The Most Overrated, Underrated, And Best Cities For You Visit, Live And Eat

Most people who would answer what cities they love, dislike, and even hate… probably haven’t been to them? I’m underweight cities in Africa but have been all over the world and have strong thoughts on the places I’ve visited. Been to most major world cities several times. And I thought I’d take a stab at tentative, reductionist thoughts describing them.

It’s not enough to go to a place once and develop more than a contingent view. Every city has both positives and negatives, and you may experience more of one or the other on a given visit but that doesn’t mean you have a full sense of the place.

If you don’t like someplace, other than Chicago and Boston, you should probably go back! That way you can discover more about it, and find the things that are good there and that others appreciate.

  • Most Overrated U.S. Cities: Denver, Chicago, Portland, Boston
  • Most Underrated U.S. Cities: Los Angeles, Falls Church
  • Most Underrated World City: Singapore
  • Best World City: Tokyo
  • Saddest World City: Hong Kong
  • Greatest Flawed City: New York
  • Cities I Still Need To Visit: Ashgabat, Pyongyang, Tehran, Riyadh
  • City I Most Want To Live In: Austin

New York is badly run, and politicians make excuses blaming others for its problems. It’s too expensive to live in too little space. And yet it brings together large numbers of exceptional and ambitious people – a cluster that makes it where you want to be for the greatest shot at success in many industries. (Sure, the Bay Area still for tech, LA for entertainment, and Boston for biotech, but otherwise New York.)


New York City


New York City

Los Angeles isn’t underrated by the people who live there, they pay a lot to live there, in housing costs, taxes and regulatory expense. But is there a better city in the country for ethnic foods? New York is good for some foods, and so is Houston, but LA is rather unmatched.

Although if there’s a city in the U.S. that comes close for ethnic foods, surely it is Falls Church, Virginia – with its Eden Center (go to any Vietnamese restaurant in the interior corridors); Elephant Jumps (still probably the best Thai restaurant in the United States); and cluster of Korean places in nearby Annandale?


Elephant Jumps


Elephant Jumps

Singapore is also underrated because it’s too often derided as sterile, because English (Singlish) is spoken, and because it’s so accessible. But it too is one of the world’s great food cities at both the high and low end, and it’s incredibly well-run. The smartest people are often part of the bureaucracy there. Where else is that true?


Singapore Hawker Center

Tokyo, too, is one of the world’s great food cities. It has New York’s density and excitement. And as an outsider I’m always amazed.


With Takashi Ono at Jiro Roppongi

Sadly, Hong Kong is a place I watch slide from the perch on which I used to hold it as it turns to the mainland and squeezes the freedoms of its own people – jailing dissidents for speaking out about their city’s future with retroactive application of ‘national security’ laws that China committed would never be applied retroactively, and which renege on commitments the country made when Hong Kong was handed over by the British. “Do You hear the people sing,” by the way, is banned in China.

Denver is cold. Traffic is a nightmare. Food is overrated. The airport is too far away – and you’re too far away even when you reach the airport because you have to go through one of the worst security screening setups and take a train to the concourses that may not work and there’s no walking alternative. Have you ever stayed in the soulless Tech Center area? It’s far worse that the suburbs of the DFW Metroplex.

Chicago is colder still, what’s the line, that a bunch of New Yorkers said ‘Gee, I’m enjoying the poverty and crime, but it just isn’t cold enough. Let’s go west?” Meanwhile Boston has all of the downsides of New York and Chicago, but without the food.

On the subject of overrated, I haven’t ever really connected with ‘Major Western European Capitals’ although that’s probably not true of London which has become underrated while Paris and Rome are overrated and Berlin, which was underrated 20 years ago, is now probably properly rated.

Vienna is incredible, but I wouldn’t want to live there though I’ve been attached to it since Richard Linklater’s 1995 classic Before Sunrise where young American Ethan Hawke is traveling Europe and meets Frenchwoman Julie Delpy on a train. They disembark together in Vienna and spend the night talking, walking the city, and falling in love.

At the end of the film they don’t exchange numbers. Instead they plan to meet up again in Europe in six months, and the film ends leaving viewers wondering whether they actually do (a question that’s answered 9 years later in the outstanding Before Sunset).

I’ll suggest that Toronto is one of the most underrated cities in the world even though it is cold and that Vancouver is excellent as well.

Amsterdam is way too crowded in the summer but when weather is less pleasant and tourists clear out it’s fantastic, walkable, and one of the best brunch cities in the world. Surinamese-Chinese food is a thing there, and much better than you’d imagine (or as good as you’d imagine). And fish! Pickled fish! Meanwhile, what frequent flyer doesn’t love stroopwafels? But boy they are so much better when they are freshly made and not packaged.

Austin is where is dream of living… which is why I live here. I moved from DC after 18 years, having ‘done my time.’ We chose Austin became we like it. It was ‘too popular’ a decade ago when we made that decision, and has become more popular since. Things have changed somewhat, with New Yorkers and Californians bringing a reservations culture to restaurants (you no longer just walk into all the top places). Outside of barbecue none of the food is world class – but it’s the world’s best barbecue, and everything else is above average. While we have good North Asian food we’re lacking in Southeast Asian.

People complain about (3) things in Austin.

  • High real estate prices because it’s expensive for Texas. Zoning and cumbersome processes within the city limits make it expensive to build, and people want to live there. But it’s not expensive compared to the Northeast or to Northern and Southern California.

  • Traffic There are certainly streets that are busy at peak times, but nothing again compared to the Northeast. I moved here and thought the traffic was downright civilized compared to the 495 Beltway at the 270 Spur around 5 p.m. on a Thursday.

  • Heat in the summer but we don’t have super cold winters, and Austin is in Central Texas. It’s not humid compared to Houston or for that matter D.C. which is built on a swamp. I’ll take 100 in Austin over 90 in D.C. any day.

No place is perfect, but I chose to move to Austin because I found it the most livable. There are more days of sunshine and plenty of parks and outdoor activities. When I first moved here there weren’t a lot of ‘great’ restaurants outside of barbecue but everything was above average. And there was culture, too, in the form of music (for which it’s known) and experimental theater. I viewed it as being like San Francisco dropped in the middle of Texas with a compact downtime and all of the administrative benefits of not being in California.

When I moved here it seemed like ‘everyone was moving to Austin’ and Jon Stewart did his show from here for a week. He covered ‘the immigration problem’ and sent a reporter to the Austin border. One ‘man on the street interview’ subject remarked that Austin was nothing like it was when they moved here six days ago.

And yet it was still underrated. Now it is probably fairly rated, although problems are starting to show. High housing prices reveal political limits to housing construction that drive up costs, a City Council that meddles in the airport and slows development, and rhetoric that is anti-police yet offers some of the most egregious contracts to police in the nation (yet delivers poorly on service).

So what does it mean to be a great city, for more than just a visit? It varies by the individual and what they are looking for. But some that are important:

  • Food matters to many, but what kind of food matters will differ. Austin is a burgeoning food city but we’re poor in Southeast Asian cuisine.
  • Weather matters, but are you looking to avoid too cold (like me) or too hot?
  • Taxes matter if you have money, regulation matters if you’re in business or looking for a job. Texas is one of the more heavily-regulated states for occupational licensing.

Ironically for an energy-producing state, one of the top issues here in Texas is the electricity grid – which comes down to an increasing demand for energy that isn’t met by sufficient growth in supply (mostly a function of federal rules).

There are of course many cities in the middle! I am torn over what I think of Bangkok, I love much of it but it’s not among my top.

I enjoy my time in the Mideast but the cities aren’t my absolute favorites in the world. Doha is worth about 48 hours in my view, go see the Museum of Islamic Art.

There’s nowhere I fall in love with in Africa, but also nowhere I’ve spent enough time in for me to actually say I hate. Maybe I ‘hate’ Mumbai, for its slums, nowhere was I sadder or angrier than the time I spent there – angry at the policies that keep people in poverty.

One question I left off is where I feel ‘most at home’ and that one was tough for me, I’ve never quite felt like I fit in anywhere. I was torn between Northern Virginia (where I lived longest), Austin (where I’ve chosen to live now), and Sydney (where I’ve probably visited most, for family). Anywhere I go though I always feel a little bit like an outsider. I keep leaving to go other places!


Sydney

How would you answer these questions yourself, and which takes of mine do you think are most right or wrong?

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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Comments

  1. Gary
    How can you not include Lima in this conversation, when a large part of your ranking is food.
    Best food city

  2. I would say that Chicago is one of the most underrated major cities in the country. I guess it sort of helps with house prices even in the nicer parts of the city (but then there are the high property taxes to catch you on the other side).

    Most Overrated U.S. Cities:
    Most Underrated U.S. Cities: Chicago, Washington (DC)
    Most Underrated World City: DC
    Best World City: DC or London
    Saddest World City: Cairo
    Greatest Flawed City: New Delhi

  3. One thing most important, after climate and scenery (urban and rural) are the people. I prefer visiting places where the people genuinely like Americans and have a positive attitude. If offshore people don’t like me as an American or are usually brusk and sometime downright rude, I do not care how good the food is when the local atmosphere is negative. I have found a second home in Cambodia where the people are smiling, many impoverished and under continuous rule by the same family for decades. No place is perfect.

    After spending cumulatively more than 12 months there in the past few years, it is a joy to converse with the locals of all social strata in English which many know. (The U.S. dollar is the major currency.). In Siem Reap crime is negligible, scenery outstanding in many national parks, and the food is quite good. Farm to table is the norm.

    Angkor Wat is a major draw, and continues to amaze, though the huge Tonle Sap (which is filled by the Mekong in the rainy season, and then is drawn down in the dry season) and Preah Vihear on the border are equally amazing. The latter has a 2,442 steps beginning in Thailand and ending at the entrance to the temple on the top of a bluff, looking over miles of northern Cambodia.

    Most of all, a genuinely sincere friendliness pervades most of the country. Sihanoukville dominated by Chinese and the capital Phnom Penh are worth visiting but not for extended stays. The memory of the Khmer Rouge lingers after 2 million were slaughtered as a result of the Nixon-Kissinger indiscriminate bombing and intervention in local affairs. The people have not forgotten, and they are not bitter, by living in the past.

  4. You’re a courageous man for doing this list, knowing what criticism you’ll provoke. The nicest comments will be the ones that propose a new list, completely different from yours. I respect you for posting this, but you’re a braver man than I.

  5. I think it is up to the person or persons to where they want to travel. Everyone has that special place around the world they like,but there might be new places to see that would interest any traveler

  6. I recently fell in love with Norwich, England. It has a wonderfully preserved Medieval/Tudor center with half timbered and ancient stone buildings, plus a stunning. Norman cathedral daring from 1101. Norwich is friendly, beautiful, and brimming with unique shops, restaurants and English charm. It’s perfect to experience an authentic English city with few tourists or tourist traps. The most underrated city in the UK, in my opinion.

  7. Oy. I always enjoy reading you, mostly because you call AA out for all of their flaws. But even as an ex-Austinite, you lost all of your credibility here.

  8. Someone actually selected the DC swamp as “underrated” and one of the best cities in the world. Unbelievable! That place is an absolute dump and is occupied by some of the worst people on Earth.

  9. James N could perhaps share with us where he has lived and tell us his idea of:

    Most Underrated U.S. Cities;
    Most Underrated World City;
    Best World City;
    Saddest World City; and
    Greatest Flawed City.

  10. So Chicago’s overrated? Fine. We don’t want you here anyway, especially if you’re from New York or Boston.

  11. Chicago is an amazing city. Frankly, your completely cliched and non-specific criticism of it calls the rest of your entires list in question.

  12. People are such wusses about the cold. Happiness studies consistently show that happiness doesn’t vary with average temperature but people utterly fail to internalize that so they end up in a mid-tier city (yes, Austin is mid-tier) convinced that it’s making their life better. If you’re willing to put up with some surface level angst/pain (which you should be, you’re an adult), you can get a spectacular deal living in Chicago. I know of no other place where the ratio of real estate price : city quality is so low.

  13. “Chapter 170A of the Texas Health & Safety Code prohibits abortions outright, except in certain circumstances. Section 170A. 002 prohibits a person from performing, inducing, or attempting an abortion. There is an exception for situations in which the life or health of the pregnant patient is at risk.”
    Would I want to live in a state that undermines the health of 50 percent of its residents? No, thank you.

  14. City I would most like to live in is Santa Barbara (although it’s too small to be a city).

    Yes, high taxes, earthquakes, occasionally loopy laws, but the weather and beaches are to die for.

  15. I’ve spent the equivalent of over two years of the last dozen in France. About three weeks of that was in Paris. I can get everything in other French cities I can get in Paris, but at a much better price with much nicer people. The exception is the museums (Musee D’Orsay, in particular). Still, I know people who love Paris. My attitude is not that they’re wrong, but that I can’t judge the accuracy of their assessment until I see _their_ Paris. The Chicago I visit is a wonderful place, despite the incompetency of the overlords. And, that is why lists like this are fun, but not something I’d use for travel planning.

  16. BTW, off point a bit, but the RATP will stop selling week and day passes for the Paris Metro from 20 July to 8 Sept. The one-use ticket goes from €2.1 to €4, with an equivalent increase for a carnet (€32 for 10 tickets). They have an option for Olympic visitors at €16 (1 day) to €70 (7 days). This would have no effect on most residents since they buy monthly or annual passes. Welcome to the Olympic$.

  17. Why the knock on cold weather places? Not everyone wants to live in swampy weather. In Chicago or Toronto you get 9-10 months of great weather while in Texas you get only 6 or so.

  18. One small correction: those New Yorkers said: “New York is cool, but it is not cold enough and there is not enough crime”. So they established Chicago…

    Given your roots, I am a bit surprised that you did not include Sydney! And as far as smaller cities go, I would say the most underrated by Americans is Cadiz, Spain. Its combination of architecture, surfing (at Playa de Santa Maria), scenery, history, and a huge selection of restaurants (almost only Spanish, very little international), along with the charming fact that almost no one speaks any English, makes it the place which I am writing this post from. Here for the fifth time, and just made AirBnB reservation for next year.

  19. In Africa: Cape Town (not as safe as it used to be but spectacular scenery and very affordable). Also Cairo for what it offers, though I wouldnt want to live there.

  20. Duluth, MN? That was a surprise to see mentioned here.

    I was just there earlier in the week and I am surprised that someone put it on the list. It’s much nicer than say St Cloud, and I like driving across the bridges between Duluth and Superior and all the water up that way, but to end up living there or being there around the year? I would like to see someone put forward that case.

  21. Love this discussion. I’ve been looking for a place that seems like home for decades. Checking out Spain (Costa del Sol, Costa de la Luz) in Sept.
    Favorite US city: Pittsburgh- culture, sports, food, medical care, recreation, walkability, transportation. And it’s beautiful. Could use more sunny days.
    I’d wanted to move back to California (Carmel) for years, but I’m over it. Internationally, same for Hong Kong. I’ll probably never see that harbor again.
    Excited to be making first trip to Australia and New Zealand in early 2025,
    Cosmic voyager, destination unknown.

  22. Boston and Chicago are not overrated – they are amazing places with so much to see and do and not as overpriced as NY/DC/LA/SF.

    SF should be #1 on the most flawed and overpriced list with garbage fees at every turn. Falls Church is not a city, it’s part of DC metro with a nice concentration of ethnic food.

    You are missing nothing in Africa.

  23. As soon as I read “except for Chicago and Boston” I knew your list would be a somewhat foolish one. Both cities have great food, fun things to do, great education, entertainment, museums. Boston has great seafood and Italian food. And for the most part, most of Chicago made me feel safer than other similar sized cities as I like to walk a lot in cities.

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