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.
Did you know? Tuscany has no less than 7 Unesco World Heritage sites! learn more abot them and find more fun facts about Tuscany here.
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Table of Contents
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.
The car is a necessity if you want to stay in the countryside and it is also the easiest way to reach many of the villages around Tuscany, harder to get to if relying on local buses only.
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
If you prefer not to drive, you will be happy to hear Tuscany has a good train system.
The trains won’t bring you everywhere in Tuscany but towns such as Florence, Pisa, Lucca have good connections. If you intend not to drive, this is the area I recommend you focus on.
For short distances and regional rains, advance booking of tickets is usually not necessary although always advisable.
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 can be 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 photographed and where you find tuscany must-see sites such as San Quirico d’Orcia, Pienza, Bagno Vignoni, Monticchiello, 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,
- Monteriggioni,
- Chianti area 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. You can find my full guide to the best thermal towns and hot springs in Tuscany here.
Where to base yourself in Tuscany with kids
Tuscany is all family-friendly and where to base yourself with children depends on the type of vacation you want.
For a sea and sun family vacation in Tuscany, I recommend the Etruscan Coast, a lovely area with sandy beaches and easy access to pretty hilltop villages, perfect to mix time on the sea and sightseeing.
For a holiday in the Tuscan hills, maybe in a villa with a pool or an agriturismo, I recommend Val d’Orcia and in particular the area of Chianciano Terme
Here you find 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: spend one day in Florence, a good amount of time for a stroll in the city center and a visit to Florence main attractions.
Make sure you stay the night and pick a hotel in a central location, to make the most of your time. Find our guide to the best area to stay in Florence here.
Good to know: while Florence city center can be seen in a day, the city has stunning museums that deserve way more than that. If you prefer to stay in Florence longer, you can follow this 2 day Florence itinerary instead.
Day 2: Take a day trip to the Chianti region, taste its beautiful wines and exolore gorgrous San Gimignano, one of the most beautiful and popular day trips from Florence
Day 3: spend the day in Siena, one of the most beautiful and important cities in Tuscany, famous especially for its UNESCO Piazza del Campo and its incredible Duomo, two of the most beautiful landmarks in the whole of Italy.
4 Days in Tuscany itinerary
With 4 days in Tuscany, I recommend the following itinerary.
Day 1: Florence and its treasures
Day 2: Siena and its beautiful medieval center, and Bagno Vignoni for a relaxing thermal baths with views over Tuscany
Day 3: San Quirico d’Orcia and Pienza for a full immersion in Medieval and Renaissance Tuscany
Day 4: Moltepulicano (return to Florence ot Rome), its historical center and wine tradition
Itinerary for 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 and its treasures
Day 2: Unesco treasure Siena and thermal heaven Bagno Vignoni
Day 3: Pienza and San Quirico d’Orcia, gems of Renaissance and Medieval times
Day 4: Montepulciano and Montalcino, wine loers paradise
Day 5: Lucca, pretty walled town for music lovers
With additional days, you can also easily add a day in Arezzo/ Cortona or head back to the North of Tuscany and visit Pisa.
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!
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