Umbria to Tuscany and Cinque Terre
September 20–October 2, 2022 (13 days)
with Optional Rome Extension
September 16-20, 2022
✔ Enjoy some of Italy’s most picturesque landscapes of verdant valleys, ancient vineyards and olive groves as you journey from the less-travelled country roads of Umbria and Tuscany to the seaside villages of Cinque Terre on the rugged Italian Riviera coastline.
✔ Stroll Assisi’s old town, explore the sun-dappled hill-towns of Gubbio, Todi, Volterra and the Etruscan town of Orvieto, stand inside one of Tuscany’s most ancient piazzas in Siena, admire the famous towers of San Gimignano and discover Florence, the “Cradle of the Renaissance”.
✔ Experience the Italian “dolce vita” as you delight in regional specialties and Italian wine.
✔ Optional pre-tour to the magnificent city of Rome
Depart Rome and proceed to Assisi, a well-preserved medieval hillside town spread across the slopes of Mount Subasio in Umbria. The UNESCO-listed town was the home of St. Francis, who left a position of wealth and turned to a life of poverty, chastity and obedience, founding the order whose followers became known as Franciscans.
See the Basilica of St. Francis during your guided tour. (D)
Assisi © Magalex
Today head north for a guided tour of UNESCO-listed Urbino, a vibrant university town, birthplace of the artist Raphael and one of the cultural capitals of the Renaissance. Urbino’s immaculate historic centre appears to have changed little since the 15th century, when it enjoyed a golden age under the powerful Duca Federico da Montefeltro. In this idyllic hill town, houses and palaces of weathered brick and pantiles cluster around steep narrow streets, surrounded by misty mountains and green and yellow hills.
Continue to Gubbio, a beautiful city that shows traces of different dominations, from the Roman to the papal. Highlights include the cathedral, the Ducal Palace, the Capitán’s Palace and the Palazzo dei Consoli. (B,D)
Gubbio © Gino Cianci, Fototeca ENIT
This morning enjoy a guided tour of Orvieto, set atop a 325-metre outcrop of volcanic tufa rock amidst vineyards, olive groves and cypress trees. Undernearth the city are thousands of caves dug out during Etruscan, Medieval and Renaissance times. The Chapel of San Brizio, one of Italy’s most famous Gothic cathedrals, is home to wonderful frescoes by Signorelli.
Continue to medieval Todi, often described as Umbria’s prettiest hill town, with views over the Tiber Valley and its river. Todi is encircled by three sets of concentric walls, each from a different historical era – the innermost are Etruscan in origin, the middle ones date from the town’s Roman period, and the “new” medieval walls survive from Todi’s heyday as a prosperous centre in the Middle Ages. (B,D)
Depart Assisi and proceed to Lake Trasimeno. With its placid waters lined by rolling vineyards and olive groves, the heart-shaped Lake Trasimeno is one of the most picturesque corners of Umbria. Enjoy a boat tour on the lake including lunch on Isola Maggiore.
Afternoon arrival at Colle di Val d’Elsa, Tuscany – your home for the next five nights. “Colle” is known for its medieval alleys, its production of crystal glassware and as the birthplace of legendary 13th-century architect Arnolfo di Cambio, who built Florence’s Palazzo Vecchio. The town is clearly divided between Colle Alta (“High Colle”) – the original medieval buildings – and newer Colle Bassa (“Low Colle”), strung around the base of Colle Alta’s long-inhabited rocky outcrop. A transparent lift runs between the two, via an ancient tunnel through the rock. (B,L,D)
Morning visit to San Gimignano – the “City of Beautiful Towers”. In the 12th and 13th centuries more than 70 towers rose above the tile roofs of the hill town, built partly to defend against outside invaders, but mostly as command centres and status symbols for San Gimignano’s powerful families. A dozen towers remain and stand tall over the surrounding vineyards, giving the town the look of a fantasy kingdom. Enjoy an unforgettable ice cream at Master Sergio Dondoli’s gelateria. Among the world champion’s famous creations are his Crema di Santa Fina gelato (cream of saffron and pine nuts) and Champelmo sorbet (pink grapefruit and sparkling wine).
In the afternoon, stop in the enchanting Gothic city of Siena for a guided tour of the old town. See one of Italy’s most beautiful squares, the seashell-shaped Piazza del Campo, on which the famous horse-race – the Palio – takes place each year. (B,D)
Explore the alabaster mountaintop town of Volterra. This former Etruscan settlement offers a splendid view of the surroundings. Enjoy a light lunch at a family-run farmhouse which procudes saffron.
Continue to Lari, a lesser known medieval Tuscan town. The Famiglia Martelli has been making pasta here since 1926. Enjoy a tour of the smallest pasta factory in the world. (B,L,D)
This morning, take a cooking class at a charming castle located in the middle of the Tuscan vineyards.
After lunch, discover the beauty of the Chianti region and proceed to a vineyard for a tour and wine tasting. You will also sample their homemade olive oil with bruschetta, mixed salumi and Pecorino cheese. (B,L,D)
Proceed to Florence, cradle of the Renaissance, for a half-day guided tour. On the banks of the Arno river, the capital of Tuscany has hardly changed and its narrow cobbled streets are a feast of elegant 15th- and 16th-century palazzis, fresco-decorated churches, marble basilicas and world-class art museums. Highlights include Palazzo Vecchio, Ponte Vecchio, the Duomo, the Uffizi Gallery and the Galleria dell’Accademia, home of Michelangelo’s David statue.
Afternoon at leisure to further explore Florence on your own, before returning to Colle for dinner. (B,D)
Depart Colle and head to Pisa for a walking tour of the historic centre including the Campo dei Miracoli. See the Leaning Tower of Pisa, known worldwide for its nearly four-degree lean.
Continue to the elegant city of Lucca, famously known as the city of a hundred churches, due to its large amount of historical religious structures. Its medieval walls encircle most of the historic old town. The only major city in Tuscany to resist the might of Florence, Lucca finally succumbed to the forces of Napoleon and was ruled for a time by his sister Elisa Bonaparte. In your free time, you might want to visit Lucca Cathedral, Piazza dell Anfiteatro or take a walk on the city walls. Late afternoon arrival in Sestri Levante – or “Sestri”, as known by the locals – on the Ligurian coast. (B,D)
Leaning Tower, Pisa © Steven Lek
Nestled between the Mediterranean’s blue waters and the rugged coastal mountains are five fishing villages that seem to cling precariously to the clifftops in a collage of rainbow hues. Together, Monterosso al Mare, Vernazza, Corniglia, Manarola and Riomaggiore are known as Cinque Terre (Five Lands). Their medieval architecture and age-old system of agriculture are protected as a UNESCO World Heritage Site. Discover these picture-book villages via train and boat (according to weather and sea conditions) and experience the daily life of this beautiful corner of Italy – from the colourful fishing boats, cobblestone streets and alleyways to the wine, olives and citrus fruit produced locally. (B,D)
Manarola, Cinque Terre
Today is dedicated to the “three pearls of Tigullio”. Start with a walk around the historic fishing village of Rapallo, and learn how to make the most classic Ligurian pasta dish – Trofie al pesto Genovese. Enjoy the results of your culinary efforts at lunch.
One of the best ways to see the glamourous Italian Riviera, with its colourful villas and cobalt waters studded with yachts, is from the sea. Take a ferry to Portofino, known all over the world for its piazzetta surrounded by pastel coloured houses, pointed-arched porticos and elegant boutiques. This simple fishing village has become a VIP holiday destination and is one of the most loved Italian places by the international jet set. Finally, take a boat to Santa Margherita Ligure, an elegant Roman town with brightly coloured houses and Liberty style hotels. Return to Sestri Levante in time for dinner. (B,L,D)
Depart for Milan, world-class stop on the international fashion stage and a wealthy city of glamourous people and stylish shopping streets. Milan is also rich in history, from its Roman ruins and soaring Duomo to a host of ancient churches, medieval castles, Renaissance palaces and Leonardo da Vinci’s Last Supper.
Enjoy a guided tour including the spectacular Gothic Duomo – the finest of its kind. See the Teatro alla Scala, one of the most famous opera houses in the world, as well as the Galleria Vittorio Emanuele II arcade, the most visited meeting point of the Milanese with its elegant shops and cafés. Celebrate the conclusion of the tour with a farewell dinner at a local restaurant. (B,D)
Galleria Vittorio Emanuele II, Milan
Transfer to the airport for your flight(s) home. (B)