Tuscany bike tour

Embark on a self-guided bicycle tour in Puglia

Starting from $ 1,998

6 Days

Level 3

Learn moreCycle over gently rolling terrain, with some occasional longer climbs. Maximum elevation is 3,600 feet.

May - Oct

Tour Overview

There’s something magical about cycling through Tuscany.

On this bike tour you will uncover the Tuscany, one of italy’s best destination  for a bike trip !

 Pedaling past vineyards and cypress-lined roads, it’s easy to understand why this region has captured imaginations for centuries. Take your time exploring medieval gems like Siena, where evenings spent in the Piazza del Campo watching the sunset are unforgettable. Local tip: visit a family-run winery near Radda in Chianti for an intimate tasting experience. From pecorino cheese to homemade pici pasta paired with Chianti, Tuscany offers endless culinary delights along your route.

Day 1 Highlights 

  • Get on your bike and ride to Montefollonico, a medieval town situated on a hill between the valdichiana and the val d’orcia.
  • Immerse yourself in the medieval charm of Montepulciano, a hilltop village in the Province of Siena, famed for its vino nobile, stunning renaissance architecture, and historic Piazza Grande. With its breathtaking views, it’s a treasure of Tuscan heritage.

  • On the edge of Montpulciano, tour a wine domaine rooted in the district of Vino Nobile.

Day 2 Highlights 

On day 2 and day 3, you will be cycling on what is often referred as the Val d’Orcia route. It a cycling route with many rolling hills but extremely rewarding views on renaissance towns, cypress tree lined roads and vineyards.

  • Discover the architectural beauty of Pienza, a Renaissance gem shaped by Pope Pius II, and savor its timeless atmosphere, reflecting the harmony of Renaissance ideals.
  • From a view point along your route, enjoy a magnificient view on the monastery of sant’anna in camprena, where many scenes of the movie the English patient which received 9 oscars were filmed.

  • Delve deeper into Tuscan flavors by participating in a culinary experience highlighting the region’s traditions.

Day 3 Highlights 

  • Cycle down one of the most beautifful route in Tuscany down, the cypress lined Montichiello road.
  • Pedal to the small hillside settlement of Bagno Vignogni famous for it’s hot spring located in the town main square.
  • Step into Sant’Antimo Abbey and if you arrive at the right time, you will see monks perform Gregorian chants in an awe-inspiring Romanesque setting.
  • If you choose the premium hotel tour, from your hotel you will enjoy views on monte amiata, an extinct volcano also the highest mountain in southern tuscany

Day 4 Highlights 

Cycle on part of the Eroica cycling route as you make your way through the Crete Senesi.

  • Indulge in a Brunello wine tasting in Montalcino, where ancient cellars produce one of Italy’s most celebrated red wines, the Rosso di Montalcino.
  • Pedal across the breathtaking Crete Senesi, an otherworldly landscape of rolling clay hill and cypress-lined roads.
  • Explore the medieval beauty and history of Siena as you wander the cobblestone streets, marveling at the charm of Piazza del Campo, home to the Palio horse race and admire its stunning Gothic cathedral.

Day 5 Highlights 

  • On day 5, you will ride on the chianti classico wine and olive oil route, passing through Radda and Gaiole in chianti.
  • Stroll through radda in chianti a medival town enclosed in large defensive walls  and surrounded by the valleys of arbia and peda

Premium Hotels

Villa Cicolina

Villa Ciccolina

Once the home of a noble family, the Villa Cicolina embodies Tuscany with its rustic charms and fresh décor. Lounge by the infinity pool in the midst of the olive grove embracing the exquisite views, or wander through the adjacent vineyards. With just 11 rooms, this heavenly villa is yours to enjoy, and the staff is attentive to all of your whims.

Castello di velona

Castello di Velona

Built in the 11th century and once the residence of noble families the Castello di Velona isolated on a hill and offers amazing views over the rolling hills of the Val d’orcia. Beyond it fairy tale setting the hotel features beautiful rooms styles with tradition in mind. Best of all the hotel is close to some of Tuscany’s most famous Brunello vineyards.

Il Fontanelle

Hotel Il Fontanelle

Located in a green setting, the Hôtel Fontanelle is a place of relaxation. However, it’s located on a hill, and you have to make one last effort before reaching it.

Casual Hotels

Il Marzocco

Il Marzocco

In the center onf Montepulciano, this hotel have been owned by the same family since the begining of the century. The rooms  either have balconies or terraces with a view on the valley or they have a view on the renaissance houses of the old town.

Si Montalcino

Si Montalcino

Small charming hotel completely renovated, is located on the panoramic road to S.Angelo in Colle, one kilometer away from the walls of Montalcino.
This hotel is on a natural terrace that dominates the valley overlooking Monte Amiata and from here you can admire the vineyards of Brunello and the towns of Pienza, San Quirico D’Orcia, Radicofani and Castiglione D’Orcia.

Villa Curina

Villa Curina

Deep in the peaceful countryside, surrounded by rolling Chianti hills and a few kilometres from Siena arises Villa Curina Resort, a little 16 th century village full of history and fascination.

Delicate decorations of walls, antique wooden floor slabs, precious fabrics, romantic four poster beds,antique furniture and of sienese craft, contribute to crate a charming and wam atmosphere typical of a countryside villa.

What’s included

Included

  • 5 nights in luxury hotels
  • 1 st day lunch
  • Daily breakfast
  • Curated restaurant list for lunch and dinner
  • Luggage and trip transfers
  • Pre-booked activities (e.g., wine tasting)
  • GPS-guided biking routes (5 days)
  • Bike rental with essentials
  • Detailed roadbook with POIs
  • Pre-trip hotel recommendations

Not included

  • Transport to get and from the trip starting location
  • Lodging before and after the trip
  • Personal expenses
  • Drinks or extras at the hotels
  • Travel insurance