Puglia

I’d probably swap Matera in Basilicata for one of those. I think you could choose Alberobello OR Locorotondo OR Ostuni and be satisfied, but I share your view that overnights can be worth the change of location.
In November, Lecce and Bari (plus Matera) would be my top choices. Enjoy!

I did a month in Puglia in November and it was delightful. Loved Lecce, stayed in PAM and choose it over Monopoli but as much as I loved PAM Monopoli is larger and would have more to see. Disappointed in Ostuni. Called the White City but don't think the residents got the memo as found it more dilapidated than white.

Make sure to stay one night in alberobello, I was there last year, very much worth it!

Thanks for the replies! Matera is actually the only place I've visited in the area, so luckily I dont have to feel I'm missing out on that. And I just booked one night in a Truli in Alberobello, so very excited about that.

But I am very disappointed to hear about Monopoli, maybe I'll watch some YouTube videos and see which would be the best destination to spend 3 nights.

The dilapidated comment was about Ostuni, not Monopoli. I found Monopoli an absolute gem so don’t have any qualms about there! I bypassed Ostuni so cannot say.
If you are driving your choices matter little, but if you are using public transport you should peruse your journey/day trip details as you choose bases.

oh yes! Thanks for the correction

Hi, I’ve stayed in the Puglia region three years in a row in May - a gorgeous area, and I have stayed in each of the cities you’re considering plus some more. Of the ones you listed, if you want to eliminate one, I would drop Bari. I stayed there twice for the Festa di San Nicola which is very much worth attending, but when I stayed there last month just as my first day arrival, it was my least favorite.

I don’t like day trips either. I love experiencing each of the cities in the evenings & early mornings. For the comments about the white cities - I have stayed in both Locorotondo & Ostuni. Locorotondo is the smaller, prettier version. I think you will like Ostuni more if you stay there before you stay in Locorotondo. There’s still a lot in Ostuni to enjoy, even without it being pristine white. I splurged & stayed one night in a fantastic B&B in Ostuni last month (Palazzo Stunis B&B) that’s an easy 5-minute walk from the main piazza. The previous time I stayed in a small hotel in the old center, but the B&B was such a great experience, and the host is one of the best.

Monopoli vs. Polignano a Mare - I’ve stayed in both. Be sure to take a quick 5-minute train ride to the other one. They both have their own characteristics. Polignano a Mare is my favorite because of the cliff/caves setting, but Monopoli was also very nice! I took lots of photos in both. : ). Monopoli has a stunning church interior, too. For November, Monopoli may be the better option if boats aren’t running cave tours because of the weather or season.

Alberobello - yes, stay in a trullo! It’s so fun to wake up and be staring at the inside ceiling cone shape!

Locorotondo is small, so if you wish, take a taxi over to nearby Martina Franca, too.

My favorites in order, not including Matera:
Polignano a Mare
Trani
Locorotondo
Monopoli
Alberobello
Ostuni
Lecce
Bari
Martina Franca

My family loved staying for a week in the oldest part of Ostuni in late March/early April 2018. Favorite town on the water was Trani.

I don't normally like day trips because i like to experience each location in the evening

These might better be thought of as "morning trips" because Puglia many shops/churches/museums close about 1pm until around 5pm and restaurants close by 2pm for the riposo. In smaller towns it is probably most. We were there in the summer but it is my understanding the riposo is year round. Tourism mainly happens before lunch or in the evenings and the afternoon is spent out of the sun or at the beach. If you do want to stay thru the evening away from your base town you'll have a few empty hours to fill.

Hopefully I can find a nice cafe/bar that's open during riposo. Best time to have a glass of wine! LOL

A lot of people are mentioning Trani. I'll have to look into this!

I did find a very nice apartment in Ostuni's old town on booking.com. Can't go wrong with free cancelation if you change your destination.

The riposo didn’t affect me that much while I was in Puglia because I like to take a little breather early afternoon to wash the outfit in the sink I wore the day before (hotel room cleaning is finished), put my feet up & recharge my phone, I go out in the afternoon & sketch, and I’ve been able to find at least a few outdoor tables open in each city to have something to drink.

It’s also a good time to be out riding a bike.

We do three things in Puglia in the afternoon in addition to rest and laundry: drive to the next place, eat lunch until 3:00pm, and go look at the facades of Romanesque churches. On last year's trip, I also found some churches opening back up at 4:00pm, like the Basilica di Santa Caterina d'Alessandria in Galatina near Lecce --- it's full of frescoes. Or the Chiesa Santa Maria al Casale near the Brindisi airport which is open all day.