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OT: "Name a city that exceeded your expectations upon your first visit."

Jackson, WY. Beautiful arrival into the airport, one of the best, most scenic flights into an airport I've ever been on. And the town itself has an abundance of great shops, great food, and great people. And you're only a few minutes from Grand Teton National Park and an hour from Yellowstone.
Is that really a surprising place when it’s literally where weather people go as a destination ?
 
This was going to be my answer also! What a cool place. The downtown park with the waterfall/rock feature was amazing and the entire downtown area was gorgeous.

Lots of great places to eat the whole way up the main drag and around the falls. I compare it with Asheville given they're only about an hour apart. It's a little like Asheville without the hipster vibe and more cultural diversity.

Also, you're close to the mountains, Clemson, and only a few hours from Atlanta or Charlotte.
 
Brisbane. Visited in winter and weather was lovely. 20-25 C each day. Would definitely be too hot for me in summer.
City is clean, and easily walkable along the developed riverfront. It is a really easy city to spend a few days in. Great seafood caught right there.
You usually think of Sydney or Melbourne when thinking of Aussie, (and I think Sydney is OK--just massive. Not been to Melbourne yet). But Brisbane surprised me and as comparatively easy for me to get to, I would go back.
 
LOL! Philthydelphia! That's hilarious!! I lived there for 2 years and was very happy to escape with my life and never looked back. Disgusting place and the people are even worse.
It honestly makes me laugh when Pittsburghers insult people from elsewhere. Whether it's Philadelphians, "rednecks", "hicks", West Virginias. Zero self-awareness; especially coming from the sizable, often miserable geriatric portion of the population.
 
For me, San Luis Obispo and it's not even close. Had no expectations and ended up loving that little town while there for work a few times. Years later, ended up taking the family while we were on vacation, wife loved it too.

On the negative side, Portland. Heard a lot of good things and I thought it was disgusting.
 
I'll co-sign on Montreal, besides what's listed above it's an amazing food city! They have a massive Little Italy, great Jewish food, French food, and French-Canadian. My biggest knock is that the subway doesn't go to the airport.

Dublin, Ireland is great and way more than touristy stuff, if the election went the other way I would have seriously thought of moving there.

Three years ago I spent a week in Birmingham, England and it was a blast even though I could barely understand what everyone was saying, reminded me of Pittsburgh and Chicago.
 
In the States: Charleston, S.C.

In Canada: Vancouver. I expected it to be nice, but not that nice.

In Europe: San Sebastián, Spain. Most beautiful small city I ever have visited. In the Basque Country on the Atlantic Ocean. Day trips from there are superb, including into the French Basque Country.

Barcelona: The most beautiful city in the world and the people are great. Had wanted to go there since the late 1980s when I saw the Whit Stillman movie “Barcelona.” Finally made it in 2013, when I rented an apartment for 3 months. Have been back almost every year since for 1 to 2 months. We had an apartment rented for 3 months in 2020, but cancelled by the pandemic. Hope to do it in 2021, and we will be looking to buy a place for a permanent move.
 
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I second everyone mentioning Montreal. It's my favorite big city so far. Obviously the foreign language element plays a role but there is also do much to see and do. Great subway system (love those subway tones and hearing every stop in french), lots of great neighborhoods that are easy to get to on said subway, and lots of interconnected underground shopping malls downtown if the weather is lousy.

And I can drive there in 8 hours. Easy drive too, aside from the border crossing.
Yes, but why is that surprising? It is one of the biggest destination points in North America. So I would have hoped you expected it to be really cool.
 
If we were going the other way, as to "most disappointing city" first and foremost to me would be Reno. It sucks.
 
Yes, but why is that surprising? It is one of the biggest destination points in North America. So I would have hoped you expected it to be really cool.

I had heard it was nice. But I've been to most of the big, hyped destination cities in North America and it was better than them all. So to me that was surprising.
 
Baton Rouge, LA. It's a college town inside of an actual city. The only place that compares is Austin.
 
Baton Rouge, LA. It's a college town inside of an actual city. The only place that compares is Austin.
I’ve been to Baton Rouge, and was not impressed.

I was, however, impressed with the footprint of Tiger Stadium. That thing is huge.
 
I’ve been to Baton Rouge, and was not impressed.

I was, however, impressed with the footprint of Tiger Stadium. That thing is huge.
It's definitely the type of city where you need a local to show you around. The downtown area and the neighborhood surrounding LSU, which I imagine are the spots where most visitors pass through, are definitely very underwhelming.
 
Cleveland. I expected it to be a trash dump from everything I heard about it. It was Pittsburgh exactly.

Baltimore. Same thing. Inner Harbor area is one of the nicest areas in any city in America.
I agree with this. Personally, I love visiting the city of Cleveland. Very underrated downtown area and lots of great neighborhoods. Has a lot more going for it than people may expect. I wish they’d develop the lakefront near the Browns’ stadium, though.
 
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Baton Rouge, LA. It's a college town inside of an actual city. The only place that compares is Austin.

Another college town I was impressed with is Tallahassee. Not because the city itself is amazing (it's pretty nice though) but the amount of outdoors recreational opportunities are everywhere throughout the city and the surrounding areas.
 
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