• Leslie

The Perfect 10 Day Itinerary for Tuscany, the Quintessential Italian Experience

Updated: Aug 30


landscape of Asciano in Tuscany
landscape of Asciano in Tuscany


There's nowhere more romantic in Italy than the stunning region of Tuscany. Tuscany is like a painting. With its cypress-lined roads, golden wheat fields, and medieval hilltop towns, Tuscany offers the quintessential Italian village experience, complete with fine wine and delectable food.


Here's my comprehensive guide to spending 10 days in Tuscany. This Tuscany guide covers all the best destinations, must see sites and attractions, and historic landmarks in Tuscany.


Tuscany boasts some of the world's best cathedrals, palaces, museums, and landscapes.

It's celebrated for its Gothic and Renaissance art. Tuscany is considered the birthplace of one of mankind's greatest adventures, the Italian Renaissance.


Here's the itinerary that I recommend for the perfect 10 day road trip through Tuscany. This itinerary is easily adjustable. You can make it shorter or longer, depending on your available vacation time.



10 Day Itinerary for Romantic Tuscany



You can also make it more leisurely by eliminating a destination or spending less time in Florence at the outset, if you'd rather see the smaller Tuscan hamlets. I also give you some options for extending your Tuscany trip at the end, if you have extra time in Italy.


Recommended Itinerary for Your Tuscany Getaway


Day 1: Arrive in Florence

Day 2: Explore Florence

Day 3: Explore Florence

Day 4: Day Trip to Arrezo or Cortona

Day 5: Pick up your car, drive to and explore Siena

Day 6: Drive to Montepulicano, stop in Pienza

Day 7: Drive to San Gimignano, overnight in Volterra

Day 8: Explore Volterra and Drive to Lucca

Day 9: Explore Lucca

Day 10: Day Trip To Pisa



map of Tuscany


This Tuscany itinerary assumes you pick up a car when leaving Florence. (You don't want to have one in Florence.) You can get around some of the Tuscan towns with public transport. But not every hill town has rail service. Tuscany and its breathtaking landscapes are best seen by car.


I like to use AutoEurope for the cheapest rates. If you can drive a manual, it's vastly cheaper.


Your overnight bases will be Florence (4 nights), Siena (1 night), Montepulciano (1 night), Volterra (1 night), and Lucca (2 nights). If this is too much moving around for you, you can skip the longer drive to Montepulciano and enjoy more time in Siena. Siena makes a great base for day tripping in Tuscany.


Here are my must know tips for traveling in Italy and tips for renting a car in Europe.



the iconic Ponte Vecchio in Florence
the iconic Ponte Vecchio in Florence


The Best 10 Day Itinerary for Exploring Tuscany


Day 1: Florence


Fly into Florence to begin your Tuscan road trip. Florence is the capital of the Tuscan region.


It's an overwhelmingly beautiful city, the "Cradle of the Renaissance." With the best Medieval and Renaissance art in Europe, Florence is a veritable art lovers paradise. Florence's entire historic center is a designated UNESCO World Heritage site. You'll need to buy your tickets for major attractions and must see sites well in advance.


On day 1, head to the historic complex of Florence Cathedral, Santa Maria del Fiore, nicknamed the Duomo. I recommend purchasing a 72 hour combination pass that allows you to see all sites within the Duomo complex -- the Duomo, the Baptistry, the Giotto Bell Tower, and the Duomo Museum. They're all eminently worth seeing.


You should start with the stunning Duomo Museum to get the historical backdrop for all these structures. The museum is housed in the Piazza del Duomo at the back of Giotto's Bell Tower, behind the Duomo apse. The museum space is a fabulous treasure box of sculpture. Its rooftop terrace also offers a mesmerizing view of Brunelleschi's dome.


READ: Visitor's Guide to Florence's Duomo Museum



Brunelleschi's dome on Florence Cathedral
Brunelleschi's dome on Florence Cathedral

the view of Florence from Brunelleschi's dome
the view of Florence from Brunelleschi's dome


Then, head to Florence Cathedral -- the most prominent, and popular, landmark in Florence. It was built over 172 years, beginning in 1296. Florence Cathedral is made of brown sandstone and beautifully faced or "frosted" with pink, green, and white marble.


Filippo Brunelleschi's magnificent terra cotta colored dome, built from 1420-36, is the highlight. The burnt orange cupola is the very symbol of Florence.


It’s decorated with frescos by Giorgio Vasari, a Florentine artist and the world’s first art historian. For panoramic views, climb up the cupola.


READ: How To Visit the Duomo and Climb Brunelleschi's Dome



the Florence Baptistery, 1000 years old
the Florence Baptistery, 1000 years old


Next, stroll to the Baptistery, in front of the main facade of the Duomo. Dating from 1059, it's over a thousand years old. The Baptistery sports three magnificent sets of bronze doors. designed by Lorenzo Ghiberti and Nicola Pisano. Inside, is a stunning golden Byzantine style ceiling mosaic telling the story of the Last Judgement.

Break for lunch and a wander, enjoying the joys of a traffic free Florence. Try Casa del Vino, where you can get sandwiches, crostini, or charcuterie plates with a delicious glass of wine. All'Antico Vinaio is also a must-try, just minutes away from Piazza della Signoria. Its sandwiches are made with a local bread called schiacciata.


Then, take the classic stroll across Florence's storybook bridge, the Ponte Vecchio. It looks like cobbled together houses suspended over the Arno River. The bridge has three arches topped with a jumble of charming shops. Nowadays, you can buy expensive jewelry on the Ponte Vecchio.



the Uffizi Gallery on the Arno River
the Uffizi Gallery on the Arno River



In the afternoon, head to the Uffizi Gallery, Florence's #1 sight. It houses the world's best and most abundant collection of Italian medieval and Renaissance art. The museum is a crowd pleaser, the third most visited site in Italy. The Uffizi deserves its accolades.


The Uffizi boasts seminal works from the 13th to 18th centuries. Here's where you'll find one of the world's most iconic paintings, Sandro Botticelli's Birth of Venus. If your time is limited, you should focus your efforts. The must see halls include the Hall 2 (Giotto), Hall 8 (Lippi), Halls 10-14 (Botticelli), Hall 15 (Leonardo), Hall 41 (Raphael and Michelangelo), Hall 83 (Titian), and Hall 90 (Caravaggio).


READ: Complete Guide to the Uffizi Gallery

For dinner, dine at Trattoria da Tito, not far from the Accademia, or Bobo's Trattoria. Or take a guided food tour for the total Florence food experience. If you need more art, the Palazzo Strozzi is often open at night with beautiful temporary exhibitions. Otherwise, you can just take a moonlit stroll through the beautiful historic center.



MIchelangelo's David sculpture in Florence's Accademia
MIchelangelo's David sculpture in Florence's Accademia


Day 2: Florence


1. Accademia Gallery


Start you morning bright and early at the Accademia Gallery. After the Uffizi, the Accademia is Florence's most visited museum. People flock in to see what is probably the world's most famous sculpture, Michelangelo's commanding statue of David.


The 17 foot sculpture is considered the embodiment of male beauty, a Calvin Klein-like model of physical perfection. David was commissioned for a niche of the Duomo. But it was considered too beautiful for that location. It's essential to have a reservation for the Accademia. Here's my guide to David and how to skip the line to see it.


2. San Marco Monastery


When you're done at the Accademia, head a few blocks to another amazing Florence art spot, the Museum of San Marco Monastery. San Marco is an extraordinary decorative complex, one of the most unusual things to do in Florence. You can admire art in its original in situ location and understand how contemporary audiences experienced it.



the facade of San Marco Monastery, filled with Fra Angelico frescos
the facade of San Marco Monastery, filled with Fra Angelico frescos



At this Renaissance convent-museum, you travel back in time to a nearly perfectly preserved 600 year old Dominican monastery.


It was paid for by Medici family money, designed by the stellar architect Michelozzo, and decorated with delicate frescos by one of the most sublime painters of the Renaissance -- Fra Angelico. The fiery preacher Girolamo Savonarola even lived there, in the monks dormitory cells.


READ: Visitor's Guide to San Marco Monastery


You're likely ready for lunch. This is a good time to explore the San Lorenzo markets. There are two of them, an outside street market and an indoor food court known as the Central Market. I can recommend a rustic gem, Trattoria la Burrasca, on the market's north corner.



the facade of Santa Maria Novella
the facade of Santa Maria Novella


3. Santa Marias Novella


After lunch, tour the beautiful Basilica of Santa Maria Novella and the Piazza della Repubblica. Santa Maria Novella Santa Maria Novella was founded in 1279 by a Dominican order. The basilica has a similar design to the Duomo, with polychrome and white marble create a striking front facade.

The interior is a true marvel. It holds one of the most famous paintings in Italy, the Holy Trinity by Masaccio. You'll want to inspect three important highlights -- the Strozzi Chapel, the Filippo Chapel, and the Spanish Chapter House.


4. Basilica of San Lorenzo and the Medici Chapel

Next, head to the monumental complex of the Basilica of San Lorenzo. The complex is a veritable haven of Renaissance art and architecture, a must see for history buffs. The complex is vast, including: the basilica itself, Brunelleschi's Old Sacristy, Michelangelo's New Sacristy, the Medici Chapel, the Medici Crypt, and the Laurentian Library.



the Tomb of Giuliano in the Medici Chapel, with Michelangelo's famed sculpture of Night
the Tomb of Giuliano in the Medici Chapel, with Michelangelo's famed sculpture of Night

Most importantly? It has the largest number of Michelangelo sculptures in Florence, quite a selling point. And a Michelangelo-designed library. If you're on the Michelangelo trail, the the Medici Chapel and the Laurentian Library are must see sites in Florence.


READ: Complete Guide to the San Lorenzo Complex and the Medici Chapel


5. Palazzo Vecchio


In the evening, head to the magnificent Palazzo Vecchio, one of the few must see sites in Florence that's open at night. The Palazzo Vecchio was the seat of government and one of the three palace-residences of the Medici dynasty.


It sits in the Piazza della Signoria, which is essentially a free open air sculpture gallery. Here's my guide to the highlights of the Piazza della Signoria.


READ: History of the Medici Dynasty



Hall of the Five Hundred in the Palazzo Vecchio
Hall of the Five Hundred in the Palazzo Vecchio, with frescos by Giorgio Vasari


It's definitely worth going inside the Palazzo Vecchio, though so many tourists don't. The Palazzo Vecchio is a doughty medieval fortress on the outside and a resplendant Renaissance palace on the inside.


Inside, you can admire the stunning Michelozzo-designed courtyard, explore the grand Hall of the Five Hundred, admire Michelangelo and Donatello sculptures, and gaze admiringly at beautiful frescos at every turn.

The Tower of Arnolfo can be climbed, and provides fantastic views over Florence and the Duomo. And the lines aren't nearly as long as for Brunelleschi's dome.

READ: Visitor's Guide to the Palazzo Vecchio



courtyard of Florence's Bargello Museum
courtyard of Florence's Bargello Museum


Day 3: Florence


1. Bargello Museum


Start your day at the Bargello Museum, Florence's underrated sculpture museum. If you need a hearty breakfast before you visit, head to The Dinner for all manner of eggs and pancakes. It's right by the Bargello.


The Bargello houses an amazing collection of Renaissance sculptures. The most important works are in the Michelangelo and Donatello rooms. Those include Michelangelo's first major sculpture, Bacchus, and his Pitti Tondo, Donatello's acclaimed Bronze David and St. George, and Gian Lorenzo Bernini's Bust of Costanza.


READ: Visitor's Guide To the Bargello Museum


2. Basilica of Santa Croce Complex

After the Bargello, visit the amazing Basilica of Santa Croce. In a city studded with magnificent churches, Santa Croce really stands out. Santa Croce has one of the greatest assemblages of paintings, sculptures, and funereal tombs in existence.



Dante statue against the facade of the Basilica of Santa Croce
Dante statue against the facade of the Basilica of Santa Croce

Michelangelo's tomb in Santa Croce, designed by Giorgio Vasari
Michelangelo's tomb in Santa Croce, designed by Giorgio Vasari


Santa Croce is a place of superlatives. It’s the world’s largest Franciscan church, a fine example of Italian Gothic style, and home to many celebrity tombs (including Michelangelo's), magnificent frescos, and Donatello sculptures. Santa Croce is a place of one stop shopping for Italian culture.


In particular, the frescoed chapels are impressive. The best ones are the Bardi Chapel, the Peruzzi Chapel, the Pazzi Chapel, the Baroncelli Chapel, and the Maggiore Chapel. You'll find frescos by Giotto, the greatest artist of the 14th century, and other Renaissance luminaries.


If you want to lunch in the Santa Croce area, try the tiny but mighty Le Vespe Cafe. There will be lines, but it's well worth the wait.


4. Florence Viewpoints


For your last evening in Florence, head to one of Florence's iconic viewpoints. Piazzale Michelangelo is the classic lookout point.


But if you hike 10 minutes further uphill, you'll come to the Basilica of San Miniato al Monte, Florence's crowning glory. The ancient church is a unique and harmonious blend of medieval architectural styles, pre-dating Florence's Renaissance treasures.


READ: Complete Guide To the Santa Croce Complex



the gorgeous setting of the Pitti Palace
the gorgeous setting of the Pitti Palace


In the afternoon, cross the Arno and head to Florence's Oltrano neighborhood, This may be Florence's most trendy neighborhood. There are three must see sites in the Oltrarno neighborhood: the Pitti Palace, the Church of Santo Spirito, and the Brancacci Chapel in Church of Santa Maria del Carmine.


If you didn't break for lunch in the Santa Croce area, there are plenty of places near the Pitti Palace in the Piazza della Passera. Other good restaurants near the Ponte Vecchio include Il Magazzino, 5 e Cinque, and Trattori 4 Leoni. Once fueled up, head to the Pitti Palace.


5. Pitti Palace


The Pitti Palace is one of Florence's must see sites, a truly wonderful experience. The palace is an incredibly unique combination of splendor, in situ art collections, and beautiful gardens.


The magnificent Palazzo Pitti was the regal home of the Medici family. The palace is the largest palace in Florence and one of Florence's most stunning architecture gems.



the Boboli Gardens behind the Pitti Palace
the Boboli Gardens behind the Pitti Palace


The palace houses 4 museums. The one you can't miss is the Palatine Museum.


It boasts an impressive collection of over 500 in situ paintings, chock a block on top of each other amid lavish stucco and silk furnishings. In the five Planet Rooms, there are beautiful ceiling frescos by Pietro da Cortona.

After gazing at these master works, head to the backyard playground of the Pitti Palace, the lovely Boboli Gardens. The gardens are the largest green space in Florence, sprawling over 11 acres. The gardens are effectively an open air museum, with hundreds of nooks to explore.


READ: Guide To the Pitti Palace


Day 4: Day Trip to Arezzo or Cortona


You have two options for day 4: a day trip to either Arezzo (for culture) or Cortona (authentic Italian charm), according to your own preferences.



Piazza Grande, the main square of Arezzo
Piazza Grande, the main square of Arezzo


1. Arezzo Day Trip Option


If you love Renaissance art, head to the cultural hotspot of Arezzo, just 30 minutes away on the high speed train. Arezzo is a compact and colorful city. It's quiet and less crowded than other Tuscan towns, but stuffed with delicious things to see and do.


In particular, you need to visit the high chapel in the town's Basilica of San Francesco. There, Piero della Francesca, painted his greatest masterpiece, still in situ. The complex fresco cycle represents the Story of the True Cross. It's considered one of the greatest and most influential frescos of the early 15th century.

The rest of Arezzo offers plenty of things to do, with many churches and museums. Arezzo Cathedral is a late 13th century Gothic church, with a rather austere exterior. But inside, you'll find a luminous Mary Magdalene portrait by Piero della Francesca and some beautiful terra cotta ceramics by della Robbia. There's also a stunning viewpoint.


Art lovers should visit the House of Giorgio Vasari, the famed Florentine architect and artist. He became the world's first true art historian, after publishing his treatise Lives of the Most Excellent Painters, Sculptors, and Architects.


READ: Art Lover's Guide to Tuscany



the beautiful Tuscan town of Cortona
the beautiful Tuscan town of Cortona


2. Cortona Day Trip Option


If you want to get off the beaten path in Italy, you can go "Under the Tuscan Sun" in hilly Cortona in eastern Tuscany. A former Etruscan town, Cortona was featured in the famous movie and book by Frances Mayes. It's a quiet charmer, seated on a commanding hill with great views in every direction.


Cortona's main street is Via Nazionale, the only flat place in town. There, you'll find a great wine bar called Enoteria. At one end of the street is Cortona's most famous piazza, the Piazza dell Repubblica, perfect for people watching. At the other lies the splendid Piazza Garibaldi.

As you walk the small streets, you'll bump into one small church after another. Most of the buildings are made of pietra serena, a type of limestone that famed Italian architect Brunelleschi liked to build with. If you continue on Via Berrettini, you'll reach Fortezza Medicea di Girifalco, which offers splendid views over the countryside.


Cortona has a wonderful little museum, the Museo Diocesano, located in Chiesa del Buon Gesù in the Piazza del Duomo. The museum has some absolutely superb paintings -- works by such Renaissance luminaries as Far Angelico and Luca Signorelli. It also houses the famed Cortona Altarpiece.


Cortona has a vibrant dining scene. For lunch or dinner, here's a list of good options.



the Siena Cathedral complex in Siena
the Siena Cathedral complex in Siena


Day 5: Explore Siena


Get up bright and early, pick up your rental car, and drive to Siena, where you'll overnight. Bella Siena is one of the best cities to visit in Tuscany for its rustic medieval beauty, tasty food, and luscious chianti. If you want to bask in medieval times, there's no better place.


You'll want to spend ample time strolling through the pedestrianized historic center. It's a well-preserved burnt orange dream littered with cute cafes and shops.


1. Sienna Cathedral


Siena's most famous site is its Duomo, Siena Cathedral. It's one of Europe's most beautiful churches, especially for lovers of all things Gothic. It's the symbol of Siena, clad all over in Siena's trademark white and dark green marble. Consistent with the Gothic ethos that "more is always better,” every inch is decorated with marble, mosaics, sculptures, and frescos.



the Palazzo Pubblico in Siena, with one of Italy's most famous fresco cycles
the Palazzo Pubblico in Siena, with one of Italy's most famous fresco cycles

cafes lining the medieval Piazza del Campo in Siena
cafes lining the medieval Piazza del Campo in Siena

To visit the Siena Duomo complex properly, you need to pre-purchase the Opa Si Pass. The Duomo complex isn't just Siena Cathedral. It also includes the Baptistry, the Crypt, the Piccolomini Library, the Facciatone viewing terrace, and the Museo dell'Opera del Duomo Museum. The Facciatone offers stunning views of Siena.


2. Palazzo Pubblico


Don't forget to tour Siena's town hall, the Palazzo Pubblico. It was built in 1297-1308 for the Council of Nine, the governing body of Siena. The palazzo is one of the seminal civic structures in Europe It's a harmonious example of early Renaissance architecture, with a curved brick facade and beautiful triforate arched windows.


Inside, you'll find the Allegory of Good and Bad Government, one of the most famous fresco cycles in Italy. Beside the palazzo soars the slender Tower of Mangia, which you can climb for more panoramic views.


Siena is a great town to indulge in an excellent Italian meal. If you're ready to splurge, your best option is either the Michelin starred La Taverna San Giuseppe or Antica Osteria da Divo. (Make reservations!) Antica is very atmospheric. It's partially housed in ancient Etruscan tombs. If you're on a budget, try Gino Cacino di Angelo instead.

READ: 24 Hours in Siena



a beautiful street in medieval PIenza
a beautiful street in medieval PIenza


Day 6: Drive to Montepulciano With a Stop in Pienza


On day 6, get up early and drive the classic Crete Senesi (Sienese Clay Hills) route to Montepulciano. This is a beautiful terrain of pointy cypresses, golden rolling hills, wheat fields, and sunflowers.


En route, stop in pretty Pienza. Pienza is a UNESCO-listed town in central Tuscany that will just take a couple hours to explore. Park in one of the lots outside the town walls.


Pienza's main square is the splendid Piazza Pio II. Designed by Renaissance architect Bernardo Rossellini, it was intended as the crowing glory of Pienza, the "ideal Renaissance city." The square is wrapped with impressive buildings, including Pienza Cathedral and the Palazzo Piccolomini (the pope's residence).


Pienza is known for its pecorino cheese. Plenty of shops hawking this delicacy are tucked away in the narrow streets. Have lunch at Trattoria Latte di Luna on the Corso Rossellini, one of Pienza's main streets.



aerial view of pretty Pienza
aerial view of pretty Pienza

the village of Montepulciano in Tuscany
the rustic village of Montepulciano


The quaint medieval town of Montepulciano is just 20 minutes from Pienza. It's famous for its Vino Nobile, a delicious violet-scented ruby red wine. The town is perched on a hilltop and encircled within ancient city walls. There are parking lots at the top of the town near the fortress and at the bottom of the town near Porta al Prato.


Hilly Montepulciano is a delight. From the Porta al Prato, it's a steep climb to the town. Along the way, you'll see a string of impressive Renaissance palaces. At the highest point is the Piazza Grande, with a never-finished and rather homely Duomo. The best views are from Piazza San Francesco.


Montepulciano is home to the Pinacoteca Crociani. The museum's showpiece is a painting attributed to Caravaggio, the greatest painter of the Baroque period. After making your own judgment about the provenance of the painting, head to one of Montepulciano's wine cellars and then dine at Acquacheta or Osteria del Conte.



spikey towers in the UNESCO town of San Gimignano