**Updating this after a few years, as I can add a few onto the list and also re-evaluate a few decisions.**
Not eligible becuase I live too close / can't speak to as a tourist attraction: New York City (obviously would be really high), The entire rest of the Northeast Corridor (Philadelphia, Boston, Baltimore, Washington), Jacksonville, Houston
Not eligible because my time there was limited to work: Raleigh, Detroit, Fort Lauderdale
20.) Atlanta (2017)
I went to Atlanta once, on a bachelor party of a family friend. It was a great time, and sure it may be hard to separate the city from the bachelor party-ness of it all (a good one is about as good a long weekend as possible), but the city itself seemed like a better, not as hot, Dallas. Really nice restaurants featuring southern cooking. We ventured out to a couple nice suburbs for meals as well. Of course, there are a few aspects of the city that make it a particularly apt Bachelor Party spot - some that are basically cultural mileposts. Won't say more. The only thing keeping it from being higher is the lack of historical importance and natural beauty; most of the cities on the list have one or the other.
19.) Orlando (1998, 2000, 2001, 2005, 2009, 2016)
Removing Disney and Universal, Orlando wouldn't be anywhere close to this. I have visited Orlando a couple times without really touching either park system and found it decent, with good shopping and decent restuarants/bars. But we can't just ignore that those two monster park systems, in Disney's case, a literal city. Those parks to have some magic to them, changing enough each half decade to not get fully old (haven't really visited any since 2009). Disney is quite a bit magical, and despite the cost, the crowds, it is one of the world's best destinations.
18.) Houston (many times)
20.) Atlanta (2017)
I went to Atlanta once, on a bachelor party of a family friend. It was a great time, and sure it may be hard to separate the city from the bachelor party-ness of it all (a good one is about as good a long weekend as possible), but the city itself seemed like a better, not as hot, Dallas. Really nice restaurants featuring southern cooking. We ventured out to a couple nice suburbs for meals as well. Of course, there are a few aspects of the city that make it a particularly apt Bachelor Party spot - some that are basically cultural mileposts. Won't say more. The only thing keeping it from being higher is the lack of historical importance and natural beauty; most of the cities on the list have one or the other.
19.) Orlando (1998, 2000, 2001, 2005, 2009, 2016)
Removing Disney and Universal, Orlando wouldn't be anywhere close to this. I have visited Orlando a couple times without really touching either park system and found it decent, with good shopping and decent restuarants/bars. But we can't just ignore that those two monster park systems, in Disney's case, a literal city. Those parks to have some magic to them, changing enough each half decade to not get fully old (haven't really visited any since 2009). Disney is quite a bit magical, and despite the cost, the crowds, it is one of the world's best destinations.
18.) Houston (many times)
It's hard to really judge Houston as a tourist destination because it hasn't been one too often for me, going there mostly for work our to visit my cousin and his family - both of those two drawing me more to The Woodlands, a posh Houston suburb that beacuse of Houston traffic is far away. That said, I've spend a decent time downtown and while Houston is as sprawling as we think, there's many cool neighborhoods, many great night spots, and it might be one of the best food cities in North America. Truly they have great food of many cuisines, having some of the best Mexican food of any American city, and extending that to Vietnamese, Nepalese and so many others. There's not too much to "see" but tehre's a lot to eat and do, which makes up for it.
17.) Portland, ME (2021)
Portland will always remain in my mind as the place I went to first during the pandemic, with four of us taking a group trip. While there were some restrictions, it was also a way to see the city and the surrounding area in the height of the fall colors without it being too busy. The place though had a lot to offer. Really nice restaurants with a great mix of high brow cooking without the fuss. A lot of great breweries, including some really great set-ups in converted warehouses. The night scene was pretty good, with its few cobblestone alleys lined with pubs and bars and the like. In the end, we had a nice time in Portland, and my only real quibble (other than the ridiculous cost of lobster rolls) is that the sights, including Acadia Park, are a bit too far away.
16.) Las Vegas (2004, 2022, 2024)
We can throw that 2004 trip out. I do remember it, but in reality this ranking is based on 2022 and 2024. There are probably few places better to spend 24-48 hours. But the second you get to that third day, things get rough. There is so much to like about the city though, to the glitz, to the food, to the life of it all. Yes, I'm nowhere near rich enough to enjoy it in full, but that doesn't stop me from enjoying it in little. What I do like in Vegas is nothing feels like a rip-off. On a recent trip there for a friend's bachelor party, we paid a decent amount to (1) go to a day-party at the MGM pool hosted by Martin Garrix, (2) eat at a steakhouse and (3) go to the Omnia Club with Zedd. All of it was at the very least worth the money. That's all one can ask for, right?
15.) Vancouver (2018, 2020)
Vancouver is beautiful, that much is obvious. With the mountains to the north a constant presence above a great modern North American city. If anything, I'll hae to give more reasons for not ranking Vancouver higher than this. The city is quite big, with potential traffic issues. There are a few nice neighborhoods, but they are hard to reach from the outsides of the city. The nice nature is a little too far. Anyway, if you have time, and a car, the city is great. The food, especially the various asian-inspired bistros, are great. The nature is wonderful, particularly if you have time to drive up the Coast.
14.) Austin (2002, 2016)
May seem low, but that more speaks to the strengths of the cities above it, which include truly unique factors, great restaurant & beer cultures, and/or historical relevance. Austin has some of these things, if not all, but not at the high degree of some of the others. The best aspects probably are the barbecue and live music, but there's other cities that do each, if not both in one case, at a reasonably good level as well, without the added heat and sprawl. Either way, Austin is a fantastic city, but is starting to get slightly too popular and slightly overcrowded to add to the fact that American does indeed have a lot of great cities.
15.) Vancouver (2018, 2020)
Vancouver is beautiful, that much is obvious. With the mountains to the north a constant presence above a great modern North American city. If anything, I'll hae to give more reasons for not ranking Vancouver higher than this. The city is quite big, with potential traffic issues. There are a few nice neighborhoods, but they are hard to reach from the outsides of the city. The nice nature is a little too far. Anyway, if you have time, and a car, the city is great. The food, especially the various asian-inspired bistros, are great. The nature is wonderful, particularly if you have time to drive up the Coast.
14.) Austin (2002, 2016)
May seem low, but that more speaks to the strengths of the cities above it, which include truly unique factors, great restaurant & beer cultures, and/or historical relevance. Austin has some of these things, if not all, but not at the high degree of some of the others. The best aspects probably are the barbecue and live music, but there's other cities that do each, if not both in one case, at a reasonably good level as well, without the added heat and sprawl. Either way, Austin is a fantastic city, but is starting to get slightly too popular and slightly overcrowded to add to the fact that American does indeed have a lot of great cities.
13.) San Francisco (1999, 2008, 2014, 2017)
San Francisco actually somewhat proves my point about Calgary maybe needing another go. Had I not spent a long weekend there in November, it would likely be higher, but there is a couple glaring issues I found this time around, mainly the almost unimaginable homeless problem driven mostly by opiods and drugs. There are streets deep inside SF's main area that are basically unwalkable. It disfigures what is a great city outside of that, with incredible food, a world-class art and drinks culture, good museums, great sightlines and parks, and so much more. The only other negative to me might be the price, which is somewhat unescapable. Either way, San Francisco has a few black marks on it that hurt it from being a truly brilliant city..
12.) Minneapolis (2022)
The only downside I can think of about Minneapolis is that they didn't have a lot of hiking, something that I probably would have realized with a bit more research ahead of time. Anyway, with that little exception, I found the rest of Minneapolis quite lovely. Great food, with some really upmarket restaurants, like an excellent tasting menu experience at Travail. Beyond that, of course there's umpteen increedible breweries that were all amazing. This wasn't a surprise at all, I was expecting some amazing brews in Minneapolis. What was more unexpected was a truly great Art museum, beyond just the normal fare with a bunch of surprisingly great Asian art. Also the city was eminently drivable, which I'm starting to think is more a localized NE problem (of course add in places like Chicago, LA).resta
11.) Portland (2017)
I went to Portland three weeks before I went to San Francisco in 2017, and found it quite a bit better. They are similar in some ways, but Portland is cheaper, with the same asian influences. Also in Portland's favor is a truly astounding craft beer culture, and great food all around, from Pok Pok's wings, to incredible biscuit sandwhiches. You also get some beautiful, remote, scenery in teh 1-2 hour perimiter of the city, from the Mt. Hood region to the East and the Tillamook Forest to the West. It's a truly beautiful city with a great sense of what it is; one of the few cities in America that define everything that a unique American city should have.
I went to Portland three weeks before I went to San Francisco in 2017, and found it quite a bit better. They are similar in some ways, but Portland is cheaper, with the same asian influences. Also in Portland's favor is a truly astounding craft beer culture, and great food all around, from Pok Pok's wings, to incredible biscuit sandwhiches. You also get some beautiful, remote, scenery in teh 1-2 hour perimiter of the city, from the Mt. Hood region to the East and the Tillamook Forest to the West. It's a truly beautiful city with a great sense of what it is; one of the few cities in America that define everything that a unique American city should have.
10.) New Orleans (2024)
I technically visited New Orleans back in 1994 or something. Obviously, I have no memories of that trip. I went again in 2024 for a friends Bachelor Party. Seems cliche, sure. and yes we spent probably too much time in the French Quarter, but go a bit astray from that and you get quite a fantastic city. The secondary drag we went to the second night - the area near Frenchman's Street - is just so perfect. There is really no American city like it - our kind of crazier, more "American-ized" version of Montreal. What New Orleans also really has going for it is its food scene - the cajun/creole food that is so uniquely its own. For weird Europeans who claim we have no culture, I submit to you New Orleans. From the music, to the unique architecture, to the food, to the culture, there is really nothing like it - even if it is a bit too trashy to really love.
9.) San Diego (1999, 2017)
We all get the jokes about San Diego, the perfect weather, the laissaz faire attitude that made a whole community do a shrug emoji when they lost their football team. The perfect nature of the city. All of it. It is all true, because we are all just jealous that a city with a perfect year-round climate was made and we don't all live there. I went in March, it was 70 each day and sunny. The city has history, with old churches and military history like the aircraft carrier musuem. It has great food - including multiple great restaurants lining the Gaslamp district. There is a great beer culture highlighted by two of the most successful craft breweries in the US in Ballast Point and Stone. And of course there are some great hiking trails and parks and sports. The city is a perfect place to live, but it isn't too bad to visit either.
We all get the jokes about San Diego, the perfect weather, the laissaz faire attitude that made a whole community do a shrug emoji when they lost their football team. The perfect nature of the city. All of it. It is all true, because we are all just jealous that a city with a perfect year-round climate was made and we don't all live there. I went in March, it was 70 each day and sunny. The city has history, with old churches and military history like the aircraft carrier musuem. It has great food - including multiple great restaurants lining the Gaslamp district. There is a great beer culture highlighted by two of the most successful craft breweries in the US in Ballast Point and Stone. And of course there are some great hiking trails and parks and sports. The city is a perfect place to live, but it isn't too bad to visit either.
8.) Toronto (2008, 2016, 2017)
I almost put The Six in the groups of cities that I can't rank as I did a project in a suburb for four months, close enough to go into the city many times, but I liked it too much to keep it out. Toronto is great, easily the best (NY excluded) mega-tropolis I've been to in the US. The positives in Toronto are endless, from the CN Tower, to the Island, to the bevy of incredible food options, and neighborhoods from Downtown, to the Distellery District, to Yorkville, to so many others. The food is great. The beer is great. The bars are great. The city is large but never has the traffic or urban sprawl problems that other huge USA cities have to deal with. Toronto also has a great comedy and music since (Drake aside), and has as much culture of its US counterparts. It's a lot larger than people realize, and still has all the cultural charms of the secondary cities, A rare combination.
7.) Phoenix (2021, 2022)
The only negative I have to say of Phoenix is that there are limited things to do. There are nice hikes and walks in nature, but its blisteringly hot. The Grand Canyon is a bit too far for me to include it and be fair to other places that I would leave out a site 3 hours away. That said, parts of Phoenix are phenomenal. Secretly, I think its one of the best food cities in America, with just superb Mexican food without the frills of SoCal (or even Texas). There is just great Mexican food everywhere. There's a surprisingly strong beer culture, including some great bottle shop/beer bars. There are some sites, including one of the better 'single focus' museums I've been to in the Heard Museum on Native American history. It's a fast growing city but still eminently drivable. There's a real lot to like, just go between October and April. **After coming back twice since writing this, my impression of Phoenix has only increased. It is the most drivable metropolis in the US, the food and beer are excellent, and the hiking within an hour of the city is great. It is also oddly one of the more green cities in America.**
6.) Salt Lake City (2018)
Of course, Salt Lake City encompasses the cottonwood canyons, and the Great Salt Lake in this ranking. I don't know if there is a US metro area that mixes urbanity and nature quite like Salt Lake (other than maybe the city at #2). The food in Salt Lake was great, with a burgeoning foodie scene. The alcohol options are more varied than you would think. The city is amazingly walkable and easy to transit around. Finally, those views, those hikes, that natural beauty. Salt Lake City's bevy of close by hiking options, all within an hours ride from downtown, are astounding. All double as great ski slopes in the winter as well, for those that like that aspect of the world. My first trip to Salt Lake City took me by surprise, and truly I can't wait to go back.
5.) Chicago (1998, 2001, 2005, 2015)
I need to go to Chicago again, because while I did go for three days in 2015, that wasn't a long enough trip to formulate a changed opinion. My memories of Chicago are more from childhood, where I remember it being somewhat a perfect American city. They have arguably the best collection of museums of any American city. They have a beach. They have incredible sports to witness, including a cathedral that is Wrigley Field. I'm sure they have food and great bars and all the rest as well. The largest four cities in the country for as long as I can remember have been NYC, LA, Chicago and Houston (just city, not metro area), and Chicago seems the least like a true sprawling Metropolis. **2024 Update: I've gone to Chicago many, many times more, mostly because my company opened an office there. In all honesty, I should remove it at this point. It's fantastic, that's all there is to say. Having not really been to Los Angeles enough to judge, Chicago is easily to me America's 2nd best megalopolis. Of course, this isn't a ranking of Megalopolises....**
I need to go to Chicago again, because while I did go for three days in 2015, that wasn't a long enough trip to formulate a changed opinion. My memories of Chicago are more from childhood, where I remember it being somewhat a perfect American city. They have arguably the best collection of museums of any American city. They have a beach. They have incredible sports to witness, including a cathedral that is Wrigley Field. I'm sure they have food and great bars and all the rest as well. The largest four cities in the country for as long as I can remember have been NYC, LA, Chicago and Houston (just city, not metro area), and Chicago seems the least like a true sprawling Metropolis. **2024 Update: I've gone to Chicago many, many times more, mostly because my company opened an office there. In all honesty, I should remove it at this point. It's fantastic, that's all there is to say. Having not really been to Los Angeles enough to judge, Chicago is easily to me America's 2nd best megalopolis. Of course, this isn't a ranking of Megalopolises....**
This is somewhat re-written after my trip in 2021, but Denver as a whole is still an incredible city but has grown a bit too big since my first trip in 2015. The food scene is still great, the natural beauty arond it in every direction is still great. The city remains really drivable and workable, and has some great night spots (the best club I've been to in the US - though granted with covid-impacted crowd control restrictions which helped). There's really no down side to Denver. The only reason it's dropped in my mind since my first visit (after which I had it at #2) is because another city leaped over it (a city that share's a lot of similarity to Denver) and because the craft beer which was such a large part of my initial ranking is something that many other cities have caught up to.
3.) Calgary (2005)
This is re-written as the first time I did this list I was only going off my trip in 2005. I went back in 2019, to experience the city itself and the surrounding area again. At the time I was worried if I overrated Calgary (I had it like 10th), having gone back, I seriously underrated it. Calgary is incredible drivable, despite being a metro of 2mm people. It has excellent food including great use of Calgary beef. The night spots were all excellent, from great and relatively low priced cocktail bars to one of the better clubs I've been to in North America (sadly, Habitat Living Social seems to have closed...). The weather is incredible (summer only, obviously), and Banff is every bit as magical as it's made out to be with Carribean-blue water mixed with incredible scenery. It truly is North America's underrated little jewel that I just wish was easier to get to.
2.) Nashville (2016, 2017)
Live music has many homes within the US, but I would argue none touches Nashville, from mainstream spots like the Grand Ole Opry or Bluebird Cafe, to the many great spots that litter Broadway on both sides, to even the others that espouse Rock and Blues. Nashville owns all cities I've been to when looking at music. Of course, that isn't where Nashville's positives ends. There are great restaurants, from BBQ to hot chicken, to a truly special burger place in Pharmacy Burger. The cities' increasingly built up outskirts push the number of restaurants and bars even further higher, The city, nestled nicely in the Appalachian plateau's even rarely gets too hot. What a great slice of Americana.
1.) Montreal (many, many, many times)
Yes, I've been to Montreal a lot, mostly during its annual Jazz Festival it hosts in the Place des Artes area - a tremendously run festival visited by millions. But even outside the festival, Montreal is an amazing city. It has sites, from Mont Royal to the various churches and buildings, to the Old Town,. It has incredible food, from French Canadian staples to world known Smoked Meat. It has a great bar culture, with some great breweries. It has live music even when you remove the Jazz Festival. It has great parks and open streets and little crowding, and crepes, and everything else. Having such a seemingly foreign city, where French reigns supreme, so close to home is fantastic, and i'm blessed to be able to visit it somewhat-annually.
Live music has many homes within the US, but I would argue none touches Nashville, from mainstream spots like the Grand Ole Opry or Bluebird Cafe, to the many great spots that litter Broadway on both sides, to even the others that espouse Rock and Blues. Nashville owns all cities I've been to when looking at music. Of course, that isn't where Nashville's positives ends. There are great restaurants, from BBQ to hot chicken, to a truly special burger place in Pharmacy Burger. The cities' increasingly built up outskirts push the number of restaurants and bars even further higher, The city, nestled nicely in the Appalachian plateau's even rarely gets too hot. What a great slice of Americana.
1.) Montreal (many, many, many times)
Yes, I've been to Montreal a lot, mostly during its annual Jazz Festival it hosts in the Place des Artes area - a tremendously run festival visited by millions. But even outside the festival, Montreal is an amazing city. It has sites, from Mont Royal to the various churches and buildings, to the Old Town,. It has incredible food, from French Canadian staples to world known Smoked Meat. It has a great bar culture, with some great breweries. It has live music even when you remove the Jazz Festival. It has great parks and open streets and little crowding, and crepes, and everything else. Having such a seemingly foreign city, where French reigns supreme, so close to home is fantastic, and i'm blessed to be able to visit it somewhat-annually.
