8 Day itinerary in Italy, Europe

Classic Tuscany

Immerse yourself in the purest beauty! This memorable bicycle trip takes you to the heart of Tuscany, among superfine red wines, olive groves, and hills designed by cypresses, wonderful historical centers, and cheerful locals. You will ride from the Crete Senesi to the lands of the Vino Nobile di Mo... Read More

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Gian Mario

By Gian Mario


Physical Difficulty


Recommended Age


Operated in

English, Spanish, French, Italian


On Some Day Trips

starting point


trip type


trip attributes

Outdoors & Nature

Food & Drink





Brunello di Montalcino, Nobile di Montepulciano and Chianti wines


The amazing towns of Siena and San Gimignano


The Crete Senesi landscape


The Eroica routes


mid-range expand_more

Day 1

place Benvenuti in Toscana

Tour briefing, bike fitting and warm up ride. Arrival in Tuscany, shuttle or individual arrival at our accommodation in Asciano countryside. Tour explanation, delivery of tour documentation, and careful bike fitting, then possibly warm up ride to the pretty medieval town of Serre di Rapolano.

Meals: Dinner


  • mid-range: Farmhouse Il Molinello
Day 2

place Asciano to Pienza

Across the beautiful villages of Montepulciano and Pienza. Today we ride through the Val d’Orcia, a quintessential Tuscan landscape, made out of rolling hills dotted with cypress trees; its landscape is listed as a UNESCO World Heritage Site. After the marvelous Montepulciano, we end in the pretty Pienza, a real model of Renaissance city.

Meals: Breakfast


  • mid-range: Hotel Corsignano
Day 3

place Pienza to Montalcino

In the land of the Brunello di Montalcino wine. From the romantic Renaissance atmosphere of Pienza, heading towards the medieval village of Montalcino, kingdom of the fine Brunello di Montalcino wine. Along the way the beautiful Orcia valley and the majestic Sant’Antimo Romanic abbey.

Meals: Breakfast


  • mid-range: Hotel dei Capitani
Day 4

place Montalcino to Siena

From the vineyards of Montalcino to the rolling hills of Siena. A beautiful ride from the vineyards of Montalcino to the rolling Crete Senesi, until the lively but still authentic Siena, the most medieval town of Tuscany.

Meals: Breakfast


  • mid-range: Hotel Italia Siena
Day 5

place Siena to San Gimignano

Across the Val d'Elsa up to the Manhattan of Medieval times. We leave Siena along the Via Francigena route, after the medieval walls of Monteriggioni we continue through the hills around the Val d'Elsa. The ride ends among the high towers of San Gimignano.

Meals: Breakfast


  • mid-range: Hotel Bel Soggiorno
Day 6

place San Gimignano to Gaiole in Chianti

An Epic day along the Eroica roads. We say goodbye to the unique skyline of San Gimignano then enter the Chianti Classico region, where we will experience some of the dirt roads that have made the Eroica famous all over the world, the iconic vintage bike ride through the Chianti region.

Meals: Breakfast


  • mid-range: Badia a Coltibuono
Day 7

place Gaiole in Chianti to Asciano

At the origins of Chianti Classico wine. We go through the Chianti wine region, discovering the stunning Brolio Castle, a true symbol of the territory, because the official method for the production of Chianti wine was established here in 1872. Then we pass through the ancient thermal baths of Rapolano before ending our day in the countryside of Asciano, chez our friends Elisa and Alessandro.

Meals: Breakfast, Dinner


  • mid-range: Farmhouse Il Molinello
Day 8

place Arrivederci!

Well, it’s time to say goodbye, but we are sure this part of Italy will touch your hearts and you’ll come again to visit more!

Meals: Breakfast

What’s Included

Accommodation expand_less

  • Farmhouse Il Molinello
  • Hotel Corsignano
  • Hotel dei Capitani
  • Hotel Italia Siena
  • Hotel Bel Soggiorno
  • Badia a Coltibuono

Meals expand_less

  • Dinner (2)
  • Breakfast (7)

Transport expand_less

  • Luggage transportation inn2inn

Extras expand_less

  • Welcome meeting and tour briefing
  • Maps, route notes or GPS tracks
  • Telephone assistance
  • Peace of mind being with our experienced team

Not Included expand_less

  • Local Taxes (approx. 10 €)
  • Drinks at Dinner

About Gian Mario


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star_outline 5 (3 reviews)

I'm Sardinian, Italian, and European, passionate about my land, culture, and outdoor activities. I love to meet people and make them feel like they are at home. It's my job, it's my passion.

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$1,300.00 USD