I'm surprised someone thought Madrid was overrated... I consider it one of the great cities of the world... you were unlucky with the robberies, so your opinion is warranted to be altered...

I believe no city in the world has so many great day excursions OUT of the city as Madrid does... most easily reachable by frequent trains. (Segovia, Avila, El Escorial, Toledo, skiing in the mountains, Salamanca...and on and on) and now with high speed trains, you can take day excursions to Cordoba and Seville.

Whereas I agree with you as far as making judgments before actually visiting, I have been to Sydney (twice) and found it to be generally dull. I didn't, and still don't, get the hype. I left with the feeling that it's "exotic" enough to be kinda cool for non-adventurous travelers, but not so exotic as to be difficult to deal with. My first trip I was there for three days and felt like I didn't miss much that I had wanted to see (and I did do my research). I was even there during Mardi Gras so things were pretty jumping throughout the city. My second trip, I did the museums and whatnot and hung out at the beach. Honestly, I was living in LA at the time of both trips, and I could have done what I did in Sydney at home. At the end of being there, I went to Asia, which I found to be exponentially more interesting, fun, and worthy of visiting.

Every time I voice my opinion about Australia, people generally complain. How could you not like Australia! (I did) It's so exotic! (Sydney isn't) They have great beer! (I don't drink) Did you go to the Rocks?!?!? (yes, see previous) Note: I enjoyed Australia very much. People were friendly (less so in Sydney, more so in Perth), it was very pretty, and the ferry from the CBD to Manley is in itself worth a visit to Sydney. Exiting Sydney harbour has to be one of the best city scenes I have ever experienced. I just don't get the fascination with Sydney. It's a lovely place to visit, but given a choice, it would be quite far in the bottom half of places I would visit if I had an opportunity.

Overrated? I would say HNL. I enjoyed my visit very much, but I don't think that it meets the hype. Felt very Disneyesque. Less so near the North Shore, which is where I would crash if I return to Oahu. Again, exotic enough to feel like you went somewhere, but not so exotic as to be difficult to go to or be in. I admit that my feelings are probably skewed by the price. For the price my better half and I spent to go for five days, we could have spent three weeks in SE Asia. The luau was fun, though. Wish there were a few less obnoxious drunks, but I guess you find that anywhere.

LOOK, turns out I was right: there is NOTHING to do/see in Sydney
 

I just noticed in my Frommer's Australia on $50 a day book, that they rate all the attractions in places between zero and three stars.

the ONLY "three star' attractions in Sydney are the Opera house view, and the $165 "tour" across the big bridge. That's it for three stars "must see". Two stars: the aquarium and a wildlife part, and Bondi beach Dec-Feb only. That's it for two stars. Nothing else...

Compare that to London, Paris, even Los Angeles... Grow up, sydney-lovers.

The day trip to the Blue mountains is a 2 star. Other day excursions got NO STARS. There are a few one star attractions/monuments, but THAT'S IT. Seems that 1/2 day in Sydney should be just fine. And I'm thinking that might be even too much.

For some reason, Sydney has this terriffic hype, that I never bought into... I'll give them credit for a good P.R. promotion... the reality is there's virtually NOTHING of interest there for tourists.... still might be a nice place to LIVE, I don't deny that... but for tourists? come on... let's be honest about this.

Shanghai was definitely a let down for me and my wife a couple of years ago. I expected so much more and it really was nothing. We had to really scrape to find anything interesting about the city. Taipei was more interesting from about every aspect....and that city isnt a lot either.

I think the area that LA covers is part of the issue. I believe it is hard to find a city with as much to do in the area that LA covers. My wife is Thai and there is a great temple with a wonderful Thai food festival one sunday per month that gives you a really great taste of thailand right in LA along with a very nice Thai temple. It is not however right across the street from Unverseral or anywhere near downtown. Plenty to do in LA just got to spend all day in LA traffic to get to it. :D I like the city.

Don't forget that one (let alone a tourist) cannot survive in LA without a car. Sydney, on the other hand, has a very convenient and extensive train and bus network.

In defense of Shanghai
 

I have spoken to a number of people who have been to Shanghai on business, and they describe it as a soulless, sterile megalopolis, "a machine for business and finance," as one has put it. And I can certainly sympathize with that perspective.

But my experience has been completely different: my s/o is a Shanghai native, and an expert in modern Chinese history and literature. The Shanghai she has shown me is one of breathtaking architectural diversity, great cultural and literary traditions, and high social cultivation during many crucial periods of history. Shanghai has had many episodes of being international, cosmopolitan, prosperous, ultramodern, as well as having those great episodes snuffed out by wicked turns of history. One of Shanghai's greatest teasures lies within the souls of its people, who have developed a polis that has been at both the top and the bottom many times throughout history, and express it in public ways that are not always obvious at first glance. Their struggles and hopes are documented in numerous superb Chinese movies, such as Suzhou River, and Shanghai Dream. History has taken Shanghai once again to the edge of modernity, and the people Shanghai are very familiar with operating in this space. To say Shanghai has no history and culture is simply not true...Shanghai's history and culture is a succession of covering and then uncovering later. Shanghai is very much a work in progress, and the people of Shanghai make no apologies about it.

There is a nice museum below the Pearl Tower that contains numerous exhibits and beautifully constructed dioramas depicting Shanghai through the ages. I would recommend it to all visitors, so they can get a sense of where Shanghai came from, and that in many ways, Shanghai is picking up where it left off before the war and revolution. The Shanghaiese are very proud of their ascendancy, but also of their cuisine, dialect, heritage, and customs. They have risen the whole Pudong district out of nothing in just 15 years -- remember that when gazing out over Pudong from the top ball of the Pearl Tower, or from the 88th floor of Jinmao. And then go over to the other side of the Pearl Tower or Jinmao observation floors, and look at old Shanghai, by the banks of the Suzhou River, between the Bayer sign and the Lenovo sign...the contrast depicts just one example of covering and then uncovering later.

Toronto and Washington D.C. are definitely overrated. I thought Toronto would be a Canadian version of my home city (New York), but it was absolutely boring! D.C. is definitely boring as well; besides the Udar-Hazy museum near IAD and the Smithsonian, there is not much to do.

what's the udar-hazy museum???

I agree with those who voted for Sydney. Other than it's harbour scenery, there isn't much to do nor enjoy. Quite dull, boring, and uninspiring.

Auckland on the other hand is one of the most underrated IMO. Spend a couple of days there for a business trip in November and found it to be more charming, scenic, and friendly than Sydney. Pity that I did not have time to do any leisurely activities nor sightseeing. But to my luck, I'll be returning there again for another corporate assignment the end of this month and I'll have one full day to enjoy for leisure in between days of sales call. ^

Great food if you know where to go. World class museums. A park where you can rent a rowboat or spend the entire day watching people. A sense that the streets are where much of life is lived. A daily clock that lets dinners start late and entertainment end later. Day trips out of town if you want to leave. Sports teams with internationally known stars. After living in Madrid (twice while in school) I find it similar to New York in many ways.

Having now read this entire thread, I think a few posters are correct -- what you want/like in your 20s may be different than what you want/like in your 30s. Also, it's not just an age thing, it also depends what else you're dealing with/searching for at that particular time. Right now I'm feeling a little tired of cities and on my vacations I want to sit on a beach or at a pool or go hiking. But that doesn't mean I always hate cities, just that right now I'd prefer something different, with a little more nature and a little less noise.

By the way, I liked Sydney when I was there 12 years ago. I like some things about LA and don't like others. I now live in SF and find the homelessness and general downtown dirtiness to be really depressing (and I moved here from NYC).

Smithsonian Air and Space Museum complex near IAD
http://www.nasm.si.edu/udvarhazy/

San Jose, but it was never overrated in the first place.