There’s obviously a ton to see in Paris, and the city center around the Eifel Tower, on either side of River Sein, is beautiful. Paris is a probably a city that certain people would love, but I am not one of them. Of course, I liked it enough to put ahead of some damn good cities, mostly on the ridiculous amounts of things to see alone. I actually don’t remember much of my Paris trip, which is strange given its relative recency, but I do remember thinking one day in the Louvre was far from enough, and the city center of Paris containing some of the best architecture of any European city. **After going back in 2018, I can say I might be being harsh on Paris, but to me it is a slightly less great version of the other great European capitals like London, Madrid, Rome - unsurprisingly all higher up the rankings.
33.) Vienna (2000 & 2009)The 2
nd time I went to Vienna was on my high school’s Orchestra’s tour of Austria during my Senior year, and much of my high ranking for Vienna is based on that trip. There is a ton of history in Vienna, with the music scene being located there (Mozart and Beethoven’s houses), with the adjoining arts scene with a bevy of theatres. If you like classical music, then Vienna is heaven. I am including the adorable little town of …… where we performed, which was half an hour outside Vienna. The best part of Vienna is how modern it is. The city center has some of the largest streets and public squares of anywhere in Europe, with grand architecture all around. The food isn’t great, but it is no worse than Germany and Switzerland, and Austria is generally less expensive. It took a second trip to get acclimated with Vienna’s charms, but they are there, and plentiful.
32.) Cusco (2016)
Full disclosure, I'm cheating by including Machu Picchu as one of the associated sites of Cusco, which is a large part of the reason it places so high. Machu Picchu is a spectacular tourist attraction, from teh never-ending views of Hauranya Picchu's face, to the cascaiding hills on every side, to the great hikes. When you peel back to Cusco proper, it remains a great secondary city, a South American, high altitude version of Krakow (next on the list). The food is great, with so many small, but fine quality, restaurants. It has a vibrant restaurant and bar scene, and quite a bit of tourism locally, including other Incan ruins near the city limits. Finally, the altitude, as Cusco us probably the highest city that is easily and heavily visited. Plus, I owe a lot to the Loki Hostel, a wondrous place of Blood Bombs and fun.
31.) Danang / Hoi An (2026)
Yeah, I'm combining them because to be honest, Hoi An is basically a suburb or extension of Danang. And if you think of them that way, what's not to love - you get great modernity, beaches, food, nightlife in Danang (including some really underrated hiking) and then you get the old town beauty of Hoi An. It is hard to describe Hoi An properly, the alleyways, the handicrafts, the colors, the lanterns - oh the lanterns that make each night something out of a movie. I could get lost on those streets of the old town of Hoi An every evening and still return abck to Danang to enjoy amazing Vietnamese cuisine, drinks and dancing. Danang is the perfect midpoint between Hanoi and Ho Chi Minh, and I ranks roughly halfway between the two as well.
30.) Oaxaca (2025)
They call it the culinary capital of Mexico, and Oaxaca is definitely that. The food is incredible, but homely Oaxaqueno food in the food markets, to refined Michelin star cuisine, to street tacos and moles. Food is the bleeding heart of Oaxaca, but the rest of the city is quite nice as well, from a few well curated museums, some great lanes decorated to the nines, some beautiful pastel colored blocks of city, all so walkable and lovely. And then the nightlife is something to behold as well. All of it high in a plateau with mountains on all sides. Just all good things.
29.) Bilbao (2021, 2026)
This second visit to Bilbao where I could spend more time in a fully COVID-free world, really accentuated how great a palce it is. The food remains nearly unparalleled - from the pintxos to places like Islares and of course Azurmendi. The sights are excellent - from the famed Guggenheim, to the churces and other museums, to walking the Northern hills. The nightlife is great - so many wonderful bars and breweries, from its old town to more far afield. Bilbao also has that Basque feeling that you are not just in Spain, but somewhere that little bit different. Even if Bilbao may not be as famed as San Sebastian in terms of food/pintxos, the other elements have me see it as better of the two.
28.) Tallinn (2024)
My parents visited Tallinn in 2011 and raved endlessly about it, and more pointedly how much I would love it. I think I'm probably a fairly different person in 2024 than 2011, but they were still very right. Tallinn's old town is among the loveliest and most picturesque that I've visited - with maybe just Krakow (to come) as better in my mind. The pastel-colored alleys and shops and cafes around it are amazing, as are the bars and restaurants hidden inside. But where Tallinn is really separating itself is what lies outside the old town, a design/modern forward city with museums, giant parks, great waterfront and incredible restaurants, like NOA Chef's Hall, one of the better tasting menus I've had in Europe. On the whole, Tallinn was a special place.
28.) Taipei (2019)
I should have figured that Taipei would be a really great city. Still, however, I was surprised by how well built, how green, how beautiful it was. The food was great, from beef noodle shops to fancy high-end restaurants. The bar scene was excellent, with a burgeouning craft beer culture was shocking. The tourism was great, with nice pagodas and temples tucked away all across the beautiful green city. If only the cuisine was slightly better Taipei would have ended up much higher. There's also a lot of hills and forests and greenery within an hour of the city in every direction. Taipei has so much going for it.
26.) Berlin (2014)Berlin is the only German city I've gone to as an adult, and from what I read it was a good one to pick. The city is sprawling, and has covered it's whole 'we had a giant wall' thing with some really modern buildings and a few nice memorials. But what it also hides is an incredible city. The main squares, or platzes are all incredible, including that entire stretch between the Brandenburg Gate, through the Tiergarten, and ending with the Berlin Island. There are various areas of the city with incredible churches, restaurants, bars (and bars, and bars) and historical buildings. The city houses some fascinating museums that touch on the long, varying history of Germany is a country. Berlin as a city is too big to do in 3 days like I did, but it is definitely alluring enough to go back.
25.) London (1999, 2000, 2010, 2017, 2018, 2019, 2022)
I probably should just go to London more, because both my Dad and my Sister, who lived there, swear by London as an incredible city. But again, I’m not ranking this by how livable they are, but how good they are as tourist destinations. London definitely has enough to see, including the nicely compact Royal stuff (palace, parliament, other stuff), and a neatly packed city center (West End, Trafalgar Square, other stuff I’m forgetting), but it is a little too big. It’s subway system is clean, but doesn’t have the expansiveness that it needs (something I give huge credit to the NYC Subway System for, no matter how dirty it is). Of course, it is damn expensive, and the weather is mostly lousy. It may get better with more trips, but I think London is too big for its own good, and a little too confused, as it tries to be both Rome and New York. **So I went here in 2017-2019 and 2022, and really have nothing more to add. I think what I wrote back then is more or less accurate. In the end, being in any English speaking city outside of the US just doesn't seem as foreign & exciting. And I really can't get over how bad the street layout is in this city. Makes me really appreciate New York being a grid.
24.) Bangkok (2003, 2013, 2019, 2022, 2024)
Here’s the gist of what I remember from Bangkok: nice Wats to see, incredible food, up all night, eating all the time. Bangkok is a food-lover’s paradise, especially for those who like Thai food. Bangkok is also close to areas where you can do all those Asia type things like ride elephants and see the jungle. The weather is surprisingly decent for a city in Southeast Asia, and from what I remember it is pretty easy to navigate. My thoughts regarding Bangkok have indeed changed with my one-plus day visit. The city is better than I remembered, with sprawling malls, an advanced metro system, and new urban centers. The weather isn’t quite as good, as it is still hard to get to different parts of the city, but the city center of Bangkok is about as good as any I’ve seen in Asia. ** After going again for a few days in 2019, my opinion of Bangkok is largely unchanged, but improved in a way. The food is great, particularly the soon to be closed Gaggan. There are some really nice districts. But what it lacks is the cleanliness and constant modernity of a Singapore. **After further going in 2022, while the food remains Top-5 in the world, the bustle, the maw, the "oversized Bangalore" of it all kind of hurts it to me. Any place with Gaggan, Le Du, #FindTheLockerRoom can't be any lower, but there's a lot to dislike amongst that brilliance.
23.) Granada (2001, 2021)
I'll admit, I have very limited memory of Granada - like I do with most of my trip to Spain and Portugal in 2001. But from what I do remember of Granada, mainly around the magic that is the Alhambra. Granada also has great food (as does most of Andalusia), including amazing seafood and lamb. Spain itself is probably my favorite country to visit, and a large part of that is even outside is major metropoloses (which are good enough to both be in Top-10 for me) it has incredible gems with incredible history and culture.
**After visiting in 2021, I'm justified in my original love of Granada. The Alhambra was as good the second time around, but the food even better. The great old town was just lovely to wander about, pick up tapas at their various tapas bars hidden down alleys with great seating spilling into the streets. That is Spain, so were teh wine bars, and even beer bars, in this beautiful little town.
22.) Buenos Aires (2017, 2023)
The only new entrant this time around, Buenos Aires was a joy to visit in full for four days. Similar to its South American counterparts in Lima and Santiago (both higher), Buenos Aitres mixed the culture of South America with the architecture of Europe, leaning a bit heavier on the European side. The neighborhoods of Palermo and Recoleta were an unending joy to stroll around in both during the day to witness the greenery, and at night to witness the joy. The food is more steak and heavy, but when steak is cooked as well as it is in Argentinean parilla's one can forgive that part as well. Someone who is more Europe leaning in their proclivities will probably rate Buenos Aires higher than Lima or Santiago. I don't, but that's more about love for the other two, and the Pacific side of Sud America, than anything negative about the people from the port.
21.) Tokyo (2013, 2023)As a tourist, I don't care what the work and life culture are of the people in the city, and good thing, because if I did I may hate Tokyo. To see people in full suit in the subway at 11 PM coming home from work is jarring. But this isn't about any of that, it is about Tokyo the city, and it is a really fabulous metropolis. Tokyo is sprawling, in a way that makes New York seem small. There are really bustling regions like Shinjuku, really fun late night spots like Roppongi. There is a ton to see, and great food options. The food may be more corporate than traditional and homestyle in Tokyo, but that isn't all bad. The biggest complaint with Tokyo is just the size. It is so big that it is tiring to navigate at times, getting from one end to the other. Even with the reliability and the local JR Train lines, it takes time to get around.
**2023 Update: Going back didn't change my opinion of Tokyo too much, just crystallized what it does so well, from its art museums, its nightlife scene, and of course the food (if you're willing to pony up). Separately, the things keeping it from being higher up, such as the truly just endless urban maw of it all, and the sheer size, are still as true in 2023.**
20.) Budapest (2024)
I had Budapest on the earlier versions of the list before I cut it because I needed slots and I only went in 2000 so barely remembered it. Well, now going in full and I probably underranked it initially if anything, Budapest is a special place, combining many of the bests of Europe without the pretension of a Paris or London. There are amazing museums, great gothic architecture, great parks and castles and palaces. The parliament building is an world-class, stunning building. And then the culture - the great food from street goulash shops to fine dining; amazing cocktail spots and a party district in the Jewish Quarter that is among the most fun, compact places I've explored. There really was no downside of Budapest. Then again, there really aren't many downsides of any of the cities to come either.
19.) Mexico City (2014, 2018)I put 2014 there, but I went to Mexico City two different times, staying in two different areas of that expansive, massive, festive city. Far safer than most areas of Mexico, La Cuidad is incredibly impressive. There are tons of historical sites, like the entire Zocalo, the Chapultepec, and La Reforma. Mexico City also has a wealth of food options, with incredibly authentic Mexican fare from around the country, including the incredible Oaxacan food. Really fun night spot as well. Mexico City blew me away also with its strange, mysterious beer culture. The City is a sprawling testament to how secretly, behind the dangerous cartels that line the exterior, the soft interior of Mexico is a gorgeous, cultural attraction that is bettered by so few cities.
**After going again in 2018, I realize how much I missed out of Mexico City's overwhelming culture. The neighborhoods of Polanco and Condesa may some of the most cultured and serene in North America. The food scene is incredible, be it world class Pujol or the street taco vendors. Just an amazing city.
18.) Dubrovnik (2017)
My expectations were raised on Dubrovnik from a number of friends and families had already visited, and oh man was it great - matching everything I would have hoped for. Dubrovnik, like many cities that line my top half of the list, aren't huge sprawling metropolises, instead smaller, untouched little power-packs of culture and beauty. The actual structure of the town reminds me of a European Cape Town, with the old town and fort replacing the V&A Waterfront area, and the hills of the newer part of the city similar to East Cape Town, and the hills in hte background, fixed with their own version of Table Mountain, being, well, Cape Town's Table Mountain. The history in Dubrovnik is amazing, with the old town such a beautiful array of nooks and crannies, with steep stairs on alleys down to the water. Within it contains history, and amazing restaurants, and, of course, Game of Thrones. Dubrovnik is one of the gems of the Adriatic Sea, right there with the other great ports of the Mediterranean.
17.) Singapore (2012, 2013, 2019, 2022)
Singapore is one of those places that has to be seen to be believed. There is no city any cleaner. There is no city as tightly situated while having enough external attractions. There is no city better built for a short stay. What doesn’t Singapore have? It has a theme park for kids. A bird park (highly recommended) and a night safari for kids and adults. It has a brand new casino for adults. It has a centralized bar/pub/club area near the waterfront. It has a preponderance of food from really, really cheap to really expensive. It has livable weather year-round. It also has the most interesting and enjoyable airport I’ve ever been to (there is a pool and gym that everyone can use for free in it!), and the cleanest, best organized subway system I’ve seen. So why is Singapore only #3? Because there isn’t that much to do, and Singapore’s not cheap enough to just sit around and eat/drink/do nothing. The sights have no historical resonance, and are replicated in other cities. Still, for a period less than a week, there is no better city to visit.
**Part of the reason I call this a living document is that I'm not going to correct where I reference Singapore at #3 which it was the first time I did this. Anyway, on subsequent trips, the sterility of the place is what drops it slightly in my mind. Still a whole lot of positives, and a "must visit" at some point, but it just doesn't have the culture some of its Asian brethren do.
16.) Krakow (2014)By rule I like smaller cities over sprawling ones. Well, while there are expanses to Krakow that extend in all directions, almost everything worth seeing in the city is in a 10x10 block radius circling the best city square (Rynek Glowny) I have seen in Europe. When you get a city that has (their claim) more bars per capita than any in the world, combine that with amazing open space and roadside/streetside restaurants, and an economy that does not use the Euro and is far cheaper than comparale cities in Western Europe, you get a pretty fantastic city. Also, you want history near its borders, you get Auschwitz about 2 hours away. Krakow is an incredible secondary city, arguably the best secondary city I've ever been to. The beer, food and endless beautiful women makes it Top-25; the sites, easily walkable goegraphy, and amazing history (Copernicus lived there too) makes it Top-15.
15.) Chiang Mai (2026)
Take all the good parts of Bangkok - namely the food - and put it in the mountains away from the urban maw, and you get a special, special place in Chiang Mai. Mountains and temples all around, but the city itself shouldn't be underrated as well - the lovely old town inside that moat, teeming with temples and beautiful architecture and shops. The sights on the hills including some of the most beautiful temples I've seen built into the cliffs. Especially when you include places like Doi Inthanon and others within my two hour radius rule, which gets you some of the most stunning temples I've seen But yeah, this is really about the food, the incredible Northern Thai food, good basically any place you go, but especially such marvelous spots like Euang Kam Sai. Add to that an amazing cocktail scene, some other great nightlife and you get a perfect little city for everyone.
14.) Sydney (2013, 2025) Take the weather and leisurely attitude of Australia, combine the waterfront facade of a Chicago, add some pub and club nightlife of any city in Europe and you get Sydney, a city that combines the great aspects of every major city I have been too. It doesn't have a true culture of its own which hurts it in my mind. What I really mean by that is, much like the problems I have with England, there are too many similarities to the US. You don't really feel you are in a foreign city too much. Of course, that all changes when you walk towards the Opera House, or go to the night spots with the Australians out partying, or eat great meats. Sydney is a wonderful city, probably the most livable of any in the Top-10 (of course, it is helped by being English-Speaking), but sometimes I would sacrifice livability for uniqueness, which is why it isn't any higher.
**2025 Update: I can't really move it higher, but to be honest prior to visiting, it was more likely to move down than up the list. Instead, it held firm and really could easily be higher. The good parts of Sydney - from the main two harbor quays, to the elevated fine dining, to the Oxford Art Gallery are special. The museums are excellent, the zoo is great. But at the end of the day, the "this is basically Chicago or Toronto, if slightly better, just 10,000 miles away" is tough to justify it going higher up.**
13.) Lima (2016, 2022)
Lima has a few things going for it. First, its culinary brilliance, with two restaurants ranking in the Top 10 in the World per San Pelligrino's list (the most accepted of that type of list), one being Maido, a Japanese-Peruvian sensation. The sites aren't the best, few major cities are in retrospect, with a few museums and halls. The real sites of Lima are the whisping cliffs, the shops and the eclectic nightlife. The best South American cities combine Andean views with European charms, and few big ones do it better than Lima. Big jump here afer my trip in 2022. The food remains incredible, adding Central to Maido on my list of culinary adventures. But also getting more time in Lima this time around, and doing a bit more research to understand neighborhoods like Barranco and others a bit better, I learned to love a lot of it. The greenery is incredible, the museums are nice. The walk along the Malecon is one of the cooler feelings out there. Everything about Lima is great. **2023 update - it moved up again. I explored more neighborhoods this time, like San Isidro and even now further away from Covid, even the historic center is a bit more vibrant. For what is also a great entry point to a brilliant country outside it, and a place with near perfect weather, Lima is stellar**
12.) Seoul (2022, 2024)
I don't know if there's a city I saw more of in my initial trip visiting a place. I went all over it, to different districts, different elevations, different stories - all of them amazing. The food, from bustling (but clean) night markets, to tasting menu bliss of Ryunique and Mingles. The cocktail houses, all inspired in their design and craft. The clubs that surround buzzing districts like Itaewon (RIP to those who dies on Halloween 2022). Everything about Seoul was great, including the sights, from large palace-come-parks in the heart of the city center, to art museums showcasing the beautiful tranquility of Korean art (white porcelain, jade, buddhas, etc.). Seoul was a masterful city, a place I easily could have spent even more time exploring different areas. Despite spending much of five days there (and the neighboring city of Suwon, that fits in my 90-minute window), I left a bit sad I didn't spend even more time - partially to get more of Seoul, and also because I want to see more of what Korea has to offer having loved their crown jewel so much. **2024 Update: No real change, because my one day in Seoul I basically just retraced steps of places I already loved. I will say, Seoul in winter is extra beautiful.**
11.) Rio de Janeiro (2025)
I probably need to add some descriptive tiers, because to be honest everything from #13 (Lima) to about #7 (Barcelona) is somewhat interchangeable. Rio could easily be higher. Hell, if I liked beaches more, it likely is a bit higher. But in reality, Rio is an incredible city - so many great neighborhoods, so much culture and joy. I've rarely been to a place with just a better overall vibe. From a natural beauty standpoint, other than my city at #1 not sure if there is a better coastal city in terms of just pure beauty. The food is great, with a mix of great low-profile steak, to high-profile tasting menus. The nightlife is endless, whether you want samba, or bossa nova, or hardcord EDM. Everything is available in Rio. Again, that beach aspect is what probably keeps it from being even higher.
10.) Ho Chi Minh City (2019, 2022, 2023, 2024)
The great food, the wide open streets and lanes, the great balloons, the sights. Ho Chi Minh City was truly a perfect Southeast Asian retreat. The place is so full of joy and pride in their city, be it the pristinely conditioned temples, the French architecture. There are great museums and sights all over. What set Ho Chi Minh City apart for me was you get the food of a Bangkok, with the infrastructure and lack of traffic of a Europe - the city so well blending their French history and Asian sensibilities. The nightlife and food was truly incredible. If not for the weather (unavoidable in that part of the world) it probably would be Top-10 for me.
**After going back in 2022, Ho Chi Minh City equaled every bit of nostalgia-fueled love and memory from the first time, arguably getting better. Each year that goes by thrusts HCMC into more and more of a first world type city, with amazing food, amazing drinks, and the best (to me) club in the world in The Observatory. There is just a joy, such an energy here. **2024 Update: Still maintains its spot, and yes every time I visit HCMC it seems a bit brighter, a bit more upscale. If anything, I hope it retains its wonderful charm in another 10 years or so as it continues its ascent**9.) Rome (2003, 2019)
Speaking of Rome, history’s most famous city checks in next. I haven’t spent any time in Rome as an adult, but I don’t think Rome is the type of city that would change much from an adult’s perspective. It is good for its history and sites first, and if you like Italian cuisine, the food second. If you include the Vatican, and as a Catholic I do, in Rome, then there is even more to see, as you have two different parts of history, the formation of the Catholic Church in the awe-inspiring Vatican grounds near and inside St. Peter’s Basilica, and the Roman history which is very well kept up. I can’t remember how their public transport was, and we went in December, so the weather was bad, but I don’t think it is a very big city. And then there is that food. I don’t want personal biases like my ambivalence towards Italian food to sway this. Many do like Italian food, and the city is even better for those people. That said, what hurts Rome in my book is I think it is too dependent on the sites, and if you aren’t there on a religious pilgrimage, I can’t imagine the allure of going to Rome more than once.
8.) Athens (2010)So Athens is very much like its historical partner, Rome, with a few less sites, a lot less crowds, less expensive, and with better weather. So does that whole equation spit out a better city? In my mind, it does. Part of this has to do with visiting Athens at the perfect time (19, during March) and Rome not (13, during December), but Athens has it all. It has a lot to see, but not so much that sightseeing takes over the trip. It has a city that is hard to navigate by car and by walking, but has an adequate subway system. It has excellent food, and a great environment that bursts with fun and enjoyment. Just a grand old time in Athens, as I’m sure it was 2,500 years ago.
7.) Barcelona (2007, 2021)
I really want to go to Barcelona again, because it could easily be #1. All the ingredients are there. Pristine weather. A people who don’t care about life, making the tourist experience more fun. Good beaches within reach. Stuff to see. An airport that is easily reachable and a city that is easily maneuverable. My issues with Barcelona (other than my dislike for the Blaugrana) are simple. There isn’t a lot to see in terms of history, mainly because the Catalans want their own history so they destroyed or shunned any Spanish national history. Barcelona is a nice city in terms of seeing the sights for a day or two and then doing nothing the rest of the time, but I do want more from my cities. **Going back in 2021 didn't really change my opinion of Barcelona at all. It remains a great city, with a whole lot to see. Getting to see the Sagrada Familia more complete - in that you could go inside - was a nice touch. The food remained excellent, from random tapas bars, to nicer restaurants.**
6.) Istanbul (2007, 2024)
Istanbul is kind of a secret still, but there is really nothing to complain about. It has a waterfront, an easily accessible city center, a lot to see (the palaces, the Bosphuros, the Red & Blue Mosques). Istanbul also has a brilliant food scene, with both Muslim and Meditterannean influences but all sorts of bases (including a ton of seafood). There is little to separate any of the cities this high in the list. My only knock on Istanbul would be the public transport is lacking without a proper Subway (this could have changed since my last visit). Overall, Istanbul combines the palate and affordability of Asia, with the energy and cleanliness of Europe, the best of both worlds. **2024 Update: Istanbul drops a bit, mostly due to some weird fogginess of brilliance I had around the city past my 2007 trip. Anyway, what it did do is remain overall just a fabulous blend of cultures. You want Eastern temples (mosques), architecture, customs? You got it. You want palaces that could rival Versaille? You got that too. You have a unique cuisine that can spread from the late-night-street-food of the world (doner kebab) to refined Michelin-star restaurants, and a burgeouning night scene to boot. The only real reason it drops is that it is a bit too big and sometimes tough to get around in, but as a city it is truly a fantastic blend of East and West**
5.) Jerusalem (2018)Religion's most important city remains the best new city I've been to since I last wrote this piece. I'm floored by how much I enjoyed every aspect of Jerusalem. The obvious important religious sites were incredible, but the food spots in the city, the areas in the old town that are disconnected to religion, the great beer bar tucked inside the great Mahane Yehuda market. All of it was excellent. If I spend more time in Tel Aviv, maybe I add that to the list to, but for Jerusalem, it was a perfect mix of history and culture. Truly, the religious sites are so enormous in their gravity it is hard to not be astounded, even for someone who is practicing but not necessarily devout. The energy in the city is just tremendous - helps we went around Christmas of course. It was a perfect mix of circumstances, but it was just incredible from start to finish, a perfect mix of first world luxuries and historical beauty.
4.) Santiago (2018, 2024, 2025, 2026)
Midway through my second day in Santiago, I started debating how high it would go. Honestly, on the initial drive to the airport, through beautiful underground tunnels and well manicured streets, it earned its place on the list. Many great meals, multiple vibrant and differing neighborhoods, enough sites to last you days, and a cleanliness of Europe and culture of the Americas, and Santiago morphed into a truly special city. You have views, like at the top of Santa Lucia Hill. You have museums. You have regal government buildings. The restaurants are amazing, going from good street food to world class tasting menus. The competing Barrio Italia, with its Portland-esque vibe, and Barrio Bellavista, with fun bar after fun bar, add the neighborhood vibe as well. It all mixed to a truly brilliant city.
***2024 Update. So, Santiago is basically as perfect a locale as I remembered, spending more time there this time and getting to see some of the best parts. The museums and cultural aspects remained great, but now let's add on top of it everything about its modernity. You really don't feel you are in South America, with its wide roads, greenery, hills and life. The restaurants like Borago are timeless. Wandering the streets of Barrio Bellavista at night is a never-ending joy. Ride that funicular and cable-car and you see a city jsut bursting with life, energy and fun.***2026 update: moving it up one spot as it continues to just amaze with its combination of North American luxuries with South American culture, food and charm - plus now we ventured out to a new day trip area. I don't think there is any place in South America better for a short visit. Plus, I love that my top-4 span four different continents now.***
3.) Kyoto (2013, 2023)
Kyoto is the 3rd biggest City in Japan, but resembles so little of Tokyo (the biggest city) that makes it seem like a different country. Sure, the food options and the bustle is still there, but Kyoto, in some ways, is like a supersized Siem Reap. The real highlight of Kyoto is the ridiculous amounts of Temples and historical Japanese
buildings. All of these are encircling the downtown area of Kyoto. Of course, that downtown is quite large, with beautiful malls, tall buildings with summer beer gardens (umlimited beer buffets for $30) and plentiful up-scale food options. Kyoto even has the most expansive Geisha area of Japan. Kyoto is the perfect city to experience what people's idea of Japan is, temples and pagodas and sushi, oh my!
**2023 Update: Everything I wrote about is true in 2023, but the stuff I didn't get overly into - mostly because I didn't focus on that as much - from the high end restaurants, to the bar & nightlife scene, upped its game. The fact the main parts of the city, be it the shopping districts, the nightlife drag, and where the sights lie, are all within sort of walking distance, ups the game for Kyoto. Also, there is a chance I was, if anything, underrating the sights. There was truly ne negative to Kyoto, other than maybe the heat but that's more on me picking this specific time of year than anything else.**
2.) Madrid (2001, 2010, 2018, 2021, 2022)I’ll never forget Madrid. It was where I turned 10 years old, in April of 2001. It was where I saw my first naked woman in real life, as I saw two nude woman near the pool in Madrid (given my age and their age, this wasn’t a good thing). It was where I first traveled alone, and where I learned the inherent joy of visiting a place a 2
nd time. Barcelona might be more ‘fun’, but I can’t think of a place that combines everything I want from a city more than Madrid. Madrid has a dependable airport, and a dependable subway system. More than that, the city is small enough in its center that you can easily walk from the Prado side on the East, to the Palace on the West and not break a sweat. It has some of Spain’s best museums. There is more than enough to see. And, of course, you are still very much in Spain. It isn’t as relaxed as Barcelona, but is just as Spanish, with open squares, easy food and drink, a lot of youngsters (and a lively area for them at night). This wasn’t a criteria, but a lot of people speak English there to boot. Madrid is basically a perfect city. Small enough to walk, with enough sites to not get bored, enough food to not go hungry, and a relaxed, but not too relaxed nature that you won’t ever get tired of doing nothing for an afternoon or two.
