I was recently in Positano, Italy for the first time and would recommend, with caveats, the town to almost anyone. I happened to take the train down from Zurich to Naples (approximately 10 hours with one change in Milan), but certainly one could fly directly into Naples from almost anywhere in Europe. From Naples, it is 1 1/2 hours by car south to Positano and is one of the most beautiful drives in the world. I’d recommend using Uber for that drive, and count on it being around €200.
Positano is expensive, and on top of that, it’s physically demanding due to the verticality of the town. Often, when a place is physically demanding, it is cheaper (think Vietnam, Thailand, Buenos Aires, etc.) but when accessible can be more expensive (think London, Paris, Tokyo, New York, etc). Positano is both physically demanding and expensive and that reduces the time frame one might have to see the town.
If one is just starting out in one’s career, then this might be too expensive a place to visit. On the other hand, if one has the financial ability to visit a place where a 10 minute taxi can be €50, then one also should consider aerobic capacity, balance, and leg strength in a town that may require climbing 1000 or more steps a day. And, some of these stairs are not uniform in height, making it even more physically demanding.
I stayed up in the Liparlati neighborhood in Positano at Soso Art B&B. This is an old style B & B, where the owner Soso makes a fabulous breakfast every morning for his guests. He grew up in Positano and before retiring and starting the B & B, he had a flower shop and a ceramics store in Positano. He has endless recommendations for the area, makes a wonderful breakfast, and if you ever get lost, mention the name Soso and the locals can point you in the right direction.
There is a Michelin 1* restaurant in Positano that I’d recommend and that is Zass. It is cliffside, it offers a tasting menu, excellent wines, fabulous service…and nosebleed prices because it is Positano. The upside? Well, as you have a drink on the terrace and look out at the water that is filled with 60 and 80 meter boats, you can rest assured that some of those owners are most likely sitting on the same terrace and enjoying the same drink you are.
Bottom line: Visit Positano when you have the money, but do it before the knees and hips begin to give you issues. It is a physically and financially challenging town, but absolutely worth visiting.
