We have 3 full days in September to visit the Tuscany region. Would it be better to stay in Florence with journeys out to the small towns like San Gimignano or would it be better to stay in San Gimignano and venture out to Florence and the other nearby small towns. Would we be missing a lot by not experiencing the nightlife in Florence?

It depends on how you are planning to travel (you haven't said). If you are renting a car, then San G is better, because a car is a liability in Florence. If it is by train or bus, then Florence offers more choices.

The Firenza nightlife is fun, the restaurants are superb and the club scene (which starts very late) is great for young people (or at least so my young people claim).

Florence is well, Florence. It's in Tuscany, bot not the "Tuscan" experience most people conjure up.

There can really be no greater disparity in the type of "Tuscan" vacation you will have based on which location you choose.

If you think nightlife in the big city is important you will not like San G, but most people who stay in San G enjoy the ancient solitude that comes at night.

And LJ is right on the car issue. If you plan to have a car Florence is no place to base yourself for day trips - it is a nightmare similar to Paris for driving.

Driving in Tuscany is a big part of the experience for many - the hills, the vistas, the towns not easily reachable by train, but it comes at the expense of the big city night time experience.

Others may disagree, but I don't think San Gimignano is a good base. To get to and from there requires traveling a long, winding road and I wouldn't want to be driving it twice a day, especially if one of the trips was after dark. Plus, if you plan to use a car to go to places like Firenze, then you are stuck in traffic trying to get into Firenze and find a place to park.

Again, others may disagree, but I don't think of Italy in general as a nightlife sort of place. When it's hot, people like to hang out in the piazza. But otherwise, only the young and single head out, and their nightlife venues are not all that fantastic.

If you really want small town Tuscany, consider staying in the Chianti region or south of Siena.

Have you been to Florence? Do you want to see Florence? If you've been there or have no interest in Florence why would you stay there? If you want the Tuscan experience why not consider southern Tuscany in the Val d'Orcia and discover Pienza, Montalcino, Montepulciano, etc. This is the area and landscape one imagines Tuscany to be. However, if it's nightlife you're looking for than I certainly wouldn't recommend this area.