Iconic Tuscany – 14 Days
Florence (5 nights) Siena (4 nights) Lucca (4 nights)
This is a sample itinerary which is completely customizable, ask us how.
Highlights of the trip
- Visit the leaning tower of Pisa
- See Michelangelo’s David sculpture
- Hike between traditional fishing villages on the UNESCO-designated Cinque Terre trail
- Make—and eat!—traditional handmade Italian pasta
- Sample fresh-pressed Tuscan olive oil & handmade chocolate focaccia
Daily Itinerary
Day 1: Welcome to Florence
Welcome to Florence
Discover Florence’s past from its Roman foundations to the Renaissance period, and soak in the modern city’s daily life.
Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, with its terracotta-tiled dome, and the Galleria dell’Accademia, which displays Michelangelo’s ‘David’ sculpture.
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
Uffizi Gallery Tour
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 from Florence
Hunt truffles
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
Pisa and its leaning tower
Head to Pisa to see the famous Leaning Tower of Pisa (tickets included) at the Piazza dei Miracoli.
Walk around Pisa’s medieval walls, as well as a tour of the Cathedral to see the Romanesque masterpieces. Learn about its origins and the engineering phenomenon as to why it leans like this today.
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 decadent gelato. Return to Florence in time for dinner.
Day 5: Leisure Day in Florence
Do Florence your way
Today is a free day to explore some of Florence‘s other notable attractions and highlights.
Recommendations for the day include:
- Basilica di Santa Croce
history museum. - Museo dell’Opera del Duomo
(history and art museum) and the Museo Galileo – Institute and
Museum of the History of Science - Shop for hidden treasures and your lunch special in the San Lorenzo market
- 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: Florence to Siena
Medieval 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 which 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.
When you are done, head downtown for dinner and wine in a family-run restaurant.
Day 7: Montepulciano and Pienza Tour
Montepulciano & Pienza
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, the idealic city of the Renaissance.
Among the many other sites, finish with 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 8: Bunello di Montalcino Winery Tour
Tuscan winery tour
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 region’s unique soils are ideal for producing elegant wines that can withstand decades of aging. 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.
Day 9: Leisure day in Siena
Stroll the streets of Siena
Make the most of your time in Tuscany with visits to Siena’s top sites. We would be happy to arrange arrangements for any of the below activities:
- National Archaeological
Museum of Siena - Opera Museum
- Learn about the ceramics manufacturing process and shop for gifts at the Ceramiche Bianco e Nero di Staccioli
- Hot air balloon over the major sites
- Rent a Vespa and explore the Tuscan hills in true Italian style
- Horseback riding in the Tuscan hills along the Via Francigena, an ancient pilgrimage route
Day 10: Siena to Lucca, with a City Tour
Lovely Lucca awaits
After breakfast take a private drive to your next destination—Lucca.
The medieval city is famous for its well-preserved Renaissance-era city walls, which have been converted to a walking promenade. The city’s foundation goes back to Etruscan and Ancient Roman times, and the city’s vibrant history is reflected in its architecture.
Explore the city on a three-hour guided afternoon tour with your knowledgeable guide. Finish your afternoon with a glass of wine or prosecco at a local enoteca, or wine bar.
Day 11: Pasta Making Class in Lucca
Become a pasta maker for a day
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 the fruits of your labor, 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 spritz or espresso and your favorite book, or spend a few hours discovering small shops in winding medieval streets.
Day 12: Cinque Terre Hiking Day Trip
Hiking in the Cinque Terre
Get an early start today for your full hiking the rugged strip of UNESCO protected coastline that includes five villages: Monterosso al Mare, Vernazza, Corniglia, Manarola, and
Riomaggiore.
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.
Day 13: Free Day in Lucca
Lucca at your leisure
Explore the city with these recommended activities:
- Piazza San Giovanni with a 12th-century church
- National Museum
- Cathedral Museum
- 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
- Stand up paddleboarding adventure on the River Serchio
Day 14: Goodbye Italy
That’s a wrap
Your journey in Italy will end after breakfast, with a transfer to the airport to catch your flight home or to your next destination. Arrivederci!
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