My Top Ten Favorite Cities

We’ve all felt it, that feeling when you visit somewhere and think: why am I not living here?! Maybe you’ll move there someday. Or maybe you and your dream city are just star-crossed lovers, always returning to each other, but never staying.

Certain cities just fit our personality. Is it big and bustling with towering skyscrapers, or is it peaceful  where you can rock on the front porch without a single car horn puncturing the silence? Maybe multiple cities as starkly different as night and day call out to you. Sometimes I think, “I need to live here in my 20’s” and other times I think, “I could definitely spend my final days here.”

I have a lot of opinions about a lot of cities, good and bad. It’s okay to not like a city. But this post isn’t about disappointments, it’s about the cities that have taken my breath away. The one’s I knew I would love and the one’s that took my by surprise. Here are my top ten cities and what I like to do in them, ranked in descending order.

10) Kilkenny


Kilkenny Castle

Kilkenny really fulfilled what I was looking for in Ireland. A country is more than a busy city or magnificent cliffs. It’s about everyday people. When I visited, I stopped in Kilkenny for a night between Dublin and Cork- both of which I also loved. Kilkenny offered an interesting history, it was beautiful to walk through, and the night scene was lively in a jovial way. I think my feelings are best described from my journal entry that day, May 16th, 2014.

“I of course was lost immediately off of the train. Just part of my process. Once I knew where I was, it hit me: I love this place. I have no idea why. The charm is intoxicating. Kilkenny is a medieval city and you can tell. It’s also a very family-friendly place; tons of adorable kids, (very) old couples, and teens in school uniforms messing about.”


Kyteler’s Inn

The top sights include the Kilkenny Castle which has a huge grass lawn where people lay out, Black Abbey from the 13th century, and Saint Canice’s Cathedral, which has a sitting Bishop. I recommend knocking about St. Kieran’s street at night to hear live music. Kyteler’s Inn is a great bar built around the legend of Alice Kyteler, considered to be Europe’s first “witch.” Also, try Kilkenny’s locally brewed red cream ale- it’s very good.

9) Chicago


Booze cruise down the Chicago River

I’m almost definitely biased towards Chicago because I grew up in the suburban outskirts. I remember taking the train in with my friends to pose in front of the bean, skate in Millennium park, and shop on Michigan avenue. I remember going downtown with my family during Christmas time to look at the Marshall Fields (now Macy’s) Christmas windows, see a show, and get deepdish pizza.


View from the John Hancock Signature Lounge

Chicago has a lot to offer: hearty food, good sports, a great night-life, and all the art and culture you could ask for. If you visit, I would recommend everything I nostalgically mentioned above. My favorite bar is the Signature Lounge at the top of the John Hancock building, where you can enjoy a spectacular view of the city. If you go late enough (11pm or later) you won’t have to wait or make a reservation. The Shed aquarium, the Science and Industry Museum, and the Natural History museum are great places for families. For a bit of art, I would go to the Art Institute of Chicago or see the Chicago Symphony Orchestra.

Sky Box in the Willis Tower

Sky Box in the Willis Tower

And, as I mentioned before, deepdish pizza. Always. Deep. Dish. Pizza.

8) Jerusalem


I went to Jerusalem during a short study abroad in college. It was an extremely enriching experience. Of course, it’s known for it’s tumultuous past and the current Israeli-Palestinian conflict. But it’s also a modern city with modern ups and downs. The mix between ancient and temporary is fascinating. Make sure to get a balanced view of your trip: don’t spend all of your time in West Jerusalem and the Old City. East Jerusalem has a lot to offer as well. Make sure to witness the separation wall with the poignant graffiti, pleading for peace.


You can also venture out to Jericho, considered the oldest city on earth where you can see the oldest known human-made structure: a 10,000 year old wall. The wall is basic but the gravity of its age will surely send anyone into a spiraling existential crisis. Empires have been born, risen, and fell. A thousand generations came and went. Entire civilizations crumbled to dust and were forever forgotten. Yet, there sits that tiny rock wall, oblivious as it all passes by. And who are we but a mere blink in the history of man? Yep. It’ll get to you.


Said earth-shattering pile of rocks

And of course, the Dead Sea is a marvel. It is the lowest point on earth and its salt content is so high that you float. It’s very fun to swim in.

7) Venice


View from the bell tower

Venice is a very unique city. There is something incredible about its winding, unnamed alleyways and canals with too few bridges that make the city a maze. The first night I was there, I went looking for the Rialto Bridge on the Grande Canal. I got lost and walked around for hours, unable to find the biggest bridge on the biggest canal! Of course, half of the fun was looking in all of the little shops and stopping for some delicious spaghetti bolognese.


I had some great pizza at that restaurant

Some of the top things to do are to visit the Doge’s Palace, the San Marco Basilica, and walk through San Marco square. I would also recommend going out to the smaller islands of Murano and Burano, which easily can be accessed by vapparetto. If you are looking for an awesome sight that is far less occupied by tourists, I suggest the Frari Church. There are huge, elaborate marble tombs seamlessly worked into the church.


Island of Murano

My fondest memories of Venice were the simplest. Sitting in a sunny square with a cappuccino, writing in my journal. Enjoying some gelato, hanging my feet over the water. Eating dinner by the canal, lit up by hanging lights.

6) Cinque Terre



Cinque Terre may be the most beautiful place I’ve ever seen. I don’t think I could live there for any extended period of time, the living is far too slow. But, if I needed to recover from some major life event or write a book, I would definitely consider Cinque Terre.


View from the trail

It is composed of five towns which you can travel between by tram. You can also hike between them for some of the most stunning views you can imagine. Truly breathtaking (the views and some of the steep hills). Cinque Terre is best experienced by living in the moment. There are no museums to wait in line for, no Basilicas named after saints. It is good food, nice people, and the beautiful coastline.

5) Washington, D.C.


Washington, D.C. is a take it or leave it kind of town. I love it but a lot of people don’t. I’m into politics and foreign policy so it’s a playground for people like me. But some find the aggressive Washington lifestyle off-putting. I don’t blame them. Living here is about committing to a lifestyle. Everyone here from the President to the night-shift office cleaners read the newspaper every morning and have an opinion on current events. Everyone I meet is sharp. And I love that.

There are two levels to Washington. The surface level is the well-beaten path of the tourists. Monuments. Museums around the mall. White House. Capitol Building. That’s not a bad thing, everyone needs to see those things in their lifetime. If you happen to be in D.C. for longer, get a second go around, or want to get off of the beaten path, there is a lot more to the city.


Georgetown canal

The deeper level has a lot to offer. If you are looking for a fun place to go out at night, you should consider Adam’s Morgan. This neighborhood offers a lively bar scene with plenty of live music. Also, no one does brunch like Washingtonians. Local 16 is a great option: $27 for an entree and bottomless mimosas. Plus, they have a rooftop garden. Capitol Steps is a very funny political sketch comedy group. All of the comedians have worked on Capitol Hill- so they know how to hit hardest. Maybe take the opportunity to get involved in politics. There is always a demonstration, a speech, or a fundraiser going on.


Hearing the President speak

Embassies regularly put on events. They have scavenger hunts, dinners, and fun activities that actually allow you to enter the embassies. Most require you to RSVP prior and have varying costs.

4) Prague


Old Town Square

Prague is a city I’d really love to know more. The cost of living is decent (but rising), the people are lively, and the city is beautiful.

The Old Square looks like it is straight out of a fairy tale. The Old Church looms in the background and storybook houses line the square. In the center is the famous astronomical clock. It is notoriously one of the most underwhelming tourist sights in the world. To get between Prague Castle and the square, you must cross Charles Bridge, easily my favorite bridge.


View from Charles Bridge

Prague Castle was cool but nothing beats the view from the gardens.


View from Prague Castle gardens

For an interesting experience, head out to Kutna Hora where there is a church decorated with human bones. Everyone reacts differently. One of my travel companions found it offensive and disrespectful. Another said it was freaky. Personally, I found it humbling and strangely comforting. We’re organic material, and eventually we’ll only be bones until we aren’t even that. Whether we rot in a coffin, are burnt to ashes, or decorate a tourist trap: who cares? We’re dead! There is no majesty in death, only life. So make this short time magnificent with as much love, laughter, and adventure as possible!

3) London



I love big cities. There are a million things to do. Restaurants and bars. Art shows and political demonstrations. Book signings and street performances. I lived in London for six months and barely scratched the surface. You could go to a different London restaurant every night of your entire life and you  wouldn’t get through them all.


Brick Lane

When you come up from the tube, every stop feels like an entirely different city! London is massive, diverse, and international. You could get lost in a place like that forever. I had an amazing time trying to sort through and understand what I could in my short period there.


Camden Lock Market

You can find the obvious places to go in a guidebook, or you could probably think of them off of the top of your head. For a fun bar, I recommend Waxy O’Connors near Piccadilly Circus. It’s a multilevel maze inside with a great atmosphere and usually has good live music. I recommend doing the Sandeman’s free walking tour of London, I learned a lot about each area of London. Brick Lane is a super hipster neighborhood that’s fun to walk through. I got an organic brunch in the back of a second-hand silver store (how random!). They also have a flea market that is about as flea as you can get. For a quality market, Camden Lock Market is a massive, permanent market.

2) Edinburgh


Inside Edinburgh Castle

Edinburgh definitely took me by surprise. I never thought I wouldn’t like it but I never expected to love it so much. It’s simultaneously modest and proud. There is a quiet dignity and permanence about it. It is mostly cobblestone streets and old stone buildings. It is remarkable how buildings that are hundreds of years old are used for such average purposes (office space?!). Yet the city is also lively and fun.

Scotland is a gorgeous country. Wild, windswept moors. Even the Romans couldn’t tame it.


View of Edinburgh from the Salisbury Crags

Everyone I met was extraordinarily kind and warm. The food was hearty and I just had to buy a cozy wool scarf. One of the rather unorthodox (in my American eyes at least) foods native to Scotland is haggis. You should try it and then look up what it is after. I got haggis deep fried the first time I had it- it was pretty good! It’s usually in a Scottish meal “haggis, tatties, and neeps” which is haggis, potatoes, and turnips. You also should take the time to do a whiskey tasting. Not a fan of whiskey, myself, but it was fun to learn about how it is made and where it comes from.


For a hostel, I strongly recommend the Castle Rock hostel. It is right next to Edinburgh castle (also a sight worth seeing) and it is cute, the staff is great, and there are activity nights. When I was there, I played in a beer pong tournament!

1) Amsterdam


Amsterdam is my favorite city in the world. The kind people, the easy going life style, the beautiful canals, and the liberal politics make it so perfect to me. You shouldn’t (and mostly can’t) bring your car, which I love. It is a great beer scene, which is my drink of choice. There is something so “come as you are” about Amsterdam that creates a feeling of acceptance. I dislike exclusivity. What’s the point?  I’m certainly not trying to impress anyone. If you want to be part of it, congratulations, you can be.


Vondel Park tulips

Amsterdam is best experienced by walking through it, dining by the canal, and biking the paths around the city. It has the Van Gogh museum, my favorite artist (like a million other people), the Rembrandt museum, Stedelijk Museum and the Rijksmuseum. Experience the tulips in Vondel Park.

Final thoughts

Well, that’s my list. Loving or hating a city is so much about gut instinct. Maybe it’s your goal to live on the road, but for most, planting roots brings contentment. Just make sure you don’t let old roots keep you from moving to your soul-city.

Which city is your star-crossed love?