Explore the birthplace of Pinnochio on this packed 15-day itinerary of the Tuscany region. Begin in Florence to see Michelangelo's 'David' sculpture and works by Da Vinci, Caravaggio, and Donatello. Hunt for flavorful truffles in the countryside, climb the leaning tower of Pisa and take a vintage Vespa out for a ride on rolling country roads. Visit the pretty medieval cities of Montepulciano and Siena, tour Tuscany's top vineyards, and handmake your own Italian pasta. Round out your trip with a hike on the historic Cinque Terre trail, which hugs the stunning Mediterranean coast.

Highlights

  • See Michelangelo’s David sculpture
  • Hike between fishing villages on the UNESCO-designated Cinque Terre trail
  • Visit the leaning tower of Pisa
  • Go hunting for truffles with trained dogs in the Tuscan countryside
  • Take a vintage Vespa out for a spin on the Tuscan hills

Brief Itinerary

Day Highlights Overnight
Day 1 Welcome to Florence!  Florence
Day 2 Uffizi Gallery Tour Florence
Day 3 Truffle Hunting Tour Florence
Day 4 Tour of Pisa & Leaning Tower Florence
Day 5 Free Day in Florence Florence
Day 6 Vespa Tour: Tuscan Hills Florence
Day 7 Florence to Siena Siena
Day 8 Montepulciano and Pienza Tour Siena
Day 9 Brunello di Montalcino Winery Tour Siena
Day 10 Free Day in Siena Siena
Day 11 Siena to Lucca, City Tour Lucca
Day 12 Pasta Making Class in Lucca Lucca
Day 13 Cinque Terre Hiking Day Trip Lucca
Day 14 Free Day in Lucca Lucca
Day 15 Goodbye Italy!  

Detailed Itinerary

Day 1: Welcome to Florence! 

Tourists viewing Michelangelo's David
Tourists viewing Michelangelo's David

Welcome to Florence, the capital of Italy's Tuscany region! Arrive at Florence Airport and transfer to the city center to check in to your hotel. Spend the rest of the day relaxing and settling in, or head out for a relaxing stroll and dinner downtown. Depending on your arrival time, you may also want to get a head start on exploring some of the city's top sites. Discover Florence's past, from its Roman foundations to the Renaissance period all the way to modern-day. 

Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, a terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's 'David' sculpture. 

Visit the Piazza della Signoria and Palazzo Vecchio, the Duomo, Pontevecchio Bridge, and the secret Vasari Corridor, as well as famous shopping streets. 

In the evening, stroll around the historic downtown for some people watching followed by dinner and drinks in the hip Sant'Ambrogio neighborhood.

Day 2: Uffizi Gallery Tour

Reflection of the Uffizi Gallery in the River Arno
Reflection of the Uffizi Gallery in the River Arno

After breakfast, make the most of your time in Florence with priority access tickets to skip the line at the Uffizi Gallery. See masterpieces by Leonardo da Vinci, Michelangelo, Caravaggio, Donatello, and others on a guided 2-hour tour. A professional art historian will guide your small group through the museum, highlighting notable works and explaining the history behind the world-famous art. 

In the afternoon indulge yourself with the decadence of Tuscany's culinary delights. Sample wares from city markets to find the best of the best. Try a truffle panini, fresh-pressed Tuscan olive oil, handmade chocolate focaccia, finished with a glass of chilled prosecco or Chianti wine.

Day 3: Truffle Hunting Tour

Bowl of whole and minced truffles
Bowl of whole and minced truffles

Today you will experience the art of truffle hunting on a tour of the Tuscan countryside (lunch and transportation from Florence included). 

Italian truffles are some of the most sought-after culinary ingredients and are a well-loved feature of Mediterranean cuisine. Often served shaved over pasta or other dishes, they add a recognizable earthy flavor that is irresistible. 

Start your day with a transfer from Florence to a prime truffle site in the heart of the Tuscan landscape. Here you will meet an expert guide who will explain the art of finding truffles using specially trained dogs. Spend the morning hunting for the rare truffles, then enjoy a packed picnic lunch complete with Tuscan delicacies and local wine. 

In the afternoon head back to Florence and enjoy a quiet evening in the local wine bar, piazza cafe, or family-run trattoria.

Day 4: Tour of Pisa & Leaning Tower

The perfect place to enjoy a gelato
The perfect place to enjoy a gelato

Head to Pisa today, located an hour and a half away on the coast, to see the famous Leaning Tower of Pisa (tickets included) at the Piazza dei Miracoli. 

Begin the tour with a walk around Pisa's medieval walls, as well as a tour of the Cathedral to see the Romanesque masterpieces. See the 12th-century Baptistery and Monumental Cemetery, then continue to see the tower. Admire the exterior, then head inside to climb the steps to the bell tower to take in the views. 

The tour concludes with a stop to see a typical Tuscan wine shop with a tasting of regional wines, followed by some souvenir shopping and a visit to the local Gelateria for a cone of creamy gelato.

Day 5: Free Day in Florence

Leather sandals at San Lorenzo
Leather sandals at San Lorenzo

Today is a free day to explore some of Florence's other notable attractions and highlights. Recommendations for the day include:

  • Learn about Florence's history in the Basilica di Santa Croce history museum
  • Explore science and art at the Museo dell'Opera del Duomo (history and art museum) and the Museo Galileo - Institute and Museum of the History of Science 
  • Visit the Chiesa e Museo di Orsanmichele, which served as the granary for the Sisters of San Michele in previous years
  • Shop for hidden treasures and your lunch special in the San Lorenzo market
  • Head to the south bank of the Arno River to the Piazzale Michelangelo viewpoint for panoramic views of the city
  • Stroll through the peaceful and relaxing greenery of the Boboli Gardens 

Head to La Terrazza Continentale next to the Ponte Vecchio bridge for a pre-dinner cocktail on the terrace while enjoying the sunset, then make your way to the Sant'Ambrogio neighborhood for dinner accompanied by a glass of Tuscan wine.

Day 6: Vespa Tour: Tuscan Hills

Vespa waiting for adventure in a Tuscan town
Vespa waiting for adventure in a Tuscan town

Take a vintage Vespa out for a spin on Tuscany's country roads during today's 4-hour tour. Follow your guide into the hills to see off-the-beaten-path sights like the 11th-century Church of San Miniato al Monte on the Piazzale Michelangelo. Stop here to enjoy the panoramic views of Florence, then continue out of the city for some fresh air and fun. 

Return to Florence in the afternoon for a well-deserved meal. Spend a quiet evening wandering the neighborhoods of Florence or shopping at the specialty boutiques which line the trendy downtown avenues.

Day 7: Florence to Siena

Brick houses in Siena
Brick houses in Siena

After breakfast, hit the road for the 1.5-hour drive to Siena, then check into your accommodation. The city's historic center is one of Italy's most popular attractions and is a UNESCO World Heritage Site. Siena is famous for its medieval architecture, museums, and for Palio, a popular horse race that takes place twice a year in the Piazza del Campo (the main square). Explore the downtown on your own before lunch, then head out for a guided two-hour tour. 

Start at the 13th-century Palazzo Pubblico which still houses the municipal administration, as well as the Torre del Magnia, a bell tower with fantastic city views. Visit these main highlights, as well as the green and white striped Duomo and its Piccolomini Library, famous for its soaring, vibrant Pinturicchio frescoes. Continue to see the Museo dell'Opera Metropolitana art museum, as well as Siena's many churches, including the Basilica dell'Osservanza, Santo Spirito, and Sanctuary of Santa Caterina

Later, tour some of the city's patrician villas, including Villa Chigi, Villa Celsa, and Villa Volta Alte. Head downtown for dinner and wine in a family-run restaurant.

Day 8: Montepulciano and Pienza Tour

Cheese aging
Cheese aging

Head out for a day trip to the medieval towns of Montepulciano and Pienza, which date back to the Etruscan era. Your local guide will accompany you through the architectural and cultural highlights of the Val d'Orcia region, considered one of Tuscany's prettiest areas. 

Start your day in the tiny village of Pienza, which stands atop a high hill above the Orcia Valley. The charming town is known as the "ideal city of the Renaissance" and was designed by Enea Silvio Piccolomini, who later became Pope Pius II. Piccolomini used his money and influence to transform his birthplace village, then known as Corsignano, into his ideal Utopian Renaissance city. 

The harmonious composition of the city includes the Cathedral, the Papal or Piccolomini Palace, the Town Hall, and the central square which sits between the buildings. Visit the Duomo or Cattedrale dell'Assunta to see unique paintings and the octagonal bell tower. Visit the Palazzo Piccolomini to see the hanging gardens, as well as the shooting locations for Franco Zeffirelli's film "Romeo and Juliet." 

Break for lunch at a traditional dairy farm, then continue to the historic village of Montepulciano, which sits along a ridge and is surrounded by walls and fortifications. Montepulciano is famous for its Renaissance buildings, churches, and historical Corso main street which leads through town, ending at the Piazza Grande—the town's main civic and religious center. 

Tour the Piazza to see the Palazzo Comunale, the castle-like town hall with an iconic clock bell. Climb to the top for views of the Tuscan hillside, then visit the spartan 15th-century Duomo, whose unfinished facade stands out from the surrounding buildings. Continue to the Palazzo Cappelli and Gothic Palazzo Neri Orselli, home to the civic museum, to see regional and national art. 

Continue to see the Church of Sant'Agnese, dedicated to Montepulciano's patron saint, and the recognizable 16th-century San Biagio, which rests on a hill below town. 

Day 9: Brunello di Montalcino Winery Tour

Shopfront selling Brunello di Montalcino
Shopfront selling Brunello di Montalcino

Spend a day sipping one of Italy’s most renowned wine, Brunello di Montalcino, on this full-day guided tour from Siena. Start at the cellars to learn about the wine's production process and meet the locals behind the wine. The name Brunello di Montalcino comes from the diminutive of Bruno (brown in Italian) and is the local name for the grape variety. Clemente Santi, a pharmacist from Montalcino, was the first to experiment with producing unblended wines with Sangiovese Grosso grapes. The region's unique soils are ideal for producing elegant wines that can withstand decades of aging. 

Brunello di Montalcino has grown in prominence since the 19th century, earning a Denominazione di Origine Controllata e Garantita (DOCG) designation in 1980. These days it is celebrated as one of Italy's best known (and most expensive) wines. 


Tour the village of Montalcino to see the imposing 14th-century fortress and climb to the top for spectacular views of the surrounding countryside. The fortress, which has remained mostly intact since the Middle Ages, now hosts festivals, concerts, and events, most notably the famous Jazz & Wine Festival held in July each year. 

Montalcino's other landmark is the tall and slender clock tower atop the Palazzo dei Priori, the city's town hall, which sits above the central Piazza del Popolo. End your tour with visits to the Palazzo Vescovile and the Sant' Agostino, Sant' Egidio and San Francesco churches, then browse arts and craft shop for gifts in the labyrinthine streets around the town center. 

Stop at a family-run winery for a traditional Tuscan lunch, then visit the abbey of Sant' Antimo before returning to Siena. The church, allegedly founded by Charlemagne in the 8th century, has roots in legendary miracles. According to the stories, the king and his army stopped here and became ill.  After an angel appeared to Charlemagne instructing him to use a local herb to cure his men, the grateful king built the abbey to honor the angel.

Day 10: Free Day in Siena

Sunset over the Tuscan hills
Sunset over the Tuscan hills

Make the most of your time in Tuscany with visits to Siena's top sites: 

  • Learn about archaeology and history at the Complesso Museale Santa Maria della Scala (the National Archaeological Museum of Siena) and Museo Archeologico di Siena (museum of archaeology and history)
  • See art at the Museo dell'Opera Metropolitana
  • Learn about the ceramics manufacturing process and shop for gifts at the Ceramiche Bianco e Nero di Staccioli 
  • Fly over the city and surrounding vineyards on a hot air balloon 
  • Rent a Vespa and explore the Tuscan hills in true Italian style 
  • Go for a horseback ride in the Tuscan hills along the Via Francigena, an ancient pilgrimage route
  • Go shopping at the Valdichiana Outlet Village, which houses over 140 famous designer and brand shops

Day 11: Siena to Lucca, City Tour

Small courtyard cafe
Small courtyard cafe

After breakfast head out the door for the 2-hour drive to your next destination—Lucca, located in central Italy on the Serchio River. The medieval city is famous for its well-preserved Renaissance-era city walls, which have been converted to a walking promenade and are popular for walks around town. The city's foundation goes back to Etruscan and Ancient Roman times, and the city's vibrant history is reflected in its architecture. 

Check in to your hotel and settle in, then explore the city on a three-hour guided afternoon tour. Highlights of the city tour include a Roman amphitheater, the 11th-century Diavolo Bridge (also known as Ponte della Maddalena), Ilaria del Carretto's Sarcophagus, and the medieval Torre Guinigi and Torre dell Ore (towers). Several famous churches, including the remarkable Church of San Michel which is mentioned first in 795 CE, the Byzantine-medieval Church of San Frediano, and the striking 11th-century Duomo di San Martino. The medieval Via Fillungo street winds through the historic downtown, connecting ancient buildings and modern-day storefronts. 

Lucca is also famous as the birthplace of the renowned composer Giacomo Puccini, whose most well-known works include La bohème, Tosca, Madama Butterfly, and Turandot.

Explore all this and more with your knowledgeable guide. Finish your afternoon with a glass of wine or prosecco at a local enoteca, or wine bar.

Day 12: Pasta Making Class in Lucca

Handmade Italian pasta
Handmade Italian pasta

Today you will learn how to make the quintessential Italian dish—handmade pasta. Discover why, exactly, handmade pasta tastes so much better during this 4-hour cooking class. Learn to make different kinds of pasta—as well as pizza and other regional specialties—before sitting down to enjoy your hard work, accompanied by a selection of regional wine. 

In the second half of the day head out to explore the city, enjoy a relaxing afternoon in a city piazza with a cup of coffee and your favorite book, or spend a few hours discovering small shops in winding medieval streets.

Day 13: Cinque Terre Hiking Day Trip

Spectacular views near Manarola
Spectacular views near Manarola

Get an early start today for your full hiking tour of the Ligurian Coast to see the beautiful fishing villages of the Cinque Terre. The Cinque Terre is a rugged strip of coastline which includes five villages: Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. The villages, the coast between them, and the surrounding hillsides are all part of the Cinque Terre National Park and are designated as a UNESCO World Heritage Site. 

The region is characterized by its abundance of Mediterranean animals and plants which cover the scrubby hillsides down to the turquoise water. The historic villages and breathtaking beauty of the region make it a popular choice for travelers who want to get out in nature.

Hiking times and difficulties: 
Monterosso-Vernazza (difficulty: average; length: 2.2 miles (3.5km); duration: 1.5h)
Vernazza-Corniglia (difficulty: average; length: 2.5 miles (4km); duration: 1.5-2h)
Corniglia-Manarola (difficulty: easy; length: 1.9 miles (3 km); duration: 1h)
Riomaggiore-Portovenere (difficulty: average; length: 5 miles (8km); duration: 3h)

Total Hike Length: 11.5 miles (18.5 km)
Total Duration: 8 hour

Day 14: Free Day in Lucca

Bronze statue of composer Giacomo Puccini
Bronze statue of composer Giacomo Puccini

Explore the city with these recommended activities: 

  • Visit the 12th-century Chiesa e Battistero di San Giovanni e Santa Reparata, a Catholic church in the Piazza San Giovanni
  • Explore art and history at the Museo Nazionale di Palazzo MansiComplesso Museale della Cattedrale, and Lucca Center of Contemporary Art 
  • Tour the beautiful English-style landscaped gardens of the Parco della Villa Reale di Marlia, the home of Elisa Bonaparte—Napoleon' sister 
  • Rent a bike and explore the city and surrounding neighborhoods 
  • Go horseback riding on the bike paths along the Serchio River
  • Learn about the Italian composer Puccini and the connections to his hometown in a concert series
  • Go for a stand-up paddleboard adventure Garfagnana on the River Serchio

Day 15: Goodbye Italy!

Little details of life in Rome
Little details of life in Rome

Time to say goodbye to the country of love! After one last cappuccino over breakfast, head to the airport for your connecting flight home. Safe travels!

Map

Map of Explore Tuscany: Florence, Siena, Pisa, & Lucca - 15 Days
Map of Explore Tuscany: Florence, Siena, Pisa, & Lucca - 15 Days