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  • Ride Overview - Chianti Hamlets and Castles Ride
    • Castles
    • Stationary
    • Villages
    • Western Saddles

    A historic horseback riding vacation in Chianti, Italy!  Chianti has been traditionally referred to as the area between Florence and Siena. This is the home of Chianti wine. Your trails will lead you through wine country and dense forests. Cypress-lined lanes will lead you to the fairytale perfect 13th-century castles and impressive sandstone fortresses.  The landscape is magical with whitewashed hamlets hidden in the rolling Tuscan hills. Gnarled vineyards and aged olive groves stretch as far as the eye can see. You will enjoy the village of Dievole which not only provides a breathtaking view but also offers a  beauty that lies in corner gardens. Your guides are distinguished for not only for providing a variety of experiences in the saddle but also for their deep knowledge of the history and culture. In addition, a non-riding tour of Siena is planned. This city has been declared by UNESCO a World Heritage Site.  A popular tourist site, it is famous for its cuisine, art, museums, medieval cityscape. Delicious Tuscan cuisine and wines will make this a horseback riding vacation to remember!   RIDING IN ITALY

    “Thanks for all your help guiding us through the many beautiful trails.  Your expert care and help with the horseback riding made our trip more interesting and fun!  Thanks for taking such good care of me in my horseback riding endeavors.” M.R.


  • Ride Itinerary - Chianti Hamlets and Castles Ride

    You will be transferred from the Siena train station to the equestrian center for a welcome cocktail and assignment of accommodation. You will meet your fellow riders and guide during dinner at the center.

    Your destination is 11th century Castello di Meleto. The castle served as a lookout position over the roads between the Chianti and the upper Valdarno valley.  The trail will lead you along the hills of Cignano where you can enjoy views of the Valle deiPasseggeri, the hamlet of Quercegrossa and Siena. Before reaching Meleto, you will cross through the hamlet Carpineto, the Mulino del Lupo and Arbia River and then past the  Castello di Tornano, a strategically situated hilltop tower dating back almost 1,000 years.

    Your destination is the 11th century Castello di Brolio. This impressive castle is perched on an isolated hill above the southern Chianti countryside. The Renaissance gardens with typical geometric shaped bushes and the English woods are stunning and from here you can admire a breathtaking view of the region. Your trail will lead you into the largest territory for Chianti Classico wine production. This wine is still produced from the original recipe created in 1872 by Bettino Ricasoli.  After a visit of the Castle,  your group will continue the journey towards the Rocca di Montegrossi which dates back to the Lombards (7th – 8th century AD). The site is long regarded as one of the finest sections of Chianti Classico and is surrounded by olive groves and forests. After your horse crosses the Arbia River, you will enter the estate of Dievole to reach the Equestrian Center. The Estate of Dievole officially dates back to the 11th century, and its vineyards and gardens are still carefully tended.

    Today, the horses will have a day of rest, while your group will go to Siena for a guided tour of the City of Palio. You will be enthralled by the Fortezza Medicea, the Piazza del Campo, the Torre del Mangia, the Cathedral and the medieval streets of this historical center.

    Your trail leads along the hills of Cignano and Quercegrossa covered with vineyards of the Chianti Classico and secular olive trees. Having left behind the Mulino di Quercegrossa, you will continue along the mining roads to the hamlet Lornano. In the midst of vineyards and forests, you will find the stoic Castello di Monteriggioni. A short trail will then lead you to the old Via Francigena which connected France to Rome. Between the clearings and thickets, you will reach the Castello dellaChiocciola. The name “Chiocciola” (snail) has been attributed to the castle because of its helical stairs in the tower. Your journey will end in Fungaia.

    Today, you will ride to  Castello di Monteriggioni. Your trail will lead you through the  Montagnola Senese territory which is one of the hilliest areas in the Siena Province. The paths at the slope of the Montemaggio will traverse to the Castel Pietraio. Considered a “hidden gem”, it is a charming Middle Age castle. You will then ride along the Via Francigena to the fortified hamlet Abbadia Isola.  The hamlet’s name was derived from the marshes that surrounded the settlement, making the fortified Abbey appear as if it was laid out on an island. Around the year 1000,  a community of Benedictine monks started a difficult marsh reclamation. Next, you will return to the 13th century Castello di Monteriggioni.  The Castle continues to be the entrance of the territory of Siena.

    Your trail will lead downstream to the Castellina in Chianti. Along vineyards and fields, your white road will end in the hamlet of Fonterutoli, an ancient Etruscan settlement. Your ride will then continue in the midst of cypress trees and forests as you return to the Equestrian Center for lunch.

    You will be transferred to the train station to begin your journey home.

  • Ride Details - Chianti Hamlets and Castles Ride

    Dates: March 8th  – 15th, May 17th – 24th, June 21st –  28th, September 20th – 27th, November 1st – 8th
    Best Months to Ride: April – June and September – October
    Train Station:  Siena
    Riding Days: 5
    Non-riding day:  1
    Daily Riding Hours: 4 – 6
    Riding Ability: INTERMEDIATE: Confident and in control at all paces including posting trots, two point canters and gallops in open spaces.
    Group Size: 2 – 8
    Maximum Weight: 210 lbs.
    Horses: Anglo-Arab, Maremanno, Quarter horse, thoroughbred
    Saddles: English and Western
    Accommodations:  3*** Tuscan townhouse and country homes.
    Price:  $3,825.00 per person, double occupancy  $970.00 single supplement
    *Price is based on dollar/euro exchange and will be fixed at final payment.

    Included: 7 nights’ accommodation,  4 1/2 days riding, 1/2 day guided tour of Siena, all meals, horse, tack, guide, transfer to and from train station
    Not Included: airfare, transfers to and from airport to train station



  • Chianti Hamlets and Castles Ride: Gallery