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 vacation begins with an overnight flight to either Florence or Pisa.

Day 2 - Montecatini

Meet your Go Ahead representative after clearing customs and then transfer via private motorcoach to Montecatini. Meet your fellow walking enthusiasts at this evening’s included dinner. (B in flight, D)

Day 3 - Montecatini

Journey to nearby Florence for a guided sightseeing tour. See the many Renaissance treasures of the city, including Ghiberti’s Gates of Paradise, Santa Croce, the Duomo and the Piazza della Signoria, home of the Palazzo Vecchio and the Uffizi Gallery. (B)

Day 4 - Montecatini

Today is free to indulge in the famous spas of Montecatini, located in the healing Valdinievole, or “Valley of Mists.” Or join an optional excursion and light lunch in Colle Verde, a typical Tuscan farm in the hills above Lucca where olive oil is produced. (B)

$99 USD

Colle Verde Visit a charming olive farm for a lesson and lunch!

Day 5 - Montecatini

This morning’s one-hour walk takes place in the Chianti region. Strolling near the vineyards where the renowned Chianti wine is produced, you’ll stop in Vinci, hometown of artist Leonardo. Then set off on another scenic walk (1.5 hours) this afternoon, passing valleys, rivers and private country homes along the route. Afterwards, sample some Tuscan vintages at a wine tasting. (B, D)

Day 6 - Siena

Take in panoramic views of the sun-warmed Tuscan countryside on your transfer south to Siena. Along the way, stop in Monteriggioni, one of Tuscany’s best-preserved medieval towns, for a 1.5-hour walk from the 13th-century ramparts. Arrive later in Siena for an afternoon guided tour. Stop at the impressively ornate Duomo for a visit to the Piccolomini Library, where you can view the frescoes depicting the life of Pope Pius II. (B, L)

Day 7 - Siena

Begin the day with an invigorating one-hour walk in San Gimignano, considered by many the loveliest of the Tuscan hill towns. Fourteen towers remain standing out of the original 70, bearing testament to the medieval rivalry between the Guelphs and the Ghibellines that shaped history in this region. Then stop in the nearby town of Volterra, which has yielded rich stores of alabaster since Etruscan times. This evening, join a special optional dinner, featuring traditional Tuscan cuisine. (B)

$69 USD

Traditional 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

Enjoy a one-hour walk this morning amid the orchards, vineyards and groves of Cortona. Then pass by Lake Trasimeno as you transfer to Chianciano, a spa town whose waters are reputed to have restorative properties. (B, D)

Day 9 - Chianciano

Today’s series of walks (2.5 hours) begins in Montalcino, famed for its fine red wine, Brunello di Montalcino. Explore the 14th-century walls before departing for Pienza. After exploring the Duomo and Gothic churches, continue to Montepulciano for a walk uphill to reach the last breathtaking view of the day. Savor authentic local dishes at our optional Country Evening tonight.(B)

$79 USD

Country Evening Feast on a traditional menu of grilled meats, roasted potatoes and local Chianti wine, topped off with tiramisu, during your Tuscan dinner at the Ristorante al Casale.

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. (B)

$79 USD

Dinner with Tenors End your day with an elegant four-course dinner in the heart of Rome. While you dine, you’ll be entertained by talented singers performing some of opera’s most beloved masterpieces. Don’t miss this festive evening, sure to leave you with wonderful memories of Italian hospitality!

Day 11 - Rome

Board your flight home, or remain in Rome for our tour extension. (B)