I will be returning to Tuscany for a third visit. Flying into Florence from Amsterdam on Monday May 5th, we will be staying at an Agriturismo outside of San Gimignano for seven nights, we will have a rental car. Looking for some help and suggestions for the following things we have not done in the area.

A cooking class near San Gimignano. There are many, many to choose from, hoping someone has first hand experience.
A wine tour or just some of your favorite wineries in the area, more a fan of white wine than red.
Tips on seeing the leaning Tower of Pisa. Never been.
Cortona, is it worth the drive?

THANKS in advance for you help.

Can't help with the cooking class or wine tour.

Pisa... If you want to climb the Leaning Tower, you need timed tickets. Pisa would be a bit too far from SG for a day trip for me. Driving would take 90 minutes or so each way, but probably more overall when you include time to find parking outside the ZTL and walk or taxi to the Tower. If the Tower/Duomo area is your only interest, there are parking lots between Stazione S. Rossore and the Tower that are outside the ZTL. If you're concerned about driving to/near Pisa, consider driving to Certaldo or Poggibonsi and taking the train to the Pisa S. Rossore station.

https://www.accessibilitacentristori...any/pisa/mappa

Cortona... With so many interesting places to visit, Cortona for me would not be "worth the drive" from SG. It's more than 90 minutes each way, not including time to park and walk into/out of the town. But you've been to Tuscany before and presumably already visited many towns/areas closer to SG, and, without knowing what you've already seen/done, it's not really possible to say whether the drive to Cortona would be worth it for you. Have you explored much of Chianti? Volterra? Abbazia di Monte Oliveto Maggiore and surrounding area?

Thank you Jean. Yes, I have explored all the places you listed and more. I was trying to see if I could find some new places to see. I think anywhere I want to go is going to be a bit of a drive at this point. Maybe I need to re-visit some places while there.

Then you're spoiled for choice... I would look at particularly scenic drives rather than destinations. I love the Chiantigiana (SR222) and could drive parts of that any time.

You might want to do a version of the drive we did a few years ago... Drive to San Casciano in Val di Pesa, a quiet town off the tourist radar with some nice sights including medieval city walls, a small but good museum, ancient churches and a water tower with a viewing platform. I would drive there via Barberino in Val d'Elsa because I always pick scenic secondary roads over more traveled "highways," but much depends on what else you want to do that day. The wine estate Cantine Antinori is near San Casciano. After San Casciano, we drove to Montespertoli which calls itself "citta del vino" (city of wine). I would add city of olive oil. There is an exhibition of local/Chianti wines in May, but we missed it. "Mostra del Chianti." Even without the exhibition, Montespertoli is a handsome town with a lovely centro storico. Next, we drove to Certaldo Alto. Lots of wildflowers along the way, and the Alto town was a nice surprise. Great views and a few interesting sights. In Certaldo, park in the "new" town below and either walk up the hill or take the funicular.

If not Montespertoli and Certaldo, you could turn the other way after San Casciano and head to Panzano, Radda (Tenuta winery nearby), Castellina... A beautiful drive.

I am going to be totally honest with you knowing that others will probably disagree. Pisa was our absolute bottom experience in three trips to Italy. We pictured an area like where we were staying (SanCasciano, Loved it!) or Lucca (in the walled town part). But you have to park somewhere (we parked at train station) and ride a crowded bus through areas of tacky strip malls and such. It is right down in the middle of a modern town area. Like others said you need tickets to go up in it. We didn't feel the need to do this. We walked around and looked in some of the buildings on the premises which were interesting. However for the time devoted to driving to Pisa, finding the train station, waiting for bus, riding said bus waiting to buy tickets then doing the reverse to get back to our car, we were underwhelmed to say the least. Yes, we got to see one of the most famous landmarks in the world, but it was just not a great experience. Couple with that.....Pisa was the only place in Italy outside of a few moments in Rome, that we were uncomfortable. There were a bunch rowdy pickpockets on the bus and they were right up against my husband. I literally had to ride with my arm around him and my hand over the zipper of his backpack the whole way back. Then once we got off (they got off at the same stop) they walked along the road leading to the station where there were outdoor eating areas. They were yelling back and forth to each other and taking food off of people's tables with them SITTING THERE! It was not a great experience at all.

Again, thanks for the information. I will look into the drives you suggested.

Thank you drenn007. I know, I know. I have heard much the same from a lot of people that have been there. But, I really want to see it in person. Thank you for all the logistical information. I am pretty sure that this will be my last time in the area and if not now.......

If you decide to go to Pisa, consider getting timed tickets for the Tower itself (stairs only). The crowds are contained and controlled to a small group, so it's actually pretty enjoyable from that vantage point.

The Duomo and Bapistry are also worth going to as well - and unless it has changed - the tourists do not flock into these areas quite as much.

I went to Pisa in 2006 well before all of the mass overtourism, which I can probably imagine what it's like now. Not going to disuade you - this is your trip. But I am actually someone who enjoyed going and seeing Pisa. I kept my expectations low and wound up being surprised. Do I need to return? No, but do not regret making the trip.

Almost welcome, caroleeschreibman554. My hub and I loved Pisa. We used it as a base:
In Defense of Pisa
We took the train for several day trips.

Thank you TDudette!

IMO, the issue is not Pisa itself but the logistics of getting there from San Gimignano.

If you drive, make sure you know where you're going to park and how you're going to get there without violating the ZTL. Signage may be better these days, but you should have a plan.

Frankly having cycled and taken the train around Tuscany I'd avoid cars, horrible and so tricky to leave somewhere. Lucca is a great visit (leave the car outside no matter what). Cole di Val d'Elsa is a great visit (you can park, outside the walls to the west).

Jean and bilboburgler, thank you. I had planned on driving and will do my research. In all the times I have been to Tuscany and all the places we have visited in the region we have never had a problem driving or parking, just lucky I guess? I will also check into the train but I know it will add time to the trip. No matter what I plan on getting there early as possible to try and avoid some of the crowds and will go on a Tuesday or Wednesday. Bilboburgler, I have been to both places you mentioned. LOVED Lucca and may go back this trip. Again, thanks.

My best times in Italy have been not about long distance travel, it is having fun with Italians, walking, tasting, breathing, enjoying the fresh everything.

Ticking off another church, not for me