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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.
tour map
tour highlights
– With your small group (maximum 22 guests), enjoy seven nights deluxe accommodations at luxurious Castello La Leccia, an impressive property amidst the serene Tuscan landscape.
– Join hands-on culinary experiences with skilled chefs to learn the secrets of preparing traditional Tuscan cuisine and desserts.
– Explore must-see highlights, including the Etruscan ruins in Volterra, plus Pienza and Siena—both UNESCO World Heritage Sites.
– Tour the grounds of Podere Il Casale, an organic farm, and learn about the owners’ passion for the slow food movement.
– 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.
– Partake in a lively cooking class followed by a lovely dinner at Badia a Coltibuono, a historic winery with origins dating back to 1051.
day-by-day itinerary
Day 1: En Route from U.S.
Day 2: Arrive in Florence, Italy | Castellina
Day 3: Castello La Leccia
Day 4: Pienza
Day 5: Cortona
Day 6: Volterra | San Gimignano
Day 7: Monteriggioni | Castellina in Chianti | Gaiole
Day 8: Siena
Day 9: Florence | Depart for U.S.
full itinerary
B = Breakfast, L = Lunch, D = Dinner
Day 1: En Route from U.S.
Thursday, October 2, 2025
Day 2: Arrive in Florence, Italy | Castellina
Friday, October 3, 2025 (D)
Upon arrival to Florence's Peretola Airport an Orbridge representative will be waiting to assist with your transfer to the property.
Dating back to the Middle Ages, Castello La Leccia exudes an aura of history—its architecture a testament to the castle's rich past. Stone walls, turrets and charming courtyards seemingly transport you to a bygone era. Stepping into your accommodations you'll appreciate the blend of classic opulence and contemporary elegance. Comfortable furnishings, plush bedding and stunning views create a quaint haven in which to retreat after enriching days of exploration.
Take time to unpack and settle in before joining fellow travel companions for a convivial four-course welcome dinner.
Day 3: Castello La Leccia
Saturday, October 4, 2025 (B,L,D)
Today meet with chefs from the property for an informative, hands-on cooking experience. Learn the secrets of preparing traditional pasta and bread, then indulge on your creations during a leisurely lunch.
The remainder of the afternoon take advantage of free time to fully immerse yourself in Castello La Leccia's varied amenities. Stroll through the meticulously maintained gardens where the fragrance of lavender and rosemary fills the air. Admire the endless panoramic views as you relax by the outdoor pool. Or opt for a rejuvenating treatment (additional fees apply) at the tranquil spa.
Later gather together for a guided tour to explore the vineyards and production area. Learn about the winemaking process and savor the varietals during a tasting.
Day 4: Pienza
Sunday, October 5, 2025 (B,L,D)
Following breakfast set out for the charming village of Pienza. Known as "the ideal city of the Renaissance," this UNESCO World Heritage Site 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 for centuries.
Continue to Podere Il Casale, a small organic farm, to 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. Join them on a tour of the vineyard, olive groves, animal sanctuary and cheesemaking workshop, and gain insight into the concept of the slow food movement. This integrated approach unites the enjoyment of growing, preparing and eating food in harmony with nature. After walking the grounds be seated for lunch featuring ingredients grown on and harvested from the farm.
Return to the property with time to freshen up before another five-star gastronomic experience—a specially crafted four-course dinner paired with wines from the region.
Day 5: Cortona
Monday, October 6, 2025 (B,D)
After breakfast travel to the hilltop town of Cortona—the adopted home of Under the Tuscan Sun author, Frances Mayes.
A local guide will escort you through neo-Gothic Santa Margherita Basilica, past Villa Bramasole, around Cortona's city center and to the Etruscan museum.
The remainder of the afternoon is at leisure. Stop for lunch at one of Cortona's many charming cafés or restaurants, then meander the winding streets exploring the various shops and boutiques.
Day 6: Volterra | San Gimignano
Tuesday, October 7, 2025 (B,D)
Today marvel at the ancient allure of 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 carve unique handmade alabaster crafts and souvenirs. Stroll through the bustling, narrow streets before reaching an overlook to view the ancient Roman theatre. Glimpse clouds of geyser steam in the distance as it escapes over the rolling hillside.
Continue to San Gimignano—the "New York of the Middle Ages" and UNESCO World Heritage Site—whose horizon of iconic towers resembles modern skyscrapers. During an inside visit of San Gimignano’s Romanesque Duomo view colorful frescoes including The Creation of Adam and Eve and Last Judgement. Learn the story of local Saint Fina, 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.
Day 7: Monteriggioni | Castellina in Chianti | Gaiole
Wednesday, October 8, 2025 (B,L,D)
Following breakfast 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. See the medieval abbey at Abbadia a Isola, then stroll through the shops in the small village of Castellina in Chianti.
This evening features an exclusive culinary adventure—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 radiates spirited fun in the kitchen while she demonstrates the simple techniques and preparations of classic Tuscan dishes.
The property itself exudes an enigmatic atmosphere—melding centuries-old history with family traditions passed down through generations. During a tour of the Renaissance garden and cellar system hear 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 developing a flourishing wine business. Since 1846 the winery continues under private ownership of the Stucchi Prinetti family.
Afterward gather together in the dining room for a special dinner.
Day 8: Siena
Thursday, October 9, 2025 (B,D)
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 join fellow travel companions for a farewell dinner at Castello La Leccia to celebrate the captivating week spent exploring Tuscany.
Day 9: Castellina | Florence | Depart for U.S.
Friday, October 10, 2025 (B)
After breakfast guests departing during the suggested times take a complimentary group transfer to the airport for flights home.
Guests continuing on the post-tour will transfer to Florence by private bus.
(Itinerary subject to change.)
Inclusions
- 7 nights accommodations
- 7 breakfasts, 3 lunches and 7 dinners served with wine
- All lessons, private tours and tastings, and unique small-group excursions noted in the 9-day itinerary
- Full guiding services of an Orbridge Travel Director and expert local guides
- 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
rates
| Category | Rate* |
|---|---|
| Superior: | $5,995 |
| Deluxe: | $7,395 |
| Single (Superior): | $9,395 |
*Special group rates; limited offer. Rates are per person based on double occupancy except where noted as Single, in U.S. dollars. Single availability limited. Airfare not included.
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.
Activity Level: 3
ModerateFull Itinerary
B = Breakfast, L = Lunch
Day 9: Depart Castellina | Arrive in Florence
Friday, October 10, 2025 (L)
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.
Day 10: Florence
Saturday, October 11, 2025 (B)
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.
Day 11: Florence | Depart for U.S.
Sunday, October 12, 2025 (B)
After breakfast guests departing during the suggested times take the complimentary transfer to Florence's Peretola Airport for flights home.
†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.)
Inclusions
- 2 nights at Hotel De La Ville (or similar)
- 2 breakfasts and 1 lunch (a 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
Rates
| Category | Rate* |
|---|---|
| Double: | $1,795 |
| Single: | $2,195 |
*Post-tour rate is per person based on double occupancy except where noted as Single, in U.S. dollars. Single availability limited. Airfare not included.
Travel Insurance
Though not required, we recommend that all guests purchase travel insurance as a means to recoup expenses if canceling or departing early from a trip becomes necessary. Information will be emailed to you with your confirmation documents. If you are on an international departure, you should purchase travel insurance that—at a minimum—provides emergency medical, evacuation, and repatriation coverage. You can call Travel Insurance Services directly at 800.937.1387 or visit www.travelinsure.com/calalumni for detailed information about various coverage options. Please indicate if you purchased travel insurance on the Guest Information Form.
Membership Statement
One traveler per room, whether an alum or friend, must be a current Cal Alumni Association member at the time of departure to participate in Cal Discoveries Travel offerings. Payment of $60 for seniors 65 years and over and $75 for others establishes a membership with all Association benefits. Memberships are for individuals only, and are non-refundable and non-transferable. A traveling pair and their children under 21 years of age may travel on one membership. Please enroll online at alumni.berkeley.edu/join.
The Cal Alumni Association (CAA) is a self-funded nonprofit organization that relies on donations to provide programs and services that support students, alumni, and the University. To make a gift, please visit alumni.berkeley.edu/donate. Thank you for choosing CAA as the recipient of your generosity.
Booking Flights
Our air partners can make flight arrangements for guests. In the event of flight delays and/or schedule changes, they will provide guests with personalized assistance. To book flight reservations with our air partners, contact (206) 319-5011 and select the option for your destination to discuss flight details with our air colleagues. Upon ticketing, a fee will be charged.
your guide(s)
Flavors of Tuscany – Insider, Interpreter, Epicure, Host
As you explore the region's culinary and cultural flavors, an Orbridge Travel Director will infuse your journey with an epicure’s appreciation of food and wine, a local’s knowledge and pride of place, and a travel aficionado’s ability to enrich the beauty of all senses to your discoveries.
Whether at a wine tasting, visiting with locals, sightseeing, or raising a glass with you over an exquisitely crafted meal, the contribution of your Travel Director is essential to the intimate and educational qualities that distinguish this program. Catch their enthusiasm and explore the flavors of this wonderful region with added confidence, understanding, and appreciation.
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