Five Cities That Deserve a Second Chance

Travel isn’t always rainbows and baby camels. 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 chance.

 Parthenon, Athens

1. Athens – I can’t believe that I actually listed Athens since not only did I not like it, I kind of hated it as I expounded upon in this post. A look at the facts though will explain my dislike. We were on a cruise (stop laughing) and had already visited a few of the idyllic Greek islands. Santorini is small, serene and shockingly beautiful, as are most of the other islands. That’s why pulling into Athens can be a bit of a culture shock. My impression of Athens was a huge city covered in soot and grime, encircled by a halo of smog and populated by thousands of pickpockets who wanted nothing more than my credit cards and cash. Standing high above the city on the Acropolis I wasn’t filled with awe and wonder, I was filled with disgust. It was swelteringly hot that day as we tried in all earnestness to explore the city and discover its hidden, very hidden, good side. We never found it and instead walked away very disappointed. Friends from that ship experienced similar emotions and a few even had their valuables stolen. As the ship pulled away from port I bade the ancient metropolis farewell, vowing never to return. Since then I’ve talked with a lot of people most of who share my opinion, but not all. There are some fervent Athens supporters out there and that makes me believe there must be something, no matter how miniscule, that can redeem this seemingly lost city. So while I may not be excited to do so, I am willing to return, briefly, to try to find this well disguised beauty in the city of smog.


Circular Quay, Sydney

2. 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. When we visited Australia the schedule was tight and only allowed for two-days in the glorious city on the bay, Sydney. We did a lot, explored the Rocks, walked the bridge and of course took a thousand photos of the famed Opera House. When our 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. Later during that trip I spent five days in Melbourne and fell in love almost instantly, which again made me think back to 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.


3. London – I have to say from the beginning that this may be a lost cause and it’s probably all my fault. When I first visited London it was at the beginning of a summer of travel around the UK. I spent a few days there, suffering the entire time from jet lag and exhaustion. That first day I pushed myself to see and do as much as possible, from Bloomsbury to watching Parliament in action. When I left for experiences further north though I was happy to leave. Since then I’ve returned to London a few times and although I’ve never had a bad time per se, I never once was sad to leave and not once have I had a strong desire to return. I’m chastised all the time by other travelers for my general ambivalence towards London, and I admit it’s strange. I’ve enjoyed everything I’ve ever done in the city, I’m a diehard Anglophile and a student of English history and yet, London does not do it for me. One problem may be that I’ve never seen the city except in a state of befuddled jet-laggyness. As a result, I’ve always been short-tempered and impossibly cranky while sightseeing. In order to determine once and for all whether or not London and I are meant to like each other, I need to spend a week or more only in the English capital and hand myself over to it lock, stock and barrel and see what comes of it. Only then will I be able to pass final judgment on the city that Wren so lovingly rebuilt.

 Toronto skyline

4. Toronto – I’ve explored a lot of Canada lately 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.” The root of my wishy-washiness regarding Toronto is the fact that the one and only time I visited was on a work trip. Now, this wasn’t my current job, but my old, soul sucking occupation so of course I didn’t really get to see the city. My initial impressions were of a very business-minded town, with lots of skyscrapers and not a ton of personality. Since then I’ve met a lot of people from Toronto and they have assured me that this is indeed not the case. They have tried to convince me that while Toronto may be large, there are plenty of neighborhoods with personality and lots to do for any style of traveler. I readily admit that I didn’t see the city in the way it should be seen and it’s not that I don’t like it, but I don’t know it. Toronto is the perfect candidate for a second chance city and given how much I love other areas of Canada, I can’t imagine I won’t soon fall in love with Toronto as well.


5. Ghent  – Ghent is often called Bruges’ ugly sister, whether that’s fair or not is not for me to say. Located in Flemish Belgium just a short train ride from Brussels, Ghent often gets a bad rap. One morning while staying in Brussels we took the train out to Bruges early in the morning for some sightseeing. Bruges is one of those classically European cities oozing with old buildings, delicious food and more charm that one place should be allowed to have. If Disney could recreate Europe, it would all look like Bruges. That’s probably why I was disappointed when I stepped out of the train station in Ghent and was met with grey skies and grey buildings. We walked into what we thought was the middle of town, saw a nice market and some pretty churches but nothing that really took my breath away. The problem here was my lack of planning of any kind. I did no research and instead relied upon locally provided tourist information to guide the way. Sometimes that works and other times, such as in Ghent, it fails. I left disappointed and a little sad that I didn’t enjoy the city. Since then I’ve seen amazing photos of the city, a city I never saw. It proved that I missed something and overlooked key areas of the city that deserve exploration, especially for a casual tourist. I failed in my duties as a good tourist and I want to redeem myself by visiting again and this time seeing everything that makes Ghent great and not just grey.

These are a few places I want to try again, what are some of yours?

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.

40 thoughts on “Five Cities That Deserve a Second Chance”

  1. This is an interesting topic and makes me think about places I should give a second chance to. Chile comes to mind, after having a wonderful several weeks in Argentina, it just could not measure up. It is interesting to hear your thoughts on Sydney versus Melbourne, as I had the opposite experience. Sydney was the first stop on our first RTW, so it holds a special place in my heart. Melbourne is a city I would love to give a second chance to – I would love to explore the food more and I would love to go there when they are not experiencing such tragedy, as we toured during the 2009 brush fires.

  2. London is a great city, but I agree it can be tiring. As you said, it might have been your mood at that time etc. Try to take it easy next time and spend some more time here. It is a city of many faces and it can amaze you very easily.

  3. I did not like Madrid the first time I was there. The airline had screwed up my trip that I was not in a good mood when I got there. I have been back two more times and really like it now.

  4. I remember my first visit to Lima, Peru. I thought it was so dirty, with no rain, all the windows looked dark and overcast. But my last visit to San Isidro area of Lima, I ended up loving it! So, it is always good to give a second chance!

  5. I hated Sydney the first time and loved it the second. The experience you have in a place and the amount of time you have to explore has a lot to do with it. I’ve just returned from several months in Canada and, like you, loved Montreal and Vancouver. Toronto as a whole I just found ‘okay’ but if you do return and want to visit a quirky, non-businesslike area, head to Kensington Market!

  6. We just visited Toronto this summer, my first trip to Canada. I absolutely loved it. But like you mentioned, everyone keeps telling me I need to see Montreal. Dublin is one I needed to visit a second and third time to appreciate. Love it now! I definitely want to go back to Kuala Lumpur and more of Malaysia. We got there half way through a month long trip in SE Asia and I really think it was more our exhaustion and need for a bit of rest than it was the city. We didn’t have the best time, but when I see other posts it looks like we missed a lot there. Great topic.

  7. Like you I had only a short time to explore and really should give it another chance to impress. Again, like you, I had more time in Melbourne and fell in love with the city. It’s a great place. Perth is another antipodean city I enjoyed. Next year it’s off to Darwin but I shall be exploring NT more than the city. Perhaps I should take time to get more acquainted with it. Thanks for a great post

  8. I think Amsterdam should be on your do-again list, Matt:) It’s such a cozy and fascinating city when you go further afield from the train station. One of my favorite cities on the planet, possibly second only to London.

  9. A very interest perspective and unique post. I guess I won’t be rushing off to Athens any time soon. I really liked London, but was also rushed and would have liked more time there. Been to Toronto many times. It does have a lot to offer if you can look beyond the CN Tower, but I do think Vancouver has an edge in terms of it’s natural beauty and also the people seem more friendly than in Toronto. Often, I think one just needs enough time to explore and dig past the major tourist attractions to really get a feel for what a city has to offer.

  10. I fully agree with what you say about Toronto. I had the same opinion until recently. I’ve spent the last 3.5 years living in the city and there are plenty of great communities and restaurants to discover. Part of the issue, in my opinion, is that most people probably spend all of their time near the major tourist attractions, which are located close to the financial district.

  11. We’re sorry that you didn’t have a great time in Ghent.
    As you mention, Ghent is sometimes called Bruges ugly sister, but you know, the ugly sister is usually a lot more interesting than the pretty one ;-)
    If you let us, we’ll show you not only a beautiful but also a quirky, fun and authentic city. Give me call, a tweet or just reply to my e-mail and we’ll make this happen!

    Nathalie Dumon @visitgent

    1. Just wanted to say that this post / offer to help show off the best of your city is great, even though not directed at me …. It also made me click through to see what I could find out about Ghent … a place I’ve never even heard of! Thanks for piquing my interest!

  12. I have promised myself that I will return to Paris. Why? Because I HATED it there (sorry, Paris-lovers!) I spent two weeks there in the summer of 2010 and had a fabulously awful time. I now credit my own terrible attitude and my over abundance of, well, ‘plans’. I will return with a better outlook and a more relaxed schedule. Or, really, no schedule at all.

  13. Very interesting post, and shows how subjective and personal travel is. Let’s face it the mood you’re in, weather, who you are with and what you choose to do with your time have a big role to play – along with pure chance. I’ve disliked places that I can only imagine would win me over if I’d met a local person or had different expectations and there are very few places I don’t want to go back to.

    As a Londoner I have to admit steam comes out of my ears when people say they don’t like London as it is a huge city which serves as such a melting pot of everything in the world in one place, because of the huge amount of variety to dismiss it as people often do frustrates me – I get the best Cambodian food I’ve ever eaten (and I’ve been to Cambodia) right by my house in Central London and there are a million quirky experiences like that here! Please give London another chance :-)

    Funnily enough I really love Ghent and have returned a handful of times, preferring it over Bruges and to Brussels too. But then when it comes to cities I like the underdog!

  14. My two cities that I ‘hated’ are Quito, Ecuador and Santo Domingo, Dominican Republic. Both cities are big, dirty and full of crime. Not places for young, blonde, solo women to travel. However, I would give either place a second chance if I had a travel companion! I believe there is much to be loved in both of the cities … I just won’t love them alone!

  15. I want to try Cape Town again. It was a beautiful city and I saw some amazing things there and in the vicinity; but I was feeling sick for much of the time I was there, so I wasn’t able to enjoy myself like I should have, and that has tarnished my memories of the trip. Also, it was raining on the day when I took the ferry to Robben Island, and due to the overcast and fog, I was robbed of some of the most spectacular views and photo opportunities of Table Mountain and the city. (That weather also made my return ferry ride very choppy and scary.). Finally, the aforementioned illness caused me to crash out at 9 pm on a Thursday night and miss the chance to go to karaoke on the only night I FOUND a place that had karaoke in Cape Town — thus preventing South Africa from being included in the 26 countries to date on my World Karaoke Tour.

  16. Great topic and read.. As a relocated Spaniard, born and breed under Alicante’s blissful blue skies, currently on his 12th year of Anglo-Saxon London life, I feel I have to share my views on two of the cities you want to visit again, and hopefully persuade you of doing so.
    I remember my disgust and disappointment when, in the summer of 2000 I took a train from Heathrow Airport to Paddington Station. I did not like the city for the first few months, considered it as an ugly, dirty, unfriendly, soul-less city.. but after 12 years of coping with ridiculous public transport services and prices, unaffordable housing and grey skies, I don’t think I have ever loved a city as much as I love this one. Crossing Tower Bridge at night, walking down the riverside paths looking at the tidal rhythms of the Thames, admiring the vastness of London from the many hills across town.. or swimming in the Hamsptead ponds in the summer.. not to mention the neverending offer of whatever you are into and how much your experience of the city changes when you manage to work / socialise and live within a couple of hoods.. Please come back to London (and get a bike to explore)!!

    The other city I wanted to persuade you to go back to is Toronto, I was there last summer using the city as a stopover between my trips to NYC. I think I would have felt differently if my visit would have been under below zero temperatures, but it was summer and it was fantastically bright and sunny throughout. So, my advice if you are to give it a 2nd chance, is GO back in the summer, where you can go to Hanlas’ Point beach and simply enjoy Canada’s great outdoors. The best thing this city has is that it is so easy to get around and although the glass and concrete clusters are dominating the downtown, there are cute suburbs with lots of interesting stuff happening.

    Happy Travels

  17. I am the only person I know who doesn’t like Barcelona. I live elsewhere jn Spain and have always disliked Catalan attitudes and politics, which have greatly tainted my views of the city. Still, my parents are dragging me there tonight for Christmas. Perhaps the fourth visit will change my mind!

  18. Totally agree with you about Toronto! It’s a great place to live (at least for me), but not the best travel destination. There is just not much to do sightseeing-wise, and you can see the whole city with all the neighborhoods in 2-3 days even if you really take your time. In fact, I kind of feel bad for tourists coming here with great expectations and leaving disappointed.

    Another one of those cities for me is Montreal. Same thing – not much to do if you are not a foodie and don’t care about street music. I know this isn’t a popular opinion.

  19. PALERMO! People would not move out of the way for me as I pulled my luggage down the sidewalk, I was ripped-off by a shop clerk within a half-hour, the restaurant manager attempted to overcharge me that night, I felt unsafe at night, garbage was piled-up everywhere and people literally yelled at me from cars (blond hair, blue eyes, pale skin: I’m clearly not from there).

    The one redeeming factor: visiting the Capuchin Catacombs, which was creepy (in a fun way).

    Glad to see you’re giving Ghent a second chance. I thought it oozed charm: fun, kitschy shops, gothic architecture, people eating and drinking outside all through the day and a bizarre contemporary art exhibit in that cathedral, which was even more spectacular than the one in Brussels.

  20. I’m living Gent along one year.. I think you forget to see a lot of things of the city. It has their special palces but you have to know where…
    I’m still investigating all the places. I have a lot of photos, with the snow, raining.. Maybe it’s kinda grey but that’s the sweet thing of the city.

    I think you have to go here again. I’m planning to visit all the secret places of Gent and taking a lot of photos.

    Gent is special if you know where you can go

  21. Interesting post! I didn’t like Paris very much, even though everyone loves it. But then again my friend got robbed at gunpoint there, which definitely tainted my view of the city. Still, I just felt like “That’s it?” the whole time. I’d like to go back just to give it another chance.

    One place I did get another chance and still did not like was Sevilla, Spain. It’s beautiful to look at, but I consistently ran into unpleasant people and situations there, and did not like the more conservative element to the culture. It’s tough to like a place after that (sorry to Cat from above!)

    1. You know, Paris is now my favorite city but that wasn’t always the case. I was an exchange student there for a month in high school and for the first three weeks I HATED it. Everything about it. But then I spent a day on my own exploring and I fell in love. It’s weird how places do or do not click.

  22. I think we all have cities that we need to try again. For me, Barcelona is one of them. It never really caught me and drew me in like other places my the architecture was stunning, but other than that I wasn’t too impressed. I haven given up though and will be giving it another shot this upcoming year when I’ll be in Spain!

  23. I feel exactly the same way about London — I studied English literature, I love everything BRitish, but the city does nothing for me. I’ve visited three times and can never get into it. I return because of the shows/activities that are there, rather than the city. Edinburgh is, to me, the highlight of Great Britain.

    1. That being said, I have my own city I need to try again — Madrid. And everyone keep their fingers crossed , because I think I’m moving there for a year for studies.

  24. I completely agree with what you said about Sydney. I spent a month there visiting family and just could not get a feel for the place. The weather was nice, it was clean, the people friendly, the food great and I saw some beautiful attractions (Harbour Bridge, Opera Hour, The Rocks, Taronga Zoo, Manly Beach) but I just didn’t love it. I don’t feel the need to ever return.

    Melbourne, in contrast, I much preferred, though still not enough to return. Maybe I’m just not compatible with Australia?

  25. I’ve the same problem with San Francisco. We landed there after an amazing road trip through Death Valley and Yosemite and San Fran was just a let down at the end, reminding us we had to go back to city life at the end of our stay there. Not fair on San Fran at all, of course.

    And Barcelona – when I was there I had a dreadful cold and didn’t appreciate the place at all!

  26. Interesting topic. I need to go to Tokyo again. We just got back but didn’t have enough time to just wander and explore the different areas.

    I had a similar experience in Ghent. When we arrived it was cold and raining. I has heard great things about the city but didn’t see much of it. We ended up leaving and heading to Bruges a day early. BTW- we had great chocolate at a shop in
    Ghent across from the tourist info office.

  27. I’m touring the Greek islands now and spent a few days in Athens beforehand. I think it’s best to do it this way around rather than taking in the beauty of the islands and then heading to the mainland like you said. I appreciated Athens in a different way. More from the perspective of the more recent history and political dynamics with a bit of ancient ruins scattered in between. While I wouldn’t want to live there, when looked at from this perspective it becomes a dynamic and edgy city that has a lot to offer. Hope you give it another chance :)

  28. Hi Matt, I’m reading this article for the second time while in Toronto. I just don’t get it. We’ve spent the last 3 days exploring the city from end to end and I still haven’t found a neighborhood or section of the city that makes me want to ever return. I also LOVE Canada so I’m disappointed. Definitely give London another try when you have the opportunity. It is one of my favorite cities in the world. As a fellow picky eater I love how easy it is for me to find great dining experiences in London. Keep up the great work!

      1. And when back in Athens, try to see it through the eyes of a local and i am sure you will absolutely love the city. It is so vibrant, lively, with great neighborhoods, sites, galleries, restaurants, bars and coffee places and amazing museums that few hours visit cannot allow you to enjoy. I could help you with that next time you visit. But in any case, you should really give Athens another chance and i am sure you will change your mind…

  29. I’m glad I went through Europe when the only American import was Coca-Cola. I must admit technology has made travelling SO much easier, but some changes are making the original character of many charming places unrecognizeable. Progress for some?

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