My boyfriend and I are traveling to Italy for the first time and we are finding ourselves a little overwhelmed with the number of options. We would love to see everything, but we only have a total of 5 days in Italy before traveling to Ireland for a wedding.

Our flight lands in Rome so we will be staying there for 2 days out of 5 days (June 3rd-8th). We aren't so worried about Rome, but it's the next step. We can't decide between staying in Florence for 2 days and doing a day trip to Greve in Chainti or San Gimignano.

Option 2 is to stay in Greve for the two days and do a day trip to San Gimignano. We would love to really relax for two days, get on a bike and check out vineyards. But, logistically speaking don't know if that would be the best thing to do considering we only have 2 days. Question is about lugging our luggage from the train and probably a bus if we choose Chianti. Another option is to rent a car from Florence, but we only drive automatic so that may be a problem.

Also, we are big foodies so would love to know if you would recommend Chianti, Sang Gimignano or Florence based on food...

We will need to make our way back to Venice on June 7th as our flight leaves early morning on June 8th. Also, does anyone know if we need to be at the airport 3 hours prior to departure for flights within Europe?

Thanks for any help in advance!