Last updated on January 21, 2024 by Stefano Ferro, founder of MEL365, following extensive travelling in Tuscany

Ultimate Tuscany Itinerary Based On Your Length Of Stay And Type Of Experience

Using this guide, you’ll discover everything you need to know about planning a Tuscany itinerary to visit the most beautiful towns, villages, countryside and wineries.

Tuscany is one of the largest regions in Italy. The sheer variety of attractions and destinations makes it easy to get lost.

In this post, you will find a few possible itineraries I designed based on how long you will stay (from 3 days to 2 weeks), how you will travel (taking public transportation or renting a car in Tuscany) and what you want to experience (art, culture, history, nature, countryside, wineries, food, SPAs and more)

But now let’s dig into it

You can read also

Beautiful rolling hills of Tuscany
Beautiful rolling hills of Tuscany
 

Best Tuscany Itinerary – In a nutshell

Here are a few quick points, however, keep reading for more detailed information

  • How many days in Tuscany: 2 weeks is plenty of time to get a good overview of the region. 10 days will give you enough time to see most of the iconic attractions, towns, and historical sights. One week is perfect for an overview of the countryside and a few towns. Five days are long enough to see the top three or four attractions. If you only have three days to spend, stay in Florence, Pisa, Siena, or the nearby Chianti region. In fact, this is one of the most common questions I get. In my view, I would recommend at least a week in Tuscany, even better 10 days. However, our society is plagued by an acute lack of time, isn’t it?
  • Tuscany Itinerary in 3 days: being this region so big I would stay close to the main airports of Tuscany. Three great places are Florence, with one of the highest concentrations of art and culture in Italy, Pisa, a great base with the Leaning Tower, or the Chianti region, the lovely countryside to explore with a rented car. Other options are however available. Read below for more details on 3 days in Tuscany
  • Tuscany Itinerary in 5 days: Tuscany can be seen in more detail by splitting your time between two locations during your 5-day holiday. You can opt for a romantic trip, a family tour, or a relaxing countryside chill-out time between medieval villages and amazing wineries. You can read all the options below in the 5 days sections
  • Tuscany Itinerary in one week: with seven days you will have plenty of time to take in the best attractions of Tuscany. You can decide to use uniquely the public transportation or be more flexible with a rented car, especially if you are after the marvellous countryside or the extraordinary free thermal areas. Read more below on my 7 days options below
  • Itinerary in 10 days: It’s plenty of time to plan either a long loop in Tuscany or a small one if you’d rather prefer to relax as well. You can even consider changing accommodations every day or so to experience it all. Read more below on my 10 days options below
  • Itinerary in 2 weeks: If you want a good overview of Tuscany then two weeks has to be. You will be able to visit the most historic towns and villages. Plenty of time for wine tasting and eating in the glorious rolling hills of the region. You can experience a few of the famous thermal baths (some with free entrance) and allocate some time even to the beach and maybe to Elba Island. Read more below on a 2 weeks itinerary
  • Tuscany Itinerary in the countryside: the most famous countryside areas of Tuscany are the Chianti region, between Florence and Siena, and Val D’orcia, south of Siena, bordering Umbria. Unfortunately, the countryside is not well served by public transportation. Renting a car will make life so much easier. You can read more about the countryside trip in my 7 days itinerary.
  • Is it recommended to rent a car in Tuscany? Public transportation (trains and buses) is great if you travel only between towns and cities. You do not need a car. However, visiting the countryside is a different business, a more complicated one. You can either decide to join an organised tour in that case or, for more freedom, rent a car in Tuscany, a game changer that will allow you to visit the most amazing corners of this region. Is driving in Tuscany difficult? The easy answer is no, except probably in Florence.
  • Best place to base yourself in Tuscany: The region is very large, so it all depends on how you feel, what you’d like to do, who you’re travelling with (partner, kids, alone), and what kind of vacation you desire. Florence, Pisa and Siena certainly top the list, but there are other stunning towns and villages near them, such as the romantic Arezzo or the unique Lucca.
  • Should I include Florence on my Tuscany itinerary? Most definitely. Besides having a UNESCO-listed historical centre, the city offers so much in art, culture and history. My suggestion is to stay at least 2 full days in Florence (read my guide on the best neighbourhood of Florence with a few accommodation suggestions). You do not need a car in Florence, in fact, it may be a problem if you have one (parking, narrow streets, limited traffic in the centre)
  • Must-see 5 places in Tuscany: here is a list of five, but I’ll elaborate more below. Shortly: Florence, Siena, Val D’Orcia, Chianti Area, Saturnia. hard to pick only 5, in fact, I will expand this list below.
  • Best 5 villages in Tuscany: Montefioralle, San Gimignano, Montepulciano, Pitigliano, Cortona. Again, impossible to select only 5, just a short list.
Ponte Vecchio at sunset
Sunset on Ponte Vecchio in Florence

Planning on hiring a car in Tuscany?

That’s an excellent idea. You can drive around Tuscany easily (except in the historic centres) and stay wherever you like, in small villages and in the lovely agriturismo, experiencing more of the local life.

It does have a few shortcomings, as you can imagine.

It is important to have full car insurance, for example, as small problems, such as scratches, happen more often than you think.

I usually get the best deal for car rentals on DiscoverCars.com, a website that compares prices and provides the best quality.

Check the car prices

Is it really necessary to rent a car?

No.

You will miss the flexibility to stop and see other attractions on the way, but I’m sure you will be more relaxed as a passenger on the bus or train.

If you would like to see the countryside, you can join one of the many tours that leave from Florence, Siena, and other major towns.

Unmissable places to see in Tuscany

Here’s a Guide to the best Tuscan attractions, as well as some secret destinations and hidden gems you should visit. 
 
Tuscany Map with attractions, towns, villages
Tuscany Map with attractions, towns, villages

The places that I consider must-sees are marked with a small star (*).

Places close to Florence

  • (*) Chianti Area: one of the most popular places in Tuscany not only for the amazing countryside but also for the famous wineries and the outstanding local food and impeccable service. It can be easily visited with a rented car following the SR222, the Chianti Road. Famous stops are Greve in Chianti, Montefioralle, Panzano, Castellina in Chianti and the Chianti Sculpture Park, just to mention a few.
  • Montecatini Terme: Montecatini has been ranked among the Top Spa Towns of Europe by UNESCO. It is possible to spend the entire day exploring the town and enjoying the famous Thermal SPA built in the 8th century.
  • San Miniato: a village famous for the white truffles that can be tasted in a few shops in the village centre (as you can imagine, it is not the cheapest experience).

Places close to Pisa/Lucca

  • Bagni di Lucca: This is a lovely town north of Lucca famous for its SPA that dates back to the Roman Empire. Just outside the town, you can also find Canyon Park, the perfect spot for some adrenaline and fun. Another attraction is the Chains Bridge, one of the most antique still-working iron bridges in the world. 
  • Castelnuovo di Carfagnana: charming old town renowned for the Ariostesca Fortress
  • Carrara: visit the unique old centre made of iconic marble and book your trip inside the cave, for an uncommon experience
  • Forte dei Marmi and Viareggio: the posh coastal towns of Tuscany, with a great long beach, perfect on those hot summer days for a swim

Places close to Siena

  • (*) San Gimignano: one of the most beautiful medieval villages in Tuscany, famous for its characteristic towers and the gorgeous white wine, the Vernaccia di San Gimignano, made there since the 12th century
  • Certaldo Alto: an hidden medieval gem
  • (*) Val d’Orcia: see more below

Places close to Arezzo

  • (*) Cortona: another characteristic and picturesque medieval village, made famous by the 2003 movie “Under the Tuscan Sun”. Try to visit it in the early morning before most of the day travellers arrive. Well connected to Arezzo by a short train trip and a quick bus.
  • Perugia: technically speaking, this is the capital city of the Umbria region. It’s, however, so well connected to Arezzo by train (less than 1 hour) that would be a pity to miss it out

Places in Val D’Orcia

  • (*) Amazing Viewpoints: SP18 ViewpointCipressi di San Quirico and Cipressi di Monticchiello and Gladiator Point
  • San Quirico D’Orcia: the most iconic Medieval town in the region
  • (*) Montepulciano and Montalcino: two medieval villages world famous for their amazing wine, the Nobile di Montepulciano and the Brunello di Montalcino, and wineries.
  • (*) Bagni di San Filippo: thermal SPA in a natural tiny river with free access
  • Bagni di San Casciano: a famous SPA village for thermal treatment in a beautiful environment including an external pool for those hot summer days

Other more hidden places

  • (*) Pitigliano: I still remember my first time approaching Pitigliano and being open mouth at the view of this town perched on top of a massive rock formation. Absolutely unique and stunning at the same time
  • (*) Saturnia: probably the most spectacular public thermal bath in Tuscany
  • Isola d’Elba: a small island off the Tuscan coast, easily reachable from Piombino. 

To find out more about the places mentioned above and other secret corners of the island, check out this guide to the top attractions in Tuscany

Read guide to the best attractions

View of beautiful Siena
View of beautiful Siena

Itinerary in 3 days

This is a very short stay in Tuscany, a region bigger than Wales and just a bit smaller than Belgium.

My personal recommendation is to stay only in one place and explore the nearby attractions.

The ideal location should be close to your airport of arrival, either Pisa or Florence.

A longer trip from and to the airport would simply take too much of your short holiday time.

You can also think to stay in the Chianti countryside, however, you would need to rent a car as public transportation outside of the main town is not that great

Lucca is another option if you fly to Pisa, and it’s ideal for families.

Florence is the romantic choice, especially if you stay in San Giovanni or Oltrarno (read more on my Florence Guide).

For more information, I highly suggest reading this comprehensive post with five day-by-day plans of possible itineraries in Tuscany based on your kind of holiday (art, culture, countryside, couples, families, history, wineries), including maps as well as photos.

3 days itinerary guide to Tuscany

3 days in Tuscany - the 5 best plans forcountryside, art, families, couples and a bit of everything
3 days in Tuscany – the 5 best plans for the countryside, art, families, couples and a bit of everything

Itinerary in 5 days

There is enough time in five days in Tuscany to plan a simple itinerary centred around two spots where you can explore the nearby attractions.

You can also choose a more relaxing getaway by staying in one town/city (or agriturismo) and exploring the attractions there (art, countryside, wineries, historical attractions).

One of my favourite bases still remains Florence, with its charming old centre and a plethora of things to do.

A stay in Florence (3 days) and Siena (2 days) is the best option if you are travelling with your partner and you are looking for a romantic gateway

Pisa is the alternative on a budget.

For families, I would still suggest Lucca together with either Pisa or the countryside, if you are keen to rent a car

You should read this comprehensive guide on 5-day itineraries in Tuscany, which includes 5 complete day-by-day itineraries with excursions, maps, as well as photos to help you choose the best option based on your kind of trip (countryside, couples, families, history, wineries).

5 days itinerary guide to Tuscany

4 or 5 days in Tuscany - the 5 best plans
4 or 5 days in Tuscany – the 5 best plans

Itinerary in 7 days

7 days in Tuscany will offer you a whole host of options.

Being an extensive region, I would suggest splitting your stay between 2 or 3 destinations and exploring from there.

You can either decide to use 

  • only public transportation to get around, which works great between towns and cities. Then you can join a local tour to explore the countryside, not really well served by either the buses or the trains. Or why not rent a Vespa for a day to explore the Chianti Area, in typical Italian style?
  • rent a car in Tuscany and be more flexible in your stops. There are so many beautiful medieval villages, charming wineries, and lovely agriturismo for the freshest local food. Or why not visit one of the many free thermal baths in the middle of nature, unique to Tuscany?

For couples, I suggest adding Arezzo and Cortona to your itinerary. Both are so romantic and picturesque, with Arezzo not as popular as the main Tuscan destinations, which means less busy, although as beautiful.

In my ultimate guide to one week in Tuscany, you’ll find 5 day-to-day plans based on what type of holiday you’re looking for (art, culture, countryside, families, couples, with or without a car). It’s a great reference with maps and photos.

7 days itinerary guide to Tuscany

7 days in Tuscany - The 5 best plans for 1 week
7 days in Tuscany – The 5 best plans for 1 week

Itinerary in 10 days

If you have 10 days in Tuscany, you will be surprised at how much you can accomplish.

Plan your itinerary ahead of time and you will avoid wasting time.

For greater flexibility, you can rent a car. For more peace of mind, only use trains and buses.

If you want to see more, try changing your accommodations every second day or so (active, but tiring) or split your stay into three or four places to enjoy a relaxed adventure while still seeing a lot of Tuscany.

Or why not spend the whole holiday exploring the beautiful Tuscan countryside?

Check out my guide with 5 types of itineraries and a daily plan for ten days spent in Tuscany whether or not you have a car.

10 days itinerary guide to Tuscany

10 days in Tuscany - The 5 best plans for 1 week
10 days in Tuscany – The 5 best plans for 1 week

Itinerary in 2 weeks, and over

In two weeks in Tuscany, you can comfortably explore Florence as well as most of the medieval towns/villages, including Siena.

In addition to experiencing the unique historical sites and the beautiful countryside, you can also take some relaxing time in an agriturismo in the Chianti Area or the Val d’Orcia.

Alternatively, why not spend some time on the beach side, or even in the Isola d’Elba?

With 14 days in Tuscany, I highly suggest using my guide to 10 days in Tuscany and adding one of the following detours:

  • sunbathing at the beach: for a posh stay, then book your extra days in Forte dei Marmi and/or Viareggio. For a more unique experience, head to Piombino and get the ferry to the Isola d’Elba, on the most beautiful islands in the north of Italy. The other possibility is to stay in the wilder Monte Argentario promontory, in the southern part of Tuscany, close to Lazio.
  • more countryside: why not explore the small region of Umbria, south of the Val d’Orcia? This is a less tourist area, probably wilder, however as beautiful and full of surprises, with the unmissable Orvieto, the historical Spoleto (founded 1,000 years ago) or the hill town of Assisi, where St. Francis (1198-1226), one of the patron saints of Italy, was born.
  • more of Italy: you will be surprised to know that Florence is only 1h30m from Rome, 2h20m from Venice and just 2h from Milan, all by an easy and quick train trip. In the 4 extra days, you could definitely think to explore another city, if you exhausted all your options in Tuscany.
Tuscany rolling hills
Tuscany rolling hills
A corner of Tuscany
A corner of Tuscany
Life in the lanes of Florence
Florence, the city of art
Florence, the city of art
The leaning Tower of Pisa
The Leaning Tower of Pisa
Lucca main square
Lucca main square
Arezzo dressed up square
Arezzo dressed up square
Siena - Palazzo Pubblico & Torre del Mangia
Siena – Palazzo Pubblico & Torre del Mangia
Stefano Ferro - MEL365.com Founder and Editor

About the Author

Stefano is a seasoned travel expert and the visionary founder of MEL365.com, a leading travel website with traffic across 6 continents. With a rich background in the travel industry, Stefano spent four pivotal years at Amadeus Travel Distribution System, gaining invaluable insights into travel technologies and distribution.

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