A horseback ride with pilgrim paths sounds fancy, but it’s also calming. You’ll get a guided trip through Montagnola Senese Park along the Via Francigena, plus a peaceful walk past the Hermitage of San Leonardo al Lago. I love that the staff feels genuinely welcoming and that the ride works for all levels. One thing to consider: it’s not for everyone physically, so check the limits before you book.

The way this is run is practical. You’ll mount with instruction, spend time getting comfortable with the horses, then set off at a relaxed pace so you can actually enjoy the countryside. With scenery that really hits (woods, hills, and golden fields), this is the kind of short experience that leaves you smiling instead of tired.

Key highlights at a glance

• Via Francigena by horse: You’ll follow the same historic route pilgrims walk, with a guide setting the pace.
• Montagnola Senese Park views: Trails through woods, rolling hills, and open fields.
• Eremo di San Leonardo al Lago: A stop with a quiet, spiritual feel while you pass the hermitage.
• Small group size: Limited to 10 participants for a more personal experience.
• All riding levels welcome: From first-timers to experienced riders, with basics explained on-site.
• Friendly, bilingual guidance: The guide speaks English and Italian, and helmets are included.

Getting to Siena’s Via Francigena starting point

Your adventure starts just outside Siena, about 15 minutes from the center. The meeting spot is Strada del Pian del Lago, 6. When you arrive, look for a shed that functions as a covered riding arena, then follow the road uphill lined with trees until you reach the guide who will route you to the group.

Plan to arrive 10 minutes early. That timing matters because you’re not just showing up for a quick photo stop. You’ll need a bit of time for the ground introduction, the horse prep, and the basics before you mount.

If you’re staying in Siena’s historic center, it’s easy to assume you can just wander there. Don’t. This one is simpler if you give yourself enough buffer to reach the countryside meeting point without stress.

Before you mount: helmets, first steps, and horse time

Once everyone gathers, the guide starts with an on-the-ground introduction. You’ll get a quick explanation of the basics of riding, which is especially helpful if you’ve never been on a horse before. There’s also time to familiarize yourself with the animals before you set off, so you’re not thrown into the ride immediately.

Helmets are included, which is a big practical plus for comfort and safety. The guide speaks English and Italian, so you should be able to understand instructions clearly, whether you’re practicing Italian or sticking to English.

You should bring comfortable clothes and comfortable shoes. Avoid sandals or flip-flops, and skip skirts, since you’ll be moving around the stables area and mounting. This isn’t a museum visit where you can sit politely the whole time.

The ride along the Via Francigena: woods, hills, and golden fields

After everyone is ready, the group leaves the stables and heads into Montagnola Senese Park on the Via Francigena. This is where the experience really becomes about the rhythm of travel. Instead of looking at the route from a road, you’re moving along it at a horse’s pace—slow enough to notice details, fast enough to feel like you’re going somewhere.

You’ll travel through trails shaped by the landscape: lush woods, green hills, and golden fields. You’ll also pass by the route that pilgrims walk, which adds a meaningful layer. It’s not just countryside scenery; it’s countryside scenery that’s been walked for centuries by people heading toward something bigger than daily life.

The ride lasts about 1 hour and 10 minutes, and the overall experience is about 1.5 hours total. That timing is ideal if you want fresh air and a new perspective on Tuscany without turning your day into a half-travel marathon.

Stop near the Hermitage of San Leonardo al Lago

One of the most memorable parts is the section of the ride that brings you into the shadow of the Hermitage of San Leonardo al Lago. You’ll pass near the hermitage, and then there’s a walk component associated with the stop.

Even without getting lost in religious details, the location does something to the mood. The hermitage sits in quiet surroundings, and that atmosphere tends to slow you down. It’s the kind of stop where you naturally lower your voice, not because you’re forced to, but because the setting feels like it asks for calm.

This is also a good moment for photos—though you’ll want to keep an eye on where the group is moving. The goal here isn’t solo exploring; it’s a guided flow, so follow the guide’s instructions and keep the group moving safely.

After the stop, you ride back toward the meeting point to finish the experience.

How long is it, and what’s your energy level expected to be?

Total time is about 1.5 hours, with the riding portion around 1 hour and 10 minutes. There’s also ground time: arriving early, introductions, mounting, and the hermitage stop walk.

The riding is designed to be relaxing, not extreme. Horses are described as experienced, which usually translates to smoother handling for riders. That said, you’re still physically involved: getting on and off a horse and being ready for the motion.

So think about it like this: you don’t need athletic training, but you do need comfort with movement and some basic balance.

If you’re expecting a fully seated, zero-effort experience, this one might feel like more work than you want. If you’re okay with a hands-on nature activity that lasts an hour, you’ll likely enjoy it.

Who this horseback tour is best for

This ride is explicitly set up for riders of all levels, from beginners to experienced riders. If you’re brand new, the introduction and the time spent with the horses before leaving the stables are a big help. If you ride often, you’ll appreciate the route length and the chance to enjoy the Via Francigena without having to plan every turn yourself.

It’s a strong fit for:

• Couples or friends who want an outdoors break from city walking
• People who like nature scenes but don’t want hours of hiking
• Anyone curious about the Via Francigena from a different angle

There are also clear limits. The tour is not suitable for:

• Pregnant women
• People over 220 lbs (100 kg)
• People over 75 years

If you’re in the gray zone on physical comfort, be realistic about mounting and the ride itself. This is guided, but it still involves the realities of horse activities.

Price and value: what $65.03 actually buys you

At $65.03 per person, this is priced like a short countryside experience—not a day-long tour with multiple stops and transport. For what you get, the value is solid, mainly because several key pieces are included.

Included:

• A guide who speaks English and Italian
• Helmets
• A guided ride and the experience elements around the hermitage stop

Not included:

• Boots (you’re expected to bring footwear)
• Pick-up and return to the hotel
• Food or drinks

That last part matters. If you’re planning to fit this into your day in Siena, you’ll want to eat before or after. The experience itself is only 1.5 hours, so you don’t want to rely on it to cover your hunger.

Where the price feels especially fair is the combination of route experience and small group dynamics. Limited to 10 participants, you’re not stuck in a huge pack, and that usually means you spend more time being guided and less time waiting.

Small-group pacing and what it feels like in practice

The small group setup can change everything. With up to 10 participants, the guide can explain basics more clearly and keep an eye on how everyone is handling the horses.

It also helps with the “feel” of the ride. Instead of rushing, the group can travel in a calmer rhythm, which matches the setting around Montagnola Senese Park and the quiet mood near San Leonardo.

From what I’d expect based on how it’s run, the staff friendliness is part of why people leave happy. When instructions are clear and the team feels welcoming, you waste less energy worrying and more energy enjoying the view.

What to wear and bring so the ride stays comfortable

This is not a fancy dress event. It’s a countryside ride, and your gear should match that reality.

Bring:

• Comfortable shoes
• Comfortable clothes

Avoid:

• Sandals or flip-flops
• Skirts

A good rule is to wear clothes that won’t restrict your movement and shoes that you can stand in comfortably around the stable area. Even if the ride is relaxed, you’ll still be dealing with boarding moments and changing positions.

If you want to take photos, plan to keep items simple and secured. You don’t want a bag bouncing around while the group is mounted and moving.

Should you book the Siena horseback tour with San Leonardo stop?

Book this if you want a short, guided way to see the Via Francigena countryside without committing to a long hike. The fact that it works for beginners, includes helmets, and keeps groups small makes it an especially comfortable choice when you’re balancing sightseeing with doing something active.

Skip it if any of these are true for you:

• You’re not comfortable with mounting and riding for about an hour
• You fall into the explicit limits (pregnancy, over 220 lbs, or over 75 years)
• You’re hoping for hotel pick-up or food as part of the package

If you’re flexible on timing and you show up ready with the right shoes and clothing, this is the kind of experience that feels like Tuscany in motion: quiet trails, historic paths, and a calm stop near Eremo di San Leonardo al Lago.

FAQ

Where is the meeting point for the horseback tour?

You’ll meet at Strada del Pian del Lago, 6. When you arrive, look for a shed that’s part of a covered riding arena, then follow the road uphill lined with trees to find someone who will take you to the guide.

How long is the ride and the full experience?

The horseback ride lasts about 1 hour and 10 minutes, and the total experience is about 1.5 hours.

What should I wear or bring?

Bring comfortable shoes and comfortable clothes. Sandals or flip-flops and skirts are not allowed.

Is this tour suitable for beginners?

Yes. The ride is described as suitable for riders of all levels, from beginners to experts, and you’ll get an introduction and basics instruction before mounting.

Who is the activity not suitable for?

It is not suitable for pregnant women, for people over 220 lbs (100 kg), and for people over 75 years.

Is there free cancellation?

Yes. Free cancellation is available up to 24 hours in advance for a full refund.