It is also a season made for lingering. Spend the morning exploring Florence, Siena or one of Tuscany's medieval hill towns, before returning to your villa for a long lunch, a glass of local wine and an afternoon beside the pool – or, as the evenings draw in, dinner around a farmhouse table. Autumn is also prime time for truffles, mushrooms, chestnuts and other seasonal produce, while the countryside is particularly beautiful for walking and cycling.
For a villa holiday, September and October have another advantage: temperatures are generally milder than the height of summer and demand is lower, making it an appealing time to experience some of Tuscany's most spectacular private estates. The Luxury Travel Book recommends early autumn as one of the finest periods for an Italian villa holiday.
Tuscan autumn escapes
Here are five particularly tempting villas to consider for an autumn escape.
Vila il Santo - Chianti
8 bedrooms | Sleeps 16 | From € 28,000 - €35,000 per week
For a classic Tuscan experience, it is hard to imagine a more atmospheric setting than Villa Il Santo. This historic estate dates back to around 1000AD and has been sensitively renovated, retaining original terracotta floors and wooden ceilings while adding all the comforts expected of a contemporary luxury villa.
The property is made up of three buildings – the Tower, Hay Barn and Pool House – giving larger groups plenty of space and privacy. The heated infinity pool has spectacular views across the countryside towards San Gimignano, while gardens, a covered outdoor seating area and loggia provide atmospheric spots for long lunches and evening drinks.
The USP: Its extraordinary history and setting. With San Gimignano, Siena and Florence within easy reach, it combines the romance of an ancient Tuscan estate with a beautifully restored, modern-day holiday experience. An arrival dinner, breakfast, daily housekeeping and a selection of Tuscan wines are also included.
Find out more
Villa Cappella Del Lupo – Chianti
5 bedrooms | Sleeps 10 | From € 10,530 - € 23,300 per week
A more contemporary take on the Tuscan villa, Villa Cappella Del Lupo sits among the hills of Florentine Chianti, close to Castelfalfi. Its interiors combine traditional wood and stone craftsmanship with sleek modern design, making it particularly appealing to those who like their countryside escape with a little polish.
There is plenty to keep everyone entertained, too: a cinema room, billiards table, football table and cigar room indoors, while outside there is a panoramic veranda with barbecue and dining area, a bocce court and an infinity pool overlooking the Castle of Castelfalfi and its golf course.
The USP: The combination of stylish interiors and serious entertaining facilities. The villa also comes with a complimentary arrival dinner, making it especially attractive for a family or group of friends looking for a relaxed autumn break.
Find out more
Villa San Leolino – Chianti
6 bedrooms | Sleeps 12 | From € 35,500 - € 42, 500 per week
History meets contemporary luxury at Villa San Leolino, an authentic Tuscan property dating back to 1368. Set between Florence and Siena and just 2.5km from the village of Panzano in Chianti, it is surrounded by vineyards, olive groves and cypress trees.
The villa has been carefully restored by its owners and combines elegant interiors with an infinity pool, fitness area, cinema room and beautiful gardens filled with herbs, vegetables, medicinal plants, jasmine, roses and lemon trees. There is also a pizza oven, sauna, hot tub, croquet and table tennis – so there is little reason to leave.
The USP: The food. A daily breakfast is included, featuring local cheeses and meats, homemade jams, seasonal fruit, granola and organic olive oil, while a Saturday-night welcome dinner is also provided. A private chef can be arranged for other meals, making this a particularly tempting choice during autumn's harvest season.
Find out more
Villa Cinigiano – Maremma
7 bedrooms | Sleeps 14 | From €15,000 - € 22,500 per week
For a taste of southern Tuscany, Villa Cinigiano is a striking choice. Set on a hill in the Maremma countryside, surrounded by vineyards and centuries-old olive groves, this former castle combines historic Tuscan character with contemporary interiors.
Inside, the open-plan living space has double-height ceilings, a statement fireplace and large doors opening onto the terrace. Seven bedrooms and suites include a particularly generous master suite with its own mezzanine lounge and office. Outside, there is an infinity pool, panoramic dining terrace, private gym, outdoor Jacuzzi and multiple spaces for relaxing.
The USP: Its location in the Montalcino/Maremma wine country. Montalcino, famous for Brunello wine, is within reach, while nearby Castello Banfi Wine Resort offers wine tastings and tours. With its combination of vineyard views, excellent facilities and concierge service, this is a villa designed for a proper autumn food-and-wine escape.
Find out more
Villa Scalabrelli, Maremma
7 bedrooms | Sleeps 16 | From €30,700 - €36,120 per week
If you want your Tuscan villa holiday to be as much about activities as relaxation, Villa Scalabrelli delivers. Set within a vast 75-acre estate near Magliano in Toscana, in the southwest of the region, this contemporary farmhouse has sweeping views across the Maremma countryside towards the Tyrrhenian coast and the Orbetello lagoon.
It is impressively well equipped: there is a private tennis court, football pitch, basketball court, infinity pool, gym, sauna, cinema room, massage room, playground and even a tree house. The property also has its own kitchen garden, with locally sourced ingredients featuring in its dining programme.
The USP: It is almost a private country-club experience. Guests can play tennis, cycle, hike, take cooking or pizza-making classes, arrange wine tastings or simply settle into the gardens and enjoy the views. Daily housekeeping and a private chef service are included, while the concierge can arrange everything from boat hire and guided walks to yoga and wine tours.
Find out more
About The Luxury Travel Book
The Luxury Travel Book is a family-run collection of luxury villas and premium apartments, with a concierge team able to arrange everything from private chefs and drivers to wine tours, cooking classes and bespoke excursions. Its Tuscany portfolio ranges from historic estates and vineyard properties to contemporary countryside retreats.
Browse The Luxury Travel Book's portfolio of luxury villas here.
