How to plan your perfect Tuscany itinerary: travel guide

All you need to know to plan a perfect Tuscany itinerary: where to base yourself in Tuscany, what to see and practical tips for a perfect trip 

Tuscany is one of those places in Italy that seem to have a special power. It envelopes visitors in all around beauty, satisfies their taste buds with gratifying food and tickles their mind with centuries old art and architecture.

The mix is intoxicating and if you add to it the physical pleasure of the sun on your skin and the sparkly Mediterranean water to refresh you, it is easy to see why Tuscany has been at the top of so many travelers’ dream list for such a long time.

I have a special connection with Tuscany, a personal  one, and I am a victim of the charm of this incredible area.

Tuscany is where half of my family is from, the place that still affect the musical rhythm of my auntie’s accent, and the place I spent most of my childhood summers in.

I love it to much we even recently relocated to Florence with the kids for a summer and we spent several holidays in different parts of this region exploring its coast and countryside.

I recommend a trip to Tuscany to everyone and in this guide, I will try and lay out all you need to know to plan a perfect Tuscany itinerary, no matter your party or time available.

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How to plan a trip to Tuscany

Tuscany is a region in the central part of the Italian ‘boot’. It is a large area, confining with Lazio (the region of Rome) to its South, Umbria and Marche to the east, Emilia Romagna and Liguria to respectively its North and north east.

To its west lies the large expanse of the Mediterranean, which the Tuscany coast follows for the whole length of the region.

To give you an idea of its location and distances between its most famous sites, these is how long it takes by car between some of its main towns:

• Florence to Lucca:  1h15 minutes
• Florence to Pisa: 1h35 mins
• Florence to Siena: 1h10 mins
• Siena to Livorno: 2h
• How to get to Tuscany

Due to its central position, getting to Tuscany is easy both from other parts of Italy and from abroad.

Getting to Tuscany by plane

Tuscany is served by 2 main airports: Florence and Pisa, catering for national and international travelers (Pisa came to the scene as a Ryanair airport and is still busy with low cost flights).

The airports are both well located to visit the rest of Tuscany and both cities offer car rental options, bus and train connections with the rest of the country.

While not technically in Tuscany, the airport of Bologna is also a good option if you are thinking of reaching this area by plane.

Please be advised that since these airport are smaller and tourism dependent, the availability of flights drastically diminishes in low season: make sure you check in advance when certain flights are available and on which days of the week.

Getting to Tuscany by train

Tuscany has a vast and efficient network of trains connecting many of its main towns and localities.

High speed trains connect Florence with the rest of the country while smaller cities are served by intercity trains and regional ones, which are slower but efficient.

With the fast trains, you can reach Florence from Rome in less than 2 hours.

Getting to Tuscany by boat

Many tourist reach Tuscany as part of a Mediterranean cruise and in that case the port of choice is the one of Livorno.

Livorno is itself a lovely town and it is very well located to be used as a base to discover Tuscany, something you can do independently or making the most of the many excursions available provided by cruise shops themselves or local providers.

You can check prices of transfer from Livorno port to Pisa and Lucca for instance here 

How to get around Tuscany

Tuscany is a large enough region and figuring out how to get from one place to the other is usually what takes up most of the time and stress when planning a Tuscany itineraries.

The good news is that traveling and Tuscany is pretty straightforward and there are several options to suit most types of travelers.

Getting around Tuscany by car

The best way to discover Tuscany is to drive your own car.

Having your won vehicle means you have total flexibility to visit not just the main cities and town but also villages and natural areas that you may otherwise find hard to reach if relying on the public transport system.

If you are thinking of driving in Tuscany, a few things are useful to know:

Tuscany has both regional/national roads and highways: the highways, like in the rest of Italy, have tolls: you collect a ticket when entering and pay at your exit. Having cash handy for this is useful.

Most cities in Tuscany have a ZTL, an area where traffic is limited to residents and permits holder. If visiting cities, make sure you keep an eye out for ZTL signals as they are not always visible and yes, they do fine you if you enter and park where you are not supposed to!

You can find tips and info on how to drive in Italy here

If driving in Tuscany with kids, remember that in Italy it is compulsory to have car seats.

You can find a selection of good car seats and booster seats for travel here 

As tempting and handy as it may be to drive to wineries in Tuscany, please stay safe and never drink and drive.

If you want to go wine tasting, get a designated driver or a private driver or winery tour instead (some recommendations at the end of this post)

Getting around Tuscany by train

As I mentioned above,  getting around Tuscany by train is easy and straightforward. For short distances and regional rains, advance booking of tickets is usually not necessary although always advisable. The best site to use is the official Italian railway site trentalia.it

You can read how to use trains in Italy here (it is geared to families with kids but not just!)

Getting around Tuscany by bus

Buses are also a good way to get around Tuscany, especially to reach smaller towns that might not have a train station or only be served by erratic train service.

there are several bus companies in Tuscany and the bus timetables are usually available in Tourist offices or in tabacconists (tabaccai) which are also the type of shops selling tickets.

the tickets need to be validated on the bus on boarding.

Where to base yourself in Tuscany

One of the most common questions about visiting Tuscany is what area or town or village is the best base for visiting the region.

The answer depends on your interests and time available but I do believe some areas are better than others and these are my top picks.

Best base to visit Tuscany for hilltop villages, food and art: Chianti and Val D’Orcia

If you are coming to Tuscany for the quintessential Tuscan experience, the one made of hilltop villages, cypress trees and amazing wineries, you will be hard pressed to find a better area as a base than the one between Florence and Siena.

This stretch of Tuscany is super rich in attractions, it is beautiful and puts you at the very centre of the action, allowing you to reach some of the most famous localities in Tuscany with short drives.

In this area you will be easily visit:

• Florence, with its incredible art and shopping opportunities
• Pisa, which is busy but still worth visiting, especially if you can stay the night
• Lucca, lovely walled medieval town
• San Gimignano, gorgeous with its turreted hilltop position
• Siena and its stunning Piazza del Campo
• Volterra and the golrosu countryside of this area
• Val d’Orcia, where the famous Tuscany shots of cypress trees and hilltop villas are shot

I am also fond of the area of Arezzo and Cortona, which puts you in a great location to discover not just Tuscany but also Umbria and Lazio.

Where to base yourself in Tuscany if you don’t want to drive

If you prefer not to drive, the best area to stay in Tuscany are:

• Florence, a great transport hub you can use as a base to take day trips by train and bus
• Siena, a great base to discover the area immediately around the town and southern Tuscany thanks to the many day tours available
• Greve in Chianti, a lovely place to stay if you want to take it slow and enjoy the countryside

This is an example of a wonderful day tour that covers some of the most beautiful areas of Tuscany

Best place to stay in Tuscany for thermal springs and wine

Tuscany has some gorgeous thermal springs and you want to experience them the best base for you would be in the South East of the region.

The area of Bagno Vignoni for example is gorgeous and great for thermal relaxation and wine (here you have Montalcino and its famous red as well as the delicious Morellino di Scansano, maybe my favorite Italian wine) and lovely is also the area of Saturnia, where you have stunning villages such as Pitigliano, quiet and rich in history.

Where to base yourself in Tuscany with kids

Tuscany is all family friendly but I have a soft spot for the Etruscan coast when it comes to recommending a destination for families.

This coastal area of Tuscany  between Grosseto and Livorno is gorgeous and has a great mix of sandy beaches, child friendly attractions and  villages like Suvereto or Bolgheri that are full of charm,

It also has some interesting archaeological sites that are easy to visit with kids and that can add an extra layer of culture and learning to your stay (more info on children attractions in Tuscany farther down in this article).

Where to stay in Tuscany accommodation options

Tuscany is very well equipped to welcoming tourism and offers several accommodation options.

Staying in agriturismo

My favourite type of accommodtion in Tuscany is agriturismo (plural: agriturismi).

Agritrismo are country homes that have opened their doors to guests and are usually in wonderful locations in the middle of the country, away from the hustle and bustle of the city and allowing you to be in close proximity to nature.

Agritutismi come in all shape and sizes: some are small and rural and still operate as working farms (or may have a farm area, often open to kids yo visit) and some are very elegant, upscale and equipped with swimming pools and more.

The choice of agriturismo in Tuscany is endless: you can find all options on agruturismo.it or even on booking.com, selecting ‘country houses’.

To give you an idea of what is available, have a look at:

Campo di Carlo (Sassetta, near Bolgheri and the coast): you can read our full review here or check our prices on booking.com here

Or

Fattoria di Maiano (Fiesole, just outside Florence): you can read our review here or check their prices and offering here 

Renting a Tuscan Villa

Many families opt for booking a Villa for their Italian stay and this is indeed an excellent option in Tuscany tnanks to the vast variety of properties available.

A great site to find villas here, to suit all budgets is Homeaway Italia that you can check out here

Campsites

Tuscany is a great area for camping too and this option is exceptionally popular with families with kids in particular.

Depending on what you are looking for and what you like, you can select small independent properties such as

Podere Pianetti, a small and perfectly kept caravan site with hot tubs and access to the beach

or all inclusive solutions like the Paradu Resort with pools, kids activities, restaurants onsite etc . The photo below is from our happy stay at Podere Pianetti and you can also check our Paradu review here

What to see in Tuscany: must see attraction

This is a daunting paragraph to write as let’s me honest: there is so much to see in Tuscany you can fill sever guidebooks just with things to see!

For the sake of this first timers’ guide to Tuscany however, I have selected a few places I do think should be visited for a great Tuscany experience and organised them in easy to follow itineraries.

Recommended Tuscany itineraries

It is hard to go wrong when visiting Tuscany, everywhere is so beautiful, but if you are short on time, having an itinerary can be handy. These are my suggestions.

3 days in Tuscany itinerary

If you only have 3 days in Tuscany I recommend you follow this itinerary:

Day 1: Explore Florence

Florence is a gorgeous city and while you can easily spend many days discovering its beauty, it is surprisingly easy to enjoy it even with a short time available.

With one day in Florence, you can visit a museum of your choice (book in advance tickets for the Uffizi and Accademia) and then you can see the best of the city taking a stroll in its ancient town center.

Even with a few hours you an see the famous Santa Maria Novella and Florence’s duomo, you can see Piazza della Signoria and Ponte Vecchio and you can also stretch to the top of Piazzale Michelangelo, which is touristy but has amazing views over the city.

Some of our favourite hotels in Florence:

• Check out Hotel Spadai, a great hotel in a perfect position in Florence city center
• Palazzo San Niccolo, on the ‘other side’ of the Arno river, in a quiet and charming part of Florence
• Palazzo Belfiore which offers great self catering apartments

Day 2: Discover Chianti and San Gimignano

On your second day in Tuscany, head to visit Chianti and San Gimignano.

I recommend you start your day from Chianti (Greve and Castellina are two great stops) and make your way to San Gimignano later in the day, planning to stay the night.

San Gimignano is a lovely town but it is overrun by tourism during the day as it is a popular day trip from Florence and it gives its best once the buses are gone and the sun starts setting over its tall towers.

A great place to stay in San Gimignano is Hotel L’Antico Pozzo

Day 3: Spend a day in Siena

On day 3 I recommend you head to Siena.

You can easily spend the whole day in this beautiful town and soak in its beautiful squares, contrade and shops  but, if you prefer, you can also take part of the day to visit the country side near it, for instance stopping in Monteriggioni on the way from San Gimignano.

4 days Tuscany Itinerary

If you have one extra day in Tuscany I would build on the itinerary above and add onhe stop in the area of Montalcino.

This area has stunning countryside and is famous for glorious food and beautiful countryside and has the added bonus of thermal baths!

This is the itinerary we followed when we spend 4 days in Tuscany and worked like a charm

Day 1: Visit Florence

For museums and its stunning city center

Day 2:  Explore Chianti and San Gimignano

To enjoy the Tuscan countryside and one of its most charming hilltop villages

Day 3: Discover Siena

And its incredible past

Day 4: Explore Montalcino and Bagno Vignoni

I highly recommend you get a car to visit this area. The countryside here is stunning and the villages make for very pleasant stops, making drive satisfying and easy.

In this area, we enjoyed staying right in Bagno Vignoni, which has several great accommodation options such as the B&B Locanda Il Loggiato 

If you have 5 days or more in Tuscany

If you have 5 days or more in Tuscany than you really are spoilt for choice on what to see Tuscany is reasonably compact and with 5 days I don’t want to say you will see the whole of it, but you can definitely cover a good bit of ground.

With 5 days i recommend you plan the following itinerary

Day 1: Florence

For museums, restaurants and shops

Day 2: Chianti and San Gimignano

For winery visits, to experience the Tuscan countryside and famous hilltop villages

Day 3. Siena

For its incredible past and medieval charm

Day 4: Add Arezzo and Cortona

Arezzo and Cortona are in the Eastern part of Tuscany and are lovely towns to visit as use as a base to discover Tuscany as well as Umbria and parts of Lazio.

If you can, It is worth spending a few hours or even a day to explore each. If you are staying in Cortona, I highly recommend a stay at Dolce Maria, right in the center of town.

I added them after Siena in this version of the itinerary as it makes better geographical sense but distances in the area are not big and reaching this area is easy.

Day 5: Montalcino and Bagnovignoni

For indulging in wine and thermal springs

Day 6: Castagneto Carducci and the coast

I am partial to this part of Tuscany as I feel it offers a wide variety of options and landscapes in short and easy to handle distance.

Here you have woodlands and hills, small villages (I love Bolgheri, Suvereto and Castagneto Carducci) but nearby you have an amazing coastline, perfect to dip your toes in the sea if visiting in the hot season.

We have spent several summers in this area and you can read here why you love it so much here.

Our agriturismo of choice in this area is the lovely Campo di Carlo (it has a pool and a lovely hilly location)

Day 7: Pisa and Lucca

Pisa and Lucca are both wonderful and yes, while many people find Pisa overrated I feel it is worth seeing it, no matter how maddening the crowds there can be.

The main thing when visiting Pisa is to be ready for the crowds and make a massive effort to see beyond them. If you can, the tower and the battistero near it ill just take your breath away. You can read here what to do in Pisa and how to spend a day there

The best way to visit is to go very early in the morning or stay the night, both options that would leave you time to visit the other gem of the area that is the walled town of Lucca.

How to visit Tuscany with kids: kid friendly attraction in Tuscany

Hilltop villages, art cities and vineyards may not conjure up the idea of Tuscany as a family friendly destination but things can be misleading.

Tuscany is a wonderful destination for families and it is a family destination for choice not just for foreigners but Italians too, who happily flock to its coastline as soon as school and work allow.

There are many reasons why going to Tuscany with kids.

Heading to Italy with the kids? Don’t miss our step by step guide to planning a family trip to Italy 

Tuscany has beautiful child friendly beaches

If you are looking for a sea and sun destination to enjoy with the kids, Tuscany offers many options.

The area of Orbetello and farther North the area of San Vincenzo and are all excellent for families and have sandy beaches in most localities as well as many tourism facilities

There are several children attractions and theme parks in Tuscany

• Tuscany has several attractions that are just for children. Some worth mentioning are:
• Pinocchio park (Pisa): small amusement park and garden decorated with statues from the famous Pinocchio story
• Water parks such as Piccolo Mondo (Pisa) waterpark with slides, go karts and kids bouncers and Aqua Village, in the Cecina and follonica area
• Il Cavallino Matto, the largest amusement park in Tuscany with rides for all ages
• Il Giardino dei Tarocchi, a wonderful sculpture gardens with artwork by Nikke di Saint Phalle
• Zoos and animal encounter opportunities, such as Pistoia zoo and the European fauna park Poppi (wildlife sanctuary)

Tuscany is perfect for matching kids and grown up interests

Thanks to the small distances between locations and the huge variety of activities, i find Tuscany one of the easiest places to mix kids and adults fun.

If you want to get the kids to splash on a gorgeous beach, discover ancient towns and have amazing meals all in one day, there is no better place to be than Tuscany!!

Great organised activities and tours in Tuscany

• Chianti half day afternoon tour from Florence with wine tasting
• Florence market to table cooking lesson
• Tuscany by Vespa, full day tour
• Children cooking class in Florence
• Florence walking tour for kids and families
• Horses and Vineyards, horseback riding in Tuscany
• Fiat 500 vintage Tuscany Tour

I hope you enjoyed this guide to planning your trip to Tuscany and it helped answering your questions about planning your best Tuscany itinerary. Safe travels!

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