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The Best of Tuscany and Umbria - Biking - Itinerary

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Day 1: BENVENUTI! Arrival in Montepulciano

The Zephyr Guide will meet you in Montepulciano, providing you with route notes and maps, fitting you to your bicycle, and answering any questions you have.

Ride Details: There is no ride today as you can arrive in Montepulciano any time you wish.

About the Town: Montepulciano is a medieval walled town built on a limestone ridge, with many beautiful Renaissance style palazzi and churches. The town is very pedestrian-friendly and a great place to walk.

Special Event of the Day: Taste the famous Vino Nobile wine from a streetside cafe in the middle of town.


The Day's Highlight: This is a fantastic loop route through the heart of Central Tuscany. Pienza, the dream town of Pope Pius II, is a place of architectural masterpieces, beautiful ceramics, and delectable pecorino (sheep's) cheese. The long route extension includes a stop in Bagno Vignoni, famous for its thermal springs!

Ride Details: MODERATE - 45 km (25% gravel, 75% asphalt) rolling hills with a longer route (65 km) available. The ride up to Pienza is a tough climb but well worth it!

Special Event of the Day: Shop for lunch in a market in Pienza and eat while overlooking the valley on top of the city walls.


The Day's Highlight: A beautiful ride including a stretch along the Lake Trasimeno bike path.

Ride Details: MODERATE - 47 km (100% asphalt) through rolling hills with a big final climb to the town of Cortona. An optional longer route of 52 km is available.

About the Town: Cortona is an ancient Etruscan hill town close to the border with Umbria. The city boasts an historic piazza with Etruscan walls and Renaissance churches and was described in the book "Under the Tuscan Sun."

Special Event of the Day: Walk along the ancient city walls of Cortona, imagining the history as you see the 5th Century BC base created by the Etruscans.


The Day's Highlight: Views of the Chiana valley and Lake Trasimeno from the slopes of the Apennine foothills before enjoying the gorgeous descent to the Upper Tiber Valley.

Ride Details: MODERATE-DIFFICULT - 75 km (100% asphalt) with a long climb to the pass and another steeper climb to the village of Montone. A longer route of 104 km is available.

About the Town: Umbertide represents your first night in Umbria. Unlike many towns in the area, it rests on the flat Tiber River valley rather than on a hilltop. The hotel is slightly out of town.


The Day's Highlight: A great ride along the Tiber Valley, passing medieval castles and abbeys, on a road flanked by fields and forests to the slopes of Mt. Subasio, where the fabulous Roman and Medieval town of Assisi lies.

Ride Details: EASY - 54 km (100% asphalt) flat ride with some small hills, including the final significant climb to Assisi. A longer route of 86 km which includes two mountain passes is available.

About the Town: You will see the town of Assisi from far off on the plains, situated as it is on the slopes of Mount Subasio and capped with both a castle above town and the giant basilica of Saint Francis. Famous as the home of Saint Francis, Assisi attracts many visitors from throughout the world.

Special Event of the Day: Hike up from Assisi's town square, leaving the crowds behind as you find a perch to enjoy the solitude of the Umbrian valley.


The Day's Highlight: The ride along the Via degli Olivi "Olive Grove Way" to Spello traverses the lower slopes of Mount Subasio, with wonderful views of the plains below.

Ride Details: EASY - 31 km (91% asphalt) ride that actually loses elevation during the day. The first 10K is on a rolling road traversing the slopes of Mt Subasio to Spello. From Spello the route goes down into the valley and then crosses the Umbra Vale to Bevagna. No longer route is available this day so enjoy the fabulous towns!

About the Town: Bevagna is a beautiful small Roman town surrounded by a moat and city walls. Unlike most of the towns on the tour, Bevagna is situated in the plains rather than on a hill.

Special Event of the Day: The picturesque town of Spello is the ideal location for a lunch stop. Pick one of the many restaurants along the main street of town.

Day 7: BEVAGNA loop

The Day's Highlight: Take a day off from riding and relax in Bevagna or make a loop ride to one of the wonderful wine towns in the vicinity.

Ride Details: MODERATE to DIFFICULT (depending on the ride). Two loop routes are available. The short option of 24 km (100% asphalt) takes you to the wonderful town of Montefalco, again perched over the valley and surrounded by vineyards and olive groves. The longer ride of 90 km takes you to Todi, voted as one of the most livable cities in Europe.

Special Event of the Day: If you choose to do a loop ride, reward yourself at lunch with a glass of the superb Sagrantino red wine, pride of Umbria. The short loop takes you past several wineries.


The Day's Highlight: If you wish to ride the short route, this will be one of the flattest rides you will experience in Italy. For longer routes, the flat riding is broken up with tough but memorable climbs to the hilltop towns of Montefalco (famous for wine) and Trevi (famous for olive oil). Enjoy!

Ride Details: EASY - 33 km (100% asphalt) through the flat plains with just a slight uphill to Spoleto. A longer route of 50 km includes steep climbs to Montefalco and Trevi.

About the Town: Although Spoleto has some fantastic Roman ruins above town, it is a perfect display of a medieval city with its winding streets and dark alleys. It also has some great cafes and nightlife and so is a perfect place to spend two nights and finish the tour.

Special Event of the Day: On the long route, the winding climb through olive groves to Trevi makes you feel as if you are on the Giro d'Italia bike race while the fast descent makes it all worthwhile.

Day 9: SPOLETO Loop (or Rest)

The Day's Highlight: This is another option day where you can choose to tour the wonderful Roman and medieval town of Spoleto or take one of three rides in this mostly unvisited area of Umbria.

Ride Details: EASY to DIFFICULT (depending on the ride). You will have three loop ride options from which to choose: 19 km, 39 km, or 69 km. All are 100% asphalt. The short loop is a two-hour jaunt while the long route includes a 700 meter elevation gain through the mountains east of Spoleto. Beautiful!

Special Event of the Day: Ask your hotel clerk to make a dinner reservation at a fantastic local restaurant and celebrate your biking accomplishments with fresh local pasta, olive oil, and wine.

Day 10: Final Morning Ride and Departure

If you rode yesterday, you might want to take the morning off before you depart Spoleto for your future travels. Alternatively, choose either the short or medium loop that you didn't do yesterday.

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