My husband and I were in Positano for seven days for our honeymoon the last week of September (+5 days in Capri afterwards - which we're posting in the Capri forum) - we wanted to share our experience for anyone who's looking for some advice:
Since we were staying a week we rented a villa from www.summerinitaly.com - Casa Clementina. It was a cute apartment with unbelievable views. We had a better view eating dinner on the terrace than any of the restaurants in town! ;) It wasn't too much of a hike up from the center of town but there was a bit of noise from the cars on the main road below.. It was nice talking with the landlord (she lives below and was extremely kind and helpful) and taking trips to the grocery and vegetable shops down the street - we felt like we were getting a bit more of the "local" life.
We loved Cafe Max in the main square. The service was excellent and they brought us complementary champagne to celebrate our engagement. The stuffed zucchini flowers (with cheese and a bit of prosciutto) were SOOO good, we talked about them so much afterwards that we had to go back at the end of the week and get them again. It seems like all restaurants in Positano get booked up early (or at least the tables with the best views) so it was good to at least call or walk by earlier in the day to make a reservation. Caffe Positano was also nice - great food and a beautiful view (once again, the tables on the edge of the terrace were the best ones!) We also got take-away pizza from the restaurant by the main beach - I think it was the Covo Sarceni (??) - the one with the gelato in the front. They have the best Pizza Primavera and if you get it take-away (for the beach, etc.) it's a very good price.
The water was SO clear, turquoise and beautiful we never even felt the desire to stray away to one of the pools in town. We loved the beach Il Fornillo, around the corner to the west. It's a short and beautiful walk over and there are less people and boats around that area. Also, we went over to a private beach in the other direction where Da Adolfo restaurant is located. You can catch the restaurant's free boat over during lunch and dinner hours or hire a water taxi to take you over. It is a small quiet beach with only the restaurant-goers around and cliffs rising straight up behind the coast. Beautiful!!!
We travelled to Pompeii one day -- buy the bus tickets in town, then you have to walk up the road (past Le Sirenuse hotel). There's a little "hut" with a bench. The bus to Sorrento comes across the street from the hut-bench, while the Amalfi bus comes to the bench side. The sita buses are blue or green - I am sharing the information because everyone was always so confused. :) It really didn't appear that the buses followed any particular schedule. We normally ended up waiting quite a while which is one reason why a week-long stay is great - you can have some days off from the bus-traveling to recover and relax in town. To go to Pompeii, you can catch the Sorrento bus, then get off in Sorrento at the Circumvesuviana train station which you can take straight to Pompeii. We spent midday in Pompeii (bring snacks in with you, it's huge!) and on the way back stopped in Sorrento. Sorrento is spread out (rather than the steep feel of Positano) and very grand - lots of old mansions, hotels, parks... And great shopping, there are so many stands it seemed a lot less expensive than the Positano ones.
We also went out to Ravello. Go early!! Take the bus to Amalfi, and then transfer right away to the Ravello (smaller) bus and PUSH to get on! It is every person for themself or at least it was in the end of September. I felt like I was on the Titanic sinking and we were trying to get into the last life boat. But Ravello, once you get there, is so beautiful. Also different from Positano in that it is in the hills above vineyards with gorgeous sweeping views of the ocean from above. If you walk through the tunnel there is a museum on the left (the concert society?) that was showing an amazing exhibit of modern art while we were there. Another pathway on the left as you come through the tunnel winds up past some ceramics shops (the ceramics are amazing) and eventually ends up at a gorgeous palace-like hotel. For a few Euros you can walk through the gardens - definitely do it because at the ocean view terrace at the end of the path, there is the most amazing views in Ravello. It was one of our favorite places of our entire trip.
We hiked up to Montepertuso and Nocelle one day. We took the inter-positano bus (the little orange one that says "Montepertuso") which we were glad of, because once in Montepertuso we hooked up with a few other couples who had hiked up and seemed a bit cranky about it. The hike from Montepertuso to Nocelle is really the whole point of going up there due to the gorgeous views of the ravines and oceans - it is uphill but not difficult as you just follow the quiet paved road. Nocelle is even more rural than Montepertuso and has a quiet charming authentic feel with once again the amazing views of Positano from above. There are supposed to be some great restaurants in Montepertuso - I can imagine a sunset trip would be really nice. The stairs going down from Montepertuso link up with Positano directly so it's a nice stroll back down - LOTS of stairs but it's downhill so it's not too bad.
We loved Positano! It was a great place to stay and take day trips from. And as a side note, Capri was gorgeous and amazing as well - definitely worth more than a day trip if you can do it!