Road trip ideas for a memorable short break in Tuscany

 *Collaborative post

Two weeks today I’ll be flying to Tuscany with 13 (yep you read that right, thirteen!) of my fellow family travel bloggers to review this gorgeous luxury  Tuscan villa and experience some of the best attractions the area has to offer.  Not only am I excited to have a few days away with friends, I also cannot wait to visit one of my favourite regions in Italy.


I cannot wait to escape the cold and miserable weather in the UK to enjoy a few days as a guest at the Country Relais and Spa Le Capanne!

One of the port’s of call I most looked forward to when I worked on cruise ships was Livorno, the main cruise port for Tuscany.  From Livorno we ran shore excursions to the lovely Lucca, Siena, Florence, Pisa and San Gimignano… deciding where to spend a day ashore was always a difficult decision!  Fast forward ten years and add into the mix 13 passionate travellers and it’s easy to see why it’s taken a while to confirm plans for our three-day road trip in Tuscany.

Road trip ideas for a short break in Tuscany

Country Relais and Spa Le Capanne is located near the historical centre of Volterra in Ulignano, close to San Gimignano.  It’s a great central location for exploring the region by car as Florence, Siena, Pisa and Livorno are all about an hour away.    

We will be picking up our hire car from Pisa airport after midday on the Friday, and leaving midday on the Monday, so our priority is to make maximum use of our two full days sightseeing. **Top tip – A useful site to compare rental car prices is EasyTerra, an independent car hire comparison site.

We originally considered combining a half day in Pisa, (very doable as the main sights – the Leaning Tower of Pisa, the Field of Miracles and Cathedral can be seen in a few hours,) with a half day in Florence.  We decided against it, as the hours spent driving would have been impractical and wasteful.  Instead we have opted for a full day in Florence and a full day in Siena to fully explore these incredible cities. (Although I have to say it was a difficult choice as San Gimignano is also spectacular!).

Saturday morning we plan to pop into Volterra on our way to Siena.  This will be my first time in Volterra.  I’m most excited to walk along the cobbled streets of the walled town, check out the medieval ramparts and visit the pastry shop owned by the Giovannini family to indulge their famous Italian pastries.

road trip ideas Tuscany

Our one hour drive from Volterra to Siena will be a very pleasant one passing by rolling hills, woods, vineyards and olive groves…  The iconic Tuscany landscapes I remember so well from my cruise ship days.

During our journey we will pass Castel San Gimignano, a popular spot which must be featured on Instagram thousands of times due to its enviable location set high on a hilltop. We won’t get time to stop during this rather short road trip but it’s not hard to see why it’s one of Tuscany’s most famous villages…

road trip ideas Tuscany - San Gimignano

Siena is a unique city, built over three hills.  Leading the way over the hills, (and helping us burn off some pizza, wine and gelato calories!),  will be our local guide who will take us on a three-hour walking tour around the main sights of the medieval city.  We plan to check out its central piazza, Il Campo, which is known worldwide as the location of Siena Palio, the famous bareback horse race, which takes place there twice a summer.  It’s a place I have been keen to visit after seeing it in the James Bond movie, Quantum of Solace.  It’s also a strikingly beautiful part of the city with unusual architecture such as the Palazzo Pubblico –

road trip ideas Tuscany - Siena



  1. 23rd May 2018 / 4:38 pm

    Awesome information! My fiance and I are honeymooning in Italy this September and we can’t wait! We’re still not so sure where we’ll go since there is just so much to see there, but Tuscany sure looks amazing! I can’t wait to eat everything. ;-p

  2. 7th March 2018 / 11:31 am

    “Watch out Tuscany!” is all I can say 😉 Oh you guys will have THE BEST time! And these roadtrip ideas are wonderful – we always love a good roadtrip, if only for the flexibility when travelling with little ones. #MondayEscapes

    • Lisa
      7th March 2018 / 7:51 pm

      Ha ha yes Tuscany certainly does need to watch out Jenny! We love the flexibility road trips can provide too:)

  3. 6th March 2018 / 9:58 pm

    I am so so excited about this trip! It is going to be amazing!! I am just deciding what shoes to take for all the sight seeing and photo taking!! 🙂

  4. 6th March 2018 / 2:21 pm

    I will be taking a Mediterranean cruise in September and will be in the Tuscan Region so I was so happy to see your post! It got me very excited for my trip!

  5. 5th March 2018 / 10:24 pm

    Any chance of making it 14 travel bloggers!! 😉 You’ve sold it too well! Sounds like a wonderful trip. Can’t wait to hear about all the adventures! #MondayEscapes

  6. 5th March 2018 / 8:11 pm

    That sounds like such a fun upcoming trip! I would love to road trip through Italy and have the flexibility of having my own vehicle. Thanks for giving me some great ideas to start from! 🙂 #mondayescapes

  7. 5th March 2018 / 2:46 pm

    Literally cannot wait, its been ages since I was in this part of Italy!

  8. 5th March 2018 / 10:04 am

    omg, omg this has made me soooooo excited, I cant wait to wander and enjoy all those beautiful sights, I think I am going to need to buy a spare camera battery just in case I know I am going to take soooo many pictures x

  9. 5th March 2018 / 9:35 am

    Tuscany is so beautiful and we have spent a couple of holidays there – the second taking in all of the places you talk about. We stayed just outside san Gimignano and walked in each evening for ice cream and to enjoy the atmosphere. I have no doubt we’ll be back

  10. 5th March 2018 / 9:07 am

    I love Tuscany! I’m looking forward to reading about the road trip!

  11. 5th March 2018 / 7:58 am

    This looks absolutely lovely. Husband and I visited Bologna last year (loved it) and can’t wait to get back to Italy!

  12. 4th March 2018 / 10:31 pm

    I’m so excited about this trip. It’s going to be awesome! I already know we’re going to be gutted that we didn’t have longer to explore!

  13. 4th March 2018 / 11:57 am

    There is so much history to see and this place looks simply wonderful for a road trip. Enjoy!

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