San Gimignano vs Siena

No question for me -- Siena -- The Campo, the amazing cathedral with one of the most stunning interiors in the world including the fabulous floor (when it is uncovered it is a real treat but they always have some of the tableau uncovered), climbing the Torre Mangia, the town hall with its mural of good and bad government -- just a wonderful place.

SG is also good although small and really suffers from being overrun with day trippers much more pleasant in the evening after the buses have gone -- Siena is larger and absorbs crowds better.

That's truly an apples vs oranges question. A provincial capital and university city known for its architecture vs a medieval hill town. I would happily spend a day or part of a day in either, depending on what I was interested in doing on the day.

Definitely Siena, I second everything janettravels44 said.

Crowding and availability of any cathedral or other tickets may affect your choice, especially in high season.

Personally, Siena without a doubt.

Siena has interesting sights and whole city to explore. SG is pretty but IMHO is a hollowed out tourist destination because of its skyline and setting. I've spent several nights in Siena and been happy but I see SG as a couple hour tour and then going onto something else because there's nothing else to see.

The fact that Siena is closer only seals the deal. I'd probably recommend Siena even if it was the further option, but all things considered it's an easy reccomendation.

My $.02,
=Tod

We spent a couple of nights in both cities in 2006. SG was overrun with tour busses and we hiked outside of the city during the day. It was wonderful in the evenings; very much a village feel.

As others have said Siena has much more to do and offer. That trip, I loved SG more, but if I returned I would go to Siena to go to sites not previously visited.

San Gimi is a very small town and doesn't need much time to see, but Siena is loaded with great sites.
Both are good, recommend you friends do some research on WHAT there is to see in each city.

TripAdvisor.com under "things to do in ...."

I personally loved both. But San Gimignano stands out for me because of the Chapel of Serafina. It played a crucial role in one of my favorite movies Tea with Mussolini. Yes, the town was packed with tourists and there was a gauntlet of shops to get through, but at the right time of day it would be lovely.

Go to Siena first, then if you have time at the end of the day, you can swing by San Gimignano for a quick visit at the end of the day. If you go at a time of the year when it gets dark later, you can probably do it. But Siena should be your priority. San Gimignano is crowded with day trippers in high season, especially weekends, but if you go later in the day the day trippers will be gone, although certain sights may be closed by 5 or 6pm.

Thank you all so much. Consensus is overwhelmingly for Siena, so that is what we are going to do. As one person said, if we have time we can always drive up to San Gimignano in the early evening after Siena and after the crowds. I appreciate all your help!