San Gimignano to Siena Bike Tour: The Heart of Tuscany

Experience Tuscany’s Iconic Landscapes with Premium Comfort and Expert Guidance

The San Gimignano to Siena Bike Tour is a premium, full-day biking experience departing from Florence. This tour connects two of Tuscany’s most iconic UNESCO World Heritage sites through the rolling hills of the Chianti region. Led by Company Owners  Piero and Elena, the itinerary also includes a visit to the Medieval fortress of Monteriggioni and offers full van support and leisurely pace, making it accessible for any skill level.

• Small groups only
• Led directly by the Company owners, Piero & Elena
• Visit three of most beautiful Medieval Towns of Tuscany: San Gimignano, Monteriggioni, Siena
• Leisurely cycling in the gorgeous Tuscany countryside 
• Flexible ride distance (10–13 miles) –
• Difficulty: easy to moderate
• Full van support throughout the day
• Electric bikes available

Tour Details & Quick Facts

• Departure : Florence
• Duration: Full Day (Pick-up 8:30AM, Drop-off 5:30 PM)
• Biking Distance: 10 to 13 miles (16 to 21 km), adjustable based on skill level
• Difficulty: Easy to Moderate 
• Route: San Gimignano -> Monteriggioni -> Siena
• Group Size: Small group (2 to 8 people). Private tour  – larger groups can be accommodated upon request.
• Minimum Age: 12 years old
• Are you traveling with younger children able to ride and love biking ? Let us know so that we can size your Private Family adventure on your need!
• Non-riding travel companions are always welcome to join the experience! Feel free to contact us for more details.

What is Included

• Round-trip air-conditioned van transfer from a designated meeting point in Florence. Please note that if you are staying outside Florence, we will be happy to arrange a customized countryside meeting point for your convenience.
• Expert guidance by owners Piero & Elena (Licensed Tour Operator since 2013)
• Full guidance and van support 
• High-quality 27-speed light-frame fitness bicycle, helmet, and water bottle
• Optional : High-end E-bikes upgrades are available upon request for an easier ride.
• Snacks and fresh fruit during the bike ride
• City maps and insider recommendations to discover Siena and lunch

Tour Highlights

• Two UNESCO Sites: Visit both San Gimignano and Siena in one day.
• Monteriggioni Fortress: Stop at the unique walled medieval castle on the Via Francigena.
• Scenic Chianti Roads: Cycle through postcard-perfect vineyards and olive groves.
• Flexible Cycling: Choose your pace and distance with our support van always nearby.
• Local Expertise: Discover hidden gems and history that only local guides know.

Ready To Experience Tuscany By Bike?

Your Itinerary Step-by-Step

1. Florence Departure & San Gimignano: Your day begins with a 8.30 AM with a convenient pick-up in Florence. We drive you to the “Manhattan of the Middle Ages,” San Gimignano. You will have time to explore its famous towers, enjoy the quiet early morning atmosphere and world-class gelato before we start our cycling journey.
2. Cycling to Monteriggioni To avoid some steep and heavily trafficked climbs, leaving San Gimignano a short van transfer brings us to our peaceful starting point, surrounded by the beautiful Tuscan countryside.
   We fit your bikes and start pedaling on beautiful, low-traffic roads. The route takes us through the classic Tuscan landscape towards the Medieval fortress of Monteriggioni, final destination of the biking portion. This perfectly preserved walled hill-top town offers a great spot for photos and a brief rest.
3. The Road to Siena Your safety first! In order to avoid busy roads the ride continues by van to Siena.
4. Siena Sightseeing & Lunch Once in Siena, we give you free time ( approx 2 hours )  to admire the city’s wonders, the Gothic Cathedral and Piazza del Campo. We provide a detailed map of the city centre and our favorite local spots for a quick, good Tuscan lunch.
5. 5. Return to Florence After a full day of exploration, our van provides a relaxing drive back to Florence, arriving at approximately 5:00 PM

Join our Florence to San Gimignano&Siena bike tour and discover Tuscany at a slower, more authentic pace.

WHAT MAKES BIKE FLORENCE & TUSCANY DIFFERENT

Bike Florence & Tuscany is a founder-led Tuscany Biking Company specializing in authentic small-group experiences departing directly from Florence and surroundings.
Since 2013, we have focused on combining:

• genuine local guidance
• scenic secondary roads
• flexible pacing
• authentic Tuscan atmosphere
• small groups
• personal attention

Rather than creating high-volume tourist experiences, our goal is to help guests experience Tuscany in a more personal, relaxed and memorable way.

FAQ

• Do I need to be an experienced cyclist? No. Most guests joining this tour are recreational riders rather than experienced cyclists.
• Is Tuscany too hilly for beginners? Tuscany naturally includes rolling hills, but this route was selected to remain enjoyable and manageable for occasional riders.
• Are e-bikes available? Yes. E-bikes are available and help make the experience accessible to a much wider range of fitness levels.
• What happens if it rains? Our support van allows us flexibility in changing weather conditions and helps us adapt the day whenever needed.
• Is van support included? Yes. Our support van is always available throughout the day.
• Is this tour family friendly? Yes. This is one of our most popular experiences for active families visiting Tuscany.
• Is lunch included in the price? Lunch is not included, allowing you the freedom to choose your preferred meal during your free time in Siena . We will provide a map and our best local restaurant recommendations.
• What should I wear? Comfortable activewear is perfectly fine. Professional cycling clothing is not required.