When most people picture Tuscany—the rolling green hills, the winding roads lined with iconic cypress trees, and the golden-hour light hitting a medieval farmhouse—they are actually picturing the Val d’Orcia. While the region is famous for its Renaissance cities, the true magic lies in its UNESCO-protected southern countryside. This comprehensive Val d’Orcia itinerary is designed to get you out of the city and straight into that postcard-perfect landscape.
Instead of battling immediate city traffic, this route has you grabbing a rental car at the Florence airport and escaping directly south. Basing out of a rural villa in Castelmuzio, you will spend your days exploring the medieval streets of San Gimignano and Siena, sampling robust wines in Montepulciano, and discovering the Renaissance charm of Pienza. To cap it all off, the road trip loops back north for a grand, three-day finale exploring the iconic art and architecture of Florence. Prepare yourself for breathtaking landscapes, rich history, and a true feast for the senses!
Why Tuscany?
Italy is an incredibly diverse country with an attractive capital of Rome, with all the Roman history and culture. The Alps and Dolomites are my natural draw to the mountains, with the Alta Via 4 Trek being a highlight. Cities such as Venice attract people worldwide for its narrow canals. The southern regions of Naples and Sicily offer warmth and coastal towns. However, since doing a day trip to Florence from Rome in School, I’ve always wanted to return as an adult!
The Tuscany countryside is beautiful, and films such as Gladiator only add to the desire to visit. Renowned for being a wine region, the vineyards and medieval towns add to the laid-back lifestyle. Staying in an Agritourism (Accommodation on a working farm) is a wonderful experience and helps you appreciate the simpler things. See our authentic Val D’Orica Itinerary below.
Val D’Orica Itinerary
Tuscany Map
Val d.Orcia Itinerary: Planning Tips
What to see?
When planning the Val D’Orcia itinerary, controversially, the Leaning Tower of Pisa is not included on this list, as I’ve had mixed recommendations about visiting. Instead, this Val D’Orcia itinerary focuses more on South Tuscany instead of visiting Pisa, Lucca or the charming coastal towns. Florence is a must-see, being the largest city in Tuscany and ever popular with tourists flocking to see the history, art plus indulge in the cuisine.
Sienna is a medieval brick city that has a magnificent Cathedral, the Piazza del Campo and Torre del Mangia to see. San Gimignano was my favourite town to visit, with its ruined towers and the best gelato in the world! Finally, Val D’Orica and Pienza are picture postcards of Tuscany and white tracks to explore among rolling hills.
Where to stay?
We stayed in Castelmuzio for our Val D’Orica itinerary to start because the countryside views from the olive grove were very attractive. A 90-minute drive from Florence and many lovely towns surrounding it, such as San Quirico d’Orcia, Pienza and Montepulciano. Hotels are available, but for an authentic Italian experience, stay in an Agritourism. This type of accommodation is on a family-run agriculture farm (a vineyard or olive grove) and usually has fresh products. For our picturesque Val d’Orcia itinerary, we spent 2 nights in an apartment in Florence via Airbnb to give us easy access to the city. Florence has an abundance of accommodations for every budget, good transport links to Rome and an international airport.
Transport
The easiest way to navigate and fully explore Tuscany and this Val D’Orcia itinerary is by hiring a car. Public transport is limited and irregular for visiting the remote countryside towns. If you’re only staying in Florence, then you won’t need a car and could book a day tour to Siena, Pisa and other attractions. We used Zest to research the different rental companies and used AutoVia, where we picked up from the Airport.
Tip – There is a free airport shuttle to the rental companies
When to visit?
The best time to visit for the Val D’Orcia itinerary would be the summer time, but most places with swimming pools don’t open them until June. So if you’re looking for a villa to relax by the pool, then wait, but be prepared for the higher prices and temperatures. We went in May, which had a nice balance of warm sunny days, lower prices and fewer tourists too. Tuscany has things to offer all year round, but be aware of Italian public and school holidays.
How long to visit?
The 8-day Val D’Orcia itinerary is adaptable for longer visits to explore northern Tuscany, such as Pisa, Lucca or the Coastal towns. However, focusing on just Florence and then a long weekend would be enough. We felt that we covered most of the main sites in 2/3 days around the city. It’s easy to combine Tuscany with a trip to Rome as well!
City Trip Essentials
Daily Val D’Orcia Itinerary
Day 1 – Castelmuzio
The start of our Tuscany adventure and Val D’Orcia Itinerary was rushed after oversleeping and needing to drop the car off at the Airport. Luckily, it all worked out, and before long, we were boarding the flight to Florence (Amerigo Vespucci) Airport. Florence was sunny in early May when we arrived mid-morning, and we quickly found the shuttle to the Car Rental.
We had to queue for an hour to collect the rental car (VW T-Roc) and then hit the road. I had the first challenge of navigating out of Florence and adapting to driving on the opposite side of the road. Soon we were away from the traffic and motoring towards the beautiful countryside of Val D’Orcia for 90 minutes.
Castelmuzio
Castelmuzio is a small hilltop village near Pienza (12 min drive) and in the province of Siena. It’s a fortified and well-kept medieval settlement with stunning surrounding views of the famous rolling Tuscany hills and fields. We stayed in an Airbnb cottage in an olive grove downhill from the main town. This gave us space away from neighbours and amazing views of the scenery. Castelmuzio has minimal shops, cafes or restaurants, which suits us for self-catering. We went to a supermarket in Siena when driving down to buy groceries to self-cater. Then popped into shops in Sinalunga near the motorway to stock up.
Day 2 – San Gimignano
The first full day to go explore, and my number one destination to see was San Gimignano. The medieval walled hilltop town is known for its stone ruined towers, such as the iconic Torre Grossa. I was first inspired to visit San Gimignano while playing Assassin’s Creed 2. It took an hour to drive over, and we found free parking outside town at Via Antonio Gramsci, then walked 10 mins to the town entrance.
Be prepared for lots of other tourists in the narrow streets! Shops are selling local produce and products, along with many souvenir shops around. As you head to Piazza della Cisterna Square, you’ll find a long queue. My advice is to join it ASAP and then savour the delightful gelato of Gelateria Dondoli.
I recommend walking to Punto panoramic, which offers fantastic views of the dozen towers and the surrounding countryside. San Gimignano has Romanesque and Gothic architecture stules to appreciate. For lunch, we picked up slices of Pizza from the affordable and tasty RiccaPizza – San Matteo. We ate them on the steps outside Duomo di Santa Maria Assunta, basking in the sun.
After hours of fun exploring the picturesque town, we said goodbye and drove back to Castlemuzio. The Airbnb had no WiFi (not deliberate when we booked), so we relaxed outside with our books and a glass of local wine. A homemade dinner eaten al fresco with a vibrant sunset was a perfect end to the day.
Day 3 – Montepulciano
Cooking Class and Wine Tasting
For Roisin’s birthday, I gifted her a Cooking Class with the Chef at Tiberini in Montepulciano. This was located at Tiberini Vineyard, where we spent the morning learning to cook authentic Pasta and Tuscan dishes. Professional chef (Samuel) and Grandma Dima supervised and guided our experience. It started by meeting the welcoming Tiberini family over an Espresso before starting to prep veg and slow-cook the main course.
Then the fun begins by making 2 different types of Pasta, an Egg Pasta Pici and a Flour-based Ravioli. It was incredible fun rolling out and making the pasta with light competition and sampling the wines from the vineyard as we cooked. It wouldn’t be an Italian cooking class without learning how to make Tiramisu! Once the cooking was complete, we had a tour of the wine cellar and the making process (unfortunately, it was raining, so not through the vines themselves). The Tiberini family enjoyed our cooking skills for lunch, along with bottles of wine.
The dishes were very flavoursome and (unbiased of course), my Spinach and Ricotta Ravioli was the best. Every dish was paired with a Tiberini wine to appreciate different flavour profiles and combinations. The owner of the Vineyard, Luca, was a wonderful host and very wise as he taught us about the laid-back Tuscan lifestyle and how to appreciate the simple things in life. After many glasses of wine and a great lunch, we brought several bottles and said farewell. This experience made my Best Travel Moments of 2024, and I would highly recommend the Tiberini vineyard!
Montepulciano
After the vineyard tour and cooking class, we went to see Montepulciano despite the rain and impending storm. Montepulciano is a medieval and Renaissance hilltop town known for its world-famous winemaking region. In particular, the Vino Nobile red wine is what the town produces best. The walk up the cobble streets is fairly steep towards the main square, with wine shops seemingly everywhere.
There are some great viewpoints of the vineyards all around Montepulciano that are worth seeing around town. The drive from Montepulciano was precarious due to a thunderstorm and torrential rain along the sweeping, narrow roads, but luckily quiet. We had another quiet evening after a long day out and cooked a simple homemade meatball dinner.
Day 4 – Pienza & Val D’Orcia
Val D’Orcia Gladiator Run
A main highlight of our Val D’Orcia itinerary was going to Pienza. I was most excited about visiting Pienza to see Val D’Orcia in full. The weather was perfect for getting photographs of the landscape made famous by Russell Crowe in Gladiator. The plan was to drive the 10 minutes to Pienza and then run along the gravel tracks to the viewpoints and get some pics with our phones (No Fujifilm for this one).
We jogged through the beautiful Pienza and found our way to the Corsignano Church before trail-running down to the famous photography spot. It was one of my favourite runs along the tracks with the green fields, cypress trees lining the roads, blue skies and hills in the distance. After the rain, however, we didn’t expect the track to turn to shoe-coating clay and turned the run into a trudging walk. Eventually, we reached the next road as the day warmed up and enjoyed a gentle pace back to Pienza.
Tip: Go Early for Gladiator Photos! We ran at 7:30 and beat the crowds there
Pienza
After our run, we got changed in the car and then walked back into Pienza for a much-needed café stop. La Posta has a prime location where we enjoyed coffee and pastries sitting outside for a reasonable price. The reviews aren’t great, but our experience was good for people-watching and soaking in the sun. We walked around the small town and narrow streets before retracing our tracks of the run to get a view down towards the Gladiator spot and take photographs of the Val D’Orica valley. We didn’t stay too long, as the rest of the day was a planned rest and recovery day around the cottage and Castelmuzio.
A hearty and healthy breakfast back at the Airbnb was necessary to refuel, and we started to love the Bialetta Mokka pot coffee. The rest of the day was very relaxing, where we lay on the sun lounges among the olive trees, reading books. We enjoyed some Limoncello and Fanta in the afternoon while listening to music and taking things slower than I’m used to.
Most of my trips are maximalist, where I plan to make the most of each day, whether hiking or in cities, so it was enjoyable to have a relaxing day (post 10K run). We wandered up the steep track from the olive grove to Castlemuzio to stretch our legs and then enjoyed another quiet evening of cooking, wine and relaxation.
Day 5 – Siena
Siena
Our last full day staying in Castlemuzio and our busiest day on the Val D’Orcia itinerary was the Siena day trip. After Florence, there is another magical city in South Tuscany to see. Siena is a must-visit city and is only an hour’s drive from Florence. The main attractions are Siena Cathedral (Duomo di Siena) and the fan-shaped Piazza del Campo with the Gothic town hall and Torre del Mangia.
Also, the Fortezza Medicea (walled fortress to walk around), Palazzo Salimbeni (gothic palace) and Fontanina Contrada dell’Oca (ancient fountain) are interesting things to see when visiting. There is an abundance of shops and an equal number of tourist groups to fight past. Whilst we visited, we didn’t go inside the Cathedral due to the long queues or up the tower, but it’s a very pretty city to roam around.
The car park was under the train station, which had very cheap parking for the day (only 2 euros!) with a 30 min walk into town after going up the escalators in the shopping centre all the way up. There is a supermarket and toilets in the shopping centre above, which was convenient before heading into the city. For lunch, La Piccola Ciacciarria was chosen and delivered amazing pizza and ciaccine for low prices! We then walked to Gelateria Artigianale for ice cream, and I was surprised it wasn’t more popular or had more reviews.
Giro D’Italia Cycling
The afternoon was spent at the side of a gravel track waiting… for context, I’m a road cycling fan, and after we booked our Tuscany trip, I found there was a stage of the Giro D’Italia only 45 mins away. It was a “Strade Bianchi” stage, which means instead of tarmac, the professionals would be racing along white gravel tracks. So I persuaded Roisin to spend the afternoon soaking up the sun and atmosphere with hundreds of other fans.
We patiently waited and got fantastic photographs of the riders and the action. It was a full day out by the time we walked to the car and drove home to our cute cottage. The evening was a treat of wine with more Al Fresco dining outside before we started packing our bags to speed up the next morning’s check-out. It was sad to be leaving the southern Tuscany countryside and ending our Val D’orcia itinerary so soon.
Day 6 – Florence
The day started with a 7Km run from Castlemuzio to Petroio and back along the road. It gave us great views of Castlemuzio and over to Pienza in the morning sun. After a last breakfast in the Airbnb, we packed up the remaining food and our bags into the rental car. We checked and cleaned the cottage before handing the keys back to the owner, who gifted us a small sculpture made from olive tree bark (a challenge to transport home!).
Then, we drove the 90 minutes along the motorways back towards Florence Airport to drop off the rental car at AutoVia, which was a simple process. Finally, we grabbed the bags and got the shuttle back to the airport terminal before buying tickets for a tram into the city. The tram was packed for the full 30min journey into the city centre as we finally arrived in Florence.
Florence
The first step was to drag the suitcase through the streets and over bridges to our Airbnb for the next few days. We stayed on the south side of the river with a 20min walk back to the central attractions. The studio flat had everything we needed for a base camp, and before long, we were ready to explore the wonderful city. It was 25 degrees, to help cool off, we headed to Gelateria dei Neri for delicious ice cream, but not quite as good as San Gimignano!
We booked an afternoon walking tour starting next to the Basilica di San Lorenzo to learn about the history of Florence. But first, I was desperate to see the Cathedral of Santa Maria del Fiore. The grand and imposing Cathedral with its famous Duomo and Tower is an absolute must-see. Tip– Be aware of pickpockets, particularly around the Cathedral! With lots of groups of tourists taking photos, it’s a prime location for theft
Walking Tour
I enjoy free walking tours to learn about the history and culture, and to pick up tips from a local guide. This tour, booked via GuruWalk, started next to Basilica di San Lorenzo and explained the origins of Florence with its connections to Rome and the influence of the Medici family. Next, at the Cathedral of Santa Maria del Fiore, we learnt about the construction of the ground-breaking Duomo, Cupola, and Bell Tower. The tour showed local restaurants and medieval buildings to visit.
The walking tour finished at the Piazza della Signoria with Palazzo Vecchio and the replica of the Statue of David outside. We learnt about the art history of the city and the secret tunnels connecting the city to Palazzo Pitti via Ponte Vecchio. After the tour, we headed back to the apartment to cook leftover pasta with homemade bruschetta and tried to finish off the Limoncello.
Day 7 – Florence
Florence Morning Run
A new concept we tried was a running tour of Florence for the places we hadn’t seen on Day 6. Starting off along the river, then chose to walk up the steep steps to Piazza Michelangelo for an incredible panoramic view of the city skyline and very quiet compared to later in the day (stay tuned).
Next, we crossed the river and headed towards the Basilica of Santa Croce for a photo stop. Then ran through Piazza della Signoria and up to the Cathedral, which was quiet at 7:30. Next, we ran to the Basilica of Santa Maria Novella before continuing up to Lidl to pick up some stuff and finished with a nice finish back over the river for a complete 10K.
Basilica of Santa Croce
After the run, we went to Wild Buns Bakery, which serves mouth-watering Scandinavian pastries and breads. Plus, it was opposite the apartment, which helped keep the coffee warm for breakfast too. The plan for the day was to visit the Basilica of Santa Croce in the morning, and then we had Duomo & Bell Tower tickets booked in the afternoon before dinner. First, we walked over the crowded Ponte Vecchio to the Basilica and weren’t turned away.
There is a dress code to make sure you’re properly covered up, which saw many tourists not get entry, which was only 8 Euros. The Basilica is home to famous Tombs & Monuments such as Michelangelo, Galileo, Machiavelli, Alfieri, Rossini and Foscolo alongside Brunelleschi’s Pazzi Chapel and Donatello’s sculptures, a real gem of history. The Cloister and chapels are beautiful and worthy of a visit.
Cathedral of Santa Maria del Fiore
Afterwards, we went in search of lunch and avoided the hyped-up All’Antico Vinaio; instead, we went to La Schiacciata next door, which had a much shorter queue, huge sizes and arguably better Schiacciata! We roamed the city until we collected the Duomo climb tickets. The Cathedral itself is free, but to climb the Duomo or Bell Tower requires tickets. I would recommend the Brunelleschi Pass (30 Euros or £25), which includes access to the Baptistery of San Giovanni, Giotto’s Bell Tower, Brunelleschi’s Dome, the Opera del Duomo Museum and the ancient Basilica of Santa Reparata.
Tip– Book the Cathedral tickets from the official website and a few weeks in advance, as it books up fast! We were late, so we paid more via a 3rd company, but still got to experience the unbelievable Cupola and city views.
The climb up the Dome (Cupola) is time-limited, whereas the rest of the Piazza del Duomo attractions are valid for up to 3 days later. It is 453 steps and is only for physically capable people. However, the exercise to reach the viewing platform is the 2nd best view of Florence. The obvious viewpoints are the Bell Tower and the reverse view of the Cupola from the Tower, which puts the engineering masterpiece into scale.
It’s a narrow walkway, and even with limited visitors, it’s crowded at the top, as seen above. Why stop climbing there after the Cupola climb when Giotti’s Bell Tower has 414 steps to scale next? Afterwards, we deserved a well-earned drink, so we stopped at La Petite near Piazza della Repubblica. We had a delicious meal at La Bussola close by, where I had the best Italian Pizza along with a lovely bottle of Montepulciano red wine.
Piazza Michelangelo
Instead of dessert, as tempting as the Tiramisu was, we spontaneously decided to rush over to Piazza Michelangelo in the hope of seeing the sunset over the city. We caught the sun setting over the river on the Ponte Vecchio before a fast hike up the hill to join the crowds. We managed to squeeze into a viewpoint and watched the pastel-coloured sky in the background of the landmarks- the best view in Florence!
The photographs were incredible, and most people felt they had left too soon once the sun had dipped behind the hills. There were some live musicians on some nearby steps, so we enjoyed the music, the sunset, and the atmosphere of all the people gathered at the Piazza. On the way back to the apartment, we searched for a Hole in the Wall bar; however, we were too late, unfortunately.
Day 8 – Florence
Our last day in Florence and of the Val D’Orcia Itinerary trip was a relaxing one, which started with a long morning walk exploring the outer areas of Florence. For the second day, we dropped by the Wild Bun Bakery to try some different pastries from Day 7. Breakfast involved finishing off as much as possible before we packed the suitcase and bags before Check-Out. To not be weighed down, we dropped off the suitcase at a luggage store near the Train Station.
Then we walked over to il Mercato Centrale Firenze to see the market and went in search of souvenir magnets. We scouted out the lunchtime restaurant before finishing off the souvenir shopping. To save on buying food at the airport, we bought Foccacia at L’Officina degli Antellesi, which was only second to La Schiacciata. We had some spare time to kill, so we visited a park to read our books in the sun.
Trattoria Za Za was the last restaurant before leaving, and we were glad we had reserved as there was a long queue otherwise. I ordered a linguine mushroom dish with white wine, and Roisin had a Ragu & Pici pasta with an Aperol Spritz. The flavours backed up the top ratings online, and I would highly recommend it for Pasta!
Afterwards, we fancied one last gelato to finish the trip, so we found Gelateria Artigianale La Sorbettiera. The best ice cream in Florence is silky smooth and delicious, with reasonable prices and a good selection! It was then that time of the trip to collect the suitcase from the storage, jump on a tram and head to the airport. Our 8 days in Tuscany were full of memories and a place I will be returning to for sure!
Budget
Italy is not the cheapest destination, so be warned! It can add up very fast when tempted by the delicious food (see below how to spend your money) and incredible drinks. And add on top all of the attractions and museums that could be visited, it’s easy to live a life of luxury and culture. We aimed for our Val d’Orcia itinerary to be a budget road trip with selected experiences to spend the money on.
The most expensive experience was the pre-booked Cooking Class in Montepulciano, costing £150 each, then the Florence Cathedral Duomo and Tower climb at £40 each. Our approach was to self-cater in the Agriturismo, so we bought 6 days of food at Lidl in Siena. And whilst in Castlemuzio, we didn’t eat out at restaurants, instead got quick food to go and then enjoyed several lovely meals out in Florence.
The 2 Airbnbs were good value at £50 a night each, with the prices below for 2 people splitting the cost. The flights worked out reasonably well as we shared a 25kg Hold Bag for clothes. To get the best of Tuscany, a car rental is advised to give maximum flexibility. As mentioned, Zest is a helpful website to filter the options from global companies (Hertz, Enterprise or Europcar) to local Italian providers (AutoVia or Alamo). It cost us £120 for the 5 days, with no additional cost for a 2nd driver with AutoVia and 50 euros to refill petrol.
Italian Cuisine
It wouldn’t be an Italian travel guide or Val D’Orcia itinerary without mentioning the cuisine. I’d travelled to Venice & the Dolomites before, where I enjoyed my food, but in comparison, the Tuscany food was streets ahead. The quality of the produce and the simplicity of the dishes we tasted in our Val d’Orcia itinerary were a refreshing contrast to other cuisines. Even the groceries from supermarkets were affordable and made into great homemade meals. We visited a famous wine region, so we rightfully had to try a few bottles, which helped convert Roisin to liking red wine. Below is a summary of my favourite Food & Drink:
- Best Pizza – La Bussola, Florence
- Best Focaccia -La Schiacciata (next to the famous All’Antico Vinaio and fewer queues)
- Best Pasta – Trattoria Zà Zà
- Best Gelato -Gelateria Dondoli
- Best Coffee – Bialetta Mokka Pot
- Best Wine – Vino Nobile Montepulciano
- Best Pastry – Wild Buns Bakery
Not Quite Renaissance Art
Val D’Orcia Itinerary: Lessons Learned
- Beauty – The main attraction for this Val D’Orcia itinerary isy was seeing the rolling Tuscany hills around Castelmuzio. The weather was perfect with lots of sun and blue skies in May, which added to the beauty. The hilltop towns were charming, and I loved the medieval style. And there are jaw-dropping Cathedrals, Basilicas and Piazzas to admire and photograph.
- Food – As explained, the cuisine is on another level with the best pizza, pasta and ice cream I’ve ever had! It’s not the cheapest place for food, but the quality is very high with many top-reviewed restaurants and places to eat, dine and drink. Any Val D’Orcia itinerary must indulge in the local culinary scene.
- Running – A new one for 2024 was to do running tours of cities and landscapes. The Florence 10K run in the early morning gave a quiet, tourist-free city to explore. And the Tuscany runs along the hills were relaxing and easily distracted by the panoramic views.
- History – Florence and Tuscany have a rich history during the Renaissance era. With so much art and culture linked to this period, and still some Roman influence too. The history of the Medici family and the Cathedral of Santa Maria del Fiore was of personal interest.
- Relaxation – The Val D’Orcia itinerary was designed to relax and rest up, but I learnt I’m not very good at having a day off! We only had the afternoon on Day 4 for reading, sketching and sunbathing, but would happily do more if the accommodation had a pool and we had longer.
Val D’Orcia Itinerary: Final Thoughts
Exploring the Val d’Orcia and the wider Tuscan region has been a massive bucket list trip of mine for years—ever since climbing the digital towers of Florence and San Gimignano in Assassin’s Creed as a teen! Finally experiencing those iconic skylines in reality as a road trip with Roisin absolutely exceeded expectations.
Structuring the trip with the Val D’Orcia itinerary to start in a rustic cottage in Castelmuzio was the perfect move. Waking up to sweeping, epic countryside views allowed us to completely decompress before transitioning into the bustling, vibrant city streets of Florence at the end of the week. Whether you want to dive deep into world-class cuisine, stretch your legs on the incredibly steep streets of Montepulciano, or simply kick back and relax at a rural agriturismo with a book and a glass of Chianti, this specific pocket of Italy delivers flawlessly.
Where is your favourite place to visit in Italy? I would love more recommendations for our next visit! If you enjoyed this Val d’Orcia itinerary, please share it with others planning their European road trips, and subscribe to The Journal—our monthly newsletter packed with travel tips and gear reviews.
FAQs
Do you need a rental car to explore Tuscany?
If you are only visiting major cities like Florence, Siena, and Pisa, you can easily rely on Italy’s excellent train network. However, if you want to explore the famous rolling hills of the Val d’Orcia, visit secluded Chianti vineyards, or stop at hidden hilltop towns like San Gimignano and Volterra, renting a car is absolutely essential to make the most of the Val D’Orcia itinerary.
Is it difficult to drive in Tuscany?
Driving in the Tuscan countryside is generally a pleasure, with well-paved, scenic rural roads. The main challenge is navigating the historical towns. Almost all historic centres in Tuscany have strict ZTLs (Zona a Traffico Limitato). If you drive into a ZTL without a resident permit, traffic cameras will automatically issue a heavy fine to your rental car company. Always park in designated lots outside the ancient city walls.
How many days do you need in Tuscany?
We recommend an absolute minimum of 5 days, but 8 days is the sweet spot. An 8-day Val D’Orcia itinerary allows you to spend 2 to 3 days absorbing the art and history of Florence, before picking up a rental car for a 5-day unhurried road trip through the countryside, vineyards, and southern hilltop towns like Montepulciano.
When is the best time to visit Tuscany?
The shoulder seasons of May/June and September/October are the best times to visit for a Val D’Orcia itinerary trip. During these months, the weather is beautifully warm, the vineyards are lush, and you avoid the massive crowds and sweltering, oppressive heat of August (when many local Italians also go on vacation and close their shops).
