Italy Guided Biking Tour – Tuscany

Tour Dates: This tour is available as a Charter Tour or Self-Guided Tour.  

This tour will be accompanied by Chuck & Judy Nichols

Welcome to biking in Italy with Nichols Expeditions!

Our Tuscany Bike Tour will take you to the Italy of your dreams. Beginning in Cortona, 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. The iconic crete landscape in Tuscany 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 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.

Join us for an unforgettable Italian cycling experience in Tuscany  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!

2022 Tour Cost: starting at €2600 euros per person, double occupancy, for a group of 8+ guests.

Price Includes:
  • 6 nights lodging
  • all breakfasts and 6 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 Cortona.  Join us for a Welcome dinner. Book your flight into Florence or Rome and and there is good train service from both cities to the start of the trip. Cortona, the setting for Francis Mayes’s best seller, Under the Tuscan Sun and a beautiful hill town to begin our tour.
Overnight in Cortona.

Day 2: Cortona – Montepulciano  – Ride 50 km

Today we will ride 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.  We’ll settle into one of our favorite villas outside of Montepulciano for 2 nights.

Overnight at Villa Cicolina.

Day 3: Montepulciano – loop ride 40 – 60 km

In the morning we will enjoy a 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.  Our guide will take us on a tour of the city including the underground channels, wine tasting options, Duomo, multiple Piazzas.

We’ll return to our lodging in the late afternoon with time to swim and relax in our amazing villa. We return to our same lodging near Montepulciano. Overnight in Villa Cicolina

Day 4: Montepulciano – Bagno Vignoni   Ride 50 km

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.

Our lodging is a romantic country inn that is a finely restored 16th century horse and carriage station where we will spend 2 nights. Overnight in Bagno Vignoni.

Day 5: Bagno Vignoni  loop ride 60 km

Our loop ride today is one one of the most beautiful in all of Tuscany!  We ride to the gorgeous abbey of Saint Antimo, a well preserved 12th-century church that still echoes with Gregorian chants. We continue to Montalcino riding past the vineyards of the famous Brunello wines. We will have lunch in Montalcino before returning back to our villa in Bagno Vignoni.

Day 6 – Bagno Vignoni – Siena – ride 60 km

The road winds through hills and oak woods to Monte Oliveto Maggiore, the most impressive abbey in Italy.  We’ll finish the ride with amazing vistas of the crete landscape and then it’s on to Siena, our final destination. Siena is one of the most beautiful medieval cities in Italy. Its famous Piazza Del Campo is an open-air museum and architectural gem.  We’ll have our farewell dinner near the famous Campo piazza in Siena.

Overnight in Siena.

Day 7 – Departure

Your tour ends after breakfast. There are both train and bus stations in Siena with easy access to both Rome and Florence.

Siena is a wonderful city worth spending an extra night if you have the time.