Tuscany
 

If you had the choice between the following two, which would you pick and why?

1. Siena + San Gimignano
2. Pisa + Lucca

To give you more of an idea of my itinerary - our base is Florence (we will not be changing this, hotels booked)
We are headed there in a couple of weeks - time of the year
And other places we are going include Rome, Montepulciano/Pienza, Lake Como + Milan
Our interests: Good food, scenery, taking in the culture.

Siena, because it's bigger, has more things to see and has a greater choice of restaurants.

https://flic.kr/p/7peinx
https://flic.kr/p/7pi8tq
I would include San Gimignano in a day tour of that region. If I remember correctly, we also visited Volterra on the same day.

https://flic.kr/p/7pi3sL

I haven't been to Pisa so can't comment, but I found Lucca underwhelming. Loved Siena and San Gimignano though I'm not sure I would want to base myself in San Gimignano as it gets very busy during the day with day trippers. It would be lovely though in the evening after the crowds left.

If this is a one-day excursion using public transportation, I'd pick Siena, and I wouldn't want to take time away to visit San Gimignano. If it's an organized guided tour, Siena and SanG are often paired, but I think time provided in both places is too brief.

I also found Lucca a bit underwhelming. We even returned to see if we just hadn't been in the right mood on the first visit. Same reaction.

Thanks so much everyone!!! So Siena it is. And if time permits we will throw in San Gimignano. Would you recommend then to visit San Gimignano after lunch before heading back to Florence? Or start in San Gimignano and end in Siena (then go to Florence)

Good choice. Siena this trip, Lucca next trip.

I would start in Siena. You may find you want to spend all your time in Siena and skip SanG. Have you checked how long you'll spend in transit... esp. if you tried to include SanG??? If you're using public transportation, it's 1+ hour from Florence to Siena, 1+ hour from Siena to SanG, and it might take 2 hours to bus from SanG to Florence.

FYI, there may be train back to Florence from Siena that departs later than the last bus. Ditto a late train back to Florence from Poggibonsi, but you'd probably have to taxi from SanG to Poggibonsi.

I would recommend a visit to San Gimignano when the Cathedral is open. These are among the greatest frescoes in Tuscany. Also, I think the food is great in SG. I might divide my time, if possible, between a morning visit to San Gimignano, see the Cathedral, and have lunch, then on to Siena for a little sight seeing. How are you getting about?

Oh dear, viranpooja, Siena and Pisa get my vote. Siena'a Duomo is incredible and the main piazza del Campo a don't miss. Pisa's Duomo is astounding and a walk away from the Field of Miracles yields an interesting city with a university vibe.


https://www.fodors.com/community/europe/in-defense-of-pisa-1702701/