Travel Recommendations: My Favorite Small Cities and Towns to Visit
Updated: Oct 15, 2020
Here’s the thing: I’ve never been a city girl. Growing up near NYC and Philly, I'd often hop on the train for a day trip. Although fun, by the end of it, I’d feel overwhelmed and overstimulated. The hustle and bustle of people everywhere. The loud honks of cars, buses, and sirens. Trying to navigate the impossible subway system. Traffic making everything take for-ev-er.
For a hot minute, I had lived in Boston. Still a suburbs girl, I’d moved to the city outskirts after living in Cambridge for my first month. I never could get used to dealing with things like grocery shopping without a car, so the surrounding towns and cities appealed to me more. Sure, I’d hop on the T and head into the city for fun or work, but I mostly spent my few years there living in the nearby towns.
Living in a city wasn’t part of my long-term plan, but I still liked taking a quick trip to get all the cultural experiences a city has to offer without regularly dealing with things that wear on me.
When I traveled more, especially to Europe, I tried to hit all the hotspots. Paris. Rome. Dublin. Vienna.
You get the picture.
CITIES. Big metro areas. And although I loved every single one of them and would go back in a heartbeat, I realized something along the way: I made some of my favorite memories while doing day trips to nearby smaller cities and towns.
Go figure. You’d think standing on top of the Eiffel Tower would have made it to the top spot for memories (trust me, it was great and still a favorite), but it turns out stopping in a local pub in a small Irish town where the older folks played fiddles while throwing back Guinnesses was the one that stuck with me more.
So, if you’re like me and prefer to find places that are a little more manageable, less hectic, and more relaxing, say no more. I’ve pulled together a list of my top 10 favorite small cities and towns in the United States and Europe.
These are fine to visit on their own or to tag on to a longer trip. For example, if you’re popping by Brussels, maybe consider doing a night or two in Bruges.
Alright. Here we go. Top 10 coming at you (listed in no particular order):
1. Charleston, SC
Okay. Before you give me shit for putting the place I currently live on this list, hear me out. This is the second time I’ve lived in Charleston. That’s right. I moved back here after my ~3 year stint in Boston.
I’m an “always moving forward” kinda gal (aka, I said I’d never move back here since I’d clearly left for a reason) and I’m also a little insane with research. So, when putting together a list of potential places to move, Charleston was top rated.
Why? Because it’s got a bit of everything. Downtown has picturesque historical architecture. There’s water everywhere, which is perfect if you love boating or the beach. And the food and cocktail scene is probably the best I’ve come across so far. Living here made me into a total food snob.
Even better, everything downtown is super walkable, making it easy to grab a cocktail and/or bite at one place and then move on to the next. It’s not uncommon for my friends and I to hit up several places each time we’re downtown because it’s easy to.
2. Killarney, Ireland
Remember that thing I said about going to a pub with fiddlers? This is the town I’d
experienced it in. After a few days in Dublin (which I’m assuming influenced Boston’s architecture since there were a ton of Irish immigrants and the cities looked strikingly similar), staying in Killarney offered a nice change of pace.
In fact, it was the type of town I’d imagine whenever I thought of traveling to Ireland. Quaint (but not too quaint) with cute little restaurants, bars, and breweries. Close by were national forests that included castle ruins, endless green fields, and waterfalls.
And, yes. The music was perfect. I loved grabbing a pint and listening to the fiddlers and accordions.
3. Portland, ME
If it weren’t for endless winter and frigid ocean water, I’d live here in a heartbeat. In fact, I loved Portland so much that it inspired the setting for my debut novel No Place to Hide.
Portland is great if you still want the amenities of the city without all the fussiness of it. Walkable, plenty of amazing restaurants and cafes, cobblestone streets, and water views make this city a perfect New England town. I loved grabbing a tea and sitting down by the port, listening to the seabirds as the boats came in and out.
Maybe I’ve gotten acclimated to the weather and warm ocean temps in the south, but I’m considering doing a long-term Airbnb rental to “live” there for at least a month soon (if COVID restrictions allow).
4. Reykjavík, Iceland
Are you thinking, “But Reykjavík is the capital of Iceland. How is that small?” Well, you have
to remember that the entire country has maybe like 300,000 people. Half of them live in Reykjavík. With that context, it doesn't seem so big, now does it?
It’s another one of those very walkable cities. I stayed in the heart of the city which made it super easy to take advantage of nearby restaurants, bars, and cafes. I’ll tell you, I was really impressed with the food in the city. It was right up there with Charleston (then again, maybe it was the hot wine that swayed me to put it high on my foodie list). I also discovered my new love for cod.
Plus, we were close to major city attractions and a couple minute walk from the bus station where tour buses would pick us up for our day tours. From there, we visited the Golden Circle, a ton of nearby waterfalls and geysers, Vik, the black-sand beaches, the Blue Lagoon, and more. We also grabbed dinner in the city before getting picked up at night to view the Northern Lights (amaaazinnng by the way).
Also, if you’re a Christmas lover like me, going in December was awesome. They love Christmas there, and their traditions are so interesting to learn about.
I could tell you this is another place I’d love to live temporarily, but I think you’re catching a theme at this point.
5. Bruges, Belgium
So. Cute. So cute. After spending time in Brussels for their Christmas market, I took a day trip to Ghent (also cute) and Bruges. If Bruges isn’t the quintessential quaint European city, I don’t know what is.
Cobblestone streets. Canals. Medieval architecture. Little town squares. It has it all. Of course, being there during Christmas also made it even that much more adorable. I loved seeing the Christmas stalls selling hot wine, chocolate, trinkets, and more, all while holiday-inspired songs were blasting throughout the market.
There were plenty of great restaurants, chocolatiers, bars, beer, and upscale shopping for all your needs.
6. Wilmington, NC
Before I ended up in Charleston more than a decade ago, I thought for sure that when I moved away from home, it would be to Wilmington. Maybe it was because I was a die-hard One Tree Hill fan growing up, but I absolutely loved this place.
Coming from a super small town on the Jersey shore, Wilmington seemed huge. Now, after living in Charleston, it seems very quiet. This makes it perfect to unwind and enjoy, especially if you take a stroll along the Riverwalk.
Plenty of the historic houses are reasonably priced Airbnb rentals and are a quick walk to downtown. And a short drive away, you'll stop at Wrightsville and enjoy a gorgeous day at the beach.
7. Prague, Czech Republic
I know this is one of those cities that seem big, but the Old Town in particular is what I’m focused on. Staying in the heart of Prague, I was a couple minute walk from the Old Town Square. All along the way, I’d felt like I had been transported into a storybook. The architecture and cobbled streets were breathtaking.
But even better were the views from above the city. I made it a point to find all sorts of vantage points, from towers to restaurants, to get the iconic red-roofed views of Prague. I’ll tell you, sipping on a glass of wine while looking down at the city, the church bells ringing in a distance...there’s nothing like it.
Plus, the US dollar went far in Prague. I upgraded to a fancy room, got massages, and went to upscale restaurants, and I felt like I had a ton of money left over. I actually had to check my bank account because I thought something was wrong.
8. Annapolis, MD
Maybe it’s because I miss small, cute New England towns, but Annapolis really hit the spot
for me. Even going during COVID with all the crazy restrictions, I found this city to be absolutely charming. With the brick-lined streets and buildings, I bet it would look picturesque during fall!
The night I got there, I stumbled upon “Dining Under the Stars.” Basically, they shut the road off to traffic and the restaurants put out socially-distanced tables so people could enjoy their meals outside. The event included a swing band, playing upbeat music that you couldn’t help but dance to.
Cute shops, good food, and seafood aside, my favorite part of Annapolis was the views. I splurged on a room with a view. Do you know how nice it was to leave the sliding door open and watch the sunrise or sunset on the harbor? I even loved the guy who stepped out on his boat one afternoon to play his bagpipes.
9. Portsmouth, NH
Right up there with Portland, Portsmouth is another perfect small New England city if you’re looking for the amenities without all the hustle and bustle. Only a quick ride from Boston, you can enjoy boutique shops, great bars and restaurants, historic architecture, and water views.
Then again, I might have loved this town because the first place I stumbled upon was a bookstore...that also had coffee and cocktails. Seriously, if I had a place like that near where I lived, it would probably be the only place I’d go.
10. Boulder, CO
Oh, mountains. Thankfully, I’d visited Boulder a couple of times because my workplace at
A quick 10-minute drive, and you can easily head to the foothills for a nice hike and beautiful views. I loved Boulder because there was a ton to do and the energy always made me feel lighter (or maybe it was the altitude). I especially liked it because I rarely get to see mountains, so having them peek out (pun intended) from every direction made me stop and pay attention.
Also, you’re a quick drive to other neighboring cities like Denver, Fort Collins, and Estes Park. Not to mention, all the wonderful outdoor recreational activities if you like to get out and enjoy nature.
Listen, making this list was tough, but I had to narrow it down, otherwise we would be here forever. Although I didn’t do a writeup of the following cities, they’re also worth considering for your next trip:
Asheville or Black Mountain, NC
Traverse City or Leland, MI
Now that I’m done writing this, all I want to do is visit all these again. Drop me a note if you’ve visited any of these places, I’d love to hear your experience!