Portland, Oregon
What’s going for it? Do you like letterpress? Do you like vintage clothes? Do you play in a nu-folk band? Then get ye to Boise, Eliot and Overlook in Portland. The city has been the capital of liberal, hipster USA for decades. The Dandy Warhols wrote Bohemian Like You about their very home town. There are some, indeed, round these parts who’d like the entire Pacific Northwest to break off from the rest of the US and go it alone. So very liberal is Portland that it’s a home from home to anyone from Europe, especially if they read the Guardian. Cyclists are loved, not loathed. There are planning restrictions on crappy developments. Portland has the highest number of microbreweries in the world. Everyone is lovely. My auntie lives there and will make you a nice cup of tea if you’re homesick. H.E.A.V.E.N. Shockingly, it still remains relatively good value. Especially the patch north of the Willamette river above the railyards. When I first visited in the early 90s, Boise, Eliot and Overlook were the kind of spots you sped through: always the first sign of a neighbourhood you should buy in. Now you can’t move for contemporary modern antiques shops and dinky record stores.
The case against Bit too cool for school. Everyone’s like you. Who will you have to hate? Oh, yes, everyone like you. The weather: like Britain, but more so… hotter and colder and danker.
Well connected? Unusually again for the US, cycle and walk without abuse: the most bike- and foot-friendly city in the country, packed with proper cycle routes (15 minutes to downtown from the northside). You may use the car. Occasionally. Perhaps for a surf trip to the coast, or a ski trip to the mountains (both 60-100 minutes).
Hang out at… A food cart: all the rage (check out foodcartsportland.com). Or, for the indulgent, Grand Central Bakery, in an old scrap metal yard. Artisan, innit.
Property The area is full of 1910s and 1920s bungalows that the local real estate guys call “craftsman style”, with handsome stoops and carved wood decoration. There are a fair few vacant lots, too, for the brave, plus 1960s and 1970s infill apartment blocks that, with a zuzz, could be nice. Look off the main drags, like Mississippi and Interstate regeneration projects. Huge detacheds, £415,000-£575,000; four-bed-plus detacheds, £225,000-£415,000; two- or three-bed detacheds, £140,000-£215,000. Condos below this.
Bargain of the week Two-bed detached on NE Sacramento, £128,000, with propertiesofportland.com.
St Pauli, Hamburg
What’s going for it? Those Beatles were on to something, you know, with their pre-fame escape to the fleshpots of Hamburg. Fifty years on, modern-day beatniks are all Berlin, Berlin, Berlin. Boring! The truly adventurous should spurn the obvious for Germany’s second city. For a start, it’s almost on the Baltic and, with Noma, Sarah Lund and all, you know how very now anything Hanseatic League is these days. Plus it’s home to HafenCity, the biggest spot of urban regeneration in Europe, bigger even than our own paltry Olympics. Despite stellar architecture and some community-minded planning, I wouldn’t recommend moving to HafenCity itself, not till 2023 or so: not unless you like cranes and high-vis jackets. But the old red-light district, St Pauli, just along the Elbe, and to the north around Karolinenstrasse and Schanzenstrasse, have been quietly simmering with revival. This was the hotbed of radicals in the 1970s and 1980s, and it still hums with alternative living. Only there’s better coffee. That’s progress. It’s still seedy, and you may have to bob and weave around the stag parties, but tucked among the porn are artists’ studios in old slaughterhouses, experimental theatre companies and, call me a capitalist, some great, and often odd, shops. Like Holy Bikes (holybikes.de). It’s more expensive than Berlin, but then Hamburg has the great advantage of a vibrant economy and jobs. You’ll need them, when all that alternative living palls.
The case against Ooh, when the wind whistles in from the North Sea: Hamburg in January – nippy. A few too many advertising agencies. For the hardcore beatniks among you, the area may have already “gone”.
Well connected? Hamburg is incredibly bike-friendly: Elbchaussee, along the river, is perfect for Sunday cycle rides, and the centre is only five to 10 minutes away; HafenCity just beyond, maybe 15 minutes.
Hang out at… Strandpauli beach bar, with one of their “special” mojitos, or Rote Flora for some improv theatre.
Property A great line in 19th-century apartment blocks and nice higgledy streets. Small flats in old buildings (60-100 sq m), £60,000-£120,000; larger flats (100-220 sq m), £120,000-£230,000. Modern blocks command higher prices: maybe £1,600 a square metre.
Bargain of the week A small flat for renovation, 75 sq m, £70,000, with grossmann-berger.de.
Northern coast, Maui, Hawaii
What’s going for it? I am not known for my surfing. But if I were, this would be the place for me. I am not known for my ability to relax. But if I were, this would be the place for me. The northern coast of Maui is where you go utterly to detach from reality. This place is so laid-back, much of it has a 15mph speed limit. Don’t even think about pineapples and grass skirts (but do think about surfboards; this is where it all began). Much of Hawaii is overloaded with kitsch. Here, there is none. OK, a very light dusting. But, mostly, the northern coast comprises a series of tumbledown, laid-back bars, waterfalls, surf spots like Ho’okipa Beach and Kapalua Bay, lush jungle, and communities of writers, artists and what my gran would have called layabouts. Avocados and guavas are as common as nettles here. As are whales. Everyone will soon know your name (the place is exceedingly friendly and community-minded). But the clincher? This is where the Japanese go on holiday. And if a place can get the Japanese to relax and try surfing, it might even work on me.
The case against A long way away from anywhere else. Don't know about you, but I'd miss good old British squally showers and snow. A bit. A volcano! Dormant, but call me nervous…
Well connected? You'll need a car, though with those 15mph limits all over the shop, it's not worth investing in a Lotus. The main airport at Kahului is about 13 miles to the west and, from Haiku, it's a 10- to 15-minute drive to the main towns at Paia and Makawao.
Hang out at… Pauwela Cafe on West Kuiaha Road. They do a mighty coffee.
Property Paia and Makawao are the most developed towns, but I'd pick the ultra-relaxed Haiku. Plantations dominated the landscape here, so expect 1850-1930 "colonial" style houses, and humbler wooden, single-storey detacheds. Two- or three-bed detacheds; £170,000-£400,000; posh detacheds with two to three acres, £400,000-£650,000. Luxury and lots of acres, above £650,000.
Bargain of the week A wooden jungle cottage, with photovoltaics on the roof and its own water supply, £164,000, with realestatemauihawaii.com.
Cihangir, Istanbul
What's going for it? I bet guide books blethered on about "where east meets west" when Istanbul was Constantinople. But at least it's finally coming true again. On account of Turkey's wooing of both the EU and east Asia, the past decade has seen the city turn from lovely-if-decrepit museum piece to lovely-if-decrepit museum piece with great bars, economic growth and an OK public transport system. Not all of the change has been for the best. But spots like Cihangir make it all seem worthwhile. This is an Orhan Pamuk kind of neighbourhood. You'll still pass woodturning workshops, button warehouses and old ice-cream parlours en route for that dark, urbane bookshop. It still feels old and ancient and unrestored and a bit shabby. There are still whiskery grocers who'll deliver figs to the door. The dervishes still whirl up the hill at the Galata Lodge. Only now there's a great rooftop bar or six with views over the Bosphorus (I'd consider moving here for the views alone) and a good modern art gallery at the bottom of the hill. What with culture and economics so shifted to the east, this feels like where the world begins.
The case against Earthquakes. They're waiting for a big one, and who knows what horrors lie within those teetering apartment blocks. Be sure to get a very, very good structural survey. Those views come with a price: exceedingly steep hills, which turn into white-water-raft courses in rain showers.
Well connected? The tottering, creaking tram plying along Istiklal Caddesi isn't just for the tourists, nor the new one up the Bosphorus and off across the Galata Bridge. In between, use your thighs, or hail one of the billion yellow taxis.
Hang out at… Susam Sokak (Sesame Street) is a laid-back cafe by day, a slinky cocktail bar by night. Good place to pretend to write that novel.
Property Recent property liberalisation means it's simpler for foreigners to buy. Think lofty, skinny apartment blocks. Fight for the views. Small flats (70-100m2), £60,000-£100,000; 100m2 flats with a good view, £100,000-£130,000; big 'uns (150-250m2), £130,000-£250,000; swanky, up to £500,000.
Bargain of the week Zillions. Start with hurriyetemlak.com.
Santa Cruz, Tenerife
What's going for it? Yes, Tenerife. But not that Tenerife. As if. No, this is The Other Tenerife. The capital bears no relation to the island more familiar to Brits. Turn a few corners on the coast road and it's like, well, Spain. Santa Cruz is magnificently, sexily exotic. Its neighbourhoods mostly date from the 1890s to the 1930s, all pastels and gin slings, though the long-lost recent economic boom has left its mark, too, with a new art gallery and public square by architects Herzog & De Meuron, and the obligatory "thing" (Is it a bird? Is it a plane?) by Santiago Calatrava. The tourist-free city is big enough not to be dull, small enough to be manageable – about the size of Leicester, only, alas, without its charms, although Santa Cruz does have bright placitas filled with orange trees and dark, drowsy coffee bars full of old men playing dominos, as well as a brilliant food market, Nuestra Señora de Africa. And when it all gets too much, there's a series of great beaches (the Las Teresitas being perhaps the best), a great coastline for swooning driving, and mountains for hiking.
The case against People might actually think you've moved to Tenerife. As if. It can be our secret.
Well connected? You'd walk, wouldn't you, with weather like this? Otherwise, a car is vital.
Hang out at… Café Numancia for a fresh-pressed naranja watching the parklife. Then Café del Principe for an ice-cold coffee. Then maybeEl Contemporáneo bar for a sundowner. Then to Calle Antonio Dominguez Alfonso in Noria for nightcaps. Oops, a day gone.
Property Noria, downtown, might be the first stop: its once dilapidated homes are being slowly restored, and the place has great life. Las Mimosas for the swankier. Small (50m2-plus) apartments in the centre or larger ones farther out, £110,000-£170,000; large apartments in the centre (100m2-plus), £170,000-£350,000; huge apartments or sprawling detacheds, £350,000-£500,000.
Bargain of the week Very large, 216m2 apartment in the centre, needing updating, £400,000, with barrespropertytrading.com.
• This article was amended on 25 January 2012. The original said: "Ooh, when the wind whistles in from the Baltic..." In fact any nippy whistling comes from the North Sea, the source of the prevailing winds. This has been corrected.
