For our honeymoon, my husband and I were lucky enough to spend a month in Tuscany. It was a brilliant idea because we got to experience things outside of the typical Florence, Pisa and Siena (ALL beautiful places with a rich history and I'm sure you have heard enough about them so lets delve into some more obscure places). Tuscany is a magical place and it's exactly as you would expect it from the movies. I remember growing up watching romantic movies set in Tuscany and thinking "wow, the rolling hills, the vineyards, the coastline...is it really like that?" I have to say, it's exactly that!
I highly recommend you spend at least 2-3 weeks travelling around Tuscany and believe me, it's best if you have your own car. Yes, Italians are insane on the road but a car will allow you to step outside of the tourist areas and experience Tuscany as the locals would.
On the Etruscan Coast, just the drive along Viale dei Cipressi towards Bolgheri Castle is magical in itself. As the name suggests, there are 5kms of Cypress trees on each side of the road and in the gaps you will see the entrance to a number of famous wineries such as Tenuta San Guido, the winery behind Sassacaia.
For me, Bolgheri truly represented the best in Italian Food, Wine and Culture. Get there before 11, walk around the quaint shops and then find a nice Enoteca and enjoy a glass of Bolgheri Rosso and the best pasta ragu you will ever eat!
2. Forte Dei Marmi (Fort of Marbles)
We visited this place with the owner of Sensi Vini. I had never heard of it before but apparently, it's the holiday destination of the rich and famous. Andrea Bocelli and his wife actually live there and the famous Italian musician Zucchero was born there!
It's a lovely sea side spot with elaborate shops, beautiful cafes and when the weather is right, you can sunbake and enjoy the waves off the coast. I really felt at home here, it could have been anywhere in the world, it didn't have the same feeling as the rest of Tuscany. Its also got a really fun nightlife so I recommend visiting in the summer and spending a couple of nights partying with the other ITALIAN tourists.
3. San Gimignano
There are plenty of old medieval towns in Tuscany but you will struggle to find one more famous than San Gimignano, home to the famous Vernaccia di San Gimignano DOCG. The only DOCG white wine of Tuscany. I warn you, there are millions of tourists that visit San Gimignano but this UNESCO World Heritage site boasts Tuscan scenic views better than I have seen anywhere. There is a beautiful Duomo to see (there are many in Tuscany) as well as Museums but simply enjoying a wine tasting flight on the balcony of a cafe with a beautiful is good enough for me!
If you want to escape the tourists but still enjoy a medieval Etruscan city, drive yourself south of San Gimignano for a couple of hours until you get to Volterra in the middle of Tuscany. Upon driving I thought, "oh my, this better be worth it!" and it didn't disappoint. There is a beautiful Romanesque Cathedral and it's own "leaning tower" which I thought was really cool. Volterra is famous for Alabaster and some of the sculptures are just breathtaking (just as is the view!) When you hike to the top, you look around and see nothing but bare land. It's really quite amazing and it makes you feel so small in terms of the size of the world. Spend a night here and enjoy dinner at a nice restaurant (I recommend checking out what rates highly on Tripadvisor), grab a bottle of wine and spend the night staring out into space.
Finally, Montepulciano! The land of the famous Vino Nobile Di Montepulciano! Not to be confused with the GRAPE from Abruzzo. It stands atop a hill in southern Tuscany and surprise, it's a medieval city! It has beautiful renaissance palaces and churches so it's perfect for history/architecture fan. If you like thermal baths, Montepulciano is also the gateway to the famous Bagno Vignoni. If you love cooking, you can stay in an Agritourismo overnight, do cooking classes and truly live like the locals!
So when are you visiting Tuscany?