Visited Santorini in the off-season using Pyrgos as a home base since it was central on the island; seemed to have more local authenticity and less tourist trappings than Oia or Fira.
The cave house was fantastic and fitted my needs perfectly as a solo traveler. I appreciated the stocked refrigerator with bread, ham, cheese, milk, OJ, an assortment of cookies, coffee, herbal teas. The style and history of the home is impressive. It has nice modern touches but still retains its classic character.
Several good Pyrgos restaurants remained open in off season. Liked Mythos Tavern the best for dinner but can’t go wrong with Penelope’s (#2) or Kounerios (#3)
Dimitra arranged arrival transport from airport for a reasonable fee. Prygos is directly on the Fira to Perissa bus route. I relied on bus transport the entire week with only minimal issues. Buses arrive about every hour 9am to 5pm during the off season. Fare is €1.80. Walking to Fira is possible, It’s not bad actually... all downhill and takes about an hour. Maybe not good in the summer heat but for a late fall/early winter visit... nice walk.
Five days really gave me an opportunity to see most parts of the island at a relaxed pace.