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If you are dreaming of a Tuscany road trip this summer, then look no further. Here is a 5 day Tuscany itinerary which will showcase all the best places to see in Tuscany from the vineyards to the ancient towns and cities. By following this Tuscany road trip itinerary, you will get to experience the best of Tuscany in 5 days

Visiting Tuscany

Why Visit Tuscany?

If you’ve seen postcards and travel brochures for Itlay, you can’t have missed the pictures of rolling hills, charming ramshackle villages, vineyards for miles and field of blazing red poppies?! The scenery is unlike anywhere else and is deserving of a spot on the front cover of any Italy guidebook.

The culture here is more laid back than you’ll find in the big cities or the coastal towns. Life is altogether slower and more peaceful in Tuscany. I stopped in a few villages in June where I barely saw anyone at all.

A Tuscany road trip is a perfect way to experience the beauty and charm of this well-known rural region of Central Italy.

countryside view of tuscany rolling hills and hay bales - one of the scenes you'll see often on this 5 day tuscany itinerary

Where is Tuscany?

As you’ll see on the map below, Tuscany is in the North/Central region of Italy and includes the cities of Florence, Siena and Pisa. Elba Island is also included, just off the coast of East Italy.

It’s actually quite a large region and you may be surprised that it reaches as far as the coast as people do not often associate Tuscany with beaches!

How to get to Tuscany

Florence is the largest city in Tuscany and is also the most central so it would make sense to start your road trip here. You could do a loop and end here too but this particular 5 day Tuscany itinerary focusses on the central, most scenic, rural part of Tuscany.

From the Val D’ Orcia, your final stop along this Tuscany road trip itinerary, you are 2 hours away from both Florence and Rome so you can choose to fly out of either airport. Since there are more flights leaving Rome, you may find flights from here are cheaper.

charming little shop in monteriggioni

Are 5 days in Tuscany long enough?

As with anywhere in Italy, you could easily enjoy long lazy days enjoying Italian food, drinking wine and taking long country strolls for many weeks at a time…

But if you only have 5 days in Tuscany then yes, this Tuscany itinerary will showcase many of Tuscany’s highlights from the city charm of Florence to the vineyards of the Chianti region to the jaw-dropping scenery of the Val d’Orcia.

If you have longer than 5 days in Tuscany then I would suggest allocating extra time to explore Siena, Pisa, Lucca or pop across to Elba island for some beautiful beach scenery.

An Overview of this 5 day Tuscany Itinerary

Day 1 – Florence

Day 2 – Florence – San Gimignano

Day 3 – Monteriggioni and wine tasting in the Chianti region

Day 4 – Siena to the Val D’Orcia

Day 5 – Val d’Orcia then back to Florence or Rome to fly home.

A Map of this Tuscany Road Trip Itinerary

Your 5 day Tuscany Itinerary

Day 1 of your Tuscany itinerary

Florence is one of the most beautiful, most popular cities to visit in Italy for good reason. Everywhere you look is like something straight out of a travel brochure. It’s absolutely deserving of a place on your Italy bucket list!

Whilst the beautiful Duomo dominates the old town, there is plenty more to see in Florence and much of it’s charm lies in the little cobbled alleys, away from the busy piazzas.

Make sure you end your day in Florence by watching the sunset at Piazzale Michelangelo which overlooks the whole city. It’s beautiful.

If there’s one thing you need to know before booking your trip to Florence, it’s that it gets busy, especially at the Duomo so you need to book well in advance for activities like the dome climb. It was sold out when I was there! Also, get up early to enjoy the city before the crowds arrive.

view of florence city with the duomo from tower climb

Things to do on day 1

  • Walk over the Ponte Vecchio bridge. This extremely old bridge is lined with jewellers, galleries and gifts shops along either side and is a popular tourist attraction in Florence.
  • Climb the tower at the Palazzo Vecchio. This is actually my favourite viewpoint as you can see the Dumo in its entirety frames by the copper coloured roofs of houses and buildings in the old town.
  • Visit the Uffizi Palace and Art galleries – one of the most important art museums in the whole of Italy.
  • Enjoy a walk through the serene Boboli Gardens, home to a beautiful palace and many fountains and sculptures. This will lead you towards Piazzale Michelangelo, where you will find the prettiest viewpoint overlooking the whole city.

Where to stay on day 1

Since you don’t have long in Florence on this 5 days Tuscany itinerary, I would recommend you stay as central and near to the old town as possible to save on travel time. Though you may not find many hotels in the old town with a car park, you don’t really need it until Day two so I recommend hiring it for when you leave Florence, headed for Chianti.

Florence is expensive so you may save money by getting an Airbnb. I stayed at Panzani 14 through Airbnb and it was extremely central, clean and the hosts very friendly. The room decor and furnishings were okay but nothing to write home about but for the cost, I felt it was reasonable value for money.

Alternatively, here are a few other options which look really lovely and are very centrally located with excellent reviews. Camerepontevechio and B&B My Way are great budget options. If you are looking for something a little more luxury, check out Ponte Vecchio Suites and Spa.

Day 2 of your Tuscany itinerary

Start your day by exploring Florence’s highlight, the beautiful Duomo cathedral and the surrounding old buildings such as St Johns Baptistery.

After your fill of cathedrals and viewpoints, head out of Florence into the Tuscan countryside and the Chianti region, known for its medieval villages and wineries. Your Tuscany road trip really begins here as you explore the town of San Gimignano in the afternoon before staying in the heart of the countryside at a beautiful agriturismo.

Things to do on day 2

  • Get up early and use your queue-jump pass (purchased well in advance) to explore Florence’s Duomo before the crowds arrive. The queues for this place get absolutely insane, wrapping around the whole cathedral by mid-morning. I wouldn’t even attempt to visit without a queue jump ticket or you may be queueing for an hour or two in the hot sun!
  • Climb either the dome or the tower. The view is better from the tower as the dome is in view. But the view is obstructed by wire mesh so you’ll get better photos from the dome climb. The dome climb must be booked well in advance and was sold out when I was there in Spring.
  • Explore one of the oldest buildings in Florence, the Baptistery of St John.
  • In the afternoon head out of Florence to San Gimignano, a charming walled city perched on a hill. It’s home to the worlds best gelato shop (it’s official, they have awards!) But the best thing about San Gimignano is just relaxing and leisurely strolling the old cobbled streets adorned with flags, visiting the many shops and restaurants before heading to the old castle ruins for stunning views onto the Tuscan countryside.
san gimignano medieval town chianti region of tuscany

Where to stay on day 2

I stayed at Borgo Gallinaio, an absolutely beautiful agriturismo. An agriturismo is a guest house within a farmhouse and you’ll find them throughout Italy. This is one of the nicest I have stayed in. With the most charming little courtyard filled with bright flowers and rooms with sloping ceilings and timber beams. There was even a swimming pool and I could happily have spent a full day just relaxing here. The food was also divine – one of the best meals I had in Italy!

room in agriturismo with beams and old furniture

If you would prefer to stay an extra night in Florence, you can also arrange many day trips into the Chianti region. Though I personally wouldn’t miss the chance to stay at a lovely agriturismo which is all part of the Tuscany experience!

Day 3 of your 5 Tuscany itinerary

Start your day exploring the beautiful Monteriggioni. A tiny medieval walled village perched atop a hill. If you happen to travel with a drone, like I do, here is a great spot for ariel photography. Otherwise, just spend an hour or so strolling the little courtyards and gifts shops, stop for a coffee or for some lunch and enjoy the countryside views.

walled village in chianti region

In the afternoon, I would suggest you take a wine tour and enjoy some wine tasting at some of the wineries that make this region famous. You can often arrange a wine tour or tastings with a winery directly or you can take a tour meaning that no one has to drive and you can experience several wineries in one afternoon.

wineries in chianti region

Alternative things to do on day 3

Day 4 of your Tuscany itinerary

Today, start early as there is lots to see. Start by driving to Siena, the largest of the towns in the Chianti Region and the one you are most likely to have heard of. Visit the ornate Duomo di Siena, climb the city tower and have lunch in Il Campo – the main piazza.

siena italy cathedral from afar

You’ll then start your journey from Siena to the Val d’Orcia, home to some of the most stunning scenery in Tuscany.

This part of this 5 day Tuscany itinerary, is not about ticking off big towns and attractions but more about enjoying the stunning scenery. I’ve listed below some of the prettiest viewpoints and best places to stop along the way.

However, the beauty of a Tuscany road trip is that you can stop wherever you like, whenever a beautiful view opens up in front of you. Just make sure it’s safe to stop – there are plenty of laybys along the road for this very purpose.

I’d recommend stopping off in sleepy Montalcino for a delicious lunch at Alle Logge Di Piazza.

Best photo stops and places to visit on Day 4

  • Cypress Tree Viewpoint 43.286258, 11.433042
  • Agriturismo Baccoleno where a winding road of cypress trees leads to a perfectly situated farmhouse (great for sunset.) 43°12’2.9755″N11°35’22.0863″E
  • The Abbey of Sant Antimo is an ancient abbey which is a great photo spot. But make sure you explore inside the old church too! 42°59’46.572″ N 11°31’12.48″ E
  • Bagno Vignoni is a little village set around a thermal spring. It is adorable. Just outside of the village you’ll find more hot springs where you can swim. 43°1’41.5488″N11°37’4.8739″E

Where to stay on day 4

I stayed at Agriturismo Lunadora and it was yet again one of those places that I wish I could stay longer. Not only was there a swimming pool with views for miles across the Tuscan countryside but there was even a mini spa room with jacuzzi and relaxation area. The breakfast, after I returned from my sunrise photoshoot, was incredible.

swimming pool at agriturismo

Day 5 of your Tuscany Itinerary

Day 5 on this Tuscany itinerary is again, a laid back day, stopping off wherever you fancy.

Today we will be focussing on the best-known parts of the Val d’Orcia. The scenery is stunning so if you are into landscape photography; get excited!

If you are a photographer then I would highly recommend getting up before sunrise to get some epic shots. Start with Podere Belvedere, a farmhouse surrounded by a cluster of trees set amidst rolling hills. The rising sun bounces off the house and if you visit in early spring, you may even get lucky with some mist to add atmosphere.

sunrise in the val d'orcia

Once you’ve finished taking your photos at all the iconic photo locations along this route (see below for suggestions and coordinates,) spend your time stopping off exploring all the beautiful towns and villages along the route. My favourite town was Pienza which was utterly charming especially with all the bright flowers decorating most of the houses.

Places to stop on day 5

Photo Locations
  • Podere Belvedere (pictured above) can be found here; 43°3’50.3319″N11°36’38.8138″E
  • Capella di Vitaleta a little abandoned chapel. You have to park your car and walk for 10-15 minutes to get here. 43°4’14.3907″N11°38’7.1896″E
  • House near San Quirico d’Orcia – a lovely country farmhouse with a long row of cypress trees leading up t it, perched on a hill. 43°3’55.6229″N11°36’43.5053″E
  • A lonely cluster of cypress trees – makes for a slightly quirky photo composition 43°3’34.947″N11°36’13.6588″E
Towns and villages to explore
  • San Quirico d’Orcia – a great spot for breakfast or a mid-morning coffee as it’s very near all the above-listed photography locations.
  • Pienza – stunning views from the walls which circle the town. The cobbled alleys and pretty streets are usually highly decorated with flower arrangements and there are many pretty courtyards with some great restaurants for lunch.
  • Montepulciano – make sure you visit the little church of San Biagio just outside the main town. Views from the road here are really pretty!

Where to stay on day 5

If you’re flying out the next day from Rome as I did, then look for a hotel near the airport – Fiumicino airport is actually quite far out of the city centre.

I stayed at Ostia Antica Park Hotel and spa. It was cheap as chips and close to the airport but the rooms were quite dated and the bed not particularly comfortable. However, I’ve still included it as an option as it’s so close and budget-friendly. If you’re arriving late and leaving early, you probably won’t care about much else!

B&B L’Ulivo Fiumicino is another budget option for under €50/night but looks pretty nice. Rome Airport Inn is a little more expensive but still very affordable and looks like a lovely place to spend your last night in Italy.

Planning a Tuscany Rad Trip Itinerary

When is the best time to take a Tuscany road trip?

Italy can get both hot and crowded in the summer months. Whilst you might not notice many crowds in the smaller towns in Tuscany, cities like Florence and towns like Siena can become very busy.

Therefore the best time to visit Tuscany will be in the shoulder seasons Spring and Autumn. Visiting In April-May and September-October will allow you to explore without the crowds and without risking sunstroke!

How to plan a 5 day Tuscany road trip

Tips for hiring a car in Tuscany

blue car in a narrow italy alley

I have hired many cars in Italy (I’m a little obsessed with Italian road trips) and not all have been great experiences! The best car hire company I have found so far is Europcar. Hiring a car was straight forward, there were no hidden extras and I even got a free upgrade.

To keep costs down, I recommend getting car hire insurance with an external provider. I get an annual Europe policy with ICarHireInsurance.com which costs a fraction of the price that you would expect to pay through the car hire company.

Another way to save money on your Tuscany road trip is by avoiding GPS hire charges by downloading maps.me on your phone and getting an air vent phone holder to use it handsfree.

Tips for driving in Tuscany

This 5 day Tuscany itinerary does involve a lot of diving but do not worry, it’s nowhere near as tricky driving in Tuscany as it is in other parts of Italy. The roads are much quieter and in good condition.

However, if at any point you go on a motorway (such as when driving back to Rome’s airport) you should be aware that there are many toll bridges which require you to pay cash so make sure you keep some on your person.


Not sure you want to hire a car to explore Tuscany? Whilst public transport probably isn’t going to cut it in rural Tuscany, you can opt to take a group tour with G Adventures, a company I trust and have travelled with many times.


I hope you’ve enjoyed reading this 5 day Tuscany itinerary and feel more comfortable about planning your Tuscany road trip!

By following this itinerary, you’ll get to see many of Tuscany’s countryside highlights as well as have the opportunity to explore one of Italy’s most beautiful cities. So make sure you remember to pin this article with the pins below so that you can refer to it later!

Any questions? Pop them in the comments section below…

Read next…

Now get planning your trip..!

Over the past 16 years of travel, I’ve picked up a few tips about how to plan my trip with ease and save a few pennies. Below are the resources which I personally use and recommend!

  • For booking hotels, I use booking.com and love the in-depth search options. If I’m looking for self-catered accommodation, I use Airbnb. Get a lovely discount HERE
  • For flights, I love Skyscanner. I always find the best deals there and the ‘search everywhere’ option is great for inspiration.
  • For day trips, my preference is to use Get Your Guide. If you’re looking for longer trips or group tours then my absolute fave company is G Adventures. Other companies I recommend are Intrepid Travel, Dragoman and Tour Radar
  • For renting cars, I use Europcar – hassle-free! 
  • And for insurance – please don’t travel without it – try Nomads!

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