My husband and I are going to Italy for the first time for 2 weeks this May. Five nights will be in Florence. We're very interested in taking some day trips out of Florence to visit wineries and nearby cities. Which do you recommend? I've heard great things about Siena and San Gimignano. Anyone been to either?

Thanks!

I've been to both and highly recommend both. Siena is a city whereas San Gimignano is a hill town. More to do in Siena. If you rent a car you can hit both in a very full day.

I have also been to both and think they are both interesting. As the previous poster said they are very different. I think that Siena merits an overnight. If you have four nights in Florence you might consider spending one in Siena and visiting San Gimigano on your way back to Florence.
We stayed in Siena for 2 nights driving from Rome to Florence and did a day trip to San Gimignano from Siena then visited a few towns in Chianti on our way to Florence. We stayed very close to the main square in Siena and loved walking in the city at night. A terrific restaurant to try is Da Divo. It was the best meal we had in Italy.

Make sure you make reservations for the museums in Florence. It will save you lots of time in line.
Have a great trip.

San Gimignano is very nice but really busy, especially in May. The town gets much nicer after about 4:00pm when all the tour buses leave. How about spending a romantic night there. We stayed in Cisterna Hotel (Sp) and had a room overlooking the square. As the sun went down, everybody sat at their open windows with their wine, it was gorgeous. Also very nice little restaurants, loads of game and regional wine. Lots of fun

Hi
scroll down on the left for postings from today and yesterday on those very topics, or just do a search in the little box above on Florence or on Siena.

From Florence there are bus tours that will take you in one day to both Siena and San G. You can also do the trip independently by bus from Florence.

Wineries are more difficult, they are scattered about, and some require advance appointments. Again, there is a company or two that offer one-day bus tours with a stop at a winery.
You could also hire a car and driver.