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Main Program: June 06, 2024 – June 14, 2024
Post-Tour: June 14, 2024 – June 16, 2024

Flavors of Tuscany

Join our small group for an unforgettable journey to Italy's enchanting Tuscany region—the bucolic, rolling countryside that provides endless inspiration for artisans, chefs, and vintners alike.


NOTE: Tour information is current as of 5/3/2024.

Program Highlights

– With your small group (maximum 22 guests), enjoy seven nights deluxe accommodations at the luxurious and exclusive Castello La Leccia in Castellina, featuring exceptional views of the lush, rolling Tuscan landscape.

– Admire the Etruscan ruins and Roman center in Volterra before visiting charming San Gimignano—the  Town of Fine Towers—which is completely encircled by medieval walls.

– Stop at the Renaissance town of Pienza, a UNESCO World Heritage Site, which sits atop a hill overlooking the Tuscan countryside.

– Discover Podere Il Casale, an organic farm. Tour the grounds while learning about the owners’ passion for the slow food movement, followed by a leisurely lunch.

– Learn secrets of preparing traditional Tuscan food in class with chefs from Castello La Leccia. 

– Visit an organic winery for a behind-the-scenes tour and tasting.

– Take a guided tour of Cortona with free time to explore afterward.

– Wander within the walled medieval village of Monteriggioni—a city along the ancient pilgrim road of Via Francigena. Visit Abbadia a Isola to see the medieval abbey and then stroll around the charming hilltop village of Castellina in Chianti.

– Savor a cooking class and dinner at Badia a Coltibuono, a remarkable winery featured on the Netflix TV show, Salt Fat Acid Heat. 

– Stroll Siena—another UNESCO World Heritage Site—with its well-preserved cityscape, celebrated Duomo, and bustling Piazza del Campo.

What's Included

  • 7 nights accommodations
  • 7 breakfasts, 3 lunches, and 7 dinners served with wine
  • All lessons and tastings as described in the 9-day itinerary
  • Private motor coach transportation
  • Luggage porterage
  • Gratuities to Orbridge Travel Director, local guides, drivers, porters, and wait staff for included meals
  • Group airport transfers for guests arriving and departing during the suggested times

Itinerary

Day 1: En Route from U.S.
Thursday, June 6, 2024

Day 2: Arrive in Florence, Italy | Castellina
Friday, June 7, 2024
Welcome to lovely Italy! After arriving at the property, unpack and relax before joining fellow travel companions for a welcome dinner. If time allows, meander Castello La Leccia's tranquil garden and courtyard with panoramic views of Tuscany's seemingly endless countryside.
Overnight: Castello La Leccia (D)

Day 3: Castello La Leccia
Saturday, June 8, 2024
Revel in la dolce vita by spending today at the wonderful Castello La Leccia accommodations and enjoy a cooking class, lunch, winery tour/tasting, and dinner. 

Here at home base, we'll learn secrets of traditional Tuscan food with an informative and fun cooking class. Experience the preparation of Italian homemade pasta and bread with chefs and then savor the fruits of the labor by dining on a sumptuous lunch. 

The afternoon is open for leisure at this wonderful property. Hike the trail surrounding the castle to take in the views, stroll the gardens, unwind by the pool, or purchase a yoga or Shiatsu class or a spa treatment (additional fees apply).

Later, delight in the panoramic views over the Chianti hills during a behind-the-scenes winery tour and tasting. 
Overnight: Castello La Leccia (B,L,D)

Day 4: Pienza
Sunday, June 9, 2024
The charming village of Pienza awaits. Known as "the ideal city of the Renaissance," this UNESCO World Heritage Site, perched on a hill in Southern Tuscany, was designed to exemplify the principles and philosophy of classical times and the great Italian Renaissance. Constructed within approximately four years, the village has remained unchanged over the centuries. 

Continue to Podere Il Casale, a small organic farm, for a behind-the-scenes look at their scenic vineyard, olive groves, animal sanctuary, and cheesemaking workshop. Meet the owners—Ulisse and Sandra—a husband-and-wife duo who moved from Switzerland to Tuscany in 1991 to pursue their dreams of creating a sustainable farm-to-table lifestyle. Gain insight into the concept of the slow food movement, which emphasizes an integrated approach that unites the enjoyment of growing, preparing, and eating food in harmony with nature.

After touring the grounds, enjoy a delectable lunch created from ingredients grown on and harvested from the farm.  
Overnight: Castello La Leccia (B,L,D)

Day 5: Cortona
Monday, June 10, 2024
After breakfast, travel to the hilltop town of Cortona—the adopted home of Frances Mayes, author of Under the Tuscan Sun. Enjoy a guided tour to visit the church of Santa Margherita, the panorama, Bramasole villa, the city centre of Cortona, and the Etruscan museum.

The afternoon is at leisure in Cortona's town center. Stop at one of the many charming eateries for lunch on your own, and explore the various small shops lining the bustling streets.
Overnight: Castello La Leccia (B,D)

Day 6: Volterra | San Gimignano
Tuesday, June 11, 2024
Enjoy a traditional Italian breakfast before setting out for Volterra—an Etruscan and Roman center high atop a hill in a volcanic region—surrounded by fortification walls. Famous for its alabaster quarries, the town's artisans produce unique handmade alabaster crafts and souvenirs. Leisurely stroll through the narrow streets before reaching an overlook to view the ancient Roman theatre. Off in the distance, glimpse clouds of geyser steam as it escapes over the rolling hillside. 

Continue to the "New York of the Middle Ages" and UNESCO World Heritage Site, San Gimignano—whose skyline from a distance resembles a modern city. During an inside visit of San Gimignano’s Romanesque Duomo, behold colorful frescoes, including The Creation of Adam and Eve and Last Judgement. Also, learn the story of local Saint Fina while stepping through a dedicated chapel, added in 1468, where the Florentine master Domenico Ghirlandaio depicted her dramatic life.

After lunch on your own, rejoin fellow travel companions in the main square for a special treat—a visit with Sergio Dondoli, master gelato creator and owner of Gelateria Dondoli—winner of numerous awards and recognitions. Sergio's boundless passion for his craft is contagious as he boisterously describes his most popular flavors, including Rosemary Baby, Cream of Santa Fina, and Zabaione di Vinsanto. Afterward, visit the gelateria for a sampling of his decadent creations.
Overnight: Castello La Leccia (B,D)

Day 7: Monteriggioni | Castellina in Chianti | Gaiole
Wednesday, June 12, 2024
Today, visit the walled medieval village of Monteriggioni—a popular stop on the Via Francigena pilgrim trail, an ancient route that connected Canterbury to Rome in medieval times. Built between 1213 and 1219, the castle's fortified walls and 14 guard towers are well-preserved today. Visit Abbadia a Isola to see the medieval abbey and then stroll around the small shops in the charming hilltop village of Castellina in Chianti.

This evening features an exclusive experience—a visit to Badia a Coltibuono winery for a cooking class with Benedetta Vitali, chef and co-founder of Cibreo and Zibibbo restaurants, as well as the author of several cookbooks. Benedetta exudes spirited fun in the kitchen while teaching the simple techniques and preparations of classic Tuscan dishes. 

During the visit, learn of the winery's history dating back to the 11th century when it was founded by monks of the Vallumbrosan Order, a Tuscan reform of the Benedictines. These monks planted the first vineyards in the northern Chianti area. Over centuries, they extended their vast land holdings to include many thousands of acres that developed a flourishing wine business. Since 1846, the winery continues under private ownership of the Stucchi Prinetti family. 

The property itself exudes an enigmatic atmosphere—melding centuries-old history with family traditions passed through generations. Tour the Renaissance garden and noteworthy cellars followed by a special dinner.
Overnight: Castello La Leccia (B,L,D)

Day 8: Siena
Thursday, June 13, 2024
Today's highlight features a visit to Siena—a UNESCO World Heritage Site—to admire its remarkably well-preserved medieval cityscape. Spared from major modern industrial development and large-scale urban extensions, Siena's original 15th-century street plan and Gothic architecture remain unchanged. Explore the celebrated Duomo, with its striking striped columns and walls, and recently excavated 13th-century frescoes. Admire the Sanctuary of Santa Caterina—a place of pilgrimage—and learn about the city’s colorful history.

During free time, wander the shell-shaped Piazza del Campo—one of Europe’s finest squares—built on the site of a Roman marketplace. 

This afternoon, meet Lorenzo Rossi, a third-generation artisan baker and owner of Il Magnifico. Lorenzo will share his special family traditions and the ingredients unique to his creations during a tasting of fresh-baked Sienese sweets.

Tonight, share your experiences from a captivating week spent in Tuscany and raise a glass with fellow travel companions one final time at Castello La Leccia during a convivial farewell dinner.
Overnight: Castello La Leccia (B,D)

Day 9: Castellina | Florence | Depart for U.S.
Friday, June 14, 2024
After breakfast, guests departing during the suggested times take a complimentary group transfer to Florence's Peretola Airport for flights home. Guests continuing on the post-tour will transfer to Florence by private bus. (B)

B = Breakfast, L = Lunch, D = Dinner

(Itinerary subject to change.)

Activity Level

Moderate

Activities are generally not very strenuous, however, this program requires individuals have higher mobility due to many steep hills, streets, and stairs in each town visited. We expect that guests can enjoy two hours or more of walking, are sure-footed on cobbled surfaces, and can walk up and down stairs without assistance. Historic city centers are usually more accessible by foot than vehicle, and often it is not possible for your motor coach to drop you off at site entrances. Due to the structure of some buildings, facilities for persons with disabilities may be limited.

Your Guide(s)

Marco Messina – Insider, Interpreter, Epicure, Host (Flavors of Tuscany Main Program)

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A native of Italy, Marco moved to Tuscany with his family as a child. Here he developed a passion for the land and culture which led to taking courses to earn credentials as an official tourism representative. Marco enjoys working as a guide for both individuals and adults, foreign and domestic, to share his love and knowledge of history, art, and local traditions. When not showcasing his homeland, Marco also delights in the roles of musician, sports enthusiast, and father. 

Accommodations

Castello La Leccia

June 7 - June 13

Become part of la famiglia as you settle into this authentic Tuscan wine estate. Sip a glass of Chianti on a sun-dappled terrace, stroll the grounds, and admire vineyards draped with Sangiovese, Merlot, and Petit Verdot grapes.

Historical sources cite that La Leccia castle’s ownership was divided among 16 owners for strategic purposes. Near the mid 1400s, the Ricasoli family dominated a large part of the Chianti Classico region, as well as the castle.

After being modified to serve more as a villa in the 18th century, the entire property was purchased in 1920 by Giuliano Daddi. Subsequently, it was the site of heavy bombardments during WWII that destroyed part of the tower and the last medieval evidence and devastated a wing of the villa.

Undergoing more than four years of careful and rigorous restoration, the castle and the surrounding gardens recently have returned to life.

With a focus on sustainability and the environment, the original spaces remain in tact but feature modern enhancements using eco-compatible materials and technologies. To warm the surroundings, wooden floors, beamed ceilings, and furniture were designed exclusively for the common spaces and made by Florentine craftsmen.

Superior: (approx. 301-484 sq.ft.) Enjoy elegant furnishings and a serene area to unwind after an enriching day of exploration.

Deluxe: (approx. 452-603 sq.ft.) Delight in absolute refinement with beautiful views of the surrounding countryside. Each room is different from the others, but all provide modern comforts and tasteful décor.

Room Amenities: Individual climate control, writing desk, LCD TV, complimentary Wi-Fi, phone, minibar, safe, and en suite bathroom with a shower or tub and shower, sundries, and hair dryer.

(Accommodations subject to change.)

Optional Post-Tour

Florence


Florence is arguably the cultural capital of Europe and the showcase of Renaissance exuberance. Lovers of beauty, art and history can extend their experience in Tuscany to embrace the treasures of this magnificent city.

Itinerary

Day 9: Depart Castellina | Arrive in Florence
Friday, June 14, 2024
Upon arriving in Florence meet a local art historian guide and set out on a walking tour of the historic city center.

In Piazza della Repubblica discover the city’s beginnings as a Roman settlement. Wander through narrow streets past the fortified houses and towers that marked the medieval town, and emerge onto the open Piazza della Signoria, the political center of the city since the Middle Ages. See the Duomo and Ponte Vecchio then cap off the morning with lunch at the local market.

Walk through the market and meet in a local botteghe where families have been serving up culinary treasures for generations. Taste different local specialties, such as not-to-be-missed finocchiona salami or Tuscan crostino, paired with a glass of fine Chianti. Afterward enjoy a delightfully sweet break with an Italian cappuccino or scoop of gelato.

In the afternoon explore the hidden craft workshops of artisans who create jewels and leather goods—flagships of Tuscan local production. And finally, weather permitting, set out on a private boat excursion on the river Arno. Sail underneath the Ponte Vecchio and capture views of the Uffizi Gallery and many palaces that are part of Florence's history.

Return to your hotel for an evening at leisure. 
Overnight: Hotel De La Ville (L)

Day 10: Florence
Saturday, June 15, 2024
Today join your guide and walk to the historic center to visit the Baptistery of San Giovanni, one of the oldest churches in Florence and a symbol of the city. With an octagonal plan, entirely covered with marble slabs and a dome decorated by a precious Byzantine mosaic, it represents a masterpiece of Romanesque architecture.

Next enjoy a tour of the Uffizi Gallery†. Commissioned in 1560 by Cosimo I de’ Medici and designed by the great architect Giorgio Vasari, the Uffizi has drawn visitors to view masterpieces by important artists of the Renaissance, including Leonardo Da Vinci, Giotto, Botticelli, Tiziano, and Michelangelo.

The remainder of the afternoon is at leisure to explore the city at your own pace.
Overnight: Hotel De La Ville (B)

Day 11: Florence | Depart for U.S.
Sunday, June 16, 2024
After breakfast guests departing during the suggested times take the complimentary transfer to Florence's Peretola Airport for flights home. (B)

B = Breakfast, L = Lunch

†The Uffizi Gallery tour is included in this itinerary because it holds a significant number of masterpieces. Touring will conclude at approximately 12:30 pm. Guests who would like to see Michelangelo’s statue of David at Accademia Gallery may additionally schedule their own visit during leisure time. We recommend securing a reservation in advance online at: https://www.galleriaaccademiafirenze.it/visita/.

Post-tour space is limited. We recommend reserving early for best availability.

This post-tour is not escorted by an Orbridge Travel Director. Included sightseeing is accompanied by a local guide.

(Itinerary subject to change.)

Activity Level

Moderate

It is our expectation that guests on this program are able to walk a mile at a moderate pace, board a motor coach, and walk up a flight of stairs without assistance. Historic city centers are usually more accessible by foot than vehicle. Due to the structure of some buildings, facilities for the disabled may be limited.

Accommodations

Hotel De La Ville

June 14 - June 15

Hotel de la Ville exudes an atmosphere of refined opulence—where classic Italian architecture and stylish contemporary décor creates an ambiance of understated luxury. Located just steps away from Florence's renowned attractions such as the Duomo, Uffizi Gallery and Ponte Vecchio, this property provides unparalleled access to the city's rich cultural heritage. Enjoy the well-appointed rooms, inviting public lounge spaces and warm hospitality. 

Room Amenities: Individual climate control, writing desk and chair, satellite LED TV, complimentary Wi-Fi, phone, minibar, safe, slippers, and en suite bathroom with sundries and hair dryer.

(Accommodations subject to change.)

What's Included

  • 2 nights accommodations at the Hotel De La Ville (or similar)
  • 2 breakfasts and 1 lunch (local market experience and tasting, featuring three courses and a glass of wine)
  • Guided art history and cultural tour, plus a panoramic walking tour of Florence's historical highlights
  • Visit to an artisanal workshop (leather or jewelry)
  • Private boat tour on the Arno River, dependent on river conditions
  • Admission to the Uffizi Gallery and Baptistery of San Giovanni
  • Luggage porterage
  • Gratuities to local guide, drivers, and porters
  • Airport transfers for guests departing during the suggested times

Terms and Conditions