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Country Roads of Tuscany & Central Italy

Country Roads of Tuscany & Central Italy

9 day tour to Italy
Tour Operator
Insight Vacations
Departures
Mar 28, 2027 – Sep 26, 2027
Prices From
$3,150
Dates & Prices
Live 'la dolce vita' during this 9-day guided tour of Italy. Explore the narrow cobblestone streets of Siena to the shell-shaped Piazza del Campo and see the Torre del Mangia, the second-tallest tower in Italy. Discover the art of truffle-hunting and learn how to make pasta from a professional before delighting in a local lunch. In San Gimignano, eat the best gelato in the world - literally. Indulge in your favorite flavors or try something unexpected. Alongside a Local Expert, marvel at the cathedral at the center of Florence: Basilica di Santa Maria del Fiore, nicknamed 'the Duomo' for its awe-inspiring crown made by a master goldsmith.

Tour Itinerary

Day 1
Welcome to Rome, a glorious city filled with classical antiquities, medieval buildings, Renaissance palaces and Baroque churches. Settle in before joining your Travel Director and get to know your fellow travelers over Roman specialties during dinner at a local restaurant.
Day 2
See the imposing Basilica of St. Peter in the Vatican City before crossing the Tiber into Ancient Rome and imagining the gladiatorial combats and sounds of roaring spectators as you visit the mighty Colosseum with your Local Expert. Journey north to the Umbrian village of Baschi. Immerse yourself in the flavors and culture of the region and learn about the secrets of Italian food culture as you join Giovanni and his dog Chris for a truffle hunting session. Afterwards, be entertained by Chef Lorenzo with a fun pasta demonstration and enjoy a delicious lunch accompanied by Orvieto Classico wine. Join a Local Expert in Perugia to navigate the underground labyrinth of little streets, alleys and arches. Walk along Corso Vannucci, resplendent in pale-pink stone, passing the princely Priors' Palace, the cathedral and the finely sculptured Great Fountain in the main square.
Day 3
This morning, during a MAKE TRAVEL MATTER® Experience, visit an artisanal workshop to meet Marta—recipient of a TreadRight Foundation grant—and her team of weavers. Discover how the fascinating art of loom weaving has been passed down through generations and learn how this ancient craft is being preserved today. Later, enjoy free time to explore the many delights of Umbria’s capital city or join an Optional Experience to Cortona. In the evening, take your pick from a hand-picked selection of Perugian restaurants for a Dine Around experience—choosing the ambience and menu that suit you best. Buon appetito!
Day 4
Journey to Assisi, one of Italy's most beautiful medieval hilltop towns, set high up in the mountains and enclosed by fortress walls. In the valley, see the famous Church of St. Mary of the Angels, much venerated as the place of St. Francis' death, then continue up Mount Subasio to the upper town. Step inside the massive, 13th-century Basilica of St. Francis with your Local Expert to learn how Giotto masterfully painted frescoes that inspired a variety of Renaissance artists.
Day 5
Follow the shores of Lake Trasimeno and continue to the narrow, cobbled streets of Siena. Standing in the shell-shaped Campo, imagine the frenzied atmosphere of the biannual Palio horse race and see the Town Hall. Explore Siena with Insight Choice. Choose to visit the medieval Cathedral or, alternatively, sample panforte, a traditional Tuscan dessert. Travel to the medieval town of San Gimignano, where your Travel Director will show you the medieval skyscrapers, serpentine streets and hidden squares. The town is also home to world champion gelato maestro Sergio Dondoli. At his artisan ice cream parlor on Piazza della Cisterna, the silky-smooth frozen treats are beautifully displayed in a range of unique flavors for you to try. Your home for the next three nights is nestled in the Tuscan countryside.
Day 6
Enjoy your day at leisure, taking in your Tuscan surroundings. Relax at your hotel or you could opt to join an Optional Experience to Lucca.
Day 7
The morning is devoted to the Renaissance city of Florence. A fascinating walking exploration with a Local Expert takes you to the marble-clad cathedral crowned by Brunelleschi's dome. See the baptistery with its beautiful Gates of Paradise and Giotto's splendid bell tower. Walk on to Piazza della Signoria with its open-air gallery of Renaissance sculptures, followed by free time to shop for top-quality Florentine leather or gold. Toast to your travels during a delicious Farm-to-Table dinner at a local restaurant and enjoy tasting flavorsome dishes prepared with locally grown ingredients, home-made pastas, traditional Chianti wine, all sourced from the farm in the Tuscan region.
Day 8
Enjoy the rolling Tuscan hills as you journey south through the Italian countryside. This morning, visit the medieval spa town of Bagno Vignoni, renowned for its mineral-rich thermal baths, then continue to the ‘model’ Renaissance town of Pienza, famous for its delicious pecorino cheese, before making your way to Rome.
Day 9
Bid farewell to the glories of Italy.

Itinerary Dates & Prices

Start Date
Mar 28, 2027
End Date
Apr 05, 2027
Our Price
$3,195
Guaranteed
Start Date
Apr 25, 2027
End Date
May 03, 2027
Our Price
$3,525
Guaranteed
Start Date
May 23, 2027
End Date
May 31, 2027
Our Price
$3,525
Guaranteed
Start Date
Jun 20, 2027
End Date
Jun 28, 2027
Our Price
$3,275
Guaranteed
Start Date
Jul 04, 2027
End Date
Jul 12, 2027
Our Price
$3,195
Guaranteed
Start Date
Aug 01, 2027
End Date
Aug 09, 2027
Our Price
$3,150
Guaranteed
Start Date
Aug 29, 2027
End Date
Sep 06, 2027
Our Price
$3,195
Guaranteed
Start Date
Sep 12, 2027
End Date
Sep 20, 2027
Our Price
$3,875
Guaranteed
Start Date
Sep 26, 2027
End Date
Oct 04, 2027
Our Price
$3,525
Guaranteed
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