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Tuscan Cultural Journey: Sun-Kissed Hill Towns, Cooking Classes, and Wine Tasting in Central Italy

Experience the sun-kissed hill towns of central Italy on a luxurious journey with unique cultural experiences. In Tuscany, spend two nights at a historic estate-turned-luxury hotel with a cooking class and a rooftop wine tasting lunch. Explore the ancient city of Arezzo and visit a winery and museum. Discover medieval Gubbio, truffle hunt, and learn about ceramics during a two-night stay at a restored monastery in Umbria. In Perugia, explore Assisi, attend an exclusive wine experience, participate in a hand-weaving workshop, and visit the "Gaite" workshops in Bevagna. Finally, enjoy an overnight in Rome with a visit to Spoleto and a guided tour of an ancient underground Roman church in Narni.

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Experience the rare and highly prized truffle hunting in the Umbrian hills with expert dogs. Meet the pooches after lunch and a tasting at a family-owned farm in Umbria.

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Explore the power of guilds in medieval Perugia on a walking tour. Visit the Palazzo dei Priori and Collegio del Cambio, headquarters of the money-changers' guild. Admire the "Sala delle Udienze" frescoes, completed by Pietro Perugino around 1500, which may have been worked on by a young Raphael.

SINA Palace, a 19th-century hilltop mansion, located in the historic center of Perugia, is filled with historical touches including antique furnishings, grand chandeliers, ornate frescoes, and a glass-bottomed swimming pool through which you can view ancient Etruscan ruins.

SINA Palace, a 19th-century hilltop mans


Florence's Peretola Airport to Villa La Massa in Candeli, Chianti wine region in Tuscany
Arrive at Villa La Massa in Tuscany for the start of the tour. Meet fellow travelers at a welcome reception and dinner at the historic luxury hotel, a former 16th-century Renaissance estate on the banks of the Arno River.
Chianti countrysde, Montefiridolfi, Fonte De' Medici agriturismo
Drive through the Chianti countryside to a farmhouse cooking school in the ancient Tuscan village of Montefiridolfi. Participate in a hands-on cooking class with the former head chef of a Michelin-starred restaurant. Enjoy a wine tasting of Antinori wines at their Fonte De' Medici agriturismo as well as a farm-to-table lunch. Join for dinner tonight at a typical Tuscan restaurant.
Travel to Arezzo, a historic Tuscan city with a wealth of architecture dating back to the Etruscans. After exploring and having lunch, continue to Gubbio in Umbria and check into a 17th-century stone monastery hotel for dinner at your leisure. Note: On some tours, there is an alternate itinerary featuring a talk by author Frances Mayes in Cortona, with a walking tour and fine dining lunch.
Gubbio in Umbria, church of Sant'Agostino, Palazzo dei Consoli
Take a walking tour of medieval Gubbio to see its preserved Roman amphitheater, Sant'Agostino church, and Palazzo dei Consoli. Explore craft boutiques known for ceramics, enjoy a truffle lunch at a castle, and go on a private truffle-hunting experience in the Umbrian woods. The evening is free to enjoy Gubbio as you wish.
Assisi, and Perugia in Tuscany and Umbria,Basilica of San Francesco
Visit the UNESCO World Heritage Site of Assisi, birthplace of St. Francis, and take a guided walking tour including the Basilica of San Francesco. Enjoy a Tauck-Exclusive al fresco lunch at the vineyards of Lungarotti Winery before traveling to Umbria's capital city of Perugia for a two-night stay in the historic heart of the city.
Perugia, Giuditta Brozzetti, Collegio del Cambio
Visit Perugia with a guided tour and explore Collegio del Cambio. Then, enjoy free time or join a short drive to Giuditta Brozzetti's workshop to witness hand-weaving on antique "Jacquard" frames. Choose to dine at your hotel's restaurant or a local taverna.
Spoleto, Narni, Rome, e Ponte Delle Torri
Drive from Perugia to Spoleto for a guided tour of the city, including a visit to the famous Ponte Delle Torri, the 12th-century Duomo of Spoleto, and free time to enjoy lunch. Then, visit the Narni Sotterranea (Narni Underground) to explore ancient Roman ruins before driving to Rome for an overnight stay and farewell reception and dinner.
Journey home from Rome
At the end of the tour, you will return home from Rome. A transfer from Hotel Indigo St. George to either Leonardo da Vinci Airport in Fiumicino or Rome Termini Train Station is included. Make sure to allow three hours for flight check-in at the airport.


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Discover the ancient city of Arezzo, with its historic architecture that dates back over a thousand years.


Airport transportation will be provided upon arrival and departure as specified.


Experience a Tuscan culinary adventure with a cooking class led by a former head chef from a Michelin-starred restaurant.


The package includes 15 meals, service charges, admission fees, taxes, porterage, and gratuities for the local guide.


Enjoy a truffle-hunting experience with a guide and their skilled dogs, followed by a delicious lunch at a truffle farm.


Peretola Airport: A modern and efficient airport that connects Florence to domestic and international destinations. Visitors can take a taxi or shuttle to Villa La Massa in Candeli, located about 25 kilometers away.

Villa La Massa: A luxurious hotel set in the rolling hills and vineyards of the Chianti region in Tuscany. The historic villa has been restored and features traditional architecture, a Michelin-starred restaurant, and a bar with a fine wine selection.

The Chianti wine region: A famous wine-producing area located in Tuscany, known for its picturesque landscape of rolling hills, vineyards, and medieval towns.

Day 01

Florence's Peretola Airport to Villa La Massa in Candeli, Chianti wine region in Tuscany

A historic city in eastern Tuscany, known for its Romanesque and Gothic architecture, including the Basilica of San Francesco and the Cathedral of Arezzo.

Day 03


Assisi: A hill town in Umbria known for its medieval architecture and religious significance. It is the birthplace of St. Francis, the founder of the Franciscan Order, and home to the Basilica of San Francesco, a UNESCO World Heritage site that houses the saint's tomb.

Perugia: The capital city of Umbria and a vibrant cultural and culinary center. The city boasts several medieval and Renaissance landmarks, including the Palazzo dei Priori, the Collegio del Cambio, and the Rocca Paolina.

The Basilica of San Francesco: A UNESCO World Heritage site in Assisi, Umbria, known for its magnificent frescoes by renowned Italian artists of the 13th and 14th centuries. The basilica is the final resting place of St. Francis and is composed of two churches, the Upper Church and the Lower Church.

Day 05

Assisi, and Perugia in Tuscany and Umbria,Basilica of San Francesco

Spoleto: A charming hilltop town in the province of Perugia, Umbria. It is known for its Roman theatre, medieval fortress, and beautiful Cathedral of Santa Maria Assunta. Visitors can explore the town's narrow alleys, taste local delicacies, and attend the famous Spoleto Festival in the summer.

Narni: A small town in the province of Terni, Umbria, known for its Roman and medieval history. The town is home to several important landmarks, including the ancient Roman bridge, the Cathedral of Santa Maria Impensole, and the Narni Underground, an intricate network of tunnels and caves.

Rome: The capital city of Italy and a world-famous tourist destination. The city is known for its ancient landmarks, such as the Colosseum, the Pantheon, and the Roman Forum, as well as its museums, galleries, and shopping districts. Visitors can also enjoy the city's vibrant nightlife, culinary scene, and cultural events.

Ponte delle Torri: A medieval bridge located in the town of Spoleto, Umbria. It spans across a deep gorge and offers breathtaking views of the surrounding countryside. The bridge is made of two towering arches and was built in the 14th century to connect the castle of Spoleto with the nearby fortress of Monteluco.

Day 07

Spoleto, Narni, Rome, e Ponte Delle Torri

The Chianti countryside: A picturesque region in Tuscany, Italy, known for its rolling hills, vineyards, and charming medieval towns. It is a popular destination for wine lovers, offering a variety of wine tastings and tours.

Montefiridolfi: A small town located in the Chianti region of Tuscany. It is known for its scenic countryside and traditional architecture, including the historic Palazzo Pretorio and the Church of San Romolo.


Fonte De' Medici Agriturismo: A charming farmhouse located in the heart of the Chianti countryside. It offers comfortable accommodations, a restaurant serving authentic Tuscan cuisine, and a variety of activities, such as wine tastings, cooking classes, and horseback riding.

Day 02

Chianti countryside, Montefiridolfi, Fonte De' Medici agriturismo

Gubbio: A charming medieval town located in the Umbria region of Italy, known for its well-preserved historic center, picturesque streets, and beautiful views of the surrounding countryside. 

The Church of Sant'Agostino: A beautiful religious building with a rich history and stunning art. It was built in the 14th century and features beautiful frescoes and paintings from the Renaissance period, including works by artists such as Ottaviano Nelli and Dono Doni. 


The Palazzo dei Consoli: A Gothic-style palace located in the heart of Gubbio's historic center. The palace was built in the 14th century and served as the seat of the town's government for many centuries. 

Day 04

Gubbio in Umbria, church of Sant'Agostino, Palazzo dei Consoli

Perugia is also home to Giuditta Brozzetti, a historic handloom workshop that produces exquisite textiles using traditional techniques. Another must-visit attraction in Perugia is the Collegio del Cambio, a stunning Renaissance palace that houses a collection of impressive frescoes and artworks.

Day 06

Perugia, Giuditta Brozzetti, Collegio del Cambio

End of the tour

Day 08

Journey home from Rome

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