Italy Self Guided Biking / Tuscany & Umbria

Tour Dates: March – October

It’s time to book the Italian Bike Tour of your dreams with exceptional riding, well planned routes and boutique lodgings! We pulled out all the stops on our Tuscany & Umbria bike tour. This unforgettable bicycle tour traverses Tuscany on quiet country roads that pass through vineyards and lead to historic medieval towns where history comes alive.

This tour is available as a Self-Guided, Guided or Charter Tour! We can customize this Tuscany & Umbria Bike Tour with shorter or longer distances and fewer or more days.

This unforgettable bicycle tour traverses Tuscany and Umbria, two of Italy’s most scenic regions where quiet country roads lead to historic medieval cities. Our tour features great riding, fantastic scenery, comfortable lodgings with all breakfasts & dinners included and luggage transfers. Our tour begins in Assisi, Umbria, where the medieval flavor takes you back to the enchantment and mystery of the Middle Ages. The province of Umbria is known as the “Green Heart” of Italy and our route is surrounded by vineyard clad valleys and hillsides covered with olive trees. Ancient walled cities, Etruscan tombs and Renaissance art are a treat for the eye, and Baci, the world-famous chocolate covered hazelnuts from Perugia, are a delicious treat for the palate! The classic charm of Tuscany is picture book perfect. The countryside is an exquisite patchwork of green fields and stately farmhouses silhouetted by Cyprus trees. Extensive vineyards and acres of sunflowers are bathed in pastel sunlight. Our route passes through several renowned wine regions and takes us to some of Tuscany’s most interesting hill top towns. Enjoy strolling centuries old streets that lead to magnificent cathedrals and grand plazas with charming shops and sidewalk cafes. All of the accommodations were specially selected to reflect the warmth and hospitality of the region and provide a real sense of the living history of the region. 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 – the Brunellos from Montalcino and the bold Vino Noble from Montepulciano.

2024 Price: €1500 Euros pp double occupancy

Single Supplement: €280 Euros Bike Rentals: Hybrid bike / € 190 euros, Road bike / € 240 euros, E bike / € 300 euros
Price Includes:
  • 9 days/8 nights
  • 8 nights hotel
  • 8 breakfasts
  • 1 dinner
  • luggage transfer
  • trip information package that includes maps, route descriptions, suggested sights to visit
  • emergency phone numbers for our Italian staff support
  • welcome orientation and bike fitting
Price Does Not Include:

International flights, bike rentals (You may choose to bring your own bike or rent one. Hybrid, Road bike and Electric bikes are available.  Contact us for prices.), lunches, 7 dinners, beverages.

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

  • Europe’s newest cycling destinations!
  • Pristine mountain valleys
  • Snow capped peaks
  • Historical cities
  • Ride in the lovely seaside city of Sarande on the Ionian Sea
  • See the archaeological wonder of Butrint

Sample Itinerary

Day 1 – Arrival

Our Italian representative will pick you up at the Assisi train station and transfer you to your first hotel. At that time they will give you a tour orientation and bike fitting. Overnight in Assisi.

Day 2 – Assisi Loop Ride: 45 Km

Enjoy the back-road to Spello, a perfectly preserved town with Roman origins. A visit to Bevagna, another wonderful medieval village. Overnight in Assisi.

Day 3 – Assisi – Solomeo Ride: 58 Km

Our route through Umbria is highlighted by a visit to Deruta, a town famous for its ceramics. Tonight’s lodging is countryside inn near Solomeo.  Overnight in Solomeo. Dinner Included.

Day 4 – Solomeo – Cortona Ride: 65 Km

A curvy road will lead us to Lake Trasimeno whose shores teem with migratory birds. You’ll cycle near beautiful olive groves to Cortona, the setting for Francis Mayes’s best seller, Under the Tuscan Sun. Overnight in Cortona.

Day 5 – Cortona – Montepulciano Ride: 50 Km

Today you will enter Tuscany through the magnificent wine country of Montepulciano, one of Tuscany’s highest hilltop towns. Renowned for its Vino Nobile, Montepulciano also boasts a unique blend of Renaissance architecture and is perched on a narrow ridge of volcanic rock. Overnight in Montepulciano.

Day 6 – Montepulciano – Montalcino Ride: 50 Km

Traveling through Pienza, home of Pope Pio II, you’ll find a unique collection of palaces, churches and a charming square. This ride takes you through the Crete landscape, one of the most famous in the world: rolling hills in all shades of brown or green; sturdy brick farmhouses or imposing mansions crowning the hilltops and cypress lined alleys design a perfect scene that inspired painters since the Middle ages. You finish your ride among the vineyards en route to Montalcino, a 13th century paradise and the home of Brunello wine. You will enjoy a two night stay within the walled city. Overnight in Montalcino.

Day 7 – Montalcino Loop Ride: 50 Km

Our loop ride takes you to the gorgeous abbey of Saint Antimo, a well preserved 12th-century church that still echoes with Gregorian chants. There is plenty of time today for shopping and sampling some of the fine Brunello wines. Overnight in Montalcino.

Day 8 – Montalcino – Siena Ride: 53 Km

The road winds through hills and oak woods to Monte Oliveto Maggiore, the most impressive abbey in Italy. Then it’s on to Siena, your final destination. Siena is one of the most beautiful medieval cities in Italy. Its famous Piazza Del Campo is an open-air museum and architectural gem. Overnight in Siena.

Day 9 – Departure

Your tour ends after breakfast. There are both train and bus stations in Siena with easy access to both Rome and Florence.

** Shorter itineraries available.