Kensington
10 Day The Flavors of Tuscany
10 Day The Flavors of Tuscany
Photogenic medieval towns, rolling countryside, Renaissance architecture, and a legacy of impeccable food and wine: Tuscany has come to symbolize everything that makes rural Italy special. Perfect for first-timers and veterans alike, this trip takes you deep into Italy’s heart and introduces you to its small-town charms, delicious gastronomy, and breathtaking art.
After arriving in ravishing Florence, the tour kicks off with a personalized walking tour of the city that gave birth to the Italian Renaissance, pausing to take in must-see sights like the Ponte Vecchio bridge, Palazzo della Signoria, and Cathedral Square en route to Galleria dell’Accademia, home to Michelangelo’s “David.” Later, explore the Roman heritage of the medieval walled city of Lucca before heading south across the glorious Tuscan countryside to your next stop: Montepulciano. In this charming hillside town, you’ll be treated to a private walking tour that takes in its dazzling Renaissance architecture and famous wine cellars before visiting the Crociani Art Gallery, home to an intriguing collection of Etruscan and Roman artworks. No visit to Tuscany is complete without plenty of time devoted to its fabled food and wine, and you’ll get the chance to experience both in fine style, first on a private gourmet food tour with tasting stops at a local Pecorino cheesemaker, a Val di Chiana farmhouse, and an organic winery, then on a private cellar tour of a pair of wineries, one of which even features its very own Etruscan tomb! From there, the scene shifts to Siena, Tuscany’s heart. First, get to know this beautiful medieval city on a privately guided walking tour of its most cherished spots (including Piazza del Campo, the Torre del Mangia bell tower, and the monuments of Sansedoni Palace), then sample its famous food while learning to prepare it yourself during a private cooking lesson at the 11th-century Castello di Melleto (complete with a tasting session of fine wines, of course). Cap the experience off in the most Tuscan way possible: wandering the olive groves of a gorgeous villa once owned by the Grand Duke of Tuscany.
Kensington Tours creates private trips from the world’s finest ingredients. Tailor-made with care by your personal Destination Expert, your personalized trip is always a one-of-a-kind experience made just for you. Expert local guidance and 24/7 service come standard.
Day 1 |
Florence (Firenze) is a compact city, but densely packed with spectacular art and architecture everywhere you look. The city center itself is a UNESCO World Heritage Site.
Birthplace of the Renaissance as well as Italy's fashion industry, Florence is imbued with an air of history and sophistication. Visitors are sure to be enchanted with the Florentine way of life, from the sensational Tuscan cuisine to the Michelangelo masterpieces. Art and food lovers will find much to embrace here. Looming over Florence is the Duomo, a red terracotta dome that is part of the Cathedral of Santa Maria del Fiore. Bellissima! |
Day 2 |
Florence (Firenze) is a compact city, but densely packed with spectacular art and architecture everywhere you look. The city center itself is a UNESCO World Heritage Site.
Birthplace of the Renaissance as well as Italy's fashion industry, Florence is imbued with an air of history and sophistication. Visitors are sure to be enchanted with the Florentine way of life, from the sensational Tuscan cuisine to the Michelangelo masterpieces. Art and food lovers will find much to embrace here. Looming over Florence is the Duomo, a red terracotta dome that is part of the Cathedral of Santa Maria del Fiore. Bellissima! |
Day 3 |
Florence (Firenze) is a compact city, but densely packed with spectacular art and architecture everywhere you look. The city center itself is a UNESCO World Heritage Site.
Birthplace of the Renaissance as well as Italy's fashion industry, Florence is imbued with an air of history and sophistication. Visitors are sure to be enchanted with the Florentine way of life, from the sensational Tuscan cuisine to the Michelangelo masterpieces. Art and food lovers will find much to embrace here. Looming over Florence is the Duomo, a red terracotta dome that is part of the Cathedral of Santa Maria del Fiore. Bellissima! |
Day 4 |
Nestled in the rolling hills of Tuscany, Montepulciano is a quintessential Italian hill town that offers visitors a perfect blend of Renaissance architecture, fine wine, and stunning vistas. Famous for its Vino Nobile di Montepulciano, this town is a paradise for wine lovers. Touring local vineyards, such as Cantina Contucci, and sampling the region’s prestigious red wines is an experience that transports you into the heart of Tuscany’s wine heritage. As you explore the town’s winding streets, you’ll also find charming piazzas, artisan shops, and historic buildings, all set against breathtaking views of the surrounding countryside. Montepulciano’s history is rich and varied. The town's Piazza Grande is a stunning example of Renaissance architecture, with landmarks such as the Palazzo Comunale and the majestic Duomo di Montepulciano. A climb to the top of the Palazzo Comunale tower rewards visitors with panoramic views of Tuscany’s iconic landscape. The town’s Palazzo Ricci is also a highlight, offering a glimpse into the grandeur of Renaissance life, while nearby San Biagio church, set in the countryside, is a marvel of classical symmetry. Beyond its architecture, Montepulciano offers a vibrant cultural scene. The Bravio delle Botti, held annually in August, is a unique barrel-rolling competition that draws visitors from around the world. Locals compete by rolling large wine barrels through the narrow streets of the town, and it’s a thrilling way to immerse yourself in Montepulciano’s traditions. Visitors can also enjoy the town’s many festivals, including food and wine fairs that celebrate Tuscany’s culinary excellence. A fun fact about Montepulciano: The town has been the setting for several films, including scenes from the Twilight Saga: New Moon, which have drawn fans to explore its atmospheric streets. Montepulciano’s timeless beauty, coupled with its wine culture and history, makes it an enchanting destination for any traveler. |
Day 5 |
Nestled in the rolling hills of Tuscany, Montepulciano is a quintessential Italian hill town that offers visitors a perfect blend of Renaissance architecture, fine wine, and stunning vistas. Famous for its Vino Nobile di Montepulciano, this town is a paradise for wine lovers. Touring local vineyards, such as Cantina Contucci, and sampling the region’s prestigious red wines is an experience that transports you into the heart of Tuscany’s wine heritage. As you explore the town’s winding streets, you’ll also find charming piazzas, artisan shops, and historic buildings, all set against breathtaking views of the surrounding countryside. Montepulciano’s history is rich and varied. The town's Piazza Grande is a stunning example of Renaissance architecture, with landmarks such as the Palazzo Comunale and the majestic Duomo di Montepulciano. A climb to the top of the Palazzo Comunale tower rewards visitors with panoramic views of Tuscany’s iconic landscape. The town’s Palazzo Ricci is also a highlight, offering a glimpse into the grandeur of Renaissance life, while nearby San Biagio church, set in the countryside, is a marvel of classical symmetry. Beyond its architecture, Montepulciano offers a vibrant cultural scene. The Bravio delle Botti, held annually in August, is a unique barrel-rolling competition that draws visitors from around the world. Locals compete by rolling large wine barrels through the narrow streets of the town, and it’s a thrilling way to immerse yourself in Montepulciano’s traditions. Visitors can also enjoy the town’s many festivals, including food and wine fairs that celebrate Tuscany’s culinary excellence. A fun fact about Montepulciano: The town has been the setting for several films, including scenes from the Twilight Saga: New Moon, which have drawn fans to explore its atmospheric streets. Montepulciano’s timeless beauty, coupled with its wine culture and history, makes it an enchanting destination for any traveler. |
Day 6 |
Nestled in the rolling hills of Tuscany, Montepulciano is a quintessential Italian hill town that offers visitors a perfect blend of Renaissance architecture, fine wine, and stunning vistas. Famous for its Vino Nobile di Montepulciano, this town is a paradise for wine lovers. Touring local vineyards, such as Cantina Contucci, and sampling the region’s prestigious red wines is an experience that transports you into the heart of Tuscany’s wine heritage. As you explore the town’s winding streets, you’ll also find charming piazzas, artisan shops, and historic buildings, all set against breathtaking views of the surrounding countryside. Montepulciano’s history is rich and varied. The town's Piazza Grande is a stunning example of Renaissance architecture, with landmarks such as the Palazzo Comunale and the majestic Duomo di Montepulciano. A climb to the top of the Palazzo Comunale tower rewards visitors with panoramic views of Tuscany’s iconic landscape. The town’s Palazzo Ricci is also a highlight, offering a glimpse into the grandeur of Renaissance life, while nearby San Biagio church, set in the countryside, is a marvel of classical symmetry. Beyond its architecture, Montepulciano offers a vibrant cultural scene. The Bravio delle Botti, held annually in August, is a unique barrel-rolling competition that draws visitors from around the world. Locals compete by rolling large wine barrels through the narrow streets of the town, and it’s a thrilling way to immerse yourself in Montepulciano’s traditions. Visitors can also enjoy the town’s many festivals, including food and wine fairs that celebrate Tuscany’s culinary excellence. A fun fact about Montepulciano: The town has been the setting for several films, including scenes from the Twilight Saga: New Moon, which have drawn fans to explore its atmospheric streets. Montepulciano’s timeless beauty, coupled with its wine culture and history, makes it an enchanting destination for any traveler. |
Day 7 |
In the walled city of Siena we stand firmly planted in the Middle Ages. Siena preserved its original character more markedly than any other city in Italy. |
Day 8 |
In the walled city of Siena we stand firmly planted in the Middle Ages. Siena preserved its original character more markedly than any other city in Italy. |
Day 9 |
In the walled city of Siena we stand firmly planted in the Middle Ages. Siena preserved its original character more markedly than any other city in Italy. |
Day 10 |
In the walled city of Siena we stand firmly planted in the Middle Ages. Siena preserved its original character more markedly than any other city in Italy. |
Travel Dates | Price | ||
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06/01/18 - 12/31/26 |
Starting At $8,338 |
Get A Quote |
Prices are per person, based on double occupancy. Offer is subject to availability and change without notice. Some restrictions may apply.