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Puglia accomodations question

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I am traveling to Italy in late July/August with my husband and son. We prefer to stay in chic but charming boutique hotels or smaller hotels in town so that we can live like locals, walk to/from dinner, etc. However, it seems to me that the nicer accommodations are in the Masserie in the countryside. We plan on renting a car and exploring the area during the day, mixing historical sights and areas of interest with beach clubs. Is having a car also going to present a major obstacle for us if we wish to stay in town? I have read that if you have a rental car, parking can be difficult as it can be impossible in some areas to drive the car to the hotel because of the narrow streets. We have approximately 1 week in Puglia before we drive to Matera and the Amalfi Coast (our base will be in Praiano). Am I wrong to focus on staying in town based on what I have told you about our plans? Will I be missing something if we do not stay in one of the Masseries that seem to popular in that region? One thought was to spend a few days in a Masserie and the other few days in town. If we were to take that approach, which town(s) do you think it would be most worthwhile to stay in where I can search for boutique hotels, and where would you suggest staying in a Masserie? Many thanks for your assistance!

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