If spending 9 days seeing top works of art and eating chocolate Foccacia sounds good, then this trip is perfect for you.  Start in Florence to see Michelangelo's 'David', tour the Uffizi Gallery, and go shopping on the medieval Pontevecchio Bridge. See the Tuscan countryside from the top of Pisa's leaning tower, then see soaring cathedrals and ancient Piazzas in medieval Siena. Explore food and wine in the Val d’Orcia before ending in romantic Lucca, where quiet courtyards, 12th-century chapels, and the perfect cup of afternoon coffee await.


  • See masterpieces by da Vinci, Michelangelo, and Caravaggio
  • Make—and eat!—traditional handmade Italian pasta
  • Visit the famous leaning tower of Pisa
  • Explore the medieval Tuscan towns of Montepulciano and Pienza
  • Sample fresh-pressed Tuscan olive oil and chocolate focaccia

Brief Itinerary

Day Highlights Overnight
Day 1 Welcome to Florence!  Florence
Day 2 Uffizi Gallery Tour Florence
Day 3 Tour of Pisa & Leaning Tower Florence
Day 4 Florence to Siena Siena
Day 5 Montepulciano and Pienza Tour Siena
Day 6 Free Day in Siena Siena
Day 7 Siena to Lucca, City Tour Lucca
Day 8 Pasta Making Class in Lucca Lucca
Day 9 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: 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.

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Day 4: 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 5: 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 6: 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 7: 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 8: 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 9: 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 of Explore Tuscany: Florence, Siena, Pisa, & Lucca - 9 Days
Map of Explore Tuscany: Florence, Siena, Pisa, & Lucca - 9 Days