6 Cities That Deserve Another Chance

Athens Greece

Travel isn’t always rainbows and puppies. Sometimes bad things happen and sometimes we visit places that we don’t like. I know, I know, there’s something good to be found everywhere; except when you don’t want to find it. Usually when I don’t like a new city or destination it’s because I was in a bad mood or something rubbed me the wrong way. I’m a fairly temperamental person and when I decide I don’t like something, I tend to never deviate from that idea. So in a spirit of reconciliation, I began to think of some destinations that I didn’t love but that I think deserve a second, or in some cases third or fourth, chance.

1. Athens
One of my earliest posts was one sharply criticizing Athens, what I routinely call my least favorite city in the world. In that post though I readily admit that my experiences in the city are very limited and started with a brief visit while on a cruise of the Eastern Mediterranean ten years ago. We had 10-hours in port and it was based on my experiences during that brief window of time that formed my entire impression of the city. But in travel first impressions really do matter and what I saw of Athens I didn’t like. At the top of the Acropolis I looked out and saw a city covered in a blanket of smog. Walking around town I found it to be dirty and disorganized, and friends of mine on the cruise were pickpocketed. I couldn’t wait to leave, but I also recognize that first impressions can be misleading. That’s why I was excited to visit a second time, again on a cruise. You know what, I didn’t care for it then either. I am though open to giving it yet another chance, although I’m not too eager for that experience to be honest.

Florence Italy

2. Florence
This is an odd city not to like, I acknowledge. On a list a dream destinations, Italy figures high and Florence even higher. It’s the city of the Renaissance, of art and beauty, in many ways it IS Italy. And yet, I had a lackluster time. Part of it has to do with my mood, I was in a bad one. My partner and I had a huge argument on the train ride down and were barely speaking during our day there. We luckily had a guide, otherwise I may have just given up and returned to our rented apartment in Milan. The walking tour helped and it was thanks our guide that we saw anything really. Florence confused me, I couldn’t get my bearings and barely found the tour guide in the first place. But the famous sights, the Ponte Vecchio, the Duomo, David, they were all fine, but they didn’t make me gush. They didn’t make me stand there in awe, desperate not to leave. No, I was quite ready to leave by the end of the day and I feel bad about that. I’d love to go back, in a better mood, and try to see if I can learn to like Florence like every normal person I know.

Walt Disney Concert Hall Los Angeles California

3. LA
I think my problem with Los Angeles was that I first visited it thinking that I would hate it. I even think that part of me wanted to hate it. That’s how intensely I personally don’t want to be identified with Southern California. I have no basis for this judgement and indeed everyone I know who lives in Southern California (well almost all) are wonderful, fun and pleasant people. So it must be movies and TV that prejudged the city for me, and I’m sorry to say that I let them get away with it. In my own defense, LA is a tough town to get to know and it takes a lot longer than a three-day weekend to discover the fun and quirky spots that make it fun to visit. Now that I have friends in the area though I’d love to return and try to learn this massive and confounding city.

Tower Bridge London UK

4. London
I really want to like London, honestly I do. I don’t know anyone that doesn’t go starry-eyed whenever the name comes up and I would love to have those same feelings for the city. I think that my next trip this fall will be my best opportunity to finally love the city, at least I hope so. I’ll be staying at a nice hotel, I’ll have lots of activities planned and it should be a great time. I also do hope that this is the time when I actually start liking London.

Sydney Opera House Australia

5. Sydney
Now before you start writing hate letters to me, hear me out. I do not hate Sydney, far from it. I even enjoyed my time there quite a bit. This post isn’t about cities I hate; it’s about cities that I need to try again. I’ve been to Sydney twice and each time it was a tight schedule. I did a lot, explored the Rocks, walked the bridge and of course took a thousand photos of the famed Opera House. When the plane left its terrestrial embrace though I wasn’t filled with a desire to return anytime soon. I felt mildly frustrated that I couldn’t get past the tourist veneer and while I enjoyed what I saw, the city and I never clicked. Contrast that with Melbourne, one of my favorite cities in the world, where I fell in love almost immediately. But it makes me wonder about Sydney. Why hadn’t I enjoyed that city more, why hadn’t we clicked? I don’t want to be disappointed in Sydney forever, so that’s primarily why I want to try it again. This time though I want to get out into the neighborhoods, I want to find hole in the wall restaurants and I do not want to climb the bridge. Sometimes a city is so famous and so well known that it can actually suffer from preconceived expectations. I think that’s what happened to Sydney and I and rather than write off this great antipodean city, I want to give it another go and reintroduce myself to her.

Toronto Canada

6. Toronto
I’ve explored a lot of Canada and I’ve enjoyed almost every minute of it. When people ask about Montreal or Vancouver, my eyes light up and I can’t wait to share my experiences with them. When asked about Toronto though, I usually give a weak smile and say, “Oh, it’s fine.” i’ve spent time there and I’ve really tried to like it as a tourist destination, but I really don’t think that it is one. I think it’s probably an amazing city in which to live with an incredible quality of life. But that doesn’t mean it’s fun to visit as a tourist. I’m willing to try again, but I continue to have my doubts.

What cities would you like to revisit?

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By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer. Also follow Matt on Twitter, Facebook and

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