Big Bend National Park and Big Bend Ranch State Park.

7) Cincinnati, Ohio

We’ve visited Cincinnati multiple times as some of our best friends live there. Even if you don’t know anyone there though, it’s definitely worth a visit.

There’s Cincinnati chili, the Smale Riverfront Park, the National Underground Railroad Freedom Center, Jungle Jim’s International Market, Trammel Fossil Park and more.

8) San Antonio, Texas

San Antonio is on this list by virtue of the truly stunning River Walk with its restaurants and bars. Without that, it might not have made it in the top 25 – that’s how much I loved the River Walk.

9) Montgomery, Alabama

It’s kind of strange that Montgomery is only 9th on the list as Alabama overall was possibly my second favorite state of 2018 after Wisconsin.

Montgomery is a great city to walk around as there’s lots to see. It’s also home to all kinds of Civil Rights history, so I learned a lot during our time there.

10) Montpelier, Vermont

With fewer than 8,000 residents, Montpelier is the least populated state capital in the US. Despite that, they rightly pride themselves on being the cutest state capital.

We booked an Airbnb that was a five minute walk from downtown Montpelier, so we walked downtown every day we were there. It’s a beautiful city near the mountains as well as Ben & Jerry’s.

Shae’s List

While Stephen experiences most places through stats and reviews, I experience them through feels and memories. Therefore my list is comprised of the places that created my favorite memories along the way and places that I’d happily go back to.

1) Enterprise, Alabama

Since visiting Enterprise all I can think about it getting back there. We made some really wonderful connections and ended up with this group of friends who took us under their wings and made sure we saw the best of Enterprise. We went to the World’s Smallest St. Patrick’s Day parade, the local homebrew competition, the US Army Aviation Museum at Fort Rucker, had Korean for lunch and then my favorite thing of all… dinner at Rob’s house with great company, food and wine. Plus, Dusty the Weimaraner.

2) Montpelier, Vermont

If we hadn’t made so many connections in Enterprise, Montpelier would be number one for me. The weather was perfect in May. My friend Stefanie came over from the UK for the week and we walked into town each day. It was just busy enough to not feel secluded, but just quiet enough to be peaceful. It was a beautiful setting and the pet store, the Quirky Pet, was worth more than one visit!

3) Charleston, South Carolina

In Charleston we met Kristie and Daryl. We did the Shrimp n’ Grits 5K with Kristie and had a couples date out to dinner and a ghost walk. I loved Market Street and this is where we found Byrd’s Cookies and 5Church. I could happily spend a lot more time in Charleston.

4) Galveston, Texas

This was just one of those perfect days. You know the kind. They’re rare, but everything goes to plan. The weather is wonderful, the food and service is great, the shopkeepers are kind and you get some quality time with your family. That was Galveston.

5) Chicago, Illinois

I love a big city. As big cities go, Chicago was great. I have a special place in my heart for NYC, so it’s hard to allow Chicago to vie for my affections, but it was pretty good. There’s so much I could list. The dog beach, the mermaid swim, the birthday hoopla, a sweet anniversary day, the contemporary photography museum, troll hunting at the Morton Arboretum and of course…. Doug. The. Pug.

6) Tulsa, Oklahoma

Sorry to my friend January – I loved Tulsa. I know you think Oklahoma City is where it’s at, but Tulsa has taken the cake. On top of the great pizza and donuts, we met Katie while staying at the Hyatt Regency. We were lucky to get to have dinner with her and then we all went to the Tulsa State Fair. Other than not getting a Dizzee the goat, Tulsa was pretty perfect.

7) Savannah, Georgia

Oh man, did I love Savannah. The more I think about it, the more I wonder if it needs to move up the list, but I’m sticking to my guns. The tandem bike ride was my favorite memory there. Just a bunch of fun and silliness with Stephen and Truffles. Much like our day in Galveston, it was just one of those times where the memory is etched in as practically perfect in every way.

8) Athens, Ohio

Honestly, I could have chosen any of the Ohio cities. We have some of our closest friends in 4 of the 5 cities we visited.

But Athens was pretty amazing. We stayed in a cabin and went hiking at Hocking Hills. Old Man’s Cave and all the subsequent waterfalls and rock formations were pretty spectacular. It was a long day since we hiked to a separate waterfall and almost ran out of water, but the good definitely outweighed the bad.

9) Nashville, Georgia

The first cabin we stayed in this year was an Airbnb in Nashville, GA. We found a great local winery, went canoeing on the lake (Truffles’s first canoe trip) and my mom and stepdad visited. It was our first ‘break’ during the trip and was really refreshing.

10) Terlingua, Texas

Cabins seem to be the theme for the end of my list. We stayed in an off-grid cabin in Terlingua. It was a tiny home and definitely gave a taste of what tiny home living would be like. We had a strenuous hike and then saw Big Bend National Park and Big Bend Ranch State Park with some more gentle hikes. I also loved going to a local community event at the star party.

Off the Beaten Path Honorable Mentions

We detoured from our journey a few times and I’d feel remiss if I didn’t mention these highlights.

Indianapolis, Indiana

I took the Greyhound Bus to Indiana from Illinois to have a girls weekend with my BFF Mary. We had a wonderful time catching up, eating cinnamon rolls, watching cheesy movies and going to the zoo where I met Frank the Flamingo (OK, his real name is Gronk, but he’ll always be Frank to me).

Toronto, Canada

We detoured from Vermont into Canada so that we could take Truffles to Woofstock. It was the 15th Anniversary and Truffles ended up getting into the VIP tent. The second day when it was just us girls was really fun as we tried a lot of things like the lure course.

Grand Rapids, Michigan

Not only did we have our friends Patty and Ed come visit us, we all competed in the Insane Inflatable 5K. After the race but before we left town, we took Truffles to her first dog beach. That was such a fun day, all the dogs, sun and sand.