Explore Mediterranean beaches, Renaissance capitals, and medieval hill towns on this delightful 13-day tour through the Italian regions of Liguria and Tuscany. Start your adventure on the west coast, where you'll discover the quaint villages, rugged shorelines, and breathtaking scenery of the Cinque Terre. Head inland to spend a day wandering through history in Pisa, before journeying west to soak up the Renaissance splendor of Florence. The final five days take you deep into the Tuscan countryside, where you'll stay at a rural agriturismo villa and immerse yourself in the culture and landscape of the Val d'Orcia—wine tasting and truffle hunting around picturesque hill towns.


  • Soak up the sun on the Ligurian Coast
  • Explore the five colorful villages of the Cinque Terre
  • Savor regional delicacies & taste local wines
  • Discover the Renaissance splendors of Florence & Pisa
  • Hunt for rare truffles in the Tuscan countryside

Brief Itinerary

Day Highlights Overnight
Day 1 Travel to Cinque Terre & Evening Cruise Monterosso al Mare
Day 2 Wine Tasting & Villages of the Cinque Terre Monterosso al Mare
Day 3 Cinque Terre Cooking Class Monterosso al Mare
Day 4 Free Day in Cinque Terre Monterosso al Mare
Day 5 Train to Pisa, City Tour & the Leaning Tower Pisa
Day 6 Florence City Tour Florence
Day 7 Free Day in Florence Florence
Day 8 San Gimignano, Monteriggioni & Asciano Asciano
Day 9 Rapolano Terme Asciano
Day 10 Truffle Hunting in Tuscany Asciano
Day 11 Benvenuti a Siena! Asciano
Day 12 A day in Val d'Orcia Asciano
Day 13 Ciao Italia  

Detailed Itinerary

Day 1: Travel to Cinque Terre & Evening Cruise

Colorful fishing boats moored at Riomaggiore.
Colorful fishing boats moored at Riomaggiore.

Welcome to Liguria!

The Cinque Terre is a rugged strip of the Ligurian coastline made up of five colorful fishing villages—Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. The coast, villages, and surrounding hillsides are all part of the Cinque Terre National Park and are designated a UNESCO World Heritage Site. The region is renowned for its natural beauty, with lush Mediterranean foliage tumbling down cliffsides to the turquoise waters below. The historic towns prohibit vehicles to preserve the traditional charm, so most travelers arrive via the train that runs along the coast or by tour boat. 

In the evening, after you settle into your accommodation, head out onto the water to enjoy a small group sunset boat tour, admiring the views of the Cinque Terre villages. You'll pass by ancient fortresses guarding the clifftops, terraced vineyards cascading down to the water, and scenic ports welcoming fishing and tour boats home. Go for a dip in the water off the deck of the boat and toast your first night on the coast, then enjoy delicious local food and snacks as you watch the sunset.

Day 2: Wine Tasting & Villages of the Cinque Terre

Riomaggiore clings to the cliffsides along the coast.
Riomaggiore clings to the cliffsides along the coast.

Spend today discovering the rugged nature and charming villages of the Cinque Terre

Start with a guided hike up to a Riomaggiore vineyard, where a local expert will explain the region's tradition of wine-making, which centers around each family owning a small piece of terraced vineyard on the steep cliffs above the village. The family lots, which pass down from generation to generation, have been terraced and cultivated in the same way for centuries. The locals take a lot of pride in growing their own family wine and taking care of the delicate grapevines the same way their ancestors did. 

The town and vineyard both enjoy sweeping views over the coastline and surrounding hills. Learn about this region’s traditional wine-making methods and centuries-old techniques as you walk through the rows. The focus here is on making high-quality wine without using any chemical products, and the results are the pride of the Cinque Terre region.  Sample two local wines to experience the delicate fruit flavors for yourself and see how organic wine-making makes a difference in taste. Nibble on traditional Ligurian focaccia bread as you learn more about the production of the wines and take in the views from the vineyard. 

After the three-hour tour, head back to town to find a family-owned cafe for lunch, then spend the rest of the afternoon exploring the Cinque Terre. The five historic villages are connected with a network of boat and train lines that ferry locals and travelers from town to town, each connected with an hourly train. Keep in mind that the train stations are located on the hillsides above, and require a bit of a walk uphill through steep streets to reach. There will be plenty of time in each village to learn about its past, explore narrow streets, and browse souvenirs before returning to Monterosso for the evening.

Day 3: Cinque Terre Cooking Class

Delicious food with an amazing view in Manarola.
Delicious food with a fantastic view of Manarola.

Today you'll discover the secrets behind traditional Italian cooking with a private 6-hour cooking class. Pick from a morning or afternoon start time, then head to the local market, where your instructor will help you pick the freshest and most flavorful ingredients for your dishes. Afterward, make your way to the nearby house of the Cesarinas, enthusiastic local chefs who love welcoming travelers into their homes to teach them the secrets of traditional Italian cooking. 

You'll spend your time learning to make three different dishes, from preparation to presentation. Start with focaccia, a delicious Ligurian bread that's typically baked with olive oil, herbs, and occasionally olives. Next, you'll make ravioli, said to have been invented in the nearby town of Novi Ligure. Your final step will be preparing Pesto alla Genovese, made with the region's famous basil. While Italy is the home of many different pestos ("pesto" refers to any paste of herbs that's ground with mortar and pestle), the Pesto alla Genovese carries a D.O.P. protection. The ingredients are simple—basil, pine nuts, Parmigiano-Reggiano, Pecorino, garlic, salt, and olive oil—but the result is mouth-wateringly delicious. 

Once you've finished learning how to cook the time-honored recipes, sit down to enjoy your meal with the perfect glass of wine from the local cellar.

Day 4: Free Day in Cinque Terre

Monterosso's picture-perfect beach.
Monterosso's picture-perfect beach.

Today is a free day to explore the area. Select from the following suggestions, then head out to make the most of your time on the scenic coast:

  • Soak in the sunshine, sunbathe on the rocks, or cliff dive into the turquoise water at one of the Cinque Terre's many beaches. The sandy Monterosso Beach has both public and private sections, Vernazza Beach is rocky and perfect for sunbathing, and Levanto Beach is long and sweeping.

  • Visit the 17th-century Chuch of San Francesco to see fine art, including a depiction of the crucifixion by Antoon Van Dyck and other notable Italian painters of the 17th and 18th centuries.

  • Tour the 1,000-year-old Castello Doria in Vernazza, the Cinque Terre's oldest surviving structure, for panoramic views of the town and harbor.

  • Climb the Scalinata Lardarina, a steep 377-step staircase that connects the harbor with the village of Corniglia, for some of the Cinque Terre's best views.

  • Dive into the 14th century at the Chiesa di San Lorenzo, an immersive journey into the art and architecture of the Renaissance.

  • Explore the 13th-century Castello Di Riomaggiore, which dominates the Cinque Terre coastline. Built to protect the town from seafaring pirates, the castle now serves as an evocative reminder of a different time, as well as a perfect spot for photographs. Head inside to see the museum exhibit highlighting centuries of town history.

  • Walk up to the Torre Aurora, a medieval castle that stands on the intersection of Monterosso's Old Town and New Town.
  • Pay a visit to Cantina 5 Terre in Riomaggiore, the Cinque Terre's only major winery, to learn about how ancient traditions mix with modern-day production techniques to produce a unique and flavorful wine. Sample the vintages, especially the excellent local white, and enjoy a relaxing afternoon among the vines.

Day 5: Train to Pisa, City Tour & the Leaning Tower

Enjoy a cone of gelato in front of the famous leaning tower.
Enjoy a cone of gelato in front of the famous leaning tower.

In the morning, head to the station to catch the train to Pisa. After taking a taxi to the hotel, leave your luggage, and set out to explore. 

The port city of Pisa sits on the right bank on the mouth of the River Arno and faces the Ligurian Sea. Most famous for the Leaning Tower of Pisa, it's also home to over 20 other historic churches, palaces, and museums that chronicle its storied history. Pisa's main tourist attractions are grouped at the site known as the Campo dei Miracoli, Italian for the Field of Miracles.

In the afternoon, take a 3-hour tour, which starts with a walk around Pisa's medieval walls, where you'll take in the extraordinary views of the Piazza dei Miracoli with its incredible white marble architecture and impeccably neat grass lawns. Tour the inside of the Cathedral to see masterpieces of Romanesque art, then head to the echoing Baptistery and cemetery. The Baptistery is a marvel of engineering whose tall dome roof allows sounds to echo for long enough to enable someone to sing a 3-part harmony with themselves. 

From here continue to the famous leaning tower. Admire the exterior (and take pictures!) before heading inside to climb the steps to the top. From here, the views of the Cathedral, Baptistery, and surrounding cityscape are well-worth the trek. Reward yourself afterward with a stop by the local gelateria for a cone of creamy gelato.

Plan your trip to Italy
Chat with a local specialist who can help organize your trip.

Day 6: Florence City Tour

Sunset over Florence and the Arno River.
Sunset over Florence and the Arno River.

This morning you'll hop on a train to Florence, less than an hour from Pisa. Spend the day exploring the city's highlights, starting with a guided half-day walking tour. Stops include the iconic Duomo, with its terracotta-tiled dome, the Galleria dell'Accademia, which displays Michelangelo's "David" sculpture, and the San Lorenzo Church, the former parish church of the powerful Medici family. 

In the afternoon, indulge yourself with the decadence of Tuscan cuisine. Discover the region's culinary history, find the best off-the-beaten-path gelato and coffee shops, and sample wares from city markets. Try specialties like truffle panini, fresh-pressed Tuscan olive oil, and handmade chocolate focaccia, finished off with a glass of chilled prosecco or Chianti wine.

Day 7: Free Day in Florence

Leather sandals at San Lorenzo Market.
Leather sandals at San Lorenzo Market.

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

  • Spend some time learning 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 you enjoy the sunset, then make your way to the Sant'Ambrogio neighborhood for dinner accompanied by a glass of Tuscan wine.

Day 8: San Gimignano, Monteriggioni & Asciano

A typical Tuscan vineyard in the Chianti region.
A typical Tuscan vineyard in the Chianti region.

Today you'll journey into the Tuscan countryside to explore the Chianti Region. Your first stop is the medieval village of San Gimignano, a UNESCO World Heritage Site located an hour away from Florence, which is famous for its Vernaccia wine and award-winning gelaterias. Explore the beautiful squares, palaces, and churches of the city before grabbing a coffee in an open-air cafe. 

Continue to the Chianti Classico wine region to visit a typical Tuscan winery. The unique characteristics of the local climate have made the region unfavorable to most crops but ideal for growing wine grapes. Alternating fields of olive orchards and vineyards characterize this idyllic landscape. Chianti wine, made primarily of Sangiovese grapes, is the local staple. Tour the cellars and vineyards, then enjoy a wine tasting accompanied by a delicious Tuscan lunch of pasta, cured meats, cheeses, and local desserts. 

Finish the day with a visit to the medieval fortress of Monteriggioni before arriving at your agriturismo in Asciano, which serves as your base for the next five nights as you explore Tuscany.

Day 9: Rapolano Terme

Sunset at a local agriturismo in Asciano.
Sunset at a local agriturismo in Asciano.

After a busy few days of sightseeing, take today to relax in the tranquil atmosphere of the thermal baths of Rapolano. This famous sanctuary has two establishments: the Terme San Giovanni, immersed in the Sienese hill, and the Terme Antica Querciolaia, close to the town. Soak in the peaceful indoor pool, then enjoy the breathtaking views from the outdoor pool overlooking the serene valley. Back at your agriturismo, enjoy an insightful olive oil tasting with the perfect extra virgin olive oil produced at the vast groves of the surrounding farm, learning how to recognize a great oil from the ordinary ones.

Day 10: Truffle Hunting in Tuscany

Hunt for truffles in Tuscany's forests.
Hunt for truffles in Tuscany's forests.

Today's activity means an early start, but you'll be rewarded with a memorable excursion into the Italian countryside in search of forest treasures. Meet Pina, a friendly truffle-hunting dog, who, along with her owner Antonio, will take you on a woodland walk through some of Tuscany's best truffle country. Truffles are some of the most sought-after culinary ingredients on earth and are a well-loved feature of Mediterranean cuisine. Often served shaved over pasta or infusing oils and sauces, they add a rich, earthy depth to many traditional Italian dishes. Discover the science and secrets of finding truffles, learn about the varieties and their ecosystems, and enjoy a tasting picnic in the woods to celebrate your finds.

Day 11: Benvenuti a Siena!

Siena's Palazzo Sansedoni.
Siena's Palazzo Sansedoni.

Today is devoted to one of Italy's most charming and authentic towns: Siena. Conquered by the Medicis in 1585, the walled fortress became a forgotten gem for centuries, making it one of Europe’s finest examples of a preserved Gothic city. With a high concentration of buildings from the 12th-14th century, Siena is also home to Il Campo, considered the most beautiful piazza in Italy and site of the famous bareback "Palio" horserace.

Your local guide will bring the history of the city to life with a tour around its major sites, ending with a visit to the cathedral to admire its medieval treasures.

Day 12: A day in Val d'Orcia

Picturesque Pienza in the Val d'Orcia.
Picturesque Pienza in the Val d'Orcia.

Today you head south through the spectacular valley of the Orcia River. Stop first in the lovely village of San Quirico, where you'll start your walk to the ancient Roman spa village of Bagno Vignoni. Afternoon visits include the enchanting Romanesque abbey of Sant’Antimo (where you may catch vespers or Gregorian chanting) before transferring to Montalcino to sip famous Brunello wine in an impressive wine cellar/fortress on the edge of town. Finally, you'll arrive at the exquisite hilltop village of Pienza, known as the “ideal city”—once considered the incarnation of a Renaissance utopia and now a treasured UNESCO World Heritage Site.

Day 13: Ciao Italia

Sunset over Florence.
Bid Florence farewell.

Your exploration of Italy ends after breakfast, with the drive from Asciano to Florence, where you'll catch your flight home.


Map of Explore Liguria & Tuscany: Cinque Terre, Florence, Pisa & Val D'Orcia - 13 Days
Map of Explore Liguria & Tuscany: Cinque Terre, Florence, Pisa & Val D'Orcia - 13 Days