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*Need help w/Puglia itinerary*

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Hello. I am traveling to Puglia with my husband and 14 year old son next summer for 10-14 days. We are flying into Brindisi in late July and may fly out of Bari. We like to explore, eat good food and wine and visiting beaches. We also wouldn't mind renting a boat for a day or more and sailing up the coast and roughing it w bit, but when we are land based we prefer staying in small quaint but hip boutique hotels.We also prefer to stay at a hotel in a town, so we can walk to/from lunch and dinner and with sea views. However, would be open to staying inland in one town if we choose 3 different locations.

I would be very appreciative of your feedback about the following:

1. Is this too much time to spend in Puglia? If so, can you suggest another area to combine it with? We have already been to Positsno, Venice, Florence. Wouldn't mind returning to Amalfi and have always wanted to visit Tuscany.
2. If we were to base ourselves in 2-3 locations, which towns would you suggest? I have liked everything I have heard about Monopoli but don't know if that is a good place up north to stay.
3. Would it be best to travel by car or train?

Many thanks!

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