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Two weeks in Puglia - Help with itinerary please

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I'm putting together a trip to (mostly) Puglia with my grandmother for the end of November. I need your help mapping out how much time to spend in each place.

We both like walking (88yo grandma can do 2-3 miles/day), love visiting UNESCO sites, always order dessert and generally travel to eat, and live for wine. I plan to rent a car. While we haven't talked in detail about the budget, DG has said this is her last trip to Europe and I want to make it really special.

Here's the trip:
Day 1 Overnight in/near Bari *we get in several hours apart, need lodging that can pick us up
Day 2 Castel del Monte & Trani; overnight in/near Bari
Day 3 Alberobello & Locorotondo; overnight in/nearMartina Franca
Day 4 Fasano & Gravina & Cisternino & Ostuni; overnight in/near Martina Franca
Day 5 Cisternino & Ceglie Messapica; overnight in/near Lecce
Day 6 Lecce
Day 7 Uggiano La Chiesa & Giurdignano; overnight in/near Galatina/Otranto
Day 8 southern Salento; overnight in/near Galatina/Otranto
Day 9 Drive to Matera
Day 10 Castelmezzano & Castelmezzano; overnight in/near Matera
Day 11 Irsina & Acerenza; overnight in/near Matera
Day 12 Miglionico & Montescaglioso; overnight in/near Matera
Day 13 Drive Grandma to Bari airport

From there I'll go on for another 3 weeks of travel in Basilicata, Calabria, and Sicily but I'll ask for your help on that later.

Questions:
Are 4 nights too many for Matera and the surroundings?
Where is a good base for Southern Salento?
Does the itinerary generally seem okay?
What are your top places that we should not miss?

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