Italy Self Guided Biking / Tuscany

Tour Dates:  8 Days, Mid-March through Mid-November

Tuscany is a charmed land of rounded hilltops covered with vineyards and acres of sunflowers bathed in pastel sunlight.

Tuscany Bike Tours are available as Self-Guided Bike Tours or Charter Tours. Check out the sample itinerary below. We can customize this Tuscany Bike Tour with shorter or longer distances and fewer or more days. Check out our guided tour of Tuscany & Umbria and this is also available as a self-guided tour.

Distant farm houses silhouetted by stately cypress trees form an age old backdrop for classic bike touring in this uncrowded region. Medieval cities with narrow winding streets beckon to be explored. There you’ll find cathedrals, grand plazas and real espresso at a sidewalk cafe nestled between 13th century sculptures. Our routes follow winding secondary roads with very little traffic. Tuscany also offers a great diversity of landscapes, from the vineyard-covered hills of Chianti and Brunello to the barren geometrical cypress-crested moulds of the “Crete”. Such incredible varieties in so short a time!

2024 Price: €1295 Euros pp double occupancy

Single Supplement: €200 Euros Bike Rentals: Hybrid bike / € 170 euros, Road bike / € 220 euros, E bike / € 300 euros

Price Includes:

  • 8 days/7 nights hotel
  • 7 breakfasts
  • luggage transfer
  • trip information package that includes maps, route descriptions, suggested sights to visit
  • emergency phone numbers for our Italian staff support
Price Does Not Include:

International flights, lunches, dinners.

Tour Difficulty

This is a moderately hilly bike tour that fit riders of all abilities will enjoy. Our routes follow winding secondary roads and average 45 – 65 kilometers per day, with more riding available for the hearty.

  • Difficulty: Moderately Hilly
  • Road Conditions: Smooth & Paved
  • Recommended Bike: Hybrid or Road

Tour Highlights

  • Ancient walled cities
  • Hillsides covered with olive trees
  • Etruscan tombs and Renaissance art
  • renowned wine regions
  • Tuscany’s most interesting hill top towns

“Our trip through Tuscany was great! Hotels were very nice and support people were all very pleasant and professional. Ebikes definitely the way to go!”

Mike H. , (Self-Guided Bike Tour of Tuscany, Italy)

Sample Itinerary

Day 1 – Arrival in Poggibonsi

You will be met by our Italian representative who will drive you to your accommodations for the night, Villa San Lucchese. This is a beautiful villa near Castellina in Chianti and is also known for excellent food.

Day 2 – Monteriggioni/Colle Vald’Elsa/San Gimignano – Distance: 37 Km, Elevation gain: 590 meters

Your first day of cycling takes you to Monteriggioni, a perfect fortress town built in the 13th century and totally encircled by high walls with 14 heavily fortified watchtowers. Continue to Colle de Val d’Elsa, take time to visit some of the glass-blowing workshops. Then it’s on to San Gimignano, the “city of beautiful towers” and one of the best-preserved medieval towns in Italy before you head back to Villa San Lucchese.

Day 3 – Villa San Lucchese/Castellina in Chianti/Siena – Distance: 35  Km, Elevation gain: 500 meters

Follow winding roads through the Chianti countryside, past lush vineyards and superb wineries, to Siena, one of the most beautiful cities in Italy. Stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for dinner.

Day 4 – Siena/Buonconvento – Distance:  40 Km, Elevation gain: 570 meters

Winding on the Chianti country roads is quite dramatic as the landscape changes from the lush vineyards to the more linear cypress-crested hills of the “Crete” near Buonconvento. Here shepherds tend the sheep whose milk is used to make pecorino cheese. You will pass through the tiny borgo of Murlo, the oldest settlement in the area, before arriving at today’s destination, a delightful agriturismo just 3 km from Buonconvento.

Day 5 – Buonconvento/Montalcino – 40 Km, Elevation gain: 700 meters

After a steep climb, pedal through the spectacular eroded hills of “Crete” and then through thick cypresses and olive groves as you approach the 14th-century Benedictine monastery of Monte Oliveto Maggiore. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. Then continue to Montalcino, a classic Tuscan hilltown renowned for its ruby-red Brunello wines, considered by some to be the finest in Italy.

Day 6 – Montalcino/Sant’Antimo/Montalcino (your choice of mileage for the day as you will not be changing hotels tonight)
Long Distance: 52 km, Elevation Gain: 1,100 meters  Shorter out and back option: 22 km, Elevation gain: 440 meters

Stroll around the town before following the trail to the abbey of Sant’Antimo, 10 km away. Few of the monastic buildings remain, but the 12th-century church is well preserved and is an outstanding example of the Italian Romanesque. With luck, you’ll visit at a time when the monks celebrate mass and the church echoes with Gregorian chants. Then return to Montalcino where you spend a second night.

Day 7 – Montalcino/Montepulciano – Distance: 50  Km, Elevation gain: 875 meters

You pass through many wonderful places today. Pause at the hot sulfurous pool in the piazza at Bagno Vignoni, then continue to Pienza, a Renaissance jewel and birthplace of Aeneas Sylvius Piccolomini who completely redesigned its center after he became Pope Pius II. Relax over a cappuccino in Montichello, a tiny walled village, and then head for beautiful Montepulciano, one of Tuscany’s highest hilltop towns and famous for its red Vino Nobile wines.

Day 8

Stroll around Montepulciano before departure. Today you will be transferred to the Chiusi train station that has access to Rome, Florence or Milan.

** Shorter itineraries available.