This is list was spurred because during this past weekend when I met 7 childhood friends for a bachelor party in Montreal, I was asked where Montreal would rank on my list of favorite cities if it was eligible. In truth, quite high! But then I got thinking, there are some great cities in the USA and Canada if we expand it. Maybe not the 40 I've listed for the non-US/Canada world, but a fair good amount. I did want to rank them, but there are two huge caveats; first is the surprisingly long list of US touchstones I either haven't visited or visited many years ago; second the cities that I've lived in, or visited too often to really be able to accurately judge.
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, Grand Rapids, Horsham, (those last two are just there for fun - random client locations, obviously had no chance to be on this list unless I went 200 deep).
Other cities that I understand are quite good but have never visited to date, or visited long enough ago I don't really remember it: Seattle, Phoenix, Salt Lake City, Los Angeles, Pittsburgh, Cleveland, Minneapolis, Milwaukee, St. Louis, New Orleans, Las Vegas, Charlotte, Memphis, Albuquerque, Boise, Honolulu, etc.
12.) 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.
11.) 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.
10.) 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.
9.) Calgary (2005)
The first time I did my International Cities list, I had Goa (admittedly, a state, not a city) ranked at #6 (out of 25). I realize that was dumb, but I had a great experience, a semi-idyllic trip. This very well could be the same thing, given my last trip was so long ago. There is a few standout features for Calgary. First is its proximity to Banff National Park (90 minutes away), a stunning Natural Park that puts most US-based ones to shame. Second is their meat, from Reindeer to Beef. Third comes from what I've read, which is an surprisingly excellent music & drinks scene that has grown rapidly in this outpost - obviously something I would not have experienced last time. I do want to make another trip to assess this initial view, but given Banff is included in Calgary's oeuvre for me, it will be hard to fall too much further than this.
8.) 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..
7.) 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.
6.) 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.
5.) 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.
4.) 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.
3.) 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.
2.) Denver (2015, 2017)
Honestly, Denver and Nashville are almost tied in my book, easily my favorite US cities that I've visited. Denver has the same cultural niceties of Nashville - incredible restaurants, great bars, a great low-key vibe. Nashville has the music, Denver has the incredible sceney with Rocky Mountain National Park, and stunning view after stunning view, an hour away. The Rocky Mountains truly are a staggering sight that Denver probably gets undue credit for, the major city with the closest ties to America's great mountains. The city has a great feeling inside, a growing city that has so much room to expand I can't foresee it ever getting too crowded. Denver is a special, somewhat untouched place that I truly need to go back to.
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.
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, Grand Rapids, Horsham, (those last two are just there for fun - random client locations, obviously had no chance to be on this list unless I went 200 deep).
Other cities that I understand are quite good but have never visited to date, or visited long enough ago I don't really remember it: Seattle, Phoenix, Salt Lake City, Los Angeles, Pittsburgh, Cleveland, Minneapolis, Milwaukee, St. Louis, New Orleans, Las Vegas, Charlotte, Memphis, Albuquerque, Boise, Honolulu, etc.
12.) 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.
11.) 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.
10.) 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.
9.) Calgary (2005)
8.) 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..
7.) 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.
6.) 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.
5.) 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.
4.) 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.
3.) 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.
2.) Denver (2015, 2017)
Honestly, Denver and Nashville are almost tied in my book, easily my favorite US cities that I've visited. Denver has the same cultural niceties of Nashville - incredible restaurants, great bars, a great low-key vibe. Nashville has the music, Denver has the incredible sceney with Rocky Mountain National Park, and stunning view after stunning view, an hour away. The Rocky Mountains truly are a staggering sight that Denver probably gets undue credit for, the major city with the closest ties to America's great mountains. The city has a great feeling inside, a growing city that has so much room to expand I can't foresee it ever getting too crowded. Denver is a special, somewhat untouched place that I truly need to go back to.
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.
