Even with all of amazing and iconic sites to see in Florence alone, a two week stay gave us plenty of opportunity to explore all of Tuscany and even into neighbouring Umbria. These days trips were highlights of our time in Italy.
We used Viator to book our excursions for no reason other than I usually do, have had no issues with them and they allow me to reserve now and pay later (a benefit for the uber early planner). Many of the same options would be available through any other booking service so do an online search or use your own. What we did end up doing is book many of these day trips through the same provider Ciao Florence , which also has their own website if you want to book directly. Having a recognizable meeting place and guides really helped alleviate the stress of finding them each time.
Our first trip involved stops at the Medieval hill towns of Siena, Monteriggioni and San Gimigiano. This trio was recommended as the most popular. It was both exhilarating and exhausting (you cannot have hill towns without hills to climb). There was a wine tasting thrown in and you could pay to participate in a group luncheon at a local restaurant in Siena, which we did.
Siena is best know for two sites; the town square with its imposing city hall, and the Cathedral and Baptistery. We were given a guided walk by a local guide which was a perk as she offered insight specific to the area and with a local flair. The town square is famous for its annual horse races, competitively fought between regions in the area. The Siena Cathedral, started in 1196 and not finished until 1348, is a fascinating mix of medieval, gothic, renaissance and baroque influences. It’s interior offers art and sculptures by renowned Italian artists such as Michelangelo, Donatello and Bernini.
Monteriggioni was originally a hilltop defensive lookout during the battle between Florence and Siena for control of the rich Chianti countryside. The battle was eventually decided by a horse race (spoiler alert – Florence won). There are only 34 permanent residents but it fills daily with tourists as it offers lots of unique shops, restaurants and great community spirit. You may recognize the town if you are a gamer – it is featured in Assassins Creed. Also Dante wrote a poem about it, ensuring it is captured in history.
Lastly San Gimigiano is a impressive walled town, again with lots of shops and restaurants and stunning views of the Tuscan countryside. Walking between stone buildings on narrow streets made us feel like we were in a medieval town in days past. The streets would open into squares surrounded by buildings that now are used by the municipality and for tourism such as museums and hotels.
One of the best parts of this and other tours like it is the stunning Tuscan countryside you can enjoy during the drive. Be sure to include a day trip to the hill towns on your next trip to Italy.