Horseback Riding in Italy

Tuscan Villages and Vintages


The Villages and Vintages horseback riding holiday in Italy is based out of a comfortable and elegant 18th century farmhouse in Chianti, Tuscany. Daily rides on well-trained horses allow you to venture through vineyards, olive groves and to medieval villages where the sound of hoof beats echo from the cobbled streets.

There is a nearby castle overlooking the grounds of the riding center, which you ride by and along cyprus-lined roads to a neighboring vineyard, where you take part in a tasting of the local wines. Other destinations by horseback include a Roman abbey, a convent converted to an organic vineyard and a monastery surrounded by the olive and grape studded landscape so typical of Tuscany. Expect lively riding with fast canters and varied terrain, with long hours in the saddle.

The itinerary also includes a visit by car to the fascinating town of Siena and other nearby points of interest. When you return each day to the riding center, you’ll have time to enjoy the pool while watching horses graze nearby. Meals are carefully prepared from local ingredients and the atmosphere is friendly and relaxed, allowing you to feel both pampered and at home.

If this type of trip looks interesting, take a look at our other equestrian wine tours

The guesthouse is an 18th century Tuscan farmhouse that has been renovated to be comfortable but to keep the original character. There are several private apartments with bathrooms and a kitchen for families or groups.

This ride allows ample opportunity to sample the well-known Tuscan cuisine and delight in “Italian style” picnic lunches.

  • Overview:
    The horses are well cared for and responsive and are also used for lessons and competition in jumping and dressage. You will be asked to assist with tacking and untacking your horse.
  • Horse Breeds:
    A variety including Dutch, Anglo-Arabians and crosses
  • Trip Pace:
    All paces
  • Tack:
    English all-purpose saddles and snaffle bits
  • Weight limit:
    190 lbs

While riders are on horseback, there are no separate activities planned for non-riders, who can enjoy the accommodations and region independently.

Montevarchi-Terranuova train station.

Tour Itinerary

Day 1

Sunday: Arrive anytime in the afternoon and enjoy a welcome drink at 7pm and dinner at 8:30pm in the elegantly restored 18th century Tuscan farmhouse that will be your home for the week.

Day 2

Monday: After a generous buffet breakfast your morning ride will take you to the Roman abbey of Badia d’Ombrone. During this ride you will be getting accustomed to your horse, who is well-trained and comfortable for the trail. Return to the farmhouse and the stables for lunch and a relaxing siesta. The afternoon’s ride takes you to the neighboring medieval Castello di Montalto, visible from the guesthouse before returning home for a relaxing dinner and evening.

Day 3

Tuesday: Today is a full day of riding on the rolling hills that take you to Arceno, a property that is centuries old and allows you to breathe in its history and beauty. Here you will an enjoy a wine tasting in a superb location with views of the vineyards and cypress-lined roads. This is the heart of Tuscany and the Sienese Chianti area, renowned for its wines. Next you visit the medieval village of San Gusme before arriving at the Etruscan site known as Campi, where you will have a picnic lunch. They view here is magnificent, as you can see 360 degrees from Monti del Chianti to Siena and Monte Amiata.

Day 4

Wednesday: Half day riding in the morning at the medieval village of Montebenichi with lunch at the riding center. In the afternoon, visit the medieval town of Montepulciano where you will taste the famous wine Nobile di Montepulciano and visit the towns which have been used as sets for many historical films.

Day 5

Thursday: Another full day’s ride to Felsina, a classic Chianti vineyard. Enjoy a picnic today on this farm before returning to your comfortable accommodations.

Day 6

Friday: Your final full day ride is today, as you pass through the “Crete senesi,” a landscape totally different from what you’ve been riding in so far, and famous for its sheep. An ancient Etruscan road takes you to an amazing view of the valley before you pass through the village of Rapale, one of the last examples of an ancient village that hasn’t been renovated.

Day 7

Saturday: A half day ride today to the Borgo monastery. This final ride will take you through the typical Tuscan countryside with which you are now familiar, through forest, vineyards and olive groves. Enjoy a last lunch at the guesthouse and then travel by car to Siena, the best conserved medieval town in Italy.

Day 8

Sunday: Enjoy breakfast and bid goodbye to your hosts.

Tour Map

Tour Dates & Pricing

Other dates can be considered for a minimum of 3 riders, please inquire!

Departure Dates

Trip Starts
Trip Ends
Apr 28, 2024
May 5, 2024
May 12, 2024
May 19, 2024
May 26, 2024
Jun 2, 2024
Sep 22, 2024
Sep 29, 2024
Oct 6, 2024
Oct 13, 2024
Oct 20, 2024
Oct 27, 2024

Pricing & Options

  • Base Price
  • $2,910

  • Non-rider Rate
  • $1,750

  • Single Supplement
  • $295

Departure Dates

Trip Starts
Trip Ends
Apr 27, 2025
May 4, 2025
May 11, 2025
May 18, 2025
May 25, 2025
Jun 1, 2025
Sep 20, 2025
Sep 27, 2025
Sep 28, 2025
Oct 5, 2025
Oct 12, 2025
Oct 19, 2025

Pricing & Options

  • Base Price
  • $3,110

  • Non-rider Rate
  • $2,270

  • Pricing Variation
  • $285

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Contact Megan Barrett

The Relaxed Tuscan ride was absolutely perfect for us - riding in the morning and afternoons open, visiting the nearby Tuscan villages, vineyards and sights of antiquity. The hosts made the experience very special and I cannot think of anything that would have improved this ride for me.

Schmall, 2021

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