The Tuscan countryside has fired the imaginations of travelers for centuries. Amid these rolling hills, recipes are still handed down through the generations and an appreciation for life’s simple pleasures finds its way into every conversation. Come discover the authentic side of Tuscany on guided walking tours through orchards, medieval hilltowns and the unforgettable cityscapes of Florence and Siena.

Detailed Itinerary

Day 1 - Overnight Flight

Your trip begins with a regularly scheduled overnight flight to Florence aboard an internationally recognized airline..

Day 2 - Montecatini

Welcome to Italy! A Go Ahead representative greets you at the airport after you clear customs and then accompanies you via private motorcoach to Montecatini, where you’ll be assisted with hotel check-in. At an included dinner this evening, meet your fellow travelers.
Included meals: breakfast (in flight), dinner

Day 3 - Montecatini

Today is free for you to relax and become acquainted with Montecatini, an inviting spa town in the hills of Tuscany. You might choose to join an optional excursion to Lucca, a walled medieval town, and Colle Verde, a typical Tuscan farm where olive oil is produced. Return to Montecatini for the night.
Included meals: breakfast

$119 CAD

Lucca & Colle Verde Visit the gorgeous Tuscan town of Lucca, famous for its Renaissance-era city walls, medieval churches and awe-inspiring towers. Then travel to Colle Verde, a farm where some of Italy’s highest-quality olive oil is pressed. During your excursion, learn about the process by which olive oil is extracted and refined. Then, enjoy a light lunch and an olive oil tasting session.

Day 4 - Montecatini

Take a day trip to the timeless city of Florence, birthplace of the Italian language, the Renaissance and opera. A guided walking tour introduces you to the city’s Renaissance splendor. Marvel at Brunelleschi’s masterpiece—Florence’s massive pink, white and green Duomo. Then discover the Baptistery of St. John.
Included meals: breakfast
Included entrances: Baptistery of St. John

Day 5 - Montecatini

Take a day trip to the timeless city of Florence, birthplace of the Italian language, the Renaissance and opera. A guided walking tour introduces you to the city’s Renaissance splendor. Marvel at Brunelleschi’s masterpiece—Florence’s massive pink, white and green Duomo. Then discover the Baptistery of St. John. You’ll have the afternoon to explore Florence on your own before returning to Montecatini for the evening.
Included meals: breakfast
Included entrances: Baptistery of St. John

Day 6 - Siena

Today’s walk is near the rounded walls of Monteriggioni, one of Tuscany’s best-preserved medieval towns. Continue on to Gothic Siena, where lunch is included after your arrival. A former independent republic, Siena was the richest city in Italy during the 13th and 14th centuries. Its architectural legacy is a testament to its former greatness. On your guided tour of Siena, enter the Campo, described by Montaigne as the most beautiful square in the world. This is where the annual Palio competition convenes. You’ll then visit the grand Piccolomini Library, a museum inside the Duomo whose well-preserved frescoes depict the life of Pope Pius II.
Included meals: breakfast, lunch
Included entrances: Piccolomini Library, Siena Cathedral

Day 7 - Siena

Today’s focus is on the fortress town of San Gimignano, with its dramatic skyline of huge, medieval towers. Fourteen of the original 70 towers remain, an ongoing testament to the Guelph-Ghibelline rivalry of the Middle Ages. Following your walk in San Gimignano is an included excursion to Volterra, a city with a history dating back 3,000 years to the ancient Etruscan civilization. Return to Siena for the night. This evening, join a special optional dinner, featuring traditional Tuscan cuisine.
Included meals: breakfast

$79 CAD

Tuscan Dinner A fascinating lesson in Tuscan culture and cuisine awaits you at this memorable dinner event. One of the region's most acclaimed restaurants, noted for its excellent food and wine cellar, serves up several courses of flavorful, culinary delights.

Day 8 - Val d'Orcia

The destination for this morning’s walk is the lovely medieval town of Cortona, one of Italy’s oldest towns, which overlooks the fertile plains of Valdichiana. Later, stop in the Umbrian region at Lake Trasimeno, site of the fiercest battle between Hannibal and the Romans in 217 B.C. Continue to Montepulciano and begin the steep walk uphill to reach the last breathtaking view of the day. After a brief stop at the church of San Biagio on your way down from Montepulciano, you’ll reach the Val d’Orcia region, where you’ll spend the next two nights. Dinner is included tonight.
Included meals: breakfast, dinner

Day 9 - Val d'Orcia

Today’s series of walks begins in the neighboring town of Montalcino, famous for its fierce battles against Florence and the Medici family’s dominion. Here, you’ll visit Sant’Antimo Abbey, a Romanesque church surrounded by rolling hills. Continue on to Pienza, “Pearl of the Renaissance,” where you’ll explore the Duomo and Gothic churches. This evening, join our optional Country Evening for Tuscan country ambiance and hospitality, as you dine on a traditional meal and sip local Chianti wine.
Included meals: breakfast

$79 CAD

Country Evening This evening, delight in Tuscan country ambiance and hospitality while you feast on a traditional three-course, family-style meal of grilled meats, a selection of vegetables and local Chianti wine, topped off with a tasty dessert.

Day 10 - Rome

The day begins with a scenic drive to the Monte Amiata region. You’ll have time to explore the charming old town of Abbadia San Salvatore before continuing on to Rome. Opt to end the day at a Dinner with Tenors, an evening of food and live music.
Included meals: breakfast

$79 CAD

Dinner with Tenors End your day with an elegant four-course dinner at one of our favorite Roman restaurants. While you dine, you’ll be treated to some of opera's best-loved arias…and you might even join the singers on stage. Don’t miss this lighthearted evening of food and fun!

Day 11 - Rome

Linger in Rome on our tour extension. Otherwise, a Go Ahead representative accompanies you to the airport for your flight home.
Included meals: breakfast
(In the case of early morning departures, breakfast may not be provided.)