We spent 3 nights in Sorrento. It was a beautiful city and I think it was a wonderful location for touring the general area. One note: there was a train strike on the Circumvesuviana the day we arrived into Naples. The platform was full of tourists and others. My advice...wait out the first train that shows up if you find yourself in this situation. When the train finally arrived everyone was shoving onto the train. The train comes fairly often and we waited for the next one and took a front car and we all got seats. This will lessen your chance of a pickpocket in my opinion. Also, if there is ever a place to wear a money belt this would be that place. My daughter actually warned someone of a person reaching into their pocket. Keep your eyes open. That being said, go to Sorrento. I had never been to this part of Italy and I absolutely loved it. Yes, there are a lot of tourists but it is a lovely city.
We stayed at Hotel La Tonnarella. It is gorgeous. The staff is wonderful. We rented their largest room as there were 5 of us. They accommodated us and the view from my shower, well...I'm still thinking of that view. I could see the entire harbor from my shower. Amazing. The rooms have gorgeous views too!
The best meal we ate was at the hotel. The food was incredible. The views were amazing. Eat here. Even if you aren't staying here eat here. Well worth it!
We asked the hotel where we should eat the second night and they suggested Ristorante Donna Sofia. They will pick you up from your hotel and bring you back. There is a reason. It is not easy to get to and the ride is quite memorable. The car goes through streets that are only the width of a car. The driver knows what he is doing. The food is very good and we enjoyed our meal. They sat us in the garden but we did move inside because of the mosquitos. The garden is lovely but I was sporting a few bites already so..
We did a ferry ride to Capri and then took a taxi to AnaCapri. I did not ride the chairlift to the top though two of our party did and loved it. We took a taxi rather than a packed bus. The bus wait was very long. The road is an experience in itself. Lots of cute shops to browse at the top. Good restaurants and gelato as well. No problem getting a taxi back down and catch the ferry to head back to Sorrento.
We also did a tour of the Amalfi coast. Take a tour. Don't drive yourself. You can enjoy the ride without the stress of the traffic and there is traffic. We saw Positano, Amalfi and Ravello. My favorite was Ravello. Far less tourists and very quaint town square with picturesque hills. The towns are all beautiful and fun to explore. The tour stopped about 1.5 hours per town and that worked well. Our guide had a lot of information about the area, each town and where and what to eat and buy. If you get motion sick take medication and stake out a seat at the front of the van. That seemed to work for those with that issue.
We did not make it to Pompeii but I always leave a place with a reason to return so...next time.