All you need to know to plan a perfect Tuscany itinerary: best places in Tuscany, where to base yourself in Tuscany, 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 minds with centuries-old art and architecture.
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 affects the musical rhythm of my auntie’s accent, and the place I spent most of my childhood summers in.
I love it so 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 share 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 (Cinque Terre) 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, this 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
Getting to Tuscany by plane
Tuscany is served by 2 main airports: Florence and Pisa, catering for national and international travelers.
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 airports 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 tourists 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 with cruise tours or independently.
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 itinerary.
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 own 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 holders.
If visiting cities, make sure you keep an eye out for ZTL signals as they are not always visible and yes, they 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 tobacconists (tabaccai) which are also the type of shops selling tickets.
Advance booking is usually not necessary.
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.
The best base to visit Tuscany for hilltop villages, food and art: Val D’Orcia / Val Di Chiana
If you are coming to Tuscany for the quintessential Tuscan experience, the one made of hilltop villages, cypress trees and amazing wineries, the best base in Tuscany is Val d’Orcia, in the province of Siena.
In this area, will find:
Val d’Orcia, where the famous Tuscany shots of cypress trees and hilltop villas are shot, where you must not miss San Quirico d’Orcia, Pienza, Montepulciano and Montalcino.
Plenty of wineries to taste the local Rosso, Brunello, Vino Nobile and Morellino
Plenty of farms and local shops with specialties such as cured meats and cheese (cacio di Pienza is amazing!)
Thermal baths, free and spas, such as those in Bagno Vignoni, Chianciano Terme and Bagni San Filippo.
San Gimignano, gorgeous with its turreted hilltop position
Siena and its stunning Piazza del Campo and Duomo, out of this world beautiful.
Volterra and the glorious countryside of this area
This is area is famous for hilltop villages, wine and food and it is perfect if you imagine your Tuscany vacation spent sitting in a medieval piazza savoring a board of cured meat and red wine (this is the area of cacio di Pienza and Nobile di Montepulciano!)
Where to base yourself in Tuscany if you don’t want to drive
If you prefer not to drive, the best place to stay in Tuscany is Florence.
Florence is a great transport hub you can use as a base to take day trips by train and bus.
From here, you can easily visit Fiesole, Lucca, Pisa, San Gimignano, Chianti and Siena by train or joining one of the many excellent available day tours.
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 is gorgeous and great for thermal relaxation and wine (Brunello and Morellino di Scansano come from here) and Saturnia is here too, now world-famous thanks to its scenic thermal waters.
Chianciano Terme, while not historical, is a great thermal town and a convenient base to explore Val D’Orcia and localities such as Montepulciano and Pienza, both worth seeing.
This is an area best discovered by car.
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 as well as the above mentioned Val D’Orcia, my favorite area of all.
While Val d’Orcia is perfect for a country experience, the Etruscan Coast is wonderful if you want also access to the sea.
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.
If you prefer a more rural location, then the area around Chianciano Terme is lovely: it has many accommodation options and the town itself has children entertainment such as a nice park with mini-golf as well as a kid-friendly thermal spa.
Where to stay in Tuscany accommodation options
Tuscany is very well equipped to welcoming tourism and offers several accommodation options.
Staying in agriturismo
Agriturismo is a country home that has opened its doors to guests.
Tre 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.
Agriturismi come in all shapes 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 thanks 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 attractions and recommended 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.
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 see most of Florence must-see attractions and possibly a museum such as Uffizi or Accademia.
If you have an extra day, even better! This is a good Florence itinerary that gives you an idea of what to see in Florence in 2 days
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 or even mix it with a stop in Bagno Vignoni, which is farther South and a nice stop for an evening meal.
If you prefer, you can also take part of the day to visit the countryside near it, for instance stopping in Monteriggioni on the way from San Gimignano.
4 days Tuscany driving itinerary
If you have one extra day in Tuscany I would build on the itinerary above and add one 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 (or Lucca)
For museums and its stunning city center. If you prefer a smaller center, I highly recommend you head to Lucca for the day
Day 2: Explore Chianti and San Gimignano
To enjoy the Tuscan countryside and one of its most charming hilltop villages, San Gimignano, famous for its towers, views and wine (vernaccia)
Day 3: Discover Siena
Discover Siena and take your time to slow down and see Piazza del Campo, Piazza del Duomo but also the surrounding hills.
You can get a step ahead and drive towards Val d’Orcia in the late afternoon too: the drive is easy and wonderful and you can have a hilltop dinner in this stunning area.
You can find my guide to a perfect day in Siena here.
Day 4: Explore Val D’Orcia
I highly recommend you get a car to visit this area and take your pick between the many beautiful towns around.
They are all small, some even tiny, and you can visit each in about half a day or less, so I suggest you plan two in a day.
I personally suggest Montalcino+ San Quirico and Pienza+Montepulciano but Pienza+San Quirico also works (and the drive between the two is stunning!)
In this area, we enjoyed staying in agriturismo in the country however, if you prefer a small village setting, we also loved 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
See above
Day 2: Chianti and San Gimignano
For winery visits, to experience the Tuscan countryside and famous hilltop villages – see above
Day 3. Siena
For its incredible past and medieval charm
Day 4: Val d’Orcia
see above, I especially recommend you seek out San Quirico d’Orcia (in the photo) and Pienza
Day 5: 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 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.
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 attractions 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
- Child-friendly beaches: Tuscany has lovely family-friendly beaches especially in the area of Capalbio, Orbetello and San Vincenzo
- 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)
You can find all of these and more in our guide to visiting Tuscany with kids here.
Great organized 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 to answer your questions about planning your best Tuscany itinerary.
Safe travels!