Italy - Castellare di Tonda
Your base for the week is Castellare di Tonda in the heart of Tuscany. This 800 acre working wine estate dates back to the Renaissance period, when it was owned by the Strozzi family of Florence. The current owners Stefano and Alessandra are passionate about their horses and riding and have invested extensively in the equestrian centre. There is a beautiful Wellness Centre which is open each day (except Tuesday). Each farmhouse has a swimming pool and there are tennis courts and many hiking trails through the surrounding hills.
The trail rides are designed to include a variety of landscapes. You ride past Chianti vineyards, through pristine forests, through medieval villages and past ancient castle ruins. There are three alternative riding itineraries.
This is a seven night itinerary with 3 full day and 2 half day rides. The week includes approximately 20 hours of riding and is suitable for strong intermediate and experienced riders who are riding fit.
This itinerary offers a more relaxed holiday and is ideal for families and friends, perhaps with mixed riding ability, who want to do more than just ride. The week includes 12 hours of riding which can be a mixture of lessons and trail rides. Subject to your riding ability and availability you may also be able to join a full day ride. A rental car is strongly advised if you book this itinerary.
This is the itinerary to chose if you are interested in learning more about and developing your skills in western riding and in particular reining. On a week long stay you have five lessons with the lead instructor Franco, as well as 5 trail rides. The Train & Trail week is suitable for strong intermediate and experienced riders.
The riding style is Western. The horses are trained to neck rein and are ridden with a loose contact. There is a herd of over fifty horses used for riding and breeding. The trail horses are a mix of breeds including native crossbreeds and Quarter horses.
The Chianti hills offer varied trails for all levels of rider. The soft Tufo sand provides excellent footing during the dry summer months when the ground elsewhere is hard. However, while the soft sand makes for excellent going in the dry, rain can make the tracks very slippery. This may affect the pace of the ride and in the case of persistent rain, it may not be possible to ride on any of the trails. If this happens, it should be possible for you to have western riding instruction in the arena. On average this happens once or twice during the season. If you are staying a full week, rain is very unlikely to affect all of your riding days.
The Medieval Tuscany is a seven night itinerary with 3 full day and 2 half day rides. The week includes approximately 20 hours of riding and is suitable for strong intermediate and experienced riders who are riding fit. Riders should be able to mount and dismount without assistance. There are opportunities for walk, trot and canter, but due to the terrain and riding style, this is not a fast ride all the time. The trails are diverse, so every day you can experience a different style of ride: take a canter alongside the river at the bottom of a beautiful canyon; discover medieval castles and abandoned churches; ride through vineyards and open pastures; stop for picnics in shady groves whilst the horses graze nearby. This itinerary is not offered in July or August since the heat makes all day rides unpleasant.
The Heart of Tuscany itinerary is a relaxed riding itinerary and is less challenging that the Medieval Tuscany. It includes 12 hours of riding which can be a mixture of lessons and trail rides. Beginner riders will start off in the arena and join trail rides when the instructor believes them safe. Subject to your riding ability and availability you may be able to join a full day ride (but note that day rides are not available in July and August).
The Castellare Train & Trail itinerary requires riders to be confident and in control at walk, trot and canter. On five days you have a western riding/reining lesson in the morning and a two hour trail ride in the afternoon (or vice versa). This itinerary is for those specifically looking to learn or improve their Western riding techniques as well as practice the more refined reining techniques of sliding stop and spins. The Instructor speaks only Italian but is accompanied by a translator.
Four night short breaks are available for the Heart of Tuscany and Train & Trail (except short breaks are not possible in July or August).
The riding on each itinerary includes steep mountain trails. You will be asked to stand in your stirrups on steep uphill sections and may be required to dismount for small sections of the trail to walk with the horses. The pace of the ride will depend on the heat so if it is very hot then the pace is likely to be a little slower. In the hot summer months, particularly late June, July and August, rides set off a little earlier in the morning.
Children aged seven years and over can have Western lessons in the arena. Children aged 12 years and over who are competent riders can join their family on trail rides within the estate. Children aged 14 years and over who are experienced riders may join their family on the longer rides outside of the estate.
Castellare di Tonda has a number of farmhouses converted into apartments. In total there are twelve restored farmhouses on the estate - each containing a number of self-catering apartments. Some apartments are on the ground floor and some are on the second floor. Riders normally stay in a farmhouse within walking distance of the stables and restaurant, but this could be a walk of about 1km. Each farmhouse of apartments has its own swimming pool which is usually open from mid-May to mid-October. If the weather permits they may be open at other times.
Couples normally have a one bedroomed superior apartment.
Two friends booking together normally have a two bedroomed apartment and so have a bedroom each with a shared bathroom (there is no single supplement for this option).
Families can book a two or three bedroomed apartment.
Single travellers will have a one bedroomed apartment by paying a single supplement. If you are willing to share a two bedroom apartment (one bathroom) and a sharer is available, then there is no single supplement. The supplement is payable in advance and refunded when we find you a sharer.
The restaurant is open for breakfast and dinner each day and lunch on Sundays. Dinner from the half board menu is included in the riding programme although it is sometimes possible to upgrade to the a la carte menu at any meal by paying a supplement locally. Lunch is not included on any of the riding programmes, except for the picnic lunches on the all-day rides in the Medieval Tuscany itinerary. If you do not have a rental car to go off-site to shop then you can order a light lunch from the bar which is open each day.
Castellare di Tonda is open from the beginning of April through to the end October. All riding programmes start on Saturday.
The Medieval Tuscany is not available in July or August. The Heart of Tuscany and Castellare Train & Trail run throughout the season. Four night short breaks are not available in July or August.
| Holiday | Experience LevelExp Lvl | Arrive - DepartArr - Dep | Price | Itinerary | Availability | |
|---|---|---|---|---|---|---|
| Castellare Train & Trail | 24 May 2025 - 31 May 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 24 May 2025 - 28 May 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 24 May 2025 - 31 May 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 24 May 2025 - 28 May 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 24 May 2025 - 31 May 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 31 May 2025 - 7 Jun 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 31 May 2025 - 4 Jun 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 31 May 2025 - 7 Jun 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 31 May 2025 - 4 Jun 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 31 May 2025 - 7 Jun 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Medieval Tuscany | 7 Jun 2025 - 14 Jun 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 7 Jun 2025 - 14 Jun 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 7 Jun 2025 - 11 Jun 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 7 Jun 2025 - 14 Jun 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 7 Jun 2025 - 11 Jun 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Castellare Train & Trail | 14 Jun 2025 - 21 Jun 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 14 Jun 2025 - 18 Jun 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 14 Jun 2025 - 21 Jun 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 14 Jun 2025 - 18 Jun 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 14 Jun 2025 - 21 Jun 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 21 Jun 2025 - 28 Jun 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 21 Jun 2025 - 25 Jun 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 21 Jun 2025 - 28 Jun 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 21 Jun 2025 - 25 Jun 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 21 Jun 2025 - 28 Jun 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 28 Jun 2025 - 5 Jul 2025 | 7 nights 7 ngts | £1,376.72 |
|
Book | |
| Heart of Tuscany | 28 Jun 2025 - 5 Jul 2025 | 7 nights 7 ngts | £1,247.73 |
|
Book | |
| Castellare Train & Trail Short Break | 28 Jun 2025 - 2 Jul 2025 | 4 nights 4 ngts | £852.17 |
|
Book | |
| Medieval Tuscany | 28 Jun 2025 - 5 Jul 2025 | 7 nights 7 ngts | £1,548.70 |
|
Book | |
| Castellare Train & Trail | 5 Jul 2025 - 12 Jul 2025 | 7 nights 7 ngts | £1,376.72 |
|
Full | |
| Heart of Tuscany | 5 Jul 2025 - 12 Jul 2025 | 7 nights 7 ngts | £1,247.73 |
|
Book | |
| Castellare Train & Trail | 12 Jul 2025 - 19 Jul 2025 | 7 nights 7 ngts | £1,376.72 |
|
Book | |
| Heart of Tuscany | 12 Jul 2025 - 19 Jul 2025 | 7 nights 7 ngts | £1,247.73 |
|
Book | |
| Castellare Train & Trail | 19 Jul 2025 - 26 Jul 2025 | 7 nights 7 ngts | £1,694.03 |
|
Book | |
| Heart of Tuscany | 19 Jul 2025 - 26 Jul 2025 | 7 nights 7 ngts | £1,565.04 |
|
Book | |
| Castellare Train & Trail | 26 Jul 2025 - 2 Aug 2025 | 7 nights 7 ngts | £1,694.03 |
|
Book | |
| Heart of Tuscany | 26 Jul 2025 - 2 Aug 2025 | 7 nights 7 ngts | £1,565.04 |
|
Book | |
| Castellare Train & Trail | 2 Aug 2025 - 9 Aug 2025 | 7 nights 7 ngts | £1,694.03 |
|
Book | |
| Heart of Tuscany | 2 Aug 2025 - 9 Aug 2025 | 7 nights 7 ngts | £1,565.04 |
|
Book | |
| Castellare Train & Trail | 9 Aug 2025 - 16 Aug 2025 | 7 nights 7 ngts | £1,694.03 |
|
Book | |
| Heart of Tuscany | 9 Aug 2025 - 16 Aug 2025 | 7 nights 7 ngts | £1,565.04 |
|
Book | |
| Castellare Train & Trail | 16 Aug 2025 - 23 Aug 2025 | 7 nights 7 ngts | £1,694.03 |
|
Book | |
| Heart of Tuscany | 16 Aug 2025 - 23 Aug 2025 | 7 nights 7 ngts | £1,565.04 |
|
Book | |
| Castellare Train & Trail | 23 Aug 2025 - 30 Aug 2025 | 7 nights 7 ngts | £1,376.72 |
|
Book | |
| Heart of Tuscany | 23 Aug 2025 - 30 Aug 2025 | 7 nights 7 ngts | £1,247.73 |
|
Book | |
| Castellare Train & Trail | 30 Aug 2025 - 6 Sep 2025 | 7 nights 7 ngts | £1,376.72 |
|
Book | |
| Heart of Tuscany | 30 Aug 2025 - 6 Sep 2025 | 7 nights 7 ngts | £1,247.73 |
|
Book | |
| Castellare Train & Trail | 6 Sep 2025 - 13 Sep 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 6 Sep 2025 - 10 Sep 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 6 Sep 2025 - 13 Sep 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 6 Sep 2025 - 10 Sep 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 6 Sep 2025 - 13 Sep 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 13 Sep 2025 - 20 Sep 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 13 Sep 2025 - 17 Sep 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 13 Sep 2025 - 20 Sep 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 13 Sep 2025 - 17 Sep 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 13 Sep 2025 - 20 Sep 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 20 Sep 2025 - 27 Sep 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 20 Sep 2025 - 24 Sep 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 20 Sep 2025 - 27 Sep 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 20 Sep 2025 - 24 Sep 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 20 Sep 2025 - 27 Sep 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 27 Sep 2025 - 4 Oct 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 27 Sep 2025 - 1 Oct 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 27 Sep 2025 - 4 Oct 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 27 Sep 2025 - 1 Oct 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 27 Sep 2025 - 4 Oct 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 4 Oct 2025 - 11 Oct 2025 | 7 nights 7 ngts | £1,237.42 |
|
Full | |
| Castellare Train & Trail Short Break | 4 Oct 2025 - 8 Oct 2025 | 4 nights 4 ngts | £759.30 |
|
Full | |
| Heart of Tuscany | 4 Oct 2025 - 11 Oct 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 4 Oct 2025 - 8 Oct 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 4 Oct 2025 - 11 Oct 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 11 Oct 2025 - 18 Oct 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 11 Oct 2025 - 15 Oct 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 11 Oct 2025 - 18 Oct 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 11 Oct 2025 - 15 Oct 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 11 Oct 2025 - 18 Oct 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 18 Oct 2025 - 25 Oct 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 18 Oct 2025 - 22 Oct 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 18 Oct 2025 - 25 Oct 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 18 Oct 2025 - 22 Oct 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 18 Oct 2025 - 25 Oct 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Castellare Train & Trail | 25 Oct 2025 - 1 Nov 2025 | 7 nights 7 ngts | £1,237.42 |
|
Book | |
| Castellare Train & Trail Short Break | 25 Oct 2025 - 29 Oct 2025 | 4 nights 4 ngts | £759.30 |
|
Book | |
| Heart of Tuscany | 25 Oct 2025 - 1 Nov 2025 | 7 nights 7 ngts | £1,108.43 |
|
Book | |
| Heart of Tuscany Short Break | 25 Oct 2025 - 29 Oct 2025 | 4 nights 4 ngts | £673.31 |
|
Book | |
| Medieval Tuscany | 25 Oct 2025 - 1 Nov 2025 | 7 nights 7 ngts | £1,409.40 |
|
Book | |
| Heart of Tuscany Short Break | 23 May 2026 - 27 May 2026 | 4 nights 4 ngts | £740.64 |
|
Book |
The above prices are 'sharing prices' based on two people in either a one bedroom superior apartment or a two bedroom classic apartment with a shared bathroom.
INCLUDES accommodation; half board; riding as per programme; twice weekly apartment cleaning. The 7 night Medieval Tuscany also includes 3 picnic lunches.
SINGLE SUPPLEMENT If you are willing to share a two bedroom apartment (one bathroom) and a sharer is available then the per person sharing price applies. If no sharer is available you will have a one bedroom classic apartment and the single supplement will apply as below. We will refund the difference if we find you a sharer.
| Single Supplement | Single Supplement | |
| 7 nights | 4 nights | |
| 18 - 25 April 2025 | £558.94 | £385.24 |
| 26 April - 27 June 2025 | £419.64 | £292.37 |
| 28 June - 18 July 2025 | £558.94 | £385.24 |
| 19 July - 16 August 2025 | £898.61 | N/A |
| 17 August - 5 September 2025 | £558.94 | £385.24 |
| 6 September - 1 November 2025 | £419.64 | £292.37 |
PAYABLE LOCALLY Lunches; drinks; optional tips; spa treatments; other activities; transfers; tourist tax (€1 per night).
NEAREST AIRPORT Pisa or Florence.
TRANSFERS We can arrange transfers from either Pisa or Florence airports (c. €190 each way for 1 - 2 pax and €220 each way for 3 - 5 pax). Since the apartments have self-catering facilities you may wish to consider having a rental car to give you independence during the week. A rental car is strongly recommended if you book the Heart of Tuscany itinerary.
We can arrange transfers from Pisa or Florence airports. Alternatively you may prefer to hire a car at the airport. A rental car is recommended for the Heart of Tuscany programme.
Please note that some transfers may be shared if there are other guests arriving at a similar time.
Check-in to your apartment is usually from 16:00 and check out on the day of departure is by 10:00. Please note that the reception at Castellare di Tonda closes at 20:00 therefore we recommend your flight arrives no later than 18:00.
Collections/Drop offs are also possible in Florence and Pisa city but not in the 'restricted areas'.
Transfers need to be booked as early as possible as they are subject to availability. Any cancellations within two weeks of travel will incur full payment for transfers.
Located in the hills of Tuscany midway between Florence, Siena and Pisa.
Spring and autumn are pleasantly warm; winters mild and summers hot. Rain is possible at any time of year but unlikely during the summer months.
I had the most amazing week at Castellare di Tonda! From start to finish this holiday was wonderful.
It was my first ever riding holiday and I travelled alone. Becky from in the saddle was incredibly helpful and informative and couldn’t have done more to make booking and holiday prep any easier - thank you Becky!
I was a little nervous as I’d had a recent bad experience riding which had massively knocked my confidence.
The team at Castellare are some of the kindest people I’ve had the pleasure to come across - non more so than Ailsa who made the week perfect!
Ailsa is a fantastic riding companion and all round wonderful human - from the first moment I was put at ease and had so much fun riding out through the most beautiful countryside.
Ailsa’s kindness and support didn’t stop with the riding - she also helped me find a lovely wine tasting for my non riding day and was on hand for any questions about anything holiday related.
I had the great pleasure of spending the week riding Rossa who is a joy! Kind and safe but will respond to your leg and seat so well which makes canters the most fun! A beautiful soul she was lovely on the ground too and I had as much fun grooming her as riding her - fell a little bit in love and if I could have taken her home I would have done!
10/10 would recommend and I’ll definitely be back! Huge thank you to Ailsa and Rossa for helping me fall back in love with riding again - I’m indebted you both.
Janette ,Ripley
Overall rating: 5/5
