There are few things more satisfying than a game of tennis in Tuscany, especially when the opponent is decent, the ball is behaving itself and the view is sufficiently distracting to provide a respectable excuse for losing. Across the region, hotels and country estates have cottoned on to the appeal, encouraged by the success of Italian tennis, pairing proper courts with the sort of surroundings that make even the most competitive set feel pleasantly civilized. From Renaissance villas and medieval borgos to wine estates and country houses, these are places where you can play a few sets before lunch, cool off in the pool afterwards and still have enough energy for an aperitivo. Here are a few of my favourites.
Tennis, then Tuscany’s great cities
For tennis-minded travellers who want to combine Florence with the delights of a country house hotel, Villa La Massa has an unusually convenient advantage. The 13th-century villa, set on the banks of the Arno, offers its own heated pool, spa and fitness facilities, while just up the road Match Ball Firenze Country Club provides a serious sporting complement, with 16 tennis courts set among lawns, olive trees and cypresses. Private lessons and tailored sessions with talented and results-focused coaches are naturally available for guests. The combination is on point for players who want proper court time without staying at a dedicated tennis resort: a morning on court, followed by a swim, spa treatment or leisurely lunch back at the villa, with Florence only a short shuttle ride away.
Just south of Siena, Certosa di Maggiano is one of the quirkiest offerings in the group. Occupying a former Carthusian monastery, the long loggias and ecclesiastical architecture gives the hotel an atmosphere quite unlikely anywhere else. Its astroturf tennis court is part of a wider collection of leisure facilities, alongside the games rooms, lush gardens and elongated pool. Here, tennis feels almost incidental, in the best possible sense. A morning game can lead to an afternoon wandering through Siena, an aperitivo beneath the Tuscan sun and an exquisite dinner based on seasonal produce in the atmospheric surroundings of a property whose history reaches back centuries. For couples looking for a hotel where sport is balanced by romance and a strong sense of place, Certosa di Maggiano is hard to overlook.
Just north of the medieval walls of Siena, Villa Scacciapensieri offers a convincing answer to the question of what a boutique tennis hotel in Tuscany should be. The 19th-century manor house sits within a romantic parkland of mature trees and Italian gardens, with terraces overlooking Siena, a panoramic swimming pool and on-site restaurant with produce from the kitchen gardens. Tucked into the grounds is a private cement tennis court, available to guests free of charge and, weather permitting, playable throughout the year and into the evening under floodlights. Equipment is provided and an instructor can be arranged, making this less a hotel that happens to have a tennis court than a small country-house retreat where tennis feels naturally woven into the experience. Plus, the showers are available even after you have checked out.
Love-all: boutique hotels with bags of charm
Design-driven wonder Casa Newton is an appealing addition due to the quality of its finishes, overall playfulness and subtle nod to tennis. This intimate boutique hotel near Pienza sits amid Val d’Orcia vineyards with views across the countryside, and guests can play on its astroturf tennis court as part of a broader collection of understated outdoor pleasures that includes bocce, e-bikes and walking among the vines. The court feels perfectly in keeping with Casa Newton’s philosophy: this is not a resort built around sport, but a beautifully designed country house where a game of tennis can be slipped naturally between time by the pool, wine tasting at Fabbrica Pienza and long, unrushed meals centred on local ingredients. For travellers drawn to the idea of tennis as part of the Tuscan dolce vita rather than a dedicated sporting programme, Casa Newton is a charming discovery.
Podere Castellare offers a more intimate take on the tennis and Tuscany experience as a boutique eco-sustainable farmhouse set among vineyards, olive groves and woodland on the slopes of the Vallombrosa hills, with sweeping vistas across the surrounding valley and hilltop villages. Its artificial grass tennis court is a hop, skip and a jump from the panoramic swimming pool, making it easy to move from a morning game to a swim and a long afternoon taking in the landscape. For fitness-minded guests, the property also has a dedicated wellness and fitness area, while Podere Castellare is closely associated with Peter in Florence, the Tuscan-made London Dry Gin created by the estate’s owners and distilled in its own micro-distillery. The combination is quintessentially relaxed: tennis, a workout, a dip in the pool and a gin in hand, all against the sigh-inspiring views of the Tuscan countryside.
For adults only, The Club House in the Castelnuovo Berardenga countryside is an intriguing proposition. The five-star luxury property has just 15 rooms and suites, yet manages to accommodate two artificial turf tennis courts, a putting green and driving range, a scenic pool and one of the most contemporary spas in Tuscany. There’s also a striking gastronomic component in the form of Il Visibilio, whose blind tasting menu carries a Michelin star. The result is a hotel for the modern sports-minded traveller: intimate enough to feel exclusive, but with enough facilities to make staying on the property for several days genuinely tempting.
The grand slams: big estates, bigger backhands
For a property that makes sport feel like a natural extension of the Tuscan landscape, Castello di Casole, A Belmond Hotel, Tuscany has an enticing tennis offering if money’s no object. Tucked beneath the estate, the new sports centre brings tennis together with padel and pickleball, with courts surrounded by oak forests and the rolling countryside beyond. Guests can book a court for a relaxed game or arrange private coaching and group sessions through LUX Tennis, while the “Beat the Pro” challenge adds a more competitive edge. The result is in keeping with the character of Castello di Casole, an active interlude in an otherwise tranquil country escape, where a morning on court can give way to the spa, a Tuscan lunch or an afternoon exploring the estate.
Then there’s Rosewood Castiglion del Bosco, near Montalcino, arguably the place that most fully embraces the idea of the Tuscan estate as a destination in itself. The sprawling property combines historic buildings and private villas with wine, golf, wellness and a formidable range of outdoor activities. Tennis is part of that offering, with two courts, while some of the private villas take the idea of sporting privacy even further with their own private rectangles. For travellers seeking discretion, space and the unmistakable drama of the Val d’Orcia landscape, it represents the ultimate version of the tennis and Tuscany equation: play a set in the morning, disappear into the countryside afterwards, and let the rest of the day take care of itself.
At Il Borro, tennis is just one element of a much larger Tuscan fantasy. The Ferragamo-owned estate occupies 1,100 hectares of organically managed countryside in the Valdarno, centred around a meticulously restored medieval village that now forms the heart of a sprawling hotel. Guests can stay in suites within the borgo or in a collection of historic villas, while days can be divided between the two floodlit tennis courts, wine tasting, horseback riding, cooking experiences and long meals built around produce from the estate. It is precisely this combination that makes Il Borro so appealing: the tennis is not an isolated sporting amenity, but part of an immersive country life in which vineyards, olive groves, food and landscape all become part of the holiday.
In the Chianti hills, COMO Castello Del Nero takes a sophisticated approach to the Tuscan country retreat. The setting is a 12th-century castle surrounded by a roughly 300-hectare estate, where Renaissance heritage is paired with contemporary interiors and the COMO Shambhala wellness philosophy. The property offers tennis on artificial turf among its wellness experiences, making it well suited to travellers who want to combine an active morning with a serious spa treatment, an unhurried lunch and an evening among the vineyards. With Florence within easy reach, it also has an advantage over some of the more remote estates. You can retreat into the countryside without quite giving up the city.
In Chianti, Borgo San Felice has the particular charm of a village that has been carefully brought back to life. Surrounded by vineyards and olive groves, the estate offers the pleasures you might expect from a Tuscan wine retreat while also providing tennis among its sporting facilities. Its appeal lies in the balance: there is enough to occupy an energetic guest, but nothing that demands an itinerary. A game can be followed by a swim, a wine tasting (try the Pugnitello native varietal) or a leisurely Michelin-starred meal, with the vineyards providing the constant backdrop. It is the sort of setting where tennis becomes another expression of the Tuscan lifestyle rather than an activity imposed upon it—vigorous for an hour, dolce far niente for the rest of the day.
Baseline by the beach
Last but not least, somewhere I go twice a year for a family-friendly, no-frills take on a tennis vacation, La Buca del Gatto along the Tuscan coast near Cecina puts tennis at the heart of a relaxed seaside escape. Set in a pine forest just 500 metres from the beach, the family-oriented resort has six tennis courts, alongside pools, a gym, buffet dinners and children’s entertainment. Tennis is sufficiently central to the property that it now has a tennis academy with coaching, while the courts are available to guests as part of the resort’s sporting facilities.
