Five More Cities That Deserve A Second Chance

Los Angeles, California

A little more than a year ago I wrote a post about five cities around the world that I needed to give a second chance. For a variety of reasons, my first visits to these places were not positive experiences and a few of them I would even go so far as to say that I hated. I didn’t (and still don’t) think that’s fair; I really believe that they deserved a second chance to experience them in a better way and I even managed to do that with two of them: Toronto and Ghent. My second visit to Toronto was just as disastrous as my first and I’d really rather not go back again. Ghent however turned out to be a wonderful do over. I spent several days in this Flemish town in Belgium and fell under its spell. It was great validation to my theory that perhaps one visit is not enough to accurately form an opinion about a new destination. So with all of this in mind, I decided to pick five more cities that I feel I need to give a second chance, to see what I missed the first time and figure out what exactly makes them loved by millions of others around the world.

1. Los Angeles – 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.

duomo florence

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.

Park Guell Barcelona

3. Barcelona – When I think of Barcelona the first word that comes to mind is, “ugh.” I’ve been through Barcelona a couple of times and aside from meeting a famous chef, I really didn’t care for the experience. It was hot, crowded and just an unpleasant place to be. The touristy areas were super-touristy, the likes of which seen only in a few places around the world. Part of that is due to the fact that Barcelona is a major cruise port, attracting millions of people every year (many from the US) to spend a couple of days before they set sail on the Mediterranean. I like cruises, but that many cruisers in one place was almost too much to take. I prefer lower key cities, with some but not too many tourists. Barcelona about did me in. Still, I think I missed something, I must have. So many people love it and I wonder what’s wrong with me? How can I not love what is purported to be one of the most beautiful cities in the world? Well, I’d like to go back and see if that might change.

Photo courtesy of of Christina Saull, My View From The Middle Seat

4. Chicago – I’m biased, mostly because my partner and many of my friends hail from the New York/New Jersey region. If you thought the ‘friendly’ animosity between the two cities is made up, it’s not and it’s almost entirely centered on food. Chicago pizza isn’t pizza, it’s a casserole of some sort and don’t even get me started on what they put on hot dogs. In spite of this prejudice, I have traveled to Chicago many times for my former job, even going so far as to take extra time to play tourist. I never understood what there was to do exactly. It reminds me of Toronto in that way. It’s a perfectly ok city, there just wasn’t a whole lot to see and do. Yes they have skyscrapers and yes they have museums. But what is there in Chicago that would draw me in, want to visit on a vacation? Nothing that I know of, which is why I’m open to the idea of going back to see if there is indeed some hidden attraction or endearing quality I have missed.

Seven Dials Covent Garden

5. London – Ok, this is a holdover from my first list for a couple of reasons. One, I haven’t had the chance to return and give it what ultimately would be its third chance and second, my partner and I have a trip planned to London in May. 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 this next time will be the best, at least I hope so. We are staying at a fabulous hotel, we have tickets to a show and plans to do a lot in and around the city. It’s going to be a packed but fun few days and I do believe that this may be the time I actually come to not loathe London.

What are some cities you would like to revisit, to give a second chance?


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.

18 thoughts on “Five More Cities That Deserve A Second Chance”

  1. I hope you get the chance to rediscover these cities!

    I traveled to Cuenca, Ecuador last July. It’s a lovely city, and I did have a good time, but something was missing. I’d always been really excited about other locations, leaving feeling inspired. But, I’m not sure I felt that way about Cuenca. Maybe I’d gotten tired of being part of a language program, adjusting my desires to those of the group. Maybe it was the gloomy weather and the cold. Whatever it was, I was not completely moved. For that reason, I’d like to go back one day, to truly explore the town and give it my all.

    I’ll also add Panama City to that list. I only spent a few hours there, so I didn’t see much.

  2. I would love to go back to Hong Kong and visit the outlying islands. Apparently the life is totally different from what you see and experience in Hong Kong (island).

  3. I feel exactly the same about Chicago: it’s a big city, and it’s a perfectly fine place, but there’s nothing truly exciting about it. London and LA, though? Both are fantastic and some of my favorite places. But they take time to get to know.

    1. I feel the same way about Chicago. It’s a fine city but it wasn’t love at first sight for me (like NYC and London).

      One needs to spend a good deal of time in one place to really appreciate a place, especially big metro cities.

      Personally I don’t know how any tourist would like Los Angeles if he/she only goes to Hollywood sidewalk, Universal Studio, Disneyland, Santa Monica, and Observatory. LA is so much more than the tourist traps. Since there’s no public transit and driving time is long due to traffic day and night, LA becomes this superficial city that most deem overhyped.

      London, Paris, and NYC don’t have the same problem because of the underground/metro convenience.

  4. I have been to London on a number of occasions and whilst it satisfies my need to travel if I go down for a day or two, I couldn’t spend much longer there. I just can’t bring myself to love it the way so many other people do. I want to give Boston a second change… of the few days I have spent there, the main thing I remember is a Thai dish that I had at a little restaurant behind the cinema where we went to The DaVinci Code with protestors outside… I don’t think that should be anyone’s main memory from any city!

  5. I love that Florence is on this list. It’s a hard city for me, too — and I lived there for four months during my study abroad! I totally get what you’re saying about not being able to get your bearings. I arrived in August, and it was the end of October before I could make it from the train station to my apartment by myself! My school buildings were spread out all over the city, and I often had to call my roommates to have them come find me, as I’d gotten desperately lost somewhere!

    Besides never knowing where I was going, I feel like I didn’t really experience Florence the same way I did with other cities I visited. I’d travel every weekend and soak up as much as I possibly could in 3 days. But I never did that in Florence. I saw a lot of the museums with my classes, but I never experienced much on my own. I never even climbed to the top of the Duomo!!! I really didn’t love Florence when I was there, and I hated having to come back after each weekend trip. But with three years between me and that experience, I look back on Florence like it was the best time of my life spent in one of the most romantic, beautiful cities in the world! It’s at the top of my list of places I need to revisit with a different perspective and attitude.

    And by the way, I share your feelings on both Barcelona and London. Those were the only two cities I really didn’t like during my weekend trips. (Rome was a close third, unfortunately!) I’d definitely give London and Rome another shot, but I don’t think I’ll work too hard to get back to Barcelona any time soon!

  6. Speaking as a native Los Angelino… YES COME BACK. I do not understand why the city get’s such a bad rap, but one thing is true 3 days is not enough time, and a local connection can make the trip more enjoyable. Much of the LA scene is in small pockets and neighborhoods separated by a 20 – 40 min. drive, roaming around hoping to stumble on coolness does not work!

    1. I know, I know. :) I’ll try it again at some point, but if three days isn’t enough time to at least see a lot of a new city, that’s not good. Compare it to London or New York, both cities you will get a great feel after just a few days.

  7. I hated New York the first time I visited and actually thought it was a shoddy version of London. Looking back now I can see that was a result of poor weather, nerves about my first big trip abroad in years and an unsympathetic travel partner. The second time I visited four years later I LOVED it! The weather was better, I was more prepared for the trip and I went with my boyfriend who was great fun to be with.

    So much can depend upon the circumstances of a trip. I also think we warm to different places at different points in our lives. I hope you have a great time in London but if you don’t then don’t beat yourself up over it. If we loved everywhere we went nowhere would stand out or be special :)

  8. Hong Kong would definitely be at the top of my list.

    I’ve been twice; I disliked it the first time and just wanted to escape it the second. The only point during my visit where I felt like I was enjoying the city was when I went to the fishing village of Tai O and meandered around the town.

    I’ve met so many people who love Hong Kong and think that, if I actually spent a decent amount of time there, I would grow to love it as well.

  9. Janika – my partner and I went to Cuenca a year ago. We were both a bit underwhelmed also. We loved the rest of our trip to Ecuador, especially Otavalo and Quito. Cuenca was beautiful but lacked something for us. Not sure what. Maybe a return is in order.

  10. I agree about Florence. I thought I would be in love but not so much. Wanting to get our affair another chance ;)

  11. I agree with Florence. I spent four nights in Tuscany on my honeymoon and only dedicated one day to Florence. That was enough. It was pretty. It was…fine. I didn’t hate it but it certainly didn’t knock me off my feet like it does for so many people.

    I did really love Barcelona – but I went in January so the crowds were much smaller (but it was still in the high 50s and sunny). I don’t think it’s a city I would enjoy in the summer.

    And Chicago….well I have a love/hate relationship with Chicago. I lived there for five years and I think (aside from the cruel winters) it’s a very liveable city, but I also think that for tourists, especially those who don’t spend much time outside of downtown, it can feel kind of generic. And don’t even talk to me about deep dish pizza. Thankfully there was excellent thin crust, as well as an awesome array of international cuisines to choose from.

  12. I used to love New York (lived there for six months) and have been back to visit a few times. But every time I come back it’s more and more generic and boring. I definitely think it’s one of the most overrated cities right now (that could of course change back in the future). Los Angeles, on the other hand, is one of the most underrated. A lot of people I know slag off Los Angeles, even if they haven’t been there, it’s like people just don’t want to like it. I’ve visited four times and had a good time each time. I love driving so that helps. I also love nature, and when you can find such beautiful and diverse nature, so close to major city, that’s a great combination. I enjoyed driving out to Topanga Canyon for a hike and then down to Venice Beach to people watch, before having dinner in Santa Monica. Or the time we decided to find the ‘hidden staircases’ of Los Angeles, or when we did a one day trip out to Joshua Tree National Park etc etc… As for London, being a Dane living in London, I definitely understand when people don’t like London, it doesn’t seem like a friendly town, it’s noisy, the architecture doesn’t make much sense a lot of the time, it’s expensive. It takes effort, it’s like it fights you to test what you’re made of and you have to fight back a little. But once you find those little pockets around town, you get rewarded; the canal walk from Broadway Market to Canary Wharf; catching a great play (and not necessarily in the touristy West End); have a picnic on Primrose Hill with the great view of London; going for a walk through Hampstead Heath and perhaps end up in Highgate Village for lunch or perhaps a walk through Highgate Cemetery (where Karl Marx is buried); go to Freud’s old house/museum in Hampstead; a Jack the Ripper walk in East London; hanging out on a Sunday around Brick Lane and Colombia Road Flower Market; go to Neasden where the (apparently) biggest Hindu temple outside of India is located, also in walking distance from Ace Cafe – an old biker cafe in the middle of nowhere but where you can get great ribs and watch bikers come and go. There are a ton of opportunities depending on your preferences, but a lot them need to ‘be found’ first :)

  13. Hi from Boston. I love what you seem to be getting at; context is key. Your Florence story is painful. Bugging out like that is a nightmare . But it sure happens.Almost need to schedule in a bad travel day. I’ve come rely on research and shaping expectations. The vitality I crave when travelling isn’t bestowed on me. I need to adjust my attitude. World of difference. Hope you see another Florence.

Comments are closed.

I help you experience the best the world has to offer!

Please enter a valid email address.
Something went wrong. Please check your entries and try again.