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Horseback Riding in Italy

Tuscan Villages and Vintages

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Overview

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

Accommodations

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.

Meals & Drink

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

Ride & Horse Details

  • 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 including canters in open spaces
  • Tack:
    English all-purpose saddles and snaffle bits
  • Weight limit:
    190 lbs

Rider Requirements

Participants should be strong intermediate riders; comfortable at walk, trot, canter in open country in English tack, and able to ride for 3 - 5 hours per day. Total hours in the saddle is about 25, over about 135 miles at all paces and terrain.
You must be a fit and confident rider, prepared for a few long stretches of cantering. There are some steep ascents and descents, including requiring you to hand walk your horse, riding over cobbled streets, below overhanging branches and along rocky trails.
Riders will be expected to assist with tacking and untacking their horses, although it's not required.
Age limit: 14 years old.

Activities for Non - Riders

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

Meeting Point

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. The 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 or the polo club VAS 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!

2026 Departures & Options

Departure Dates

Trip Starts
Trip Ends
May 3, 2026
May 10, 2026
May 16, 2026
May 23, 2026
Sep 26, 2026
Oct 3, 2026
Oct 17, 2026
Oct 24, 2026

Pricing & Options

  • Base Price
  • $3,680

  • Non-rider Rate
  • $2,445

  • Single Supplement
  • $310

Request Booking

Tell us more about your riding experience and trip preferences below so we may find the perfect options to meet your needs. We will research availability and get back to you with a booking confirmation detailing suggested departure, cost and extended ride itinerary.

Meet your tour consultant Megan Barrett

About: I'm Megan (with my horse, Willow!). Based in Dubois, Wyoming, I started as a wrangler at our home ranch, the Bitterroot. I've been with Equitours since 2013 and look forward to helping you plan your perfect riding adventure!

Do you have questions about this tour itinerary? Do you want to make sure that this it is the right tour for you? Or are you ready to book? Please call or email our experienced and friendly ride consultants for more detailed information. With first-hand knowledge of the exciting tours we offer, the tour consultants at Equitours look forward to answering any questions you might have

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Speak with our reservation team directly.

1.800.545.0019

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Contact Megan Barrett

Our group of six were very experienced, allowing for frequent trots and canters. It was thrilling to canter alongside and through olive groves and hay fields. We were immersed in the beauty of Tuscany. It takes a fair amount of skill and experience to ride at different paces in varied terrain and be in the saddle for six hours a day. The ride was challenging, the countryside beautiful, the food delicious, and the hosts were great. We’ve taken four Equitours trips over the past seven years. We hope to ride again next year.

Mastejulia, 2024

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