Italy Bike Tours: Tuscany, Siena and Lazio

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.

   • Accommodation in Siena
   • Dinner

   • 

     Sangallo Park Hotel

     A 3-star laid-back hotel with cozy rooms.

   • 

     Sangallo Park Hotel

     A 3-star laid-back hotel with cozy rooms.

   • 

     Sangallo Park Hotel

     A 3-star laid-back hotel with cozy rooms.

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. 

   Elevation: 1,150m/3,773ft

   • 45.4 miles
   • Accommodation in Siena
   • Breakfast and Dinner

   • 

     Rolling hills and vineyards

     Immerse yourself in the breathtaking sights of Tuscany

   • 

     Sangallo Park Hotel

     A 3-star laid-back hotel with cozy rooms.

   • 

     Sangallo Park Hotel

     A 3-star laid-back hotel with cozy rooms.

   • 

     Sangallo Park Hotel

     A 3-star laid-back hotel with cozy rooms.

3. Day 3Siena - Montalcino

   After a delicious breakfast, you’ll set off toward Monteroni d’Arbia, riding along quiet secondary roads through the stunning Val d’Arbia. From there, you’ll continue on to Asciano, where you can admire the magnificent Monte Oliveto Maggiore abbey. The route takes you up and down rolling hills lined with iconic cypress trees before arriving in the charming village of Buonconvento, nestled in the Ombrone Valley.
   
   The final stretch of your ride leads you to Montalcino, your destination for the day. This hilltop town is famous for its Brunello wine, which is never released less than five years after the grape harvest and earns the title “Riserva” only after six. You’ll end the day with a warm welcome, a delicious dinner of local cuisine, and a well-deserved glass of wine.

   Elevation: 1,200m/3,937ft
   
   

   • 44.7 miles
   • Accommodation in Montalcino
   • Breakfast and Dinner

   • 

     Hotel Dei Capitani

     An 18th century hotel nestled in the Tuscan countryside

   • 

     Hotel Dei Capitani

     An 18th century hotel nestled in the Tuscan countryside

   • 

     Hotel Dei Capitani

     An 18th century hotel nestled in the Tuscan countryside

4. Day 4Montalcino Loop

   Another unforgettable day awaits you. Today, you’ll immerse yourself in the beauty of the Val d’Orcia, cycling along peaceful back roads through this iconic landscape. Your ride begins with a descent from Montalcino to Torrenieri, followed by a rolling route that winds through charming ancient villages—perfect for a well-earned cappuccino or espresso break.
   
   Next, you’ll visit the stunning town of Pienza, where you can enjoy lunch at a traditional *trattoria* and recharge before tackling the challenging climb back to Montalcino. This ascent spans 10 km with a 500-meter elevation gain—demanding but rewarding.
   
   As the day winds down, a memorable dinner in this fairytale village awaits, bringing your fourth day of cycling to a perfect close.
   
   You’ll spend the night in Montalcino.

   Elevation: 1,000m/3,281ft
   
   

   • 42.3 miles
   • Accommodation in Montalcino
   • Breakfast and Dinner

   • 

     Hotel Dei Capitani

     An 18th century hotel nestled in the Tuscan countryside

   • 

     Hotel Dei Capitani

     An 18th century hotel nestled in the Tuscan countryside

   • 

     Hotel Dei Capitani

     An 18th century hotel nestled in the Tuscan countryside

5. Day 5Montalcino - Acquapendente

   Another superb day of riding awaits, taking you through villages surrounded by breathtaking natural beauty. Your first stop is the charming town of San Quirico d’Orcia, followed by its nearby hamlet, Bagno Vignoni, known for its historic thermal baths. From there, you’ll continue on to Radicofani, a picturesque hilltop village crowned by a dramatic medieval fortress.
   
   As you ride into the Lazio region, you’ll arrive in Acquapendente, where your efforts are rewarded with a visit to the historic center and a well-deserved dinner featuring local flavours.
   
   Tonight, you’ll stay at the peaceful Sant’Apollinare Farmhouse.

   • 47.2 miles
   • Sant Apollinare Farmhouse
   • Breakfast and Dinner

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     Bagno Vignoni hamlet

     See the historic Bagno Vignoni which is also famous for its thermal baths.

6. Day 6Acquapendente - Lake Bolsena

   Today’s ride brings a refreshing change of scenery. You’ll briefly re-enter the Tuscany region and arrive in the striking hilltop town of Pitigliano, known for its unique historical center, nicknamed “Little Jerusalem” due to its long-standing Jewish heritage.
   
   From Pitigliano, you’ll continue your journey toward the sparkling shores of Lake Bolsena, marking your return to the Lazio region. Along the way, the remarkable village of Civita di Bagnoregio awaits—its dramatic setting offering a striking contrast to the landscapes you’ve seen so far.
   
   You’ll end the day in the lakeside town of Bolsena, where a scenic evening and a delicious dinner in good company bring your ride to a memorable close.
   
   Overnight in Bolsena.
   
   

   • 37.9 miles
   • Accommodation in Bolsena
   • Breakfast and Dinner

   • 

     Civita di Bagnoregio

     The medieval hilltop town of Civita di Bagnoregio will mesmorize you with its enchanting romantic beauty

   • 

     Hotel Royal

     The oldest hotel in the town of Bolsena with elegant rooms and outdoor pool.

   • 

     Hotel Royal

     The oldest hotel in the town of Bolsena with elegant rooms and outdoor pool.

   • 

     Hotel Royal

     The oldest hotel in the town of Bolsena with elegant rooms and outdoor pool.

7. Day 7Departure

   There is breakfast to be devoured before it’s time to board a transfer to the airport or station.

   • Breakfast