Tuscany is a vast and beautiful region in Northern Italy, known for its picturesque landscape, influential and historic cities, and incredible cuisine. There’s so much to explore that it may be hard to figure out how to see it all.
So we created one week Tuscany itinerary ideas to help you plan your trip. We provide two Tuscan itinerary options — each with a different focus — so you can choose the one that best fits your interests.
This article assumes you’ve already spent a few days in Florence, as this capital city alone requires at least three days to visit all its highlights. If you’re short on time, however, you can add these Tuscan itinerary destinations as day trips from Florence instead.
It also assumes you will be driving as your easiest option for getting around in Tuscany will be to rent a car from Florence. This will give you more flexibility and save you some time, as much of Tuscany has unreliable and slow public transport.
Now that you know what to expect and how to get around, let’s jump right in and discover all that Tuscany has to offer.
Option 1: 7-Day Highlights of Tuscany Itinerary
The first itinerary focuses on the regions around Chianti, Pisa, Lucca, and the Tuscan coast, passing through some of the best towns in Tuscany.
Choose Your Base
Your perfect Tuscany trip itinerary will start in Greve in Chianti. By the middle of your itinerary, you’ll relocate to the city of Lucca, where you’ll need to secure a second accommodation.
You’ll find some lovely agriturismi in this area of Tuscany. These are farms that offer accommodation and food — often grown on the farm but always local.
Day 1 – Greve and San Gimignano
On day one, pick up your rental car at Florence airport. It is the closest airport to Greve in Chianti and has the best variety of rental options. Greve is less than an hour’s drive from Florence via the SR222 provincial road.
Greve in Chianti
Greve in Chianti is a small but busy medieval town in the Chianti region, which sits about halfway between Siena and Florence. It’s surrounded by rolling hills and vineyards, so you’ll be spoiled with brilliant vistas wherever you look.
Stop by Pasticceria Chianti for a caffè and pastry before wandering around the town.
In Greve, you’ll find the bustling, triangle-shaped Piazza Matteotti framed by shops, restaurants, and the Church of Santa Croce. Nearby, the quaint village of Montefioralle awaits, boasting its original defensive walls and houses and streets made of stone. Don’t forget to bring your camera along!
San Gimignano
This hill town is less than an hour’s drive from Greve. It is often referred to as ‘San Gimignano delle belle torri’ (roughly translating to ‘town of the beautiful towers’) for all its towering structures. At one stage, there were over 70 of these structures adorning the skyline.
The most famous tower in this UNESCO World Heritage Site is Torre Grossa (Great Tower). Standing at 177 feet, it’s the tallest remaining tower in the town. If you’re up for the roughly 200 stairs to the top, you’ll be rewarded with sweeping views of the Tuscan countryside.
Other things to do in this town include visiting the Duomo of San Gimignano, a medieval church consecrated in the 12th century. It sits on the triangle-shaped Piazza della Cisterna, a great place to stop for lunch or gelato.
While the church appears quite minimalist from the outside, the interiors are covered in frescoes by some of Tuscany’s most renowned artists.
Once you’ve wandered about town, you can explore more of the countryside with a classic Vespa tour of the Chianti hills. The half-day tour includes a Tuscan lunch and wine tasting at a winery, and you’ll travel through lesser-known regions far from the tourist crowds.
This may mean that you’ll have less time to wander through San Gimignano, but the tour definitely offers a memorable and unique experience.
Alternatively, opt for a traditional cooking class, and learn how to prepare authentic Tuscan cuisine at a farmhouse. You’ll prepare a 5-6 course meal with the help of two locals.
Day 2 – Siena and A Winery Dinner
Siena is about an hour’s drive south from Greve in Chianti via the SR222 — also known as Via Chiantigiana.
This picture-perfect destination seems frozen in time, boasting medieval and gothic architecture and winding narrow streets.
One of your first stops should be Piazza del Campo. It’s the site of the twice-yearly Palio di Siena horse race and is surrounded by plenty of attractions worth visiting.
Head to the square to admire the unique architecture and vibrant frescoes of Palazzo Pubblico before climbing (or simply appreciating) the Torre del Mangia next to it.
There’s also a Museum of Torture in Siena, with displays of various torture devices used throughout history. There are other branches in Lucca, Volterra, and Montepulciano. It may not be for everyone, but it provides some great insights into the darker side of mankind.
A short walk from Piazza del Campo, you’ll come across the Duomo di Siena and its museum. This 13th-century cathedral has a black-and-white-striped marble facade, further enhanced by intricate detailing and a large round window.
The dome of the cathedral and its accompanying tower dominate Siena’s cityscape. Inside, you’ll be treated to a visual delight of frescoes, arches, chandeliers, and sculptures.
If you’re an art fan, be sure to stop by the Salvador Dalí Art Museum down the road. A bit further from the Duomo, you’ll find Pinacoteca Nazionale, an art gallery housing works from some of Siena’s greatest artists.
End your second day in Tuscany with dinner at a winery in San Gimignano on your way back to your base town. You’ll enjoy traditional Tuscan cuisine prepared with local ingredients while seated among the vineyards. You’ll also get to sample a wide range of regional wines.
READ: Our guide to the Best Things to do in Siena.
Day 3 – Arezzo and Cortona
On your third day, explore the lesser-known yet beautiful towns of Arezzo and Cortona. Arezzo is just over an hour’s drive from Greve, while Cortona is about a 40-minute drive from Arezzo.
Arezzo
This charming, small city southeast of Florence is a bit off the beaten path. But you might recognize Arezzo if you’ve watched Roberto Benigni’s award-winning film, La Vita è Bella (Life is Beautiful).
Head to Piazza della Badia to see the site of the “Good morning Princess!” scene. Follow along Via Cavour towards the Basilica di San Francesco, opposite which Caffè dei Costanti (another film location) used to be.
The Basilica is known for housing renaissance-era frescoes by the artist Piero della Francesca. You need to book a ticket ahead of time as a limited number of people are allowed to enter at a time.
From there, head to the Arezzo Cathedral to wonder at the colorful frescoes on the ceilings. You’ll also want to stop by the Basilica di San Domenico to admire the painted crucifix by Cimabue.
If you’re an art lover, head to Casa Vasari, a short walk away. This house museum contains frescoes, sculptures, and paintings done by Giorgio Vasari.
Down the road from this museum, you’ll find the National Museum of Medieval and Modern Art. The art is arranged in a way that recounts the history and progression of art in Arezzo.
Cortona
Cortona is another one of Tuscany’s prettiest towns perched atop a hill. This beautiful town served as the setting for the 2003 movie ‘Under the Tuscan Sun’, adapted from a memoir by Frances Mayes.
Stop by Piazza della Repubblica in the historical center, where you’ll find spots like the Palazzo del Popolo and the Palazzo Comunale.
Further up from the historical center, you’ll find Piazza Luca Signorelli, which is framed by the MAEC – Museo dell’Accademia Etrusca e della città di Cortona. This important museum is housed in Palazzo Casali and boasts a large collection of artifacts and mosaics from the Etruscan and Roman eras. These include ceramics, bronze tablets, jewelry, and art.
Next, visit Piazza del Duomo to visit the Cortona Cathedral and the Diocesan Museum. This museum houses works by the likes of Fra Angelico, Luca Signorelli, and Francesco Capella.
Day 4 – Drive to Lucca
On your fourth day in Tuscany, you’ll drive to your second home base in Lucca. The drive should take about two hours. But there are a few destinations worth stopping for along the way, like Prato and Pistoia, so you may as well make a day of it.
Prato
Prato is a city with lots of interesting attractions. The city had a thriving textile industry and is the home of some famous foods like Mortadella Salami and Prato Biscotti.
The city also boasts some impressive structures, like the 11th-century Cattedrale di Santo Stefano, with its distinct striped facade and frescoed interiors by artists such as Filippo Lippi.
Another interesting sight is the white stone Castello dell’Imperatore, a 13th-century medieval castle overlooking the city.
Prato also has a collection of curious museums for every interest. These include the Museum of Planetary Science, the Museum of Calculators, and the Textile Museum — a must-visit when in Prato.
For art, stop by the Museo di Palazzo Pretorio di Prato to see works by the likes of Filippo Lippi, Andrea della Robbia, and Donatello. The Luigi Pecci Centre for Contemporary Art is a curious-looking modern art museum that features works by a wide range of internationally renowned artists from the last few decades.
And, of course, before leaving Prato, be sure to stop by Biscotticifio Antonio Mattei (or any other biscuit shop) to purchase some biscotti for the road.
Pistoia
Pistoia is about a 20-minute drive from Prato and was designated the Italian Capital of Culture in 2017.
Head to the Piazza del Duomo, where you’ll find some of the most significant buildings related to the city’s history. These include Palazzo Pretorio, Palazzo dei Vescovi, and the ornate San Zeno Cathedral. You’ll also find the Palazzo Communale, which houses the Museo Civico, home to painted works from the 14th to the 19th centuries.
Pistoia has plenty of intriguing churches worth admiring, like the Church of San Giovanni Fuoricivitas, which boasts a densely striped facade. The Church of Sant’Andrea, with its carved marble pulpit, and the frescoed Church of San Francesco are also beautiful attractions.
An even more intriguing sight is the Pistoia Sotterranea (Pistoia underground). You can take a tour of the tunnels running below the Ospedale del Ceppo. This hospital looks somewhat similar to a hidden gem in Florence, the Ospedale degli Innocenti.
You’ll love the glazed marble frieze at the entrance of the building, created by Giovanni Della Robbia and Santi Buglioni.
After spending some time in Pistoia, continue on to Lucca to settle into your new accommodation.
READ: Our guide on Where to stay in Lucca.
Day 5 – Lucca
Lucca is a picturesque city with various attractions to explore. Its well-preserved Renaissance-era walls are an impressive sight, as is the historic center.
Start your day in Lucca with a coffee and fresh pastry at Pasticceria Dianda. Then head to Piazzale Ricasoli near the train station to start your cycling tour of Lucca — you’ll have to book ahead.
The three-hour tour is a great way to familiarize yourself with this stunning destination, as you’ll cycle along the city walls and learn about Lucca’s history. You’ll also stop to sample some wine and local bites like cured meats and cheese.
After your tour, you can revisit some of the highlights of this city. This includes the Piazza dell’Anfiteatro, an oval-shaped site of an ex-Roman amphitheater that is now abuzz with restaurants and shops.
Nearby, there’s the Basilica di San Frediano with its mosaic facade and Palazzo Pfanner — which boasts a charming garden with statues and fountains. The nearby 12th-century Chiesa di San Michele in Foro is a standout church with an ornate exterior and interior boasting art by Filippino Lippi and Luca della Robbia.
For the ultimate display of opulence, head to the National Museum of Mansi Palace to see the sumptuous interiors and a large collection of art, period clothing, and antique furniture.
READ: Our guide to the Best Things to do in Lucca.
Day 6 – Pisa
On day six, you’ll head to Pisa, the birthplace of Galileo Galilei. This iconic city boasts more than just its leaning tower. It has plenty of architectural marvels to admire and has the Arno River flowing through it.
You can get there by car in about 30 minutes or take a train. Trains leave from Lucca to Pisa hourly, and tickets cost around €5.
Once in Pisa, head to nearby Piazza dei Cavalieri. On this square, you’ll find a stunning palace decorated with patterns and ducal statues. From there, you can head to the 14th-century leaning Tower of Pisa. If you’re up for it, you can climb the roughly 300 steps to the top of the tower for incredible views.
There are many other attractions around this tower, like the Pisa Cathedral, an expansive and ornate church filled with frescoes and statues. To access the cathedral, you need to book a ticket from the ticket office. Tickets are free, but a limited number of people are allowed to enter every hour.
Standing in front of the cathedral is the medieval Baptistry of Saint John, completed in 1363. The baptistry features a pulpit created by Nocila Pisano and other elements by artists like Guido Bigarelli da Como and Italo Griselli.
The best way to see all these attractions is with a guided Pisa tour. This way, you don’t have to organize tickets for each spot, and you’ll learn some interesting information about the attractions.
Other sites worth a visit include the Museo delle Navi Antiche di Pisa, a museum dedicated to the naval history of Pisa. The museum houses antique boats and remains of Etruscan pottery.
Stroll along the Arno River to Piazza Garibaldi, where you’ll find the start of Borgo Stretto, a road filled with beautiful architecture and high-end shops.
Day 7 – Explore the Tuscan Coast
On day seven, head to the beautiful city of Viareggio or Cinque Terre to enjoy the Tuscan seaside. Trains run regularly between Lucca and Viareggio and take less than 20 minutes. Alternatively, you can drive to Viareggio in less than 30 minutes. The best way to get to Cinque Terre is with an organized day tour.
Viareggio
Viareggio is popular for its sprawling beaches and the Carnival of Viareggio. It’s one of Tuscany’s largest beach towns and boasts over 10 kilometers of sandy beaches. Most of these beaches require payment to enter but offer great amenities like changing cabins and showers in return.
There are also some green areas to explore, namely Pineta di Ponente and Pineta di Levante, where you can take a stroll or cycle.
Some of Viareggio’s top attractions besides the beach include the Citadel of the Viareggio Carnival, which encompasses a museum and contemporary art gallery. Villa Paolina also houses various intriguing museums, including an archaeological museum and a museum of instruments.
Be sure to take a stroll along the Margherita Walk parallel to the Viareggio seafront. This street is the site of the yearly Carnival of Viareggio and is lined with Art Deco and Liberty architecture.
You’ll find plenty of lovely restaurants and gelaterias here, as well as attractions like the Palace of the Muses with its beautiful collection of art.
Cinque Terre
The alternative option is to head to Cinque Terre for the day. You can take a day tour from Lucca so that the transport and itinerary are arranged for you.
Cinque Terre is famous for its cascading cliffs toppled with colorful houses overlooking the azure coast. It’s a great destination to snap some photos and enjoy a swim. This area also produces some incredible regional wines — like the sweet Sciacchetrà Wine.
Option 2: Tuscany Itinerary for Wine and Luxury Lovers
It’s no secret that Tuscany produces some of the best wines in Italy. So if your ideal vacation includes sampling different regional wines and enjoying the best of Tuscany’s luxuries, this second itinerary option is for you. You’ll explore top wine destinations like the Chianti region, Val D’Orcia, and Saturnia.
Choose Your Base
For this itinerary, your ideal bases will be in Greve in Chianti, south of Florence, and Pienza. Opt for agriturismi for the best experience of the Tuscan countryside.
LISTEN: To our podcast on Staying in an Agriturismo.
Days 1–2: Greve, San Gimignano, and Siena
Days one to two are the same as the first itinerary. You’ll explore your base town of Greve in Chianti, with much of its attractions centered around the triangle-shaped Piazza Matteotti, before heading to San Gimignano.
Tour the town of towers, climbing the Torre Grossa for stunning views of the landscape. Admire the San Gimignano Duomo and take a tour of the countryside on a Vespa, stopping for lunch and a wine tasting.
On the second day, you’ll head to Siena. Visit the Duomo and its accompanying tower and stop by the Salvador Dalí Art Museum and Pinoteca Nazionale. End your day with a relaxing and romantic dinner at a winery before heading back to Greve in Chianti.
Day 3 – Drive to Pienza
On day 3 of your one week in Tuscany, you’ll transfer to your accommodation in Pienza. This charming town is about a 2-hour drive from Greve in Chianti, but you’ll pass near towns like Arezzo and Cortona, which are both worth a stop.
Arezzo
Arezzo is just over an hour’s drive from Greve. It’s featured in the award-winning film La Vita è Bella and has plenty of sights to adore.
Stop by the Basilica di San Francesco to admire the Renaissance-era frescoes done by Piero della Francesca, or go to the Basilica di San Domenico to see Cimabue’s painted crucifix.
There are also some exciting art museums like the National Museum of Medieval and Modern Art and Casa Vasari.
Cortona
Cortona is a picture-perfect hilltop town that served as the setting for the 2003 movie ‘Under the Tuscan Sun’.
Head to the Piazza del Duomo to admire the Cortona Cathedral and the Diocesan Museum, which houses work by artists like Francesco Capella and Fra Angelico. Or stop by Piazza della Repubblica to admire stunning palaces like Palazzo del Popolo and the Palazzo Comunale.
Next, visit the important MAEC – Museo dell’Accademia Etrusca e della città di Cortona, hosted in the Palazzo Casali. This museum boasts a collection of Etruscan and Roman artifacts like mosaics, ceramics, bronze tablets, art, and jewelry.
Day 4 – Montalcino
Montalcino is about half an hour’s drive from Pienza. This hilltop town is known for its production of two local wines, Rosso di Montalcino and Brunello di Montalcino.
If you’d like the day arranged for you, you can opt for this full-day wine tour of Montalcino. The tour includes a hotel pickup and dropoff around Siena and lunch. You’ll stop by three different historic wineries in Montalcino to learn about the production of this regional wine.
Alternatively, if you’d like more time to explore the town, you can opt for this shorter Brunello wine tasting and lunch — in a Tuscan castle, no less.
During your free time, stop by the Montalcino Rocca, a 14th-century fortress dominating the town’s skyline. The main piazza nearby is worth a visit to admire the architecture and enjoy some people-watching. The square often hosts jazz concerts in the evenings.
You can also wander about the narrow streets exploring the churches and shops and perhaps buying some Montalcino wine as a Tuscan gift to take home.
READ: Our guide to visiting the Val d’Orcia.
Day 5 – Saturnia Hot Springs
Prepare yourself for a relaxing day with a trip to Saturnia on day five. Saturnia is known for its spectacular hot springs and cascading blue pools.
The waters are heated by a nearby volcano, Monte Amiata. These thermal waters are free to visit and are said to have healing properties. They do have a bit of a sulphuric smell which may take some getting used to.
Your easiest option is to book a full-day trip to Saturnia’s springs, with a sunset picnic among the vineyards included. This option covers the transport and all the necessary arrangements for you to have a relaxing day.
You can also head to Saturnia on your own. The drive from Pienza is just under two hours long. Try to make it to Saturnia early to enjoy the baths when they’re less crowded. You can also book a wine and EVO oil tasting during the day. The tasting includes samples of cheeses, meats, and Tuscan bread.
Day 6 – Pienza and Montepulciano
On day six, you’ll explore your home base and the medieval town of Montepulciano — known for its red wine, vino nobile.
Pienza
Set among rolling hills and vineyards, Pienza is a picturesque town filled with charm.
Much of the town’s construction today can be credited to humanist Pope Pius II, who wanted to turn Pienza into the “ideal town.” The products of this ambition include the Cathedral, the Piccolomini Palace, and the Town Hall, all surrounding the central square, Piazza Pio II.
Pienza is also popular for its cheese, especially the Pecorino of Pienza — a versatile sheep’s milk cheese. Be sure to stop by a few cheese shops to sample and purchase some of it.
If you visit in early September, be on the lookout for news about the famous Fiera di Cacio, a festival celebrating pecorino cheese and other regional products. You’ll witness folkloric games like the ancient Palio del Cacio Fuso.
If you’re hungry, stop by the restaurant Baccus L’Osteria to sample regional cuisine like pici (handmade pasta) and cacio e pepe. They also serve Florentine steaks if you’re looking for something more hearty.
Montepulciano
This town is about 20 minutes from Pienza and offers some of the most incredible views of the countryside. Montepulciano boasts beautiful Renaissance palaces, charming piazzas, and the red vino nobile di Montepulciano.
Wander along the corso starting at Montepulciano’s city gate, Porto Prato, and stop by the various shops along the way. You’ll find stores selling everything from wine and olive oil to textiles and kitchenware.
After that, head to the Piazza Grande, where you’ll find the Duomo and a historical well topped with two stone lions holding up the Medici crest. Follow the alleyways leading from the square, and you’ll come across terraces facing the rolling hills and vineyards below the town.
A further walk from the piazza will lead you to the Fortress of Montepulciano, which now hosts the Consorzio del Vino Nobile di Montepulciano. This site has picture-perfect gardens and a tasting room where you can sample regional wines.
Day 7 – Pitigliano and Lago di Bolsena
On day seven, you’ll visit southern Tuscany to explore a town perched on volcanic stone, Pitigliano and Lago Bolsena.
Pitigliano
This town looks a bit different from the other Tuscan towns, as it’s perched on volcanic rock that blends in with the color of the city walls. It sits near the Tuscany and Lazio border and was home to a thriving Jewish community around the 16th century — thus its nickname, “Little Jerusalem.”
This town also produces a distinct regional wine, the Bianco di Pitigliano — made with the Trebbiano Toscano white grape variety. Another consumable local to this region is the Sfratto — a stick-shaped biscuit filled with orange peel, ground walnuts, honey, and nutmeg.
Visit the Jewish Museum of Pitigliano to learn more about the history behind the Jewish community. You’ll also enjoy the interesting churches in this town, including the medieval Santi Pietro e Paolo Church and its 35-foot bell tower and the nearby Sinagoga di Pitigliano.
There’s also the Santa Maria and San Rocco Church, thought to be the oldest church in Pitigliano, and a small cave temple called the Tempietto (“small temple”). Its original use is unsure, but it may have served as an Etruscan tomb, shrine, or Roman temple.
To learn more about the archaeological history of this town, be sure to stop by the Civic Archaeological Museum of Pitigliano and the Alberto Manzi Outdoor Archaeological Museum.
Lago di Bolsena
Bolsena Lake is the largest volcanic lake in the entire European continent, covering about 44 square miles. It sits just across the Tuscany and Lazio border and is about a 40-minute drive from Pitigliano.
It’s a great site for water activities like swimming, kitesurfing, and fishing. There’s also a Bolsena lake ferry that takes you around the lake’s islands for about €10.
The spectacular lake is surrounded by small villages. One of the most important towns on the coast of this lake is Bolsena, a site inhabited by Romans since about the third century BC. The town features a beautiful hilltop castle, Rocca Monaleschi Cervara, and several beautiful ancient churches.
This town is also the site of the famous Eucharistic Miracle of 1263, where a German priest discovered blood seeping out of a consecrated Host during Holy Mass.
Getting Around in Tuscany
The best way to embark on your Tuscany adventure is by renting an Italian car. You can pick up your rental at Florence Airport and return it at the end of your trip to Tuscany. If you’re taking on the second itinerary, you could also opt to go through Rome’s airport and collect a rental car there.
The area around Lucca is well-serviced by trains, but many small villages and towns are not as well-connected. In these cases, using public transportation can be time-consuming and unreliable. So a car is your best option overall.
Where to Stay in Tuscany
You’ll find some of Italy’s best agriturismi in Tuscany. These are usually farms that offer accommodation among the rolling hills and vineyards of the countryside and will be the best option for a scenic stay when you visit Tuscany.
READ: Our guide to the Best Tuscan agriturismos to help choose your stay.
Lucca has many excellent boutique hotels on offer, like Palazzo Dipinto or Lucca in Villa Lucrezia, situated in the historic center.
DISCOVER: More amazing destinations in Where to stay in Tuscany.
Best Tuscany Tours
Looking for an organized tour that’ll cover all the logistics for you? Consider our Untold Italy Tuscany in spring itinerary to explore the region in bloom. Or have a look at our fall itinerary for Tuscany to visit beautiful Toscana at the end of the vendemmia (grape harvest).
What’s on Your Tuscany Itinerary?
Tuscany is a dreamy destination, which is why it’s no surprise that it’s the site of many romantic movies and novels. With wine galore and historic hilltop villages, this region oozes charm and fantasy.
We hope these two Tuscany itineraries have given you some inspiration for your own itinerary. If you’d like to learn more about this region, have a look at this Tuscany travel guide.
Our team of writers and creatives at Untold Italy are experts in keeping you informed and inspired about travel in Italy. Our team collaboration involves writers, photographers and editorial staff dedicated to sharing accurate Italy travel information.
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