This is actually, a very hard list to order – mainly because the particular time and experience I had in each place weighs just as heavily as the place itself. I didn’t realize that ranking these would be so difficult. Not only is it hard to rank the best from the places I’ve lived – it’s equally hard to rank the worst. In the middle, each place had positive and negative qualities that would change the ranking. Perhaps the only way to do this is to rank these places based on whether I would want to move there again with all other things being equal.
After getting started, I’ve realized that it only makes sense to rank the Top-10. As for the others, I’ve put them in an approximate order – but in general aside from general top and bottom of the list groupings – it’s pretty hard to juggle or rank them.
Looking at this list – it’s interesting to see that I’ve lived in six countries and seven U.S. States. My top 4 all have more than 1-million people. I’ve lived in four state capitals and nine cities of 500,000 population or more. I’ve lived in the largest cities in Turkey, Oregon, Washington, and Hawaii. In my top-10 are cities in Turkey, Hawaii, Washington State, Oregon, and Indonesia. I’m surprised that California isn’t in that group. The bottom line is that I like living in large cities next to the ocean, preferably with a Mediterranean or tropical climate, plenty of diversity, and at least one university and plenty of public transit options.
Izmir is a special place. It’s a port city on the Aegean and the gateway to the Turkish and Greek Aegean Islands. Izmir is cosmopolitan, modern, ancient, and laid back all at the same time. Izmir literally has it all. The caveat, of course, is that since I was last there in 2012 – a lot has happened. The Syrian civil war changed the population dynamic and the heavy hand of Erdogan and his process of re-Islamization may have drastically changed Izmir from my memories. Certainly it has changed, I’m just not certain how much.
No matter if Istanbul has changed or not – there is no place like it in the world. There are two places that I consider to be the center of the world. Istanbul is one of them and see below for the other. The entirety of human history and civilization meets in the crossroads of the planet. This astounding place with so many stories, so many traditions, and so many people. Istanbul contradicts itself. It is both East and West, a land city and a water city, secular and religious, expensive and cheap, easy and difficult. Every big city is a masterpiece – but Istanbul – it is more.
Honolulu is the other city I consider to be a center of the world. If you were to poke a straight hole through the globe, you could almost run it straight from Istanbul to Honolulu. Much smaller than Istanbul, much less history, and much less important in terms of human culture and politics – and yet – Honolulu is where the entire world dreams of going and you can meet anyone from anywhere on Oahu. It truly is ‘The Gathering Place’. Oahu is expensive, crowded, and remote – but the weather is beautiful, the people are generally peaceful and kind, and while very small in comparison to the world- it has an outsized place in the imaginations and dreams of humanity. At number three is living pretty much anywhere on Oahu including Honolulu, Lanikai and Kailua, the North Shore, etc.
I didn’t like the weather very much during my time in London, but the museums, the access to Europe, the ease of finding something to do made it rank high on my list.
Bellingham will always be a place that I hold dearly in my heart. The sheer magnitude of outdoor beauty from Mt. Baker to the San Juan Islands. Sitting between Seattle and Vancouver, British Columbia. The terminus for the Alaska Ferry. The great beer, the hippie/environmental vibe combined with a great university. It’s just a cool place. I made a great decision when I decided to live there.
Like Bellingham but bigger and with a more robust tech industry, amazing museums, great architecture, and instead of being between Seattle and Vancouver, it’s between Vancouver, Bellingham, and Portland. Great music and art, lots of cool neighborhoods, amazing restaurants.
I enjoyed living in Fez. It’s an exotic city with a lot of the amenities of the West and great markets, food, entertainment, and a robust community of expats and educated locals. Fez is the only place in my Top-10 that isn’t a water city.
Kapa’a is one of only two small towns that made it onto my top-10 list – the main reason is because I lived right next to the beach there for a couple of years. Kapa’a itself had a pretty great selection of restaurants and diversity of cultures for such a small town – but really it was waking up and going for a swim every day.
#9 Parapat, Sumatra, Indonesia
Parapat is the other small town that made it to my list. I’m sure it is a totally different experience now – but swimming in Lake Toba, taking the trip to Samosir Island, drinking that coconut wine and playing guitars with the Batak men in the evenings, hiking into the jungle and finding giant fruit bats and orangutang – these were high points in my life.
Portland is a cool place but I’d never live there again. It’s gotten too expensive, too big, too weirdly politically correct. I love the food, the quirky neighborhoods, the music, the markets, Powell’s books – but I wouldn’t live there again. I will be happy to visit over and over again though…
The following are the cities that I would live in again – if there were no other choices available. They are good places.
Tacoma seems like it just might be cool. I need more information but if I had to choose one town from all of those not in the Top-10, Tacoma would probably be it because of proximity to Seattle, Portland, Canada, the Pacific and the universities, art, music, and culture.
I didn’t really live in Mazatlan long enough to be able to judge it. I was a child and not there all that long. I think I would like it if I were to go back.
Mendocino is beautiful and honestly, I would consider living there – but it suffers from the same issues as a lot of towns on the bottom of this list – too far from a city, not close enough to warm oceans.
Alaska is amazing. I would never want to live there because the winters in Southeast are wet and long and dark. I want to go back to visit. If I had to live there, I don’t think it would be too bad.
Manisa was exotic and cool but the summers were sweltering and the real attraction was being close to Izmir. Three things I did love about Manisa – the hiking, the wild horses in Niobe, and the Messer Festival.
I liked Sacramento but it just got too hot. A big house with air conditioning would probably make it livable but there are better choices nearby.
I feel lucky to have grown up in Big Bear Lake. I also recognize how limiting that was. It’s a beautiful place. If I were to live in Southern California again, however, I would be more towards the San Diego area.
I liked Sefrou but it’s a bit too big and a bit too small. If I were to go back to Morocco, I would pick a city or town on the coast that was either bigger or smaller. The biggest draw to Sefrou for me would be friends and family who are there.
Florence is cool but the ocean is so cold you can’t really swim in it. Florence needs a university.
Raleigh was another city I appreciated and enjoyed. Simply too far from the beach and the whole Southern approach to history including confederate monuments etc gets under my skin.
As for these last places (below), I guess I’ve said all I needed to say about them. I have no desire to visit or live in any of these places again. Reedsport is the only one that I ever loved – but it broke my heart and I have no desire to ever go back. I also loved being a farm kid in Myrtle Creek, I loved our property but not all that went with it, not the community, not the people, not the horror of my experience there.
I’ve already written so much about 
I sold my antique shop for a fire-sale price. My best inventory wasn’t in it when I put it up for sale. That inventory came to Hawaii with us in a box trailer along with our possessions. I began learning the ins and outs of antique dealing in Hawaii. Most of the stuff I had brought with me was premium goods in Oregon but hard to sell in Hawaii. It’s a very different market here. I was still selling things on Ebay and began using the 
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Honolulu, Hawaii