Two weeks in Puglia

We spent a couple of weeks in Puglia in 2022 and just adored it. We stayed at a terrific Agriturismo, Masseria Aprile in Locorotondo followed by 4 nights or so in Lecce at B & B Centro Storico, also fabulous.
Masseria Aprile was a great base for taking day trips to Alberobello and other spots within an hour’s drive. Fabulous breakfast and proprietors.
We also loved Lecce and the B& B there; found easy street parking w/in 5 min walk as the center of Lecce is pedestrian only.
I strongly recommend that you extend a bit and spend 1-2 nights in Matera in nearby Basilicata, a UNESCO World heritage site (Google it if you’re unfamiliar with it- like no place we’ve ever been). Stay in a cave B & B or hotel and take a guided tour. It’s unforgettable. We stayed 1 night and wished we’d stayed longer.
Wherever you go in Puglia you’ll have wonderful food & make incredible memories. We def want to return.

Thank you so much, Elizabeth! This all sounds great. I will look into both of these places and we will for sure go to Matera and do two nights! Appreciate your help!!

I sort of break it into "zones" (depending on time of year), and I consider Matera (yes, Basilicata), Lecce, and [pick your village] in the Itria Valley three great bases. Early October or late October? In early October you might like being on the seaside, but you are never far from the coast--if you like scenic drives, the coastal road south of Otranto is nice.
One thing to consider especially for Puglia is in you want to stay in a masseria or in a town.

@ valadelphia , skip Bari or day trip?

Bari--it depends! I stayed in the old town for one night on both trips, as we arrived in evening and wanted to pick up the car the next morning. The old town is atmospheric and pleasant, has great restaurants.
That said, I certainly understand having limited time a trip, and I have a preference for smaller towns, so I would only urge those who are especially interested in it to go.

Thank you so much, Val! We will be there early to mid-October. If we could actually swim in those gorgeous waters at this time, we would be all for it! Do you know if this is possible then or is it too late?

One never knows these days--I would consider early October a definite possibility for a warm enough sea for swimming. Since it takes such little space, I'd pack a suit just in case. Weather likely takes a turn in mid to late October, so you could also just check the ten-day forecast right before you leave.

We found the book "Lonely Planet Puglia & Basilicata" useful in understanding Puglia and planning our visit last fall. It's about 15 years old but the towns haven't changed that much. Two other resources are looking online for blogs reporting on travel in Puglia, and YouTube videos such as walking tours.

We were only there for 6 nites so stayed in Lecce. Since Puglia stretches almost 200 miles long with two weeks your plan for a few bases makes sense. I'd suggest the Gargano Peninsula (Vieste, etc) which we visited on a daytrip a few years ago and thought was a beautiful area. As for swimming, I think October is becoming the new September and you'll still be able to swim. You can see historical temperatures for the past few years at https://www.timeanddate.com/weather/@3173131/historic?month=7&year=2023

Many Puglia threads on this forum, such as: https://community.ricksteves.com/travel-forum/italy/puglia-itinerary-ideas

But to find them, since the search here is clunky, the easiest way is to google on Rick Steves Italy forum Puglia.

To answer your question about towns to base in (not counting Matera), I'd say Trani, Ostuni, and Lecce --- wonderful towns that are different from each other and you can get to anywhere in Puglia from one of them. If you want an alternate base to Ostuni, I warmly second the recommendation to stay at Masseria Aprile in a trullo.