About this trip
Our standard package includes a minimum stay of 4 nights for 2 people (double room accommodation). Contact us to tailor the trip to your needs.
For Players
Tuscany follows its own rhythm, and so does Castiglion del Bosco. Wake up to the scent of cypress trees and sun-warmed stone before heading down to a clay court framed by vineyards. Here, the game follows the sunlight: rejuvenating rallies in the morning or late afternoon sessions when the hills turn to gold.
With courts reserved exclusively for guests, the only sounds are the bounce of the ball and the breeze through the olive trees. Four days is the ideal amount of time to find your balance: a routine of tennis, slow breakfasts, and relaxation, with plenty of time to explore the 4,200 hectares of the Val d’Orcia.
For Companions
For those who don’t play tennis, the estate reveals an entire universe of Tuscan pleasures. From the infinity pool to the Spa, the estate offers bespoke experiences: tastings in the private Brunello winery, cooking classes, truffle hunting, and horseback riding. For those wishing to explore the region, iconic villages like Pienza and Montalcino are just a short drive away.
Everything is seamless and included: daily breakfast, a fully stocked minibar, Kids Club, and full access to the wellness and sports facilities. No logistics, no stress—exactly how a Tuscan getaway should be.
Travel Program
Arrival in Val d'Orcia
Afternoon: private arrival at Castiglion del Bosco, welcome and check-in at the Borgo Suite
Late afternoon: orientation walk through the borgo and the estate
Evening: aperitivo and dinner at one of the estate's restaurants (on own account)
*The program is subject to change according to the coach's or student's requirements
Package details
What's included
- For all guests
- 4 nights in a Borgo Suite at Rosewood Castiglion del Bosco (17–21 September 2026)
- Daily breakfast for two
- Minibar fully restocked each day (alcoholic beverages excluded)
What's not included
- Flights and transfers to/from the hotel
- Lunches and dinners (restaurants on the estate and in the area, billed directly)
- Alcoholic beverages from the minibar
- Tennis coaching, hitting partners and racket stringing (on request, billed separately)
The venue
Explore our premium training locations and world-class facilities. Discover where your experience takes place, featuring top-tier courts and services.
Rosewood Hotel - On-estate tennis court
Included Accomodation
Rosewood Hotel
Castiglion del Bosco is a restored medieval borgo on a 4,200-hectare private estate in the heart of southern Tuscany, between Montalcino and Pienza. It's one of the most exclusive addresses in Italy: a working Brunello di Montalcino winery, a private golf course, a spa, a Michelin-level dining scene, and just a handful of suites and villas spread across restored farmhouses.
Guests are accommodated in a Borgo Suite: characterful suites woven into the original village architecture, blending antique Tuscan craftsmanship with contemporary comfort — terracotta floors, wood beams, bespoke furniture, and views over the vineyards or the medieval piazzetta.
On the Map
What's your level?
LEVEL GUIDE
Starter
Developing basic strokes.
Understanding the rules.
Learning ground strokes techniques.
Becoming familiar with court positioning.
Cancellation policy
Free cancellation up to 30 days before departure
Until 30 Days Before
Cancel early for the highest refund.
70%
Between 30 and 10 Days Before
Partial refund within this window.
30%
Less than 10 Days Before
Late cancellations can't be refunded.
Non-refundable
