The medieval hilltop town of Civita di Bagnoregio will mesmorize you with its enchanting romantic beauty
Surrounded by a ravine and with a breathtaking skyline, the picturesque town of Pitigliano is a Tuscan dream
Enjoy fantastic local produce while taking in the beautiful vistas.
Journey through lovely towns and come face to face with history
Cycle into Montalcino, a town well-known for its Brunello wine
See the historic Bagno Vignoni which is also famous for its thermal baths.
Start and finish the tour in an unforgettably beautiful place
Combining the fun of cycling and beauty of the region leads to a trip well worth it

Italy Bike Tours: Tuscany, Siena and Lazio

Duration
7 days
Site savings
$54
From
$2,619 USD

Pedal straight into the middle of a fine, Italian dream as you cycle through the glorious regions of Tuscany, Siena and Lazio. Bask in the gorgeous valleys, pretty villages and unique medieval hilltop towns while clocking up the kilometers before sitting down at the end of every day to rest your legs and enjoy the finest Italian cuisine and delicious wines. What could be better!

  • Category
    Road Cycling
  • Type
    Fully Guided
  • Duration
    7 days
  • Culture Level
    Familiar
  • Skill Level
    3 - Intermediate
  • Activity Level
    3 - Active
  • Elevation
    3 - Intermediate
  • Terrain
    Hilly
  • Distance
    217.5 miles
  • Avg. Daily Distance
    43.5 miles
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Quick Stats

  • Duration
    7 days
  • Main Destination
    Tuscany
  • Distance
    217.5 miles
  • Avg. Daily Distance
    43.5 miles
  • Elevation
    3 - Intermediate
  • Terrain
    Hilly

Route Map (click to view larger image)

Itinerary Details

  1. Day 1Settling into Siena

    Tuscany is where your bike ride begins and it is in the medieval city of Siena where the group meets for the first time. Arrive here by your own means to a warm welcome from the staff.

    There will be a briefing about the trip with details of what you can expect. Your bikes will also be assembled and prepared for the action tomorrow. Finally it’s time for some excellent Italian cuisine and drinks before retiring for the evening.

    • Sangallo Park Hotel
    • Dinner
  2. Day 2Loop through Siena and Chianti

    One thing you can be certain of on this voyage is that the food will never fail to impress. After a splendid breakfast, settle onto the saddle and begin your ride. Siena’s streets are a delightful place to begin winding your way out towards Gaiole in the hills of Chianti. Along the way be mesmerised by the rolling hills, enchanting vineyards and scenic landscapes.

    Head for Chianti’s medieval capital, Radda. Amidst its quaint cobblestone and tall stone facades, enjoy a cup of cappuccino and cornetto, the perfect Italian snack! Feeling reenergised, hop back on the bike and continue riding through breathtaking views of vineyards and historic villages.

    With a day full of riding, wind down with a dip in the hotel’s swimming pool and prepare for a delicious dinner in Siena.

    • 43.5 miles
    • Sangallo Park Hotel
    • Breakfast and Dinner
  3. Day 3Calm village life and peaceful nature accompanying every push of the pedals

    Start the day with another delectable breakfast. Settle yourself again on the saddle and expect another day of thrilling rides and fantastic views. Find your way towards Monteroni D’Arbia as you go through the less travelled and quieter secondary roads. Along the way you’ll pass through Val d’Arbia, renowned for its alluring landscapes.

    Heading for Asciano, you’ll also pass by the impressive Oliveto Maggiore abbey. This is cycling at its best, particularly when you breeze up and down between hills and cypress trees.

    The final destination today is Montalcino, known for its production of the Brunello wine. This wine is not sold before five years from harvest. After learning more about the wine, you’ll be treated to delicious local food and of course, some wine.

    • 46.6 miles
    • Hotel dei Capitani
    • Breakfast and Dinner
  4. Day 4Luscious landscapes and challenging ascents in Tuscany

    More unforgettable Italian towns beckon to be explored today. Riding through more peaceful backroads, you’ll soon find yourself in the unique Val D’Orcia. This region is the quintessential landscape of southern Tuscany with its cultivated hills bordered by towering cypress trees.

    It’s going to be a challenging morning as you deal with the descent from Montalcino to Torrenieri. The ups and downs continue through ancient villages but will be punctuated with a stop for a cappuccino or espresso.

    Lunch will be a fun affair as you reward yourself with delicious food at a typical trattoria. It’s the best way to recover your energy from the demanding Montalcino ascent which is 10kms (6.2mi) long and has an altitude of 500m (1,640 ft).

    To close up a fabulous day, dinner will be at a fairy-tale village.

    • 42.3 miles
    • Hotel dei Capitani
    • Breakfast and Dinner
  5. Day 5Incredible Tuscan villages

    The villages in this region of Tuscany are a sight to behold. Their simple but beautiful architecture dotted around breath-taking nature makes for a compelling ride today.


    San Quirico d'Orcia is the first village you enter and its stunning Bagno Vignoni spa lends the area its fame. Next along the route, the village of Radicofani gained its reputation through a dominating castle that will have you fumbling for the camera.


    Eventually, you will enter the region of Lazio at Acquapendente. This historic spot is where you will rest your head tonight after another delightful dinner.

    • 44.7 miles
    • Sant Apollinare Farmhouse
    • Breakfast and Dinner
  6. Day 6A change of scenery

    Today you get to sample some new scenery with a shift back into Tuscany, to the town of Pitigliano.

    With its historical center called "Little Jerusalem", the town is perched on a ridge and surrounded by a ravine, ensuring a striking skyline. The 500-year-old synagogue is a must-see.

    Leaving behind Pitigliano the group heads for the calming waters of Lake Bolsena. This also happens to bring you back over the border and into the Lazio region. The eventual target for the end of the day is Civita di Bagnoregio.

    This medieval hill town is picture perfect and presents a new landscape for you to marvel at. Relish in the romantic settings of Italy as you enjoy dinner here tonight.


    • 40.4 miles
    • Hotel Royal
    • Breakfast and Dinner
  7. Day 7Shooting back to Siena

    There is breakfast to be devoured before it’s time to board a transfer back to Siena and bid farewell to everyone.

    • Breakfast