Tell me if this is a good itinerary!?

If it’s Tuesday, this must be Belgium.

And how do you intend to travel from one location to the next?

It’s a lot of real estate that you are covering.

I would make Sicily a different trip. Too much traveling for a couple days.

Traveling by car, most likely. Thought the flow of it would be okay… but I could totally adjust.

hey hey amanda.muoio
welcome to the forum
@Roberto LOL
to be very blunt, it is very crazy. so stressful reading this itinerary. where are you flying in from USA/Canada? plan sicily on another trip.
many newbies want to see so much without spending time in your cities to enjoy, always on the go driving. spend more time in the bari/lecce area. italy is a big country you can not see it all.
all drivers will need an IDP (aaa.com/IDP), read rules, laws, signage, ZTL zones, speed, etc good luck
aloha

If you drive and you have 2 weeks you can probably cover Puglia pretty well and possibly some of Calabria. Just be aware that 6 hours are barely enough to drive from Lecce to Tropea (or Scilla) once you take into account pit stops for gas and food. Puglia alone, from the Gargano peninsula in the north to the tip in Santa Maria di Leuca, is a 6 hour drive. All those places look close on a map, but on the road you’d think that you will never get there.

Sicily alone can easily take two weeks to visit in a decent way.

Haha. I’m okay with being blunt. It just felt like a shame to not do Sicily when it’s a ferry away. But I will take your advice and nix it. Happy to slow it down a bit. Which towns do you suggest as bases? Was originally considering ostuni for 2 nights and otranto as well. Also would monopoli be a better base than polignano?

Otranto is an absolute must for the Salento area. An excellent base. If you go in summer and enjoy beaches, that’s a minimum 4 nights for me. I prefer it to Gallipoli or S.Maria di Leuca. Gallipoli is an easy day trip from Lecce, 30 min and you are there.

Monopoli and Polignano are both nice. As a base Monopoli may be better if you intend to use it to visit Alberobello, Locorotondo, Ostuni, Martina Franca, Grotte di Castellana.

If you plan to spend more time in Puglia I also recommend to stay in the Gargano peninsula (Vieste?) a few nights. Vieste, Peschici, Vico del Gargano are very quaint. I can give you some nice accommodations to consider in Vieste.

You will love Puglia and you can easily spend your entire two weeks in that region alone.

Thank you @roberto! Happy to take any accommodation recommendations you have to offer! 😀

Since I travel in July, places have to have a pool. Puglia is hell hot in summer.

Vieste (great and reasonably priced not fancy resort), only 10 min drive from the big parking lot at the port (historical center).
https://maps.app.goo.gl/utsrNDN47rSFCZ9EA?g_st=ipc

If you stay in Alberobello. This is more upscale resort spa, but reasonably priced.
https://maps.app.goo.gl/kkkUAyqKyrVJTfhL8?g_st=ipc
I used Alberobello as a base for a lot of places, including Matera, but if you prefer to stay on the coast, then Monopoli is a great choice. To stay in Monopoli I had considered the resort below, just north of Monopoli on the beach (Pool and preferably parking is a must for me traveling in summer), but then we decided to base ourselves above in Alberobello, in the last two years.
https://maps.app.goo.gl/e3rZw8wnxxW2KFL39?g_st=ipc

Otranto (near the beach, with garage and pool, only 15 min walk from the fortress in the historical center).
https://maps.app.goo.gl/dvLcUHPPocdrF1c49?

In Lecce I stayed at the hotel below. The location was good (walkable to the city center), and the hotel was nice (with pool of course) but the parking situation wasn’t (street parking only), so if you have a car, maybe you can find something equally nice with parking, or deal with street parking like I did.
https://maps.app.goo.gl/vTjGyqXVNGNFrFLN6?g_st=ipc

hey hey amanda.muoio
you will always get great advice from Roberto "the crazy italian stallion of travels in italy" since he's from there and will tell it like it is.
one thing to be very careful about him, when reading his posts do not be having a drink of anything over your computer, your chances of spitting it out are 99%!!! mahalos Roberto
aloha