Tuscany Week Long Road Trip

After a busy time of Rome, Japan and Marrakesh, we thought we would round the year off taking in the scenic roads of Tuscany. Getting legless on delicious wines and driving drunk without a care in the world. Tuscany is a relaxing destination and one where it is very easy to gain weight.

Pizza, pasta, cheese, coffee, calzone, bread, cheese, pasta, pasta and the best damn mashed potato, I’ve ever had. Seriously. Covering central Italy, Tuscany spreads over 23,000 kilometres with its rich landscapes, winding roads and vineyards. Tucked away beneath those hills are hundreds of tranquil, traditional Italian towns, almost none of which I can confidently pronounce.

Keeping that in mind, we explore the smaller populated areas such as San Gimignano and Monteriggioni. Next we venture to the larger cities like Sienna. Driving further north we take in the beauty that is Florence. And finally we head to Pisa, where never before had subsidence been such a celebrated occurrence. This is Suitcase Monkey eating over 6 nights in Tuscany.

My new favourite Italian word, San Gimignano was conveniently en route to our hotel. San Gimignano is a walled in medieval town, around an hours drive from Siena and the whole city just wreaks of a time gone by, but but without being lost in it. I strongly recommend. After a few hours spent in San Gimignano, we took a 40 minute drive to the Aquaviva Hotel & Spa. Located in the commune of Casole d’Elsa, we chose the location since it was a pretty central part of Tuscany so most places on our list were a few hours drive away, in either direction. For us, it was the perfect blend of the conveniences of a small hotel, whilst still feeling that Tuscany vibe and a room with a view to die for. It had been a long first day so that evening, we relaxed with some wine and a well earnt dinner.

After over indulging once again, we got some rest knowing that tomorrow we would be exploring Sienna, which is a must do for every Tuscan traveller. (Car sounds, clicks, tyres screeching, Horns beeping) On the way to Siena, we made a brief stop at my new favourite Italian word, Monteriggioni. Its main attraction is this medieval wall which circled the entire commune and offered up some more stunning views.

The couple of Euros it costs to ascend the wall also includes what might goes down in history as the quaintest museum in the world. Containing 4 rooms, the museum allows the chance to step back to an age gone by when people wanted to take back control and make Tuscany great again. Whilst you only need a couple of hours in Monteriggioni, its unique enough to warrant a visit if you are in the area. As you would expect, we ended our time here, eating too many carbs.

To help anyone who is planning a Tuscany driving holiday I have a very important message for you: Parking anywhere near a populated zone in Tuscany is a big fat pain in the ****hole. Looking back on the footage we have from this trip, I really wish we had captured the stress, pain, and anxiety it takes to find a suitable resting place for your temporary vehicle. Instead, lets show you some tranquil shots taken of better times whilst I explain. First of all, coming from merry ol’ England, the gear stick being on my right hand side kind of made me wish we’d have got automatic transmission.

Second, Italian drivers either just know EVERY single road by Osmosis, or they are born with the innate ability to see round corners. I can’t tell you how many times I crept around a bend while a 10 foot wide HGV came at me, almost in a post Brexit outrage. Yet, Italian drivers seem quite happy taking this bend, at great speed, in the middle of the road, without any consequence. But mainly, its that there are almost never any available parking spaces where you want them to be: Remember San Gimignano? 30 minutes to find a space. Siena? 20 minutes.

Along with a spot of driving the wrong way down a one way street. Great times. Usually the solution was parking somewhere a good walk away, but all I’m saying, is work that INTO your schedule or take a good look at all possible parking options before you start driving… And just be prepared from an expectation point of view and all will be well. With that mind, following a tip off from, the internet, we were super ready for some Florence parking action. We parked near the Co-Op of all places, situated right in front of my new favourite Italian words the Nenni – Torregalli Tram stop, making the journey into central Florence a breeze.

I’ve linked a Trip Advisor discussion about this below. The tram takes around 15 minutes and gives a nice view as you cross the Arno River arriving at Alammani Station. Florence is the capital city of the Tuscany region and is considered the birth place of the Renaissance. Packed with cathedrals, town squares, a bustling energy, magnificent architecture, shopping, culture, museums and much more, you could easily spend days here.

For us, we were more than happy to wander the streets aimlessly and see where we ended up (SAT NAV: In 200 meters, your destination is on the right.) If you’re going to Tuscany for more than a few days, I would really recommend splitting your hotels over 2 locations. By the last few days of the trip we did feel stuck to one area, without wanting to endure 10 hours of round trip driving. Some of the best highlights in the last few days included the time we visited Volterra, a medium sized town, with plenty of shops and climbable high towers with rewarding views.

Or the time we visited the nearby tiny town in Casole D’elsa. A picture postcard collection of sunny streets and alleyways. Or even the time we actually listened to some advice given to us during our stay, and we drove all the way to the “coastal town” of Livorno. We heard canals and thought Venice.

But this video here literally is the only nice shot taken after this 3 hour journey. Not wanting to be beaten, having got all the way to the west coast, we took the scenic drive south to Cecina. Here, we found a calm, quiet area where trees and water and beach and rocks all combined for a relaxing break in the afternoon. Then, of course, throughout all this, there were all the times we enjoyed the amazing Italian food.

Finally, on our last day, we had a few hours to spare before boarding our flight. After dropping off the car at the airport, the Pisa Mover takes you to a 30 minute walk way from the Leaning Tower itself. Due to the time constraints we had, we pretty much made a bee line towards the famous landmark but I reckon you couldn’t go far wrong spending a whole day here. If we had the luxury of time, I would have enjoyed heading inside the tower to feel the slant under my own feet. Still, the Leaning Tower of Pisa itself is a great sight to behold.

Even after seeing so many photos of it, witnessing that iconic lean with your own eyes is really impressive and was a great way for us to round of another Suitcase Monkey adventure. If you’ve enjoyed this vlog, you really will be doing us a big favour by liking this video, along with subscribing for all future trips and clicking that notification bell as we maybe only post once a month on average. In the meantime, why not watch our recent travels to Rome, Japan, Kenya and Marrakesh to name a few. And keep up to date with all the behind the scenes stuff on Facebook, Instagram and Twitter.