You're very welcome! Some days there are lots of posts, some days less and eventually I hope to catch up and answer everyone's questions. I enjoy helping out and helping plan out trips by answering doubts and questions, often makes me realize I need to myself get out to explore more to offer even more suggestions ;-) As weather warms up, that will be easier on the weekends!
Yes, you should definitely ALSO always explore the areas you stay in - I say it for everyone staying anywhere in Tuscany, not just for Castelfiorentino.
While the big, popular destinations always come up - Florence, Siena, Chianti, Pisa, Lucca, San Gimignano, Montepulciano to name some of the more popular ones - every single area in Tuscany has its own smaller gems. These include small, parish churches and the small, hilltop towns spread throughout the Tuscan countryside. They usually are not often named as a top destination in itself because of their SIZE - maybe because there are just a few attractions there, such as the castle and village around it but if you're in the area, definitely stop by and take a look!
There are many of these delightful towns all across Tuscany - from
Poppi in Casentino to
San Donato in Poggio near Castellina in Chianti to
Massa Marittima in the Upper Maremma - that hardly are ever mentioned in the "top itineraries" since those are aimed at visiting the top sights if 1. you're here for the very first time, 2. have limited time, 3. think this is your only chance to visit Italy and want to see the main sights. But if you've already been to the top cities, have more time, or love Italy and plan on returning, then we highly recommend spending more time exploring the rest of Tuscany ;-).
Having said all that, I've just visited Castelfiorentino once and it was just as a stop for lunch and quick walk as we headed to Volterra so I really need to go back and see what's there and in the area. There are various churches with important works of art - see
http://en.wikipedia.org/wiki/Castelfiorentino but likely the most interesting is the
BEGO museum with two major frescoed tabernacles by Benozzo Gozzoli from the late 15th century. Walk into practically any church, they all have frescoes and paintings by more or less important painters. Many of the most important works are actually no longer in the very small churches as they cannot be safely protected so are often in
museums of "sacred art" in the larger towns in the area. If you stop by the tourism office in Castelfiorentino ( via Ridolfi 1, right next to the train station), they will give you maps, brochures and more info on all there is to see in the area and nearby. I'd recommend visiting Certaldo, Montaione and San Miniato for sure - the views of the countryside as you drive around will be worthy of your time as well.
If you're in
Lucca, you could end up spending the entire day there - see this
itinerary - but if you're also interested in some beach time, head to
Viareggio. It is the closest, with sandy beaches and a very nice boardwalk to just enjoy some time at the sea. Keep in mind the beaches there are mostly with paid establishments that provide sun chairs and umbrellas so if you want to lay down your stuff and go in the water, look for the areas where there are no rows beach chairs/umbrellas but where people have planted their own from home. That is the best indication of the "free" stretches of beach - just find a spot in between and make yourself comfortable! In late May, expect weekdays to be better for beach time than the weekends, that's when all the locals are there too ;-)