One extra day to spend anywhere...

I vote an extra day in Tuscany just because I love it! But it looks like you do seem to be going to the big sights...

Haven't been to Lucca, so I can't comment on that one

Personally, I'd choose Lecce. There's lots to see in the city itself, as well as many interesting small towns nearby. I'd say they have mostly old, atmospheric areas rather than important museums, though.

However, you have 6 one-nighters in a row later in the trip... I can't imagine doing that, especially on a 23-day trip. I'd be certifiable by the mid-point. You may need that extra night around Day 14 or 15.

Nicole
Your itinery sounds ambitious. I stay in Puglia for 10 days and feel as though I missed so much. To go from Sorrento to Matera is a good ride. Keep in mind Puglia is not as accessible as some of the other stops you have planned on going to. Good you have a car. Public transportation is not as available in Puglia. If you are planning on being in Puglia on a Sunday almost everything is closed and other days many places close mid day and reopen in the evening. I was in Lecce on a Sunday and saw nothing except a few churches. Even restaurants were closed. With that being said, I'd spend an extra day in Lecce or the region. We rented a trulli in Cisternino at La Fogliarella, check it out.

Have fun
Lorieann

Add a night to Puglia or Lucca.

Your itinerary looks fine to me, according to your description of your travel style.

As art lover and arriving in Pisa, I find it so sad that you do not pay any attention to Florence. There is so much to see! Pisa for me is worth 2 hours - not much more. Lucca is cute and one day is ok. Siena could do with 2 days. If you do the Amalfi coast I would not do Cinque Terre and devote this time to some time in Florence and maybe one more night in Rome or a day in Tarquinia (wonderful!)
I was in Puglia (North) and Basilicate (Matera) and did it all by train. We really enjoyed Matera and had a really nice BnB near the station owned by very nice young people.
It gave us time to watch. We did also walk a lot. True what

Nice to have a car in Puglia as you are doing all of Puglia.
For Tuscany, not useful for Pisa Lucca and Sienna. For the other part it is nice to have (Montepulciano, Volterra).
Viterbo is also another idea to go to.
Enjoy your stay in Italy

We recently returned from a month in Italy. You say you are history buffs and love museums - and you are leaving Florence out of your itinerary with it's fabulous art and history. Siena is on your list and is a little over an hour by train, I think I'd find a way to get to Florence. But if you are set with the cities on your list then I'd spend my extra day in Lucca or Siena. My wife really liked Lucca and my choice (guess) was Siena. Either way I would happily return to either.

I know you said you are young and active but I don't think your itinerary is going to allow you enough time to really explore, absorb and take in what Italy and the Italian lifestyle is about (culture). When in Tuscany I found it would take longer to get from one town to another than what google maps said it would.

Good luck with your planning and however your itinerary turns out I am sure you will have a fabulous trip.

Jim

Thank you guys so much!!

We've actually been to Florence several times, but I agree... its a wonderful place to visit! If we had more time we would certainly go back, but we decided to skip it this trip.

I wouldn't add the night to Lucca because you have a pretty short drive from Monterosso and it's quite compact, flat, and easy to visit.

I would sleep the extra night in either Volterra or Montepulciano, where you have more driving and more to see within the multiple towns listed for those days. Don't miss Volterra's Etruscan museum.

I also think that Siena deserves a full day, which might mean departing later on the train toward Venice.

I see you have planned Orvieto and Civita for one day. I would add my extra night to Orvieto as going to Civita will take most of the day. You aren't leaving much time for Orvieto!