Italy Guided Biking Tour – Tuscany

2024 Tour Dates: September 15 – 22

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. 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.

The classic charm of Italy is picture book perfect with stately farmhouses set amid a patchwork of green fields silhouetted with Cyprus trees. Vineyards line the quiet country roads and acres of sunflowers bathe in pastel sunlight. Our route passes through several renowned wine regions as it takes us to some of Italy’s most interesting hill top towns. Enjoy strolling the narrow winding streets that lead to magnificent cathedrals and grand plazas with charming shops and sidewalk cafes.

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.

2024 Tour Cost: €3.000 Euros per person double occupancy

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 tour is for experienced riders. This region of Italy is quite hilly and each day you can expect 50 to 80 km of riding. Many days include hill climbs of more than 3,000 feet. If you are not accustomed to this amount of climbing, we strongly suggest that you rent an ebike.

  • 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 afternoon orientation and bike fitting. Book your flight into Florence or Rome and there is good train service from both cities to the start of the trip. Cortona, the setting f or Francis Mayes’s best seller, Under the Tuscan Sun and a beautiful hill town to
begin our tour.

Day 2: Cortona – Cortona Loop ride (50 km, Ascent 1,000 m.)

Our ride today dips into Umbria where you’ll enjoy scenic overlooks of Lake Trasimeno. We’ll ride seldom used backroads returning to Cortona for one last night.

Day 3: Cortona – Montepulciano – Monticchiello – Bagno Vignoni (65 km, Ascent 900 m)

We ride through the iconic hilltowns of Montepulicano and Monticello. Cycling through the vineyards of Vino Noble, having lunch in a piazza iin Montepulicano, cycling down the famous switchbacks to Monticchiello for a gelato stop en route to Bagno Vignoni – life is good! Our home for the next 2 nights is in the countryside – a little paradise with a swimming pool and we are just a short walk away from the hamlet of Bagno Vignoni.

Day 4: Bagno Vignoni – Montalcino – Sant Antimo Abbey loop ride (55 km, Ascent 900 m)

Layover day. This will be a great spot to satisfy a variety of desires for the day. Bagno Vignoni is a short distance away and this is a spa town. There is also a wonderful loop ride to the vineyards of Montalcino, a 13th century paradise and the home of Brunello wine. The route continues to the abbey of Saint Antimo, a well preserved 12th-century monastery that still echoes with Gregorian chants. Then you’ll return to Bagno Vignoni for another night.

Day 5: Bagno Vignoni – Sovana (70 km, Ascent 1500 m)

You’ll cycle up to Arcidosso on the slope of Mt. Amiata and then enjoy a great downhill as you enter the Maremma region in the very southern tip of Tuscany where the vegetation and climate are greatly influenced by the Mediterranean. Your destination for the next 2 nights is the tiny hamlet of Sovana.

Day 6: Loop Ride Sorano – Ptigliano, Saturnia (75 km, Ascent 1200 m)

Cycle the splendid route in the Maremma region of Tuscany. This spectacular stretch of roads is literally carved into the tufa There are many options today to shorten the route if you prefer. Sorano is a very picturesque ancient city perched on a cliff. Saturnia is known for its thermal baths.

Day 7: Sovana to Port Santo Stefano, on the sea! (70 km, 800 m)

Our final ride takes us from the Maremma region of Tuscany all of the way to the Mediterranean. Our hotel tonight is on a small beach on the sea.

Day 8: Departure Tour ends after breakfast

There is a train station in nearby Orbetello and private transfers can also be arranged.