DP and I stayed in a villa near San Miniato which is midway between the two. I would possibly try somewhere like that, very beautiful countryside, while having easy access to the larger more touristy areas. Train network is good as well if you didn't want to drive everywhere.

Ooh I did this with DS in October. He wanted to go to Italy and Pisa was cheap! It was cheap because there isn't much there to do but we really enjoyed it. We had 1.5 days in Pisa and a day in Florence. There is loads to do in Florence so just google it but in Pisa you have the tower, square, chapel and basilica which you can walk around or go in if you want to spend €€. You can walk the city walls for €3. There is a little museum called the blue house, we went to a lovely park with a great play area (can't remember the name but google it) Pisa is really tiny so you can walk most places. We actually walked to the airport with stops at the park and a cafe, took about 45 minutes altogether.

I wouldn't try to do Florence in a long weekend let alone combine it with walking and/or Pisa.

I did this for my hen! We stayed in an airbnb, went on a wine tour in Chianti and ate in some good restaurants. Make sure you visit the two famous galleries, including the one that houses the David. I didn't see the cathedral regrettably, but we did get to the Leaning Tower. A great visit!!

Bus to Pisa from the airport and then train to Florence is very easy and cheap. I would stay in Florence rather than Pisa. Florence is stunning and needs more than a couple of days. Pisa could be done in half a day. I adored Florence - the museums and art galleries, the cathedral, the bridges, the food all amazing. There is an indoor market with a central bar and lots of little shops selling all sorts of food - quite cheap and really tasty.

I need to go back to Florence.....

Book any 'sites' or museums you want to visit online, well in advance. At that time of year, there may not be tickets available if you just rock up to buy them.

Book any 'sites' or museums you want to visit online, well in advance. At that time of year, there may not be tickets available if you just rock up to buy them.

And/or queues, of course.

Pisa is lovely and has a train station that can get you to Florence as well as other places. We spent 5 days there aan didn't get to visit the country park (we saw it on the red bus tour). The Piazza Del Duomo can take half a day, and there are other things too. We loved Viarregio, an Art Nouveau/Art Deco seaside resort you can get to by train. Lucca is lovely, and Monticatini Terme is a lovely resort in the Tuscan hill, which also has a railway station if you wanted to use it as a base instead.
It is a wonderful part of the world.

Don’t stay in Pisa. There’s not much to do. Get a train in the morning from Florence then you can head back after the tower and square

I did this for my 40th. Train from Pisa airport to Florence. Didn’t do too many sights as in a small group. We made it to the Uffuzi but queued for an hour as we hadn’t booked in advance. Was well worth it, fabulous.

Didn’t make it to the Duomo due to ridiculous queues. We were there over Easter hols though. Had a lovely stroll in the Boboli Gardens. Generally wandered around in the Spring sunshine eating fab food and enjoying the architecture. I’d love to go back to do more museums and galleries out of season.

We stopped at to look at the leaning tower of Pisa on the way back to the airport for obligatory cheesy photos of us holding it up.

Lucca is lovely . I would stay there. The train to Florence is great. Florence is mental these days everywhere is crowded, lucca is more chilled

I’d skip Pisa and do either just Florence (there’s a lot to cover!) or a day trip to either Siena or Lucca by train, both nicer than Pisa!

I agree with Siena rather than Pisa. Siena is lovely.
If you go to Florence don't go on the open top bus tour. It's very long and takes you away from the beautiful bits of Florence to the modern not so beautiful bits.

Agree with pp that Lucca is beautiful - walk round the town walls and mooch round the lanes. We spent about 3 hours on the field of miracles in Pisa but very little time in the rest of the town.

We stayed in the countryside near Pistoia where there is a good Sunday market.

Florence has so much going on - the obvious, Ponte Vecchio, The Uffizi, Pitti Palace (which we loved, was a lot quieter than many of the other museums/galleries), Boboli Gardens. Check out Santa Maria Novella including the pharmacy.

I've just been trying to find details of a restaurant we went to near the Boboli Gardens - it was hands down one of the best meals I have ever eaten, but can't remember the name - sorry ! It was on a square and I'm sure it had the word Antica in the name. Not expensive or posh, just superb antipasti, pasta etc.

Gelato from La Carraia.

Bologna over Pisa any day, plus it's easier to get to from Florence than Pisa will be. Sorry that's not what you asked

Ah we hated Pisa, nothing to do, stayed there 45mins tops! 😆

However, Lucca - that was beautiful and we enjoyed it there even more than Florence.
Definitely check out Boboli gardens in Florence, but get up early to skip the queues!

Just come back from Florence with 2 teen boys. We stayed for 3 full days and visited Pisa for half a day from Florence - that is all you need for it. Stayed in central Florence - it is so small that you can easily walk around it.

We did an evening tour on the first night to get us acquainted with the city. Next day a Medici Tour with WithLocals which gave us an insight into the Medici family and included a tour of Palazzo Vecchio.

Then when on an eco tour which took us to Piazza Michaelangelo - great views. Then a tour of Palazzo Davanzati Museum.

Next day climbed Duomo cuppola and museum visit. You need to book timed tickets for the climb of the cupola. The museum ticket then allows you 72 hours to visit all the associated sights - baptistery, giotto's tower and museum. We took the audio guides and the teens enjoyed it.

We then we to Pisa for the afternoon - again you need to book timed tickets to climb the tower. We got tickets for the other sites there through Tiquets.

Last day we got timed tickets for The David at Academia through Tiqets, did a food tour around San Ambrogio area/market - eating the local dishes. San Croce church is amazing.

Just eat loads of pasta and gelato whenever possible!

The part of Pisa with the tower is tourist tat hell. The old town is lovely. But I’d just spend it all in Florence personally. We had a longer trip and stayed near Volterra which is small and absolutely beautiful. I wish I could go back to Florence - one day!