I always met a ton of people. This is easier if you go to cities with big digital nomad/expat/erasmus communities. I used to research the social life of a city

I always met a ton of people. This is easier if you go to cities with big digital nomad/expat/erasmus communities. I used to research the social life of a city in advance by checking Facebook groups like "Digital Nomads Chiang Mai" or "Lisbon Expats" and meetups on meetup.com If you want generic ideas for cities you can see http://nomadlist.com/ http://nomadlist.com/ but you still need to research it. Depending on your continent the easiest places to start digital nomading are like Lisbon/Barcelona/Budapest/Chaing Mai/Bali/Medellin. There is a ton more and you will discover them after talking with digital nomads about their previous trips.