The Best of Umbria and Tuscany

You will be met at the train station and driven to your accommodation for the night. In the afternoon there will be time to see some of the city’s artistic highlights. You could visit the magnificent Basilica of San Francesco, painstakingly restored after the recent earthquake.  The basilica complex is composed of two churches built one above the other, the lower one dating from 1228 – 1230 and the upper one from 1230 – 1253. Inside the lower church are beautiful frescoes by famous artists such as Lorenzetti and Giotto, and the wonderful Chapel of St. Martin is completely frescoed by Martini with scenes of the saint’s life. It’s one of the most beautiful works of the painter and a masterpiece of Gothic art. It’s the upper church, however, where you’ll find Giotto’s frescoes illustrating the life of St. Francis and one of the most important cycles of paintings in the history of Italian art. Unforgettable masterpieces! In the Piazza del Commune you’ll see a 14th century pulpit and the Roman Temple of Minerva with a well-preserved exterior.

Today you’ll cycle through beautiful olive groves along a ridge with delightful views to the small town of Spello, a perfectly preserved town still encircled by Roman walls on the Subasio slopes. Later you’ll ride through olive groves with no major uphills except for the final climb back to Assisi. On the return trip you can visit Bevagna, going through the most famous wine area of Umbria, the Montefalco Sagrantino “Denominazione di Origine Controllata e Garantita” (DOCG). Alternatively, you could decide to stay in Assisi today and have more time to explore the fabulous “pink city.”

Elevation gain: 1646 Ft (502 m)

As you cycle through the heart of Umbria on your way to Lake Trasimeno, you’ll pass through two of the region’s cultural treasures.
Your first stop is Deruta, world-famous for its beautiful ceramics that have been crafted here for centuries. Take a little time to wander through its charming streets and browse the many workshops filled with colorful hand-painted pottery.

Elevation gain: 1391 Ft (424 m)

Next, you’ll reach Torgiano, home of Umbria’s finest wines produced by the Lungarotti family. If you wish, you can visit their fascinating wine museum, where ancient tools and medieval presses tell the story of winemaking in the region.

From here, the route continues through soft rolling hills and quiet villages, surrounded by olive groves and vineyards.

It’s a scenic but fairly demanding day with several ups and downs, so you’ll be glad to arrive at Borgo Mandoleto, near Solomeo also known as the “cashmere village.” Enjoy a well-earned rest at this welcoming countryside retreat after a day full of beauty and culture.

Today you’ll glide by Lake Trasimeno, whose shores shelter migratory birds that nest in the bamboo that surrounds the lake. All around you’ll notice lovely villages surrounded by olive groves. There will be time to take a boat to Isola Maggiore where old ladies still weave traditional lace, fisherman mend their nets, and where you can savor some delicious fresh fish at Sauro’s Fish Restaurant. You can also climb to the highest point on the island, crowned by the 14th century Church of San Michele. Later you’ll continue and cross into Tuscany while biking to your hotel in Cortona, the setting for Frances Mayes’ best seller “Under the Tuscan Sun.” Cortona is a small but fascinating city in the province of Arezzo, situated on a commanding hill overlooking Lake Trasimeno. Its massive walls, still in great part preserved, are said to be 3,000 years old. It was one of the twelve cities of Etruria and in its vicinity there are many ruins and Etruscan tombs. It’s a wonderful place for an afternoon sightseeing stroll.

Elevation gain: 2457 Ft (749 m)

Today you’ll cycle in Tuscany through the wine country of Montepulciano. The route will lead you past some of the small Chiusi and Montepulciano lakes. Then you’ll head for beautiful Montepulciano, one of Tuscany’s highest hilltop towns and known worldwide for its fabulous red Vino Nobile wines. You can visit the superb Cantina del Redi with its vaulted cellars in town, or have a taste of the Nobili wines at Crociani winery, a small, friendlier “enoteca.”

Elevation gain: 1702 Ft (519 m)

You’ll pedal through many wonderful places today. After a visit to the San Biagio Church you’ll ride to the perfect Renaissance town of Pienza, an architectural jewel famous also for its wonderful cheese, the pecorino di Pienza. Pienza was planned and built from 1459 – 1462 by the famous Florentine architect Gambarelli at the request of Pope Pius II. Walking through the narrow streets of this walled city is a photographer’s delight, and the cathedral and the Pope’s residence are well worth a visit.  You’ll continue on a small road to Monticchiello, a tiny walled village in the middle of the incredible Crete Senesi landscape with its barren hills that appear eerie in some lights. Later you’ll make a short detour to the ancient spa of Bagno Vignoni. You can soak your feet in the warm sulfurous waters – appreciated since Roman times – that bubble up into a large pool constructed by the Medici family in the picturesque Piazza. From here you’ll pedal on to Buonconvento where you’ll spend the night in a charming agriturismo or in a modern 3-star hotel in the city.

Elevation gain: 3303 Ft (1007 m)

After a steep climb, you’ll pedal through the spectacular eroded hills of Crete Senesi and then through thick cypress and olive groves as you approach the 14th century Benedictine monastery of Monte Oliveto Maggiore, one of the best known Benedictine monasteries in Tuscany. The monastery was founded for hermits in 1313 and was suppressed by Napoleon in 1810  After restoration it was made a national monument, though some monks remain as caretakers. Ancient pines surround the cloister and the walls are decorated with gorgeous frescoes detailing the history of St. Benedetto and the Benedictine Order. You can contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict, then continue on to Asciano, a small town in the heart of the Crete Senesi. From there it’s to Siena, one of the most beautiful cities in Italy. After Florence, Siena (once Florence’s most powerful rival) is by far the most interesting town in Tuscany and offers many treasures. Highlights are the dazzling Cathedral and the Palazzo Pubblico, both gorgeous Gothic buildings, and the Piazza del Campo, one of the most remarkable squares in Italy and the site of the yearly “Palio” horse races in July and August. You can stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for your farewell dinner tonight.

Elevation gain: 2480 Ft (756 m)

You can walk around Siena and visit some of its museums before you depart. It’s a short cab ride from the hotel to the train station in Siena.