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Calling Ekscrunchy and other pugliaphiles: Puglia itinerary in progress

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My husband and I will be visiting Puglia in mid-September, and I'd love input on the itinerary I've got partly laid out.
Also, very interested in restaurant "musts". I'll definitely be using Ekscrunchy's trip reports for that.

First, our priorities: great food, pretty, not-too-touristy towns, sea views, nice hotel rooms, hotels in walking distance of restaurants (which is why we probably won't do a masseria, unless someone persuades me otherwise).

We will have a car, but enjoy being able to walk places from wherever we're staying, especially at night so my husband, who's the only decent driver, can get his drink on at dinner.

Having most trouble with my Salento choices, and with the masseria/ no masseria debate. Are we giving up something essential if we don't stay in one?

Now, the plans and choices so far:

NORTH: TRANI
Arrive in Bari Sept. 15th, spend 3 nights in Trani at Hotel Mare Resort
http://www.mareresort.it/

MIDDLE: OSTUNI OR FASANO
Sept 18-21: 3 nights in Ostuni at La Sommita, room with private terrace
http://www.lasommita.it/
OR
3 nights in Fasano at Masseria Torre Maizza (tempting but probably not, since it requires driving to anywhere else)
http://www.masseriatorremaizza.com/

SALENTO
Sept 21-24: 3 nights in Lecce? Or 3 in Gallipoli? Or split between them?

Lecce: Hotel Risorgimento
http://www.risorgimentoresort.it/

Gallipoli: Corte Palmieri
http://www.hotelpalazzodelcorso.it/hotel/it/hotel-puglia/relais-puglia.html

This part I'm having a tough time with. Don't want to do too many hotel changes. More fun to stay in Lecce and visit Otranto/ Gallipoli as day trips? Or vice versa?

The seafood in Gallipoli sounds amazing, and ditto for the sunsets. I'm a sucker for both.

Then again...nicer hotel in Lecce, I think. Would driving in and out of Lecce be a nightmare? Would we be bored by 3 nights there?

NAPLES
Sat Sept 24: Drive to Naples, spend 2 nights there (haven't picked a hotel yet) and fly home on Monday the 26th.

Thanks in advance for your input!

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