Just for reference here is the largest US metropolitan regions:

Cities ranked by urban agglomeration population.
 
City Name
 Inhabitants
New York (NY) 21,199,865
Los Angeles (CA) 16,373,645
Chicago (IL) 9,157,540
    
Washington (DC) 7,608,070
San Francisco (CA) 7,039,362
Philadelphia (PA) 6,188,463
Boston (MA) 5,819,100
Detroit (MI) 5,456,428
Dallas (TX) 5,221,801
Houston (TX) 4,669,571
Atlanta (GA) 4,112,198
Miami (FL) 3,876,380
Seattle (WA) 3,554,760
Phoenix (AZ) 3,251,876
Minneapolis (MN) 2,968,806
Cleveland (OH) 2,945,831
San Diego (CA) 2,813,833
St Louis (MO) 2,603,607
Denver (CO) 2,581,506
Tampa (FL) 2,395,997
Pittsburgh (PA) 2,358,695
Portland (OR) 2,265,223
Sacramento (CA) 1,796,857
Kansas City (MO) 1,776,062
Milwaukee (WI) 1,689,572
Orlando (FL) 1,644,561
Indianapolis (IN) 1,607,486
San Antonio (TX) 1,592,383
Norfolk (VA) 1,569,541
Las Vegas (NV) 1,563,282
Columbus (OH) 1,540,157
Charlotte (NC) 1,499,293
New Orleans (LA) 1,337,726

Most fun I’ve had in the CONUS, to the point it scared me a little. I have friends that live in the area, and there’s NO WAY I could be that close to that much debauchery.

I like St. Louis, friendly ppl. Chicago, while big, has a lot of friendly nice ppl also, as long as you stay north of the Cell or Old Comiskey or whatever they call it now. I had a lot of fun on the North Side….. I also like Louisville, it reminded me of Grand Rapids, except the ppl were friendlier in Louisville. Cincinnati I had fun in too. People there seemed really nice and I found it easy to get around. Downtown Manhattan was fun, but then I knew ppl there and so all I had to do was follow them around, not try to find my way around. It was fascinating seeing all those ppl and going through Little Italy, Chinatown and all the other ethnic neighborhoods. They do everything much different there and it was fascinating to watch.

Cities I hate with a passion… Detroit. It is a huge crap hole and the ppl are nasty and except for where that stinkin new ball park is at it looks like a war zone. If they ever voted to cede it to Canada I would support it. Washington DC is unfriendly and the wheel set-up of the streets is a pain in the butt to navigate. I didn’t like Atlanta either. But, thats my 2 cents for whatever its worth….

Of the cities I’ve visited, my five favorite:

Boston
Minneapolis
Chicago
NYC
Denver

I think I would also really like Seattle, Portland, and San Francisco, but I haven’t made it out to those yet; I’ve heard good things about Pittsburgh but haven’t made it there, either. If you include Canadian cities, Montreal and Toronto would be up there with these.

Oh, and cities I’ve visited and absolutely hated:

Houston
Atlanta
Anything in Florida

Although I haven’t been back since the hurricane, no other city felt quite so perfect to me as New Orleans. The food, the music, the drinking and the male prostitutes….ahh, sweet. It was just dirty enough, just gloomy enough, just secretive enough, and just Tom Waits-ish enough to really please me.

And a strong second is Vegas. I dig it too, jch. I loved Vegas’ obviousness, and its openly gaudy, decadent demeanor. An excess of everything. More, more, more. Vegas doesn’t pretend to be anything other than its tacky, rock out with its cock out self. Love it.

I lived there for 2 years and I can’t wait to move back. I just like all the opportunities it offers. You’re never bored either. The only thing I don’t care for are the Cuns fans.

I really liked Ann Arbor, Michigan when I visited my sister there. It’s just such a charming little town. Not really much of a city, though.

For a real city…Boston is great, unless you want to drive around it. (And it does suffer from an infestation of Red Sox fans. ;-) New York is not as pretty, but it’s got an excitement Boston lacks.

I haven’t seen much of Chicago, but downtown is very cool, with all those drawbridges.

Least favorite US city…um, probably Newark, NJ. The people are very nice, but the city is dump, and a traffic nightmare. I’m not too wild about San Francisco, either. It’s beautiful, but I’ve found that in general, the people there are a lot ruder and a lot crazier than, say, New Yorkers.

I’m not wild about Atlanta, either. It’s a Kunstlerian nightmare. I vacationed there a few years ago, and stayed at a hotel downtown. It had a big sign outside advertising “the best salad in Atlanta.” So of course, my friends and I ordered salads for lunch.

It was probably the worst salad I’ve ever seen. A few leaves of brown, soggy iceberg, an unripe tomato wedge, and some shreds of carrot. With French dressing that had a distinct chemical flavor. That horrible salad is still a running joke whenever I see the friends I was traveling with that time. Somehow, the sheer audacity of serving something that awful while claiming it’s the best in the city just boggles the mind.

The restaurant made me really uncomfortable, and not just because of the awful salad. All the wait staff were black, and all the customers were white. I’m sure it was just the demographics of the area, but it kinda made me feel I was back on the plantation or something.

it’s in the middle of nowhere, but the downtown area is very nice

who puts LA on his list of “best” places. maybe i should start traveling more.

others:
savannah, ga
st. augustine, fl
burlington, vt
DC

“worst”:
newark
tallahassee, fl

I may go to Portland in a bit, but I really dug Nashville. My all-time favorite so far, though is San Antonio, Texas. I just really like the Texas-y-ness of it. Not the Texas stereotype, but theres actually a lot of diversity of opinion, upbringing, food, etc. in a relatively small area. And the riverwalk is one of the most atmospheric places I’ve been.

My top 5 would be: San Antonio, Albuquerque/Santa Fe (I split my time between the two, and loved them both), Nashville, Salt Lake City (but could never, ever, live there. Great place for a conference, though!) and Richmond. I don’t really have a specific order after SA.

Least favorite may be DC…there’s really no time where I’ve taken a deep breath and gone, “ahhh, Washington! Breathe! It! In!” but that may just be a factor of College Park. Pittsburgh also makes me kind of sad/heartbroken. I have yet to form a memory of Cleveland, and I’m writing this from the 216 right now.

Montpelier- the quaint capital of Vermont, great sledding hills in quiet forests

Kansas City- spent a weekend there one summer and had a blast, might have been more about the experience than the city, but it somehow had San Francisco-minus-the-bay feel

Philadelphia- think it is my favorite east coast city, lots of cool stuff happening but a whole lot more manageable (on bikes) than New York, DC and from what it sounds like, Boston.

Internationally…

Copenhagen, Denmark-
Prague, Czech Republic
Guadalajara, Mexico
Toronto, Canada
Sao Paolo, Brazil

ive been to more international cities than US cities. my wife and i have decided that seeing more of our native land is a top priority and plan on headin’ west for a while in the next year. that said, the best towns in America:

Brooklyn, NY. i might still be suffering from the contact high from visiting my brother-in-law there last weekend, which could be artificially inflating its ranking, but it really is a great place. it seems like a hundred small towns all clustered together. each neighborhood is different from the next, but just similar enough to maintain continuity. and there are like a million hidden little secrets that “you just have to see”. and its just a subway ride away from the heart of western civilization. and pizza.

Columbus, OH. i live here and i dont plan on moving. small enough to not suffocate you, but big enough to have a thriving arts and intellectual community. Ohio Theatre, Gallery Hop, the Newport, the zoo, Cabot Rea…we just need reliable public transit. and cages for the undergrads.

i also liked DC and Indy. Nashville, Austin, and Milwaukee are on my to-do list.

i really didnt like Boston. 3 separate cab drivers in a two day period gave me east coast bullshit for being from Ohio. fuck them. the Sam Adams brewery was nice though.

internationally, Florence, Italy is the tops. the whole town is on permanent vacation. and the architecture alone is enough to bring you to religion. London is great too. the greatest museums in the world and they are all free!

Here in Columbia, MO. I’m not gonna lie, it’s pretty much perfect for me. To be honest I’d kinda like to live out in the country… own a good bit of land, and be able to bug hunt all day long… :D

Some other cities I’ve enjoyed-

San Francisco- although I wouldn’t want to live there or in any city with a comparable population size.

not being much of a traveling type, and only having lived in 2 cities (Columbus, OH and Asheville, NC). It’s funny, I hated Columbus when I lived there as a kid but like it more and more every time I come back to visit the family. Case in point, I’ve been up here a week for Thanksgiving and have loved it, so go figure. As a comparison, I go to school in Charlotte. They’re right next to each other in terms of population and Columbus wins in a landslide. Absolutely no culture whatsoever.

As for Asheville, it was a lot better 10 years ago before it was ranked as the best place to live in every guide book in the U.S. But… it’s got beauty surrounding it that you can’t find much anywhere else. I love living outside of town in the mountains, it’s gorgeous. Definitely worth a visit for all you midwesterners.

small college towns are the best

worst: Tucson, AZ .. lived there for a couple of years … the traffic is brutal.

Likes:
New York
London
Cuzco
Arequipa
Chicago
Charleston
Lexington Va.
Boulder
Seattle
Ann Arbor
Yellow springs Oh
San Antonio
Santa Fe
Boston

Worst:
Columbus Oh
Oakland Cal
Waltham Mass
Boynton beach
Atlanta
Portland Oregon (Rain Capital)
Nashville
St. Louis
Any City in Mexico

Best Places I’ve lived:

Cincinnati
San Francisco
Boston
Madison Wisconsin
Phoenix
Oxford, Oh

Worst places I’ve lived

Delaware Oh
Urbana Oh
Marshall Wisconsin
Berkley Cal.

But this weekend, Dayton was like comfort food in municipal form. I had a wonderful time back home.

and I enjoyed it, except for the part where despite flying it took 14 hours to get from my friends apartment in Boston to my apartment in Ada. If you ever find yourself in Boston check out the Harpoon Brewery. They have a free tasting 3 times a day, you basically get all the beer you can drink in there period of time, and it is all fresh brewed on cite or in Vermont.

My favorite city is Chicago. I just love that town, I can’t get there enough, and I hope to earn my MA at Chicago Loyola if I can get in, and Roosevelt is my backup. I love the food, the art museum, music, 2nd city, and the just the feel of the city. The only problem is there are a couple of Cubs fans up there.

Pittsburgh really surprised me. I was expecting it to be dead inside much like Cincinnati, but it is actually quite vibrant, which is good since I spend about 1 weekend there a month with my girlfriend.

D.C. is a great city, I don’t think I need to cover anything more about it.

Milwaukee also surprised me this summer. Best German food ever in America is at Madre’s in Milwaukee. If you find yourself in town take a lakefront brewery tour, show up early and you can get a start on the basically all you can drink before the tour starts. It is only $6 and the tour is given by one of the two brothers who owns the brewery, who was shitfaced when he gave our tour. At about every stop you can fill up your cup, and you get a free glass for taking the tour.

I loved Denver. It is still a rising city, but it was amazing, I am really glad the DNC choose Denver. The mountains are beautiful, the food is excellent.

Havana is not a place to spend more than a few days in. The food is terrible, the service awful, and it is a cultural wasteland because of a ‘“top-down” gov’t created culture. You can spend 45 minutes at an uncrowded restaurant waiting for food that requires very little preparation. The mass transit sucks, and cabs are expensive. Plus the old Soviet cars and trucks make a filtered cigarette or cigar the safer way to breath.

Rome-I didn’t care that much for Rome. I preferred Sorento, which had better food, nicer people, and less street crime. I want to go back to Rome, because I did not see all the historical attractions I wanted to, but the Gypsy’s, and the militarized feel of the city left me feeling uneasy and in need of Xanax.

Shanghai-Probably my favorite foreign city. The food (American, European, and Chinese) was excellent and cheap. The way the city has grown is really amazing, and the city is a cite to see.

Beijing-I preferred Shanghai but Beijing was excellent too.

It was at a Marine Post. I won’t go into the details but I was deferred pending physiological counseling.

All I remember was that the city was bleak and run down. Maybe it was the gram of hash I ate for breakfast.

*jch lit her smoke, a full size CIGAR.

*I couldnt understand her at all, i caught every 7th word. Maybe. And i used to have Filipino in laws straight whom I could have conversations with easily. And half their words were Tagalog.

*She was dead in my smartass cross hairs til i learned her mom passed away. I didnt buy she was from Key Largo, however.

*She forgot her name for a good 20 count after being asked. High Comedy! Higher comedy was seeing her dance on an empty dance floor with palms on floor, head near floor and everything else sky high. i need a beer, asap. (shudder)

*JCH’s lady can sing. ive seen her in two different locations belted some tunes. She has yet to top my rendition of Purple Rain, however. (long story)

*Yes I was asked to dance also, it seems, but couldnt decipher the code of consonants said rumpshaker was uttering. jch’s quasi sister in law saved the day by proclaiming we were married. GREAT first impression, she earned a captain and coke for that kick save.

I am available for a small fee, next time.

Quickly:
1) NYC – hands down.
2) San Francisco
3) Raleigh/Chapel Hill/Durham
4) Cleveland – lived there for a year and it really gets a bad rap. The west side is a lot of fun.
5) Pittsburgh (architecture)