Butteri on Maremmano horses at a demonstrationButteri at a demonstration in Tuscany · Photo alexcap76, CC BY-SA 2.0, Wikimedia Commons
Trail guideTuscanyTrot & Taste

Five rides in Tuscany, from San Gimignano to Pisa

San Gimignano had 72 towers, and 14 still stand.

You do not ride Tuscany in one place. In San Gimignano the towers shape the skyline, near Montepulciano it is a limestone hill, near Montieri the forest. In Florence the rides begin in the hills outside the city, near Pisa in the coastal park. We show five areas with offers. For each we say who it suits and what to watch for.

By the Saddle Atlas editorial team · 11.10.2026 · 4 min read

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San Gimignano

The towers of San GimignanoSan Gimignano · Photo Efrem Efre, Pexels

San Gimignano sits on a hill in the Val d'Elsa, 56 kilometres south of Florence. The town has been a World Heritage Site since 1990. It probably had 72 tower houses, some up to 50 metres high. 14 survive. The town lay on the Via Francigena, a resting place for pilgrims on the way to Rome. The town lies in the Valdelsa area. The white wine Vernaccia is produced only in these hills. The long rides name a winery and lunch.

Who it suits. Riders who want to combine a ride with a place and a tasting, and do not need pace.

What to watch. The length. A day programme comes with breaks, so plan time for food and wine.

  • Confirmed: location, World Heritage 1990, 72 towers, 14 surviving, Via Francigena (UNESCO); Valdelsa, Vernaccia (Visit Tuscany).
  • From the provider: starting point, route, level, group, tasting schedule.
  • Clarify before booking: how much of the day is spent in the saddle and whether wine and riding are kept apart in time.
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A selection, not a complete market overview. Offer texts in the provider's language.

Montepulciano and Val d'Orcia

Montepulciano stands on a limestone hill, on the ridge between the Val d'Orcia and the Valdichiana. Hills and golden fields with cypresses stretch far. Vino Nobile contains at least 70 percent Sangiovese.

Who it suits. Riders who want hills and open fields, and a ride between a short outing and a day tour.

What to watch. Heat and shade in summer. Cypresses and fields give little cover.

  • Confirmed: limestone hill, location between Val d'Orcia and Valdichiana, hills, fields, cypresses; minimum Sangiovese share (Visit Tuscany).
  • From the provider: duration, starting point, level, food at the farm.
  • Clarify before booking: where the ride starts and how much shade the route has.
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Montieri and the Colline Metallifere

Montieri lies in the Metalliferous Hills of the province of Grosseto, on the slope of a wooded hill with chestnut forests. In the area stand red slag heaps, the Roste near Boccheggiano. Hiking trails lead through the Park of the Metalliferous Hills. Mining took place here between the 11th and 14th centuries. The area belongs to a geothermal basin, and since 2014 steam from the ground has heated houses through district heating. It is the only area in this article with multi-day rides: the offers include rides of several days.

Who it suits. Experienced riders and anyone who wants to spend several days in the saddle.

What to watch. The duration. On multi-day rides, luggage, accommodation and fitness for rider and horse matter.

  • Confirmed: location, forest, chestnuts, Roste, park, mining 11th to 14th century, district heating since 2014 (Visit Tuscany).
  • From the provider: level, accommodation, luggage transport, group.
  • Clarify before booking: how many hours are ridden per day and how the horses are looked after between days.
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Florence and the hills

Three horses in a meadow near Rignano sull'ArnoHorses near Rignano sull'Arno, near Florence · Photo Anna.Massini, CC BY 4.0, Wikimedia Commons

You do not ride in Florence itself. The offers start in the hills outside the city, with villas, castles and forests. The forests of Vallombrosa and Reggello have centuries-old trees and are popular with Florentines according to Visit Tuscany. Many name an aperitif, a wine tasting or a tasting. In the city the Ponte Vecchio is one of the oldest bridges.

Who it suits. Travellers who want to combine Florence with a short ride, and riders who enjoy food and wine.

What to watch. The meeting point. "From Florence" does not mean a start in the centre, so ask about the journey.

  • Confirmed: hills, villas, castles, forests, Vallombrosa, Reggello, Ponte Vecchio (Visit Tuscany).
  • From the provider: meeting point, duration, group, food, minimum age for a children's ride.
  • Clarify before booking: where the ride begins and how long the journey takes.
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Pisa and the coastal park

Rider in silhouette on the Tuscan beachRider on a Tuscan beach, coast near Pisa · Photo Anna.Massini, CC BY-SA 4.0, Wikimedia Commons

Near Pisa lies the nature park Migliarino, San Rossore and Massaciuccoli. We have not confirmed whether a ride runs inside the park. The offers name the hills of Pisa, the Valgraziosa and the Certosa.

Who it suits. Travellers with little time who want to add a short ride to a Pisa visit.

What to watch. The expectation. The rides name the hills, not the coastal park.

  • Confirmed: only the name of the park (Visit Tuscany). We could not confirm vegetation and extent at the original and leave them out.
  • From the provider: starting point, route, level, duration.
  • Clarify before booking: whether the ride runs in the park or in the hills.
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Season in wine country

The vine year sets the pace in much of Tuscany. In Chianti Classico the vines bud in the first or second ten days of April according to the consortium, the grapes ripen from the third ten days of September to the second ten days of October, and the leaves fall in the second half of November. This applies to Chianti, not automatically to each of the five areas.

Questions before booking

  1. Where is the meeting point and how far is the journey?
  2. Which riding level and weight limit apply?
  3. How long is actually spent riding, and how long eating or tasting?
  4. How large is the group and how many guides accompany it?
  5. What happens in heat or rain?
  6. What is included in the offer and what is not?

What we could not confirm

For none of the five areas did we find climate values (temperature, rain), elevations or riding rules. The vine cycle above applies to Chianti. Riding itself, meaning trails and terrain, is confirmed nowhere, only through the providers' details. Offers in other areas (Pistoia, Garfagnana, Chianti near Siena, Lucca and others) are not part of these five.

Sources (retrieved 11 October 2026)
  1. UNESCO World Heritage Centre, Historic Centre of San Gimignano, whc.unesco.org/en/list/550
  2. Visit Tuscany, San Gimignano, visittuscany.com/en/destinations/san-gimignano/
  3. Visit Tuscany, Montepulciano, visittuscany.com/en/destinations/montepulciano/
  4. Visit Tuscany, Montieri, visittuscany.com/en/destinations/montieri/
  5. Visit Tuscany, Florence, visittuscany.com/en/destinations/florence/
  6. Visit Tuscany, Pisa, visittuscany.com/en/destinations/pisa/
  7. Consorzio Vino Chianti Classico, vine cycle, chianticlassico.com/en/wine/harvest
  8. Offers: Viator and GetYourGuide, as of 11 October 2026

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