Luxury Tennis Holiday in Tuscany
Castiglion del Bosco, Italy · 5 days
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.
Technique
Tactics
Play
Tennis
Relax
At a Glance
Travel Program
WHO IS THIS FOR?
- Couples and pairs of friends wanting a luxury tennis holiday without the intensity of a camp
- All playing levels — the court is private, pace is set by the guests
- Travellers who value privacy, wine, wellness and landscape as much as tennis
Dates, room type and experiences can be tailored on request. Companion programmes, coaching, transfers and extended stays available upon booking.
DAY 1
Thursday 17 September:
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)
DAY 2
Friday 18 September:
Morning: breakfast, then a one- to two-hour hit on the private clay court
Afternoon: infinity pool and wellness, or optional Brunello tasting at the estate winery
Evening: dinner in Montalcino or on the estate
DAY 3
Saturday 19 September:
Morning: tennis or long breakfast, followed by a drive to Pienza and San Quirico d'Orcia
Lunch: pecorino, pici and Brunello in a village trattoria (on own account)
Afternoon: return to the estate, pool and spa time
Evening: dinner at the estate's restaurant
DAY 4
Sunday 20 September:
Morning: late-afternoon tennis session on clay
Afternoon: optional companion experience (cooking class, truffle hunt, horseback ride)
Evening: final dinner on the estate
DAY 5
Monday 21 September:
Breakfast and check-out by 12:00.
Private departure
The venue
Rosewood Hotel - On-estate tennis court
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)
Included Accomodation
Rosewood Hotel
Cancellation policy
Until 30 Days Before
Get 70% of the total price back
Between 30 and 10 Days Before
Get 30% of the total price back
Less than 10 Days Before
Non-refundable
