Are there any places in Europe that stay reasonably mild during winter? Like at least 10-20 degrees C most days?
Bonus points for hiking or surfing opportunities 
You might want to check out the Canary Islands. According to a local I met last night, at sea level it’s about 18-22 degrees celcius during the winter months. It gets colder in the mountains, of course. 
Thanks @tkrunning, I didn’t think of the Canaries, but that’s quite obvious. I wonder how much there is to do there and how touristic it is. Does anyone know?
Canary Islands is the place to go. Also Cyprus is quite nice and the weather is awesome.
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The weather in Athens in fantastic! Lots of hiking opportunities in the mountains around Athens and all around Greece. There are some surfing spots in Greece too, but I really don’t know about the quality. The average temperature in winter is little above 10 degrees even in December and January, but there might be a little snow some evenings. And there’s snow in mountainous areas, so in winter months you can enjoy sunny and warm days in the city and snow in the mountain villages 
Have you looked into Malta? In the winter when it rains it really pours (November has an average of 108 mm of rain) but it stays between 13-20 throughout it all. Malta also has plenty of hiking/trekking/walking paths. A friend of mine is going to Malta next January to learn how to windsurf (yeah, not the same but maybe worth learning a new skill?).
How’s the tech scene in Canaries, Cyprus or Malta? From the forums I read on European south, Lisbon sounds a good spot, also Sofia (Bulgaria), Cluj (Romania) and Toledo (Spain) have good reviews.
I can’t speak for the Canaries or Cyprus, but in Malta 
it’s heavily dominated by the e-gaming industry. It seems that most expats you meet work in either e-gaming 
, aviation 
or financial services 
.
While e-gaming or banking might not be the tech industries that get you most excited, at least Malta has a highly developed tech scene given it’s tiny size. But it’s definitely no SF, Berlin or London.
Madeira is where many go to escape winter thanks to its mild temperatures and as much as ten hours of sunshine a day in January. A gem worth discovering at any time of year, Madeira is especially great to visit in winter months due to the reduced numbers of visitors and the low cost of living will make it a very affordable trip after your Christmas splurging.
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