We went to Sorrento last Sept for a wedding, we had a great week.. staying a little out of Sorrento in St Agata at a beautiful villa ( Li Galli...under the villa description of Villa ruoppo ) the buses were dirt cheap & took about 20 mins (takes that to get across most big towns here!) and they ran regularly... it was great to have the day in Sorrento then retire to a villa in the middle ...(as in outside the windows in our garden) of a lemon grove..last bus home was about 11.30pm.. The villa cost us 950 euros for the week and the views were breathtaking.. I see that the prices are the same this year although they have added a pool..you can get everything you need in St Agata...the rep & company were excellent, you can chat to them online before going or talk on the phone, they are based in Scotland but are Italian with great english. The flights are sitting at about £270 each with Travelocity from Scotland but maybe cheaper for you. This was a holiday which was different class & we did'nt find it all that expensive to eat ect...if you go enjoy the meloncello....mmm nicer than the lemon..lol
The website for that company is
http://www.holidaysnoproblem.com
They also do villas slightly closer to Sorrento on the same bus route.. in Massalebruense... which also looked gorgeous and will try the next time
There is also a very easy to find/use & cheap ferry service from Naples to Sorrento. My son is 8 and we went to the beach and he also loves Roman history, was'nt bored & watched cartoons occasionally...lol even tho he could'nt understand them he said it was OK cos he'd seen them all before & knew what was happening!
Truly is a beautiful place