Hill Town Gems of Italy

Spoleto, Umbria, Italy
May 4, 2018
12 Days
Escorted Journeys
14 Guests
From $10,690

Additional Departure: September 21, 2018


Below please find the day-by-day itinerary for this expedition. Unless otherwise noted, daily excursion options are included in the cost of the trip. We do our best to adhere to the scheduled itinerary, but in the spirit of our expeditionary style of travel we may deviate slightly to take full advantage of encounters with the destination and its people, culture, and wildlife.

Hill Town Gems of Italy Map

Brindisi / Lecce

May 4

Upon arrival in Brindisi, transfer to Lecce, the “Florence of the South.” Check in to your Deluxe room at the Patria Palace Hotel with the rest of the day at leisure.       


May 5
Olives, Italy

This morning, embark on a guided tour of the wonders of Lecce, a town with more than 2,000 years of history. During the 16th – 18th centuries, the “Lecce Baroque” style developed, and today the town is a treasure trove of artistic monuments. Visit the castle of Emperor Charles V and the eclectic Sant’Oronzo Square, dominated by an imposing statue of the Saint, built in 1666 with marble from the ancient Roman columns along the Appian Way. Next, explore the grand 2nd-century AD Roman amphitheater, followed by “Il Sedile,” a stately Baroque-Renaissance construction, dating back to 1592. See San Marco Church, a Venetian masterpiece; the Adorno Palace; the Basilica of Santa Croce, a triumph of Lecce Baroque design; and the charming Piazza Duomo. Continue along the Via Libertini, lined with churches decorated in the Lecce Baroque style, ending at the Rudiae Gate, the ancient entrance to Lecce.

For lunch, drive into the countryside to Manduria in the heart of the Primitivo wine district. Surrounded by more than 50 acres of vineyards and centuries-old olive groves, enjoy a delicious lunch paired with Primitivo wine at the wonderful 17th-century Masseria Le Fabriche fortified farmhouse. Learn about this burgeoning wine region while sipping their fresh reds and whites, see their production plants, explore their cellars, and enjoy an educational tasting of their artisan wines. Return to Lecce, and take advantage of the Dine-Around program with dinner at a restaurant of your choice.

Lecce / Matera / Monopoli

May 6
Matera, Italy

This morning, depart Lecce and drive north, up the heel of Italy’s boot, to the ghost town of Matera. The town is stunningly situated on the crest of a deep ravine, with overhanging rocks under which the Gravina River flows. A UNESCO World Heritage Site, this city of stone has been inhabited since the Paleolithic era. The numerous grottoes in the deep canyon were the perfect homes for prehistoric man, and ancient inhabitants built cave-homes and cave-churches in the easily worked tufa stone. Visit the ancient section called “Sassi,” and as you explore these deserted houses and temples, it is amazing to realize you are actually inside the mountain.

After a savory lunch at a local restaurant, continue to the Adriatic coast and the port town of Monopoli, a city first settled by the Greeks more than 2,000 years ago. Check in your Deluxe Room at the Il Melograno, a “fortified farmhouse,” with the rest of the afternoon at leisure to simply relax and enjoy the hypnotic atmosphere of southern Italy. Tonight, enjoy dinner at a delightful seaside restaurant.

Monopoli / Alberobello / Ostuni / Monopoli

May 7
Alberbello, Italy

Your full day of exploration begins with a drive to Alberobello, best known for its legendary trulli, the “White Cones of Puglia.” A trullo is an oddly shaped, squat white stone house with a conical stone roof. Some of the roofs are decorated with crosses, while others are adorned with stylized suns, geometric patterns, or shapes painted all in white to stand out against the gray stone of the roof. Visit several of Alberobello’s 1,500 trulli, which are used as restaurants, shops, lodging, and private homes. Enjoy lunch at a local restaurant.

Continue to Ostuni, one of the most stunning cities in southern Italy, famous for the dazzling effect of its whitewashed houses. Explore the jumble of staircases, small roads, alleys, and arches where hints of the Middle Ages can be seen around every corner. Return to Monopoli by late afternoon. 

Monopoli / Bari / Pescara / Ascoli Piceno

May 8
Hotel Residenza 100 Torri, Ascoli Piceno, Italy

Today, board a high-speed train in Bari for a scenic ride to Pescara, a lively city with one of the largest marinas on the Adriatic. Enjoy lunch at a lovely seaside restaurant.

Continue to Ascoli Piceno, a town of fewer than 5,000 people, that lies at the confluence of the Tronto and Castellano rivers in the Le Marche region. Called the “City of Travertine” for its honey-hued facades, Ascoli’s historic center is an architectural gem. Make a stop at charming Caffe Meletti, which features a wonderful Art Deco interior, for a taste of the local aniseed liquor. The terrace is the perfect place to relax and watch the bustle of activity in the Piazza del Popola. Check in to your Superior room at Hotel Residenza 100 Torri, set in the heart of the historic center. Enjoy a dinner of traditional cuisine at Risotrante Il Desco.

Ascoli Piceno (Hill Towns)

May 9
Ascoli Piceno, Italy

Today, explore some of the small towns that dot the hills surrounding Ascoli Piceno. Begin in Offida with a tour of Santa Maria della Rocca, one of the most notable buildings of the region. As the name suggests “on the rock” this Romanesque-Gothic church is perched on an outcropping at the edge of the city and is surrounded on three sides by steep ravines. The compact city center offers twisting alleys, a pretty piazza flanked with grand buildings, and an unhurried atmosphere. This is also a center for lace production and several vintages of wine that are highly prized throughout Italy. Continue to Moresco to see the unusual seven-sided watch tower—on a clear day views from the top stretch across the Adriatic to the coast of Albania. Drive through hills and valleys, with their patchwork of forest and cultivated fields, to Macerata to view the massive 7,000-seat Sferisterio arena, and take a stroll past the striking Renaissance architecture of the central Piazza della Liberta. Then attend a cooking class where you will learn to make the regional specialty, olive all’Ascolana, followed by lunch accompanied by regional wine. Your last stop of the day is Amandola, which boasts a well-preserved medieval center, and ancient walls, towers, and gates.

Ascoli Piceno / Fabriano / Gubbio / Perugia

May 10

After breakfast, head deeper into the hills to visit the charming town of Fabriano. Fabriano has been synonymous with high quality paper since the 12th century—a very prosperous industry that helped to fund grand medieval buildings that stand to this day. At the Paper and Watermark Museum, learn about techniques of paper production from ancient to modern times. After lunch, continue to the ancient town of Gubbio, which boasts a Roman theater, the grand 12th-century Duomo, and the massive 14th-century Palazzo dei Consoli, which has been converted into a museum.

In the late afternoon, arrive in Perugia, a city famous for its chocolates, and ancient architecture, from the Etruscans, the Roman Empire, and the Middle Ages. Settle into your Deluxe Room at the Sina Brufani, your home for the next four nights.  


May 11

Today, explore Perugia, a once powerful community that patronized artists and architects into creating a treasure trove of frescoes, paintings, and sculptures. Perugia today is a cosmopolitan city, yet with historical traditions and beautiful old buildings found around every picturesque corner. The monumental center of Perugia is the Piazza IV Novembre, the nucleus of the old city, with steep alleys leading to the ancient Etruscan walls and gates. Tour the Palazzo dei Priori; built in the 15th century, it was the home to political leaders and the powerful Bankers Guild. Inside the Palazzo, explore the National Gallery of Umbria, and its important collection of Medieval and Modern period art. Visit the Collegio del Cambio to view the work of the city’s most honored son, Pietro Perugino; he is also one of the earliest Italian practitioners of Renaissance painting in Italy.

After a break for lunch, taste some famous Perugia chocolate before enjoying some time at leisure to explore this warm and friendly city on your own. 

Perugia / Assisi / Torgiano / Perugia

May 12
Fried Olives, Italy

This morning drive to Assisi, the “crown jewel of the medieval hill towns,” and home to the patron saint of Italy, St. Francis. In the 13th century, the greatest masters of the time (Cimabue, Giotto, Simone Martini, and Pietro Lorenzetti), were summoned to Assisi to paint the new St. Francis Basilica, a church built to house the body of St. Francis,. Today, the Basilica di San Francesco is one of Italy’s most outstanding art museums, and you will tour all three levels of the cathedral. Then explore the Piazza del Comune, Assisi’s main piazza, graced with a medieval bell tower, elegant civic buildings from the 13th and 14th centuries, the stately Temple of Minerva, and the Gothic Basilica di Santa Chiara, where St. Clare of Assisi is buried.

After lunch, depart for Torgiano, the vineyard capital of Umbria. The Lungarotti Family, whose estate produces wines such as Rubesco, San Giorgio, and Torgiano Bianco, is the small town’s majority proprietor, with a stake in nearly every facet of its existence. Originally an Etruscan enclave and later a Roman fort, the town sits on a magnificent hilltop above the confluence of the Tiber and Chiàscio Rivers, looking out onto a panorama of fertile valleys and acres of vineyards. Visit the intimate Wine and Olive Oil Museum, and learn about the history of wine and its role in different cultures over the centuries. A companion museum houses an array of fascinating exhibits on the history of olive oil, its use in Umbrian cuisine, and the cultivation of olives. Return to Perugia in the late afternoon.

Perugia / Spoleto / Spello / Perugia

May 13
Spoleto, Italy

This morning, drive to Spoleto, a picturesque city positioned on a small hill, and crowned with the majestic fortress of Rocca Albornoziana. Spoleto is well known for its important archaeological, medieval, and Renaissance monuments, as well as the world-famous Spoleto Festival of the Arts. Begin with a visit to the 13th-century cathedral; adjacent to the great bell tower, the upper section of the Romanesque façade is decorated with a magnificent mosaic from 1207. The city is overflowing with Roman ruins and buildings, all so well preserved they were incorporated into later construction projects. The Basilica of San Salvatore is one such example, fusing the chamber of a Roman temple into early Christian architecture. See the landmark Ponte della Torre (Tower’s Bridge), spanning 750 feet and 262 feet above a deep gorge that separates Spoleto’s castle from the fortification tower on the other side. Dominating Spoleto’s skyline is the Rocca Albornoziana, built for Cardinal Albornoz from 1359–1370, and noted for its six sturdy towers as well as its 15th-century frescoes. Fully restored, the fortress is now a museum. Continue across the scenic Umbrian plain to the town of Spello for a delightful lunch of Umbrian delicacies and a tasting of Umbrian wines at Enoteca Properzio.

In the afternoon, tour the city of Spello, an ancient village whose history goes back to the Roman Age. Most buildings are of the local pink limestone quarried on Mt. Subasio, giving Spello a unique rosy hue, particularly at sunset. Visit the two well-preserved Augustan gates, which surround the town, and Porta Venere, with its towers Porta Consolare and Porta Urbicale. Then view the most precious treasure of Spello, the wonderful frescoes of Pinturicchio, in the church of Santa Maria Maggiore. Return to Perugia in the late afternoon.

Perguia / Orvieto / Rome

May 14

Bid arrivederci to Perugia, as you drive through Umbria to Rome. En route, make a stop in the medieval town of Orvieto. Starting at the heart of the town’s old quarter, take a stroll through the tranquil central square to the breathtaking Gothic Duomo of Orvieto, one of the most important examples of Gothic architecture in Italy. Enjoy one last lunch in the Umbrian countryside before arriving in Rome and checking in to your Deluxe room at The St. Regis Rome. Built in 1894 as the first luxury hotel in Rome, the hotel is within walking distance of the Spanish Steps, the Trevi Fountain, and Via Veneto. Every guest room has a unique hand-painted fresco depicting a Roman scene above the bed’s headboard, and a Murano glass chandelier. Enjoy the rest of the afternoon at leisure. In the early evening, view the “Eternal City” from a horse-drawn carriage. The ride ends at the hotel for a farewell cocktail and dinner with your Travel Director and fellow travelers to toast your journey to bella Italia

Rome / Departure

May 15

Board your independent homeward flight.