This adventure of a tour does more than just walk you through Tuscany, known for its landscapes and its artistic legacy. Through wine tastings, walks and explorations, you'll experience this beautiful countryside at its best, discovering cities and towns that have cemented Tuscany’s reputation as one of the world's most breathtaking destinations. End your journey in ancient Rome, where you’ll be engrossed in culture, tradition and allure of the Eternal City.

Detailed Itinerary

Day 1 - Montecatini

Your trip begins with a regularly scheduled overnight flight to Florence or Pisa (arrival city will vary by departure) 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 checkin. 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

$99 CAD

Lucca & Colle Verde This pastoral excursion begins with a visit to Lucca. You’ll have free time to browse in this inviting town before continuing on through the rolling green hills above Lucca to Colle Verde, a rural retreat and farm where some of Italy’s best-quality olive oil is pressed. During your half-day 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 - Florence

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

Spend the morning walking through the worldfamous region of the Chianti Region, land of the Chianti League, recently restored in order to preserve the name and trademark of the Chianti wine. You’ll then attend a wine tasting to sample the region’s most famous local product, red wine. On an afternoon walk, view a delightful panorama of valleys and rolling hills, ending in the town of Vinci, birthplace of Leonardo. Dinner is included in Montecatini tonight.
Included meals: breakfast, dinner
Included entrances: Tuscan wine tasting

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

Day 7 - San Gimignano

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

$69 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 - Chianciano

The destination for this morning’s walk is the lovely medieval town of Cortona, which overlooks the fertile plains of Valdichiana and is one of Italy’s oldest towns. Later, stop in the Umbrian region at Lake Trasimeno, site of the fiercest battle between Hannibal and the Romans in 217 B.C. Finally, reach Tuscany’s premier spa town, Chianciano. Dinner is included tonight.
Included meals: breakfast, dinner

Day 9 - Chianciano

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.” After exploring the Duomo and Gothic churches, 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, return to Chianciano. 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 Delight in Tuscan country ambiance and hospitality, while you feast on a traditional meal of grilled meats, roasted potatoes and local Chianti wine, topped off with a tasty tiramisu.

Day 10 - Rome

Transfer to the Monte Amiata region, where you’ll have time to explore the charming old town of Abbadia San Salvatore before continuing on to Rome for the night. Attend this evening’s optional Dinner with Tenors, featuring fine food and live opera music.
Included meals: breakfast

$79 CAD

Dinner with Tenors End your day with a delicious four-course dinner in the heart of Rome. While you dine on a savory meal, you’ll be entertained by talented singers performing some of opera’s most beloved masterpieces.

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 included.)