Italy Guided Biking Tour – Tuscany

2023 Tour Dates: September 13 – 20

This tour will be accompanied by Chuck & Judy Nichols

Welcome to biking in Italy with Nichols Expeditions! Riding across Italy is a rare chance to see, feel and taste the wonderful differences Tuscany, Umbria and Le Marche have to offer. The food and wine is legendary and the scenery is the Italy you dream about. Beginning in Cortona, Tuscany, we ride through vast rolling hills covered with wheat fields and vineyards and topped with picturesque hilltop towns. We cross into Umbria and enter the “Green Heart” of Italy. Vineyards and olive groves share space with ancient walled cities, Etruscan tombs and Renaissance Art. Le Marche is Italy’s hidden gem and you will get the feeling you have discovered an un-touristy region known only to Italians. We will pass through the Apennines and cycle the forested valleys that lead to Pesaro on the Adriatic.

The accommodations we have selected reflect the warmth and hospitality of the region and feature a splendid assortment of charming country inns that provide a real sense of living history. The scrumptious meals served on the tour are made with local ingredients and seasoned with tasty olive oil and fresh herbs. You will have a chance to sample some of Italy’s best cheeses and most famous wines.

2023 Tour Cost: TBA

Price Includes:
  • 7 nights lodging
  • 7 breakfasts and 7 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.  Our routes follow winding secondary roads and average 40 – 55 kilometers per day.

  • 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 in Cortona

We meet in Cortona. We’ll have a late af ternoon orientation and bike fitting. Book your f light into Florence or Rome and there is good train service f rom both cities to the start of the trip. Cortona, the setting f or Francis Mayes’s best seller, Under the Tuscan Sun and a beautif ul hill town to
begin our tour.

Day 2: Cortona – Citta di Castello – Distance: 52 km, elevation gain: 720 meters

We’ll take the backroads departing the Tuscan countryside and enter Umbria. We will cycle among the green hills of the Upper Tiber Valley, in luminous landscapes and an intensely cultivated countryside, to the art city of Città di Castello. Enclosed in a ring of Renaissance walls and surrounded by arable farmland, Città di Castello’s streets are lined with grand palaces, yet still has a genuine, lived-in charm. The town occupies the site of ancient Tiberinum . We’ll
spend 2 nights here.

Day 3: Citta di Castello – loop ride Distance: 40 km, Elevation gain: 645 meters

On our loop ride we’ll visit the many small villages with a highlight being, Santa Maria Tiberina. Full of charm, this village is described as having ancient Etruscan roots but a fully medieval heart. It is situated in a very panoramic position, offering unparalleled views. Fortresses and castles dot the summits. In between are patches of olive groves and vineyards. It’s a postcard -like setting.

Day 4: Citta di Castello – Sant’Angelo in Vado Distance: 48 km, Elevation gain: 875 meters

Sant’Angelo in Vado is one of the most f ascinating places to visit in the province of Pesaro e Urbino. The town is of Roman origin and located in the high valley of the Metauro River and surrounded by some of the most the picturesque countryside of Le Mar che region. The original Tif ernum Mataurense can still be seen f rom the spectacular ruins of the ancient Roman Villa of Domus del Mito with its magnif icent mosaics which date from the I century BC. This is the most important archaeological f ind of the last 50 years in this the region.

Day 5: Sant’ Angelo in Vado – Urbino Distance: 46 km, Elevation gain: 650 meters

Winding countryside roads take us to Urbino. Perched high up on one of Le Marche’s hills, Urbino is a city that delights both history buff s and foodies. Its architecture, art, and history rival any of Tuscany’s f amous masterpieces and you’ll surely understand why this is a UNESCO Heritage Site.

Day 6: Urbino – Gradara Distance: 50 km, Elevation gain: 700 meters

Today’s ride takes us across the region of the Marche to the border of the Northern Italian region of Emilia-Romagna and then we return to the Marche to the fortified medieval village of Gradara. With a majestic castle that, throughout the centuries, has been home to some of Italy’s most famous noble families, Gradara is a delight to explore. Especially, if you have always wanted to find yourself in a fairytale-like medieval setting that was declared Italy’s most beautiful village in 2018.

Day 7: Gradara to Pesaro – Distance: 30 km, Elevation gain: 450 meters

Today’s ride takes us to Pesaro on the Adriatic coast. We enter the town on a bike path and get to see f first-hand why Pesaro is known as the”City of Bicycles”, thanks to its big net of bicycle paths. Pesaro received this award by Legambiente, the most important ecologist society in Italy, in 2015, because it is the city with the biggest bicycle use in Italy. We will spend our f inal night at Hotel Vittoria, the most charming hotel in the town with its own private beach.

Day 8: Departure

There is a train station in Pesaro and we can also assist with transfer suggestions to Florence, Bologna, Rome and Venice airports are all options.