Cities or towns...
1. Akaroa, New Zealand - I wanted to move here when I visited in 2009. Founded by the French who didn't realise the English had already colonised the nation this small town on a cute peninsula with an exquisite, snaking bay, inspires bad writing like this sentence. Great food, places to stay, and one of the world's smallest species of dolphins make Akaroa a winner.
2. Colonia, Uruguay - Europeans say it is too European to impress them, but this little town with its old Spanish forts and cobbled streets has more charm than Jack Nicholson when you are drunk. Its quaint charm is balanced by ease of access to the insanity that is Buenos Aires, a mere hour's ferry ride across the staggeringly wide (50km) Rio Plata.
3. Sydney, Australia - this is not just because I am from there. Go to Balmoral beach on a sunny day, and you will understand why Stephen Fry once asked "Why would a sensible person want to live anywhere else?"
4. Damascus, Syria - The most welcoming people in the world. If you have been to Cairo with its ceaseless and offputting harassment, it is easy at first to mistake Damascans politeness as a sales pitch. But they genuinely just want you to like their city, their country, and the most amazing culture that has developed in the world's most continuously occupied city.
5. San Francisco, U.S.A. - another place I have lived, and it gets the nod for it - great food, possibly (and this is controversial) better than New York. You can walk San Fran and each block reveals something new, something so dramatically different it is as if you stepped through a portal.
Other notables ; Kyoto, Japan; Boston, U.S.A.; Capetown, South Africa; Santiago, Chile; Buenos Aires, Argentina; New York, U.S.A; and many more than pisco sours allow me to remember...
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