Italy Guided Biking & Walking Tour – Tuscany & Umbria

Tour Dates: 9 Days, September 9 – 17, 2019

This tour will be accompanied by Chuck & Judy Nichols

Welcome to biking in Italy with Nichols Expeditions!  We have added a walking tour option on this tour and we will have a local guide to lead the cyclists as well as the walkers each day.

Our Tuscany and Umbria Bike Tour will take you to the Italy of your dreams. Beginning in Assisi, Umbria, this remarkable bicycle tour traverses a countryside rich in history and scenery. Quiet country roads pass through majestic vineyards and lead to beautiful medieval towns where history comes alive. As we enter Tuscany, the crete landscape lends a softness to the horizon and the stately hilltop towns give us commanding views of the vineyards and surrounding countryside.

We rate the Tuscany and Umbria Bike Tour moderately difficult. There are E-bikes, hybrids and road bikes for rent, and each day a support van travels with us for anyone wanting a lift. We will be riding well-planned routes on quiet roads.  We rate the walking portion of the tour moderate.  Distances will vary between 6 –  12 km each day and more walking is available from the towns.

Join us for an unforgettable Italian cycling experience in Tuscany and Umbria where each day is filled with exceptional cycling, incredible hilltop towns, amazing Renaissance art, boutique lodgings, great food and exceptional wine. We hope to see you in Italy!

2019 Price: €2,700 Euros
pp double occupancy

Single Supplement: €350 Euros Hybrid Bike Rental: €175 Euros Road Bike Rental: €200 Euros Electric Bike Rental: €270 Euros
Price Includes:
  • 8 nights lodging
  • all breakfasts and 8 dinners
  • luggage transfers and van support with local guide/driver
  • maps and route directions
  • Chuck and Judy Nichols will personally accompany this tour and be there to handle bike maintenance and logistics.
Price Does Not Include:

International flights, bike rentals (you may choose to bring your own bike), lunches, beverages

Tour Difficulty

This is a moderately hilly bike tour that fit riders will enjoy.  We also have electric bikes available to ease the climbs. Our routes follow winding secondary roads and average 45 – 55 kilometers per day, with more riding available for the hearty.

  • Difficulty: Moderately Hilly
  • Road Conditions: Asphalt
  • Road bike, Hybrid bike and electric bikes are available

Tour Highlights

  • Iconic Medieval towns
  • Excellent cuisine and wines
  • Stunning landscapes
  • Charming accommodations
  • Great cycling


Day 1: Arrival

We meet in Assisi for a mid afternoon orientation and bike fitting. Join us for a Welcome dinner. Airlines from a variety of European cities fly into Perugia and the airport is close to Assisi. Trains from Rome, Florence and Milan service Assisi. Overnight in Assisi.

Day 2: Assisi Loop 

Cyclists: Enjoy the back road to Spello, a perfectly preserved town with Roman origins. A visit to Bevagna, another wonderful medieval village & a special wine tasting are afternoon highlights. Ride: 45 kms

Walkers: Walkers will visit to Spello followed by a walk from Bevagna to the Dionigi wine cellar.

The entire group will meet for lunch and a wonderful wine tasting in a family operated vineyard.

Overnight in Assisi.

Day 3: Assisi – Poggiolo  

Cyclists: Our route through Umbria is highlighted by a visit to Deruta, a town famous for its ceramics. Ride: 52 kms

Walkers: Today’s walk will be on a portion of the Valbabrrica where St. Francis walked from Perugia to Assisi

Overnight in a special villa in Poggiolo.  Tonight will be one of the best dinners of the trip.  We’ll go to a nearby farmhouse of one of our friends who used to be a chef in a restaurant.

Day 4: Poggiolo – Cortona 

Cyclists: A curvy road will lead us to Lake Trasimeno whose shores teem with migratory birds. We’ll cycle near beautiful olive groves to Cortona, the setting for Francis Mayes’s best seller, Under the Tuscan Sun.  Ride: 55 km

Walkers: Transfer to the hills above Cortona and enjoy a beautiful walk to the hill town of Cortona.

Overnight in a wonderful hotel just a stone’s throw from the Piazza.

Day 5: Cortona – Montepulciano 

Today we will enter Tuscany through the magnificent wine country of Montepulciano, one of Tuscany’s highest hilltop towns. Renowned for its Vino Nobile, Montepulciano also boasts a unique blend of Renaissance architecture and is perched on a narrow ridge of volcanic rock. Overnight in Montepulciano.

Day 6: Montepulciano 

Today most folks will enjoy spending the entire day visiting Montepulciano.  Our guide will take us on a tour of the city including the underground channels, wine tasting options, Duomo, multiple Piazzas.

Cyclists: Can opt for a morning  loop ride to Montefollonico, a lovely 12th century hilltop town. We’ll also reach Montepulciano by lunch, where we’ll have time to visit the town and can also sample the Vino Noble wines in many of the local wine shops.

Walkers: plenty of walking on the tour of Montepulciano!

We’ll return in time to enjoy an afternoon swim and relax in our amazing villa. We return to our same lodging near Montepulciano.

Overnight in Villa Cicolina

Day 7: Montepulciano – Bagno Vignoni 

Cyclists: Today we ride an amazing Cyprus lined downhill to Monticchiello, climb to Pienza for lunch, descend to San Quirico and continue to our lodging near Bagno Vignoni, a famous Roman spa town. Ride: 50 km

Walkers: Transfer to Pienza where you will begin your walk that crosses a beautiful region of rolling hills, oak woods and lovely villages. Your destination tonight is Bagno Vignoni, a thermal spa town where the main square is a basin of steaming hot water. This is considered by many to be the most charming village in all of Tuscany!

Our lodging is a romantic country inn that is a finely restored 16th century horse and carriage station. Overnight in Bagno Vignoni.

Day 8: Bagno Vignoni to Montalcino

Cyclists: Our ride takes us to the gorgeous abbey of Saint Antimo, a well preserved 12th-century church that still echoes with Gregorian chants. We finish our ride among the vineyards en route to Montalcino, a 13th century paradise and the home of Brunello wine. Our ride is shorter today and we plan to arrive in Montalcino at lunch time, so you will have plenty of time today for shopping and sampling some of the fine Brunello wines. Ride: 30 km

Walkers: Today’s walk takes you along dry river beds in a rather wild environment to reach the Abbey of St Antimo. Few of the monastic buildings remain, but the 12th-century church is well preserved and is an outstanding example of the Italian Romanesque.

Overnight in Montalcino.

Day 9: Departure

After breakfast, we will transfer you to Siena where there is good train access to all of Italy.  Siena is a wonderful city and worth spending a night if you have the time.