Tuscany Umbria Spirit

The simple and the sacred.

Saints. Artists. Wines.

Tuscany is perfection and Umbria is its humble neighbor; the home of Saints Francis, Clare, and Benedict . The two regions bring balance and depth to our Italian bike tour that is laced with spirit. Bike the emerald green hills lined with tall, narrow Cyprus trees and criss-crossed with vineyards. Explore churches enriched by frescoes and paintings. Experience the simple ingredients of the life here and see how they become part of a deeper rhythm and an elevated lifestyle: The wonderful Tuscan wines of Montalcino, Montefalco, and Montepulciano. The importance of Umbria’s favored olive oils. And the care taken to produce artisanal cheeses, each with a unique character.

Bike the soul of Italy with Siciclando and be inspired!

General Info


$ 5220


8 days/7 nights



Cycling Ability

Active Cyclists

Siciclando Equipment

Choose Your Bike!

Airport Options

​Roma Fiumicino Leonardo da Vinci or Firenze-Peretola Amerigo Vespucci Airport

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2020 Tour Dates

April 18

Open/awaiting reservations

September 6

Open/awaiting reservations

Do you have a different date in mind?

Email us the tour and dates that work for you.

Pedal picturesque landscapes: rolling green hills, ancient olive groves, and along Lake Trasimeno.
Sample the chocolate of Perugia – where Bacios were born
Bike “Under the Tuscan Sun” and stroll the winding streets of charming Cortona
Explore Tuscany’s wonderful red wine country – Brunello di Montalcino, Vino Nobile di Montepulciano, and Chianti
Taste the true Pecorino di Pienza sheep cheese – a highlight of this area
Enjoy Siena! Home of the famous horse race

The Soul of Italy


Welcome to Umbria!  

We begin in Umbria’s main city, the medieval town of Perugia. Enjoy a walk along the Corso Vannucci, the elegant main street of Perugia that winds through the town like a slow river. Take time to view the treasures of the National Gallery of Umbria or Perugino’s frescoes housed at the Collegio del Cambio. We will meet in the afternoon for a walking tour to hear the rich story of Perugia. And… if you like chocolate you are in the right place: Perugia is known for its “bacio” chocolate kiss. Dinner is included all together this night

DAY 2 – Bike Under the Tuscan Sun (35 Miles/59 kilometers)

Our ride today will take us along the north edge of Lake Trasimeno, the largest lake in central Italy and home to a wondrous bird population.  Our route brings us to Cortona, one of the iconic villages of Tuscany. The town is embraced by a medieval wall cloistering delightful boutiques and cafés.  Cortona is the setting for the famous book and film “Under the Tuscan Sun.”  Despite its fame, this lovely town has not lost its quaint charm or authenticity and is well worth exploring. Breakfast and a light lunch are included today.

DAY 3 – Ride the Renaissance (29 miles/49 kilometers)

From Cortona we begin our ride with a downhill and then an enjoyable ride into the quiet countryside of Tuscany. The destination today is Pienza, a town completely restored as an ideal Renaissance town by Pope Pio II beginning in 1459. This was the beginning of urban planning concepts with the central square surrounded by important buildings (palaces, cathedrals, and clock towers). Pienza became a UNESCO World Heritage Site in 1996 due to its cultural significance in urban planning. Breakfast is included today.

DAY : 4 – Criss-crossing Tuscan hills (26 miles/43 kilometers)

Enjoy a bike loop which will take us to Montepulciano, one of the most famous towns of Tuscany. The route will take us through charming villages and wonderful landscapes, along forests and among the typical countryside that makes Tuscany so famous. We’ll visit the wine cellars of one of the oldest wineries in the area, carved into the basement of a noble palace in town. We will enjoy a cooking class this afternoon where we will learn traditional recipes of the area and make our dinner.  Breakfast and dinner are included today.

DAY : 5 – Ancient Roman waters (31 miles/52 kilometers, optional extra ride to hotel 31 miles/24 kilometers)

We’ll bike Tuscany’s rolling hills to Montalcino, the home of Brunello wine. Take time to stroll through the village and perhaps taste the wines or prized olive oil at a sidewalk café.  We will take a private van shuttle to our hotel at Bagno Vignoni, known for its thermal waters since ancient Roman times.

Meals:  Dinner included in the hotel this night

DAY : 6 – Biking and Brunello! (23 miles/38 kilometers)

Our ride takes us from the top of Mount Amiata through chestnut forests and small villages where we arrive at Sant’Antimo Abbey, a beautiful Romanesque abbey. After the abbey, we’ll stop at a Brunello winery for a tasting and light lunch. Brunello is produced with 100% Sangiovese grapes and is one of Italy’s best known and most expensive wines. After lunch we will transfer to our hotel in Bagno Vignoni.

DAY 7 – Race to Siena! (option 1 ride: 30 miles/50 kilometers, option 2 ride: 44 miles/73 kilometers)

Enjoy our final Tuscan bike ride to beautiful Siena and more picturesque landscapes along the way.  We offer two ride options today: the shorter ride ends 20 kilometers from the hotel in Siena, where a private shuttle takes you to the hotel, while the longer route allows you to bike directly to the hotel. Once in Siena, consider a slow walk, as the locals do.  There is so much to explore including the well-known oval shaped central plaza – the Piazza del Campo adorned with the Mangia Tower.  This is the gathering place for Siena and is the site for the Palio horse race that takes place twice a year; once in July and once in August.  We will have a walking tour of the city this afternoon.  Tonight we will have our farewell dinner together.

DAY 8- Departure Day

Breakfast and end of services.



Additional options

  • 7 nights in 4 star accommodation;
  • 7 breakfast
  • 4 dinners (D1; D4; D5; D7)
  • 1 cooking class (D4)
  • Chocolate tasting in Day 1
  • 2 lunches and 1 picnic style lunch (D2; D6 and D3)
  • 2 Wine tasting D4; D6
  • Guided walking tour in Siena on Day 7
  • One English-speaking trip leader
  • Baggage transportation between hotels
  • GPS tracks and route information and maps
  • Hybrid bike rental
  • Van support
Not included
  • Admission to museums and archaeological sites
  • Tickets for trains or any public transportation
  • Wine or beverages
  • Airfare
  • Transfers to the starting point or from the finishing point unless specified; we can assist you in planning and arranging for any necessary shuttles
  • Transport of bike case (for guests who bring their own bike)
  • Personal expenses (laundry, personal supplies, phone calls, etc.)
  • Gratuity

Payment Options: credit card; wire transfer


“LOVED IT! We are your #1 fans.”

Sally Ann and Jeff F
“Entirely enjoyable!  Best of the three bike trips we have taken with various tour companies.”Doreen and Bob

Siciclando carefully chooses every aspect of a tour, including the accommodations.

Our choices are based on comfort and quality. We often choose hotels that are family-owned and operated because they provide a richer experience and because it is important to us to support the efforts of these individuals. We have developed relationships with many wonderful hotel operators. Here is a sample of the hotels on this tour for the “guided” version (please, ask us the hotel list for the “self guided” version which, due to the logistic, may be different).

Tour accommodations will be based on availability and the time of year. Once you have made your final payment for the tour, we will send you a confirmation letter that includes daily accommodations and contact information.

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Along The
Meet The Team!
Giuseppe CrinòCompany FounderGiuseppe loves to bike and he is responsible for our custom tours & it...
Daniele TarozziTour LeaderDaniele enjoys sharing his country and culture: the food, wine, art, a...
GiorgioCertified Olive Oil TasterFourth-generation olive oil producer…olive oil is in his blood. In add...