Day 1: Siena
◉ Accommodation in a 4* or 3* hotel.
◉ We chose the city of Siena for its charm, wealth of historical, cultural and gastronomic proposals, as well as an excellent position to explore the territory.
◉ Free dinner.
Siena, in Tuscany
We chose the city of Siena for its charm, wealth of historical, cultural and gastronomic proposals, as well as an excellent position to explore the territory. We will spend three days in this enchanting city full of options to explore. We will visit the towns of Chianti and taste a flavorful and genuine local wine; we follow the hills of the Crete Senesi surrounded by cypresses that enchant the landscape; we will pass through villages and castles such as Monteriggioni and San Gimignano. This is a private trip, you can choose your date and check availability with us.
From 01/04 to 31/10 2026
Visual Experience: Tour Images
GPS Route and Elevation
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WhatsAppTour Details
- Tour type:
- Tour Guided
- Difficulty Level:
-
Easy
- Meeting Point:
- Siena
- Best Period:
- March, April, May, June, July, August, September, October
- Duration:
- 5 Days / 4 Nights
- Bike Type:
- E-mtb
- Suitable for:
- Cycle Touring
Itinerary in Brief
- Day 1: Arrival in Siena
- Day 2: The heart of Chianti – 50-80km | 800-1500m D+
- Day 3: Crete Senesi – 50-80km | 800-1500m D+
- Day 4: Monteriggioni and San Gimignano – 50-100km | 700-1800m D+
- Day 5: End of the trip
Itinerary Details
Day 2: Chianti
◉ At 9.00 Bike tour with bike guide.
◉ The heart of Chianti. Come and discover the secrets of this wonderful territory between vineyards and olive trees that give flavor to our ride! We will visit one of the oldest wineries in Chianti, where all the tradition and history that enchants the international world originated. We will pass through small villages like San Gusme and Villa Sesta, which enchant with their simplicity and beautiful cypress road.
◉ Route: ride 80km 1,500+, enjoy 50km 800+
◉ Type: asphalt and white roads (strade bianche).
◉ Accommodation in Siena
Day 3: Crete Senesi
◉ At 9.00 Bike tour with bike guide.
◉ Territory that needs no introduction... there will be breathtaking panoramas, between cypresses and olive trees, flavors and aromas that give spice to this corner of Tuscany. We will dive into bucolic fields and hills that represent the postcard of Tuscany.
◉ Route: ride 80km 1,500+, enjoy 50km 800+
◉ Type: asphalt and white roads (strade bianche).
◉ Accommodation in Siena
Day 4: Monteriggioni and San Gimignano
◉ At 9.00 bike tour with guide.
◉ To close our journey on a high note, we will cycle through scenarios that seem to have come directly out of a fairy tale, immersed in immense natural and historical beauty, between the enchanting villages of Monteriggioni and San Gimignano, in the region of Tuscany, Italy. Monteriggioni, with its almost intact medieval walls, transports us back in time, allowing us to experience the unique atmosphere of the Middle Ages. This fortress, mentioned by Dante Alighieri in the “Divine Comedy”, is a vivid testimony of Italian history.
◉ Continuing our ride, we approach San Gimignano, known worldwide as the “City of Towers”. This village is famous for its preserved medieval architecture, with stone towers that rise proudly towards the sky, creating an unmistakable and magnificent skyline. San Gimignano, a UNESCO World Heritage Site, enchants not only for its architectural beauty but also for its rich history, culture, and an atmosphere that seems to suspend time.
◉ The route between these two villages is framed by breathtaking landscapes, with hills covered with vineyards, olive groves and cypresses that outline the path, offering a visual spectacle and an unparalleled sensory experience.
◉ Route: ride 100km 1,800+, enjoy 80km 1,100+, easy only Monteriggioni 50km 700+
◉ Type: asphalt and white roads (strade bianche).
◉ Accommodation in Siena
Day 5: Departure
◉ After breakfast, end of the trip
Terms and Conditions
Included
- 4 nights in Siena, 3 and 4 hotels
- 4 breakfasts
- a TYPICAL Tuscan lunch
- isotonic drinks, bars and hydration
- 3 guided bike tours with local guide
- 1 Chianti wine tasting
- bike rental
- helmet rental
- travel and health insurance for bicycle touring
- trip cancellation insurance for documented health reasons
- bike delivery and return directly to the hotel
Not Included
- Flight
- Tips (at your discretion)
- Everything not indicated as included
- Tourist tax
Payment Conditions
check the direct link or contact our staff at the time of booking
Cancellation Policy
- Cancellation policy:
- for any reason up to 120 days from the trip, penalty of € 350 per person
- between 119 days and 30 days from the trip, penalty of 50%
- from 29 days until the day of the trip, penalty of 100%
- If cancellation occurs due to international health reasons, such as travel impediment by public order, the trip will be rescheduled at no cost to the client, or they may have the option of a voucher for the amount paid to date.
- Our price already includes a 10% administrative fee which will not be refunded in case of cancellation.
- In the case of changes to the trip by the client, such as date, rooms, name of participants, there is an additional fee of € 75 per person and per change.
- NOTE: cancellation must be made by email until 14:00 (ITALY time).
Notes
THIS TOUR CAN BE PERFORMED ON VARIOUS DATES (minimum of 2 participants). from March to October.
Various Info
Attention: The text above may contain some errors, so we advise you to always ask for the link to the reservation form to ensure all items included, not included, payment and cancellation.
On Request
This tour can be done on several dates (minimum 2 participants).
When
- From 01/04/2026 to 31/10/2026
Our Bicycles
Road Bike
For speed and efficiency enthusiasts on the road.
E-Gravel
Adventure on varied terrain with the perfect electric assistance.
Gravel
Ideal for those seeking to explore mixed terrain with versatility.
E-MTB
For adventurers wanting to tackle trails with electric technology.
FAQ - Frequently Asked Questions
Can I choose the date?
Yes, this is a private tour. You choose the start date that best suits your schedule (between March and October).
What type of bike is included?
Bike rental (E-mtb) is already included in the package.
Is the hotel always the same?
Yes, we will be based in Siena throughout the tour, which provides greater comfort without the need to pack and unpack daily.
Is it suitable for beginners?
Yes, the level is easy and with the use of E-bikes the tour is accessible to everyone.
What meals are included?
All breakfasts and a typical Tuscan lunch are included.
Is there support during rides?
You will have experienced local guides accompanying you along the entire route.