Italy is an ideal destination any time of year, but if you want to immerse yourself in the beauty of the countryside there’s no better time than the later months of the year. That’s when the rolling hills of Tuscany come alive with vibrant color and sunny days of sightseeing finish in snug evenings beside the fireplace. Fall is harvest season all over Italy, and if you’re in Tuscany you’ll see the grape and olive picking activity, mountains of chestnuts at the local market and restaurant menus boasting fresh truffles on nearly every plate. When the heat of summer subsides, towns and cities around the country come alive with the markets, festivals and activities that Italians themselves love to enjoy. You’ll be far from the madding crowds of summer travel and have the opportunity to experience some of the most beautiful (and delicious!) traditional Italian autumn foods.
Of course, any great holiday starts with the ideal place to rest your head after a day of taking in the sights, and Tuscany has plenty of fantastic options to base yourself and your friends or family during a vacation. With cities like Florence, Siena or Pisa all within driving distance, you’ll have the option of relaxing in the countryside or taking in the culture of some of the most famous landmarks in Italy. And along the way, there’s so much to see that you might just spend the entire day cruising through the incredible landscape of a region that has captured travelers’ imaginations for centuries. After all, it’s not the destination but the journey that counts.
Located in the countryside around Florence, the Gabbiano Villa makes getting to the Cradle of the Renaissance a simple affair, with the train station in nearby Figline Valdarno only a few kilometers away. Yet, you may just find yourself too busy wandering the gardens of your villa to notice. The Gabbiano’s manicured property can host up to 10 guests with a private guest cottage giving room for 6 more, and its location on the sumptuous Vecchietto Estate means that you’ll have access to tennis courts, yoga lessons and cooking courses right at your doorstep. However, there is plenty to tempt you out of your nest: the Valdarno antiques fair comes to Montevarchi on the second Sunday of every month, which is just 15 kilometers from the Villa. For those looking for a little more modern shopping, the Leccio Outlet offers a full range of luxury and Made in Italy brands that will make your Christmas shopping a breeze. And, of course, both offer international shipping to keep your suitcases from bursting.
Also on the Vecchietto Estate, the Tucano Villa and Cottage is perfect for intimate groups of up to 8 guests in the main house and 3 more in the cottage on the property. The sprawling loggia is perfect for alfresco lunches and the traditional Tuscan style living room comes complete with a working fireplace for crisp autumn evenings, and guests can avail themselves of all of the amenities that the estate offers. Along with its location near the best shopping that Italy offers, the Tucano Villa is close to the famous towns of Greve in Chianti and Gaiole in Chianti, which live up to their names by hosting some of the best wineries and producers in all of Italy. Make a day out of visits to both towns, as one naturally leads to the other, and enjoy the market squares that fill up with organic vegetables and foods from the area. If you’re in the area in October you may just catch the fabulous Eroica, a cycling event that began in Gaiole in Chianti and returns there every autumn. Cheer them on from the sidelines with a glass of Chianti Classico in hand!
If you’re looking for all of the amenities of the Vecchietto Estate and a combination of modern comfort and classic Tuscan style, the Maragone Villa is the perfect refuge for an autumn getaway. It’s tucked away in one of the most exclusive corners of the estate and offers ample space for up to 10 guests to enjoy the privacy and peace that this magical location has to offer. Make it a base for exploring Florence, which is only a short car or train ride away, or plan an excursion to the hilltop town of Arezzo, the medieval city of Siena and the famous leaning tower of Pisa, all of which are reachable within a couple of hours. You’ll see these historic locations at their very best, when locals return from their summer holidays and are happy to share their food, wine and culture with visitors who know that fall is when their cities shine brightest. And after a day spent pounding the cobblestones, return to your sanctuary for a fabulous meal at the Estate’s on-site restaurant, from award-winning chefs.
If you’re looking for the ultimate Tuscan experience, you couldn’t do better than La Rosetta Villa, a sprawling compound nestled in the countryside between the storied towns of Greve and Ponzano in the heart of the Chianti region. Particularly well suited to larger groups, the villa offers a main house with accommodation for up to 12, with another 4 in the two bedroom cottage and 4 more in the 2 bedroom barn. With multiple lounging areas and a large fireplace in the living room, there is ample space to gather together for celebrations and long evenings together. The postcard perfect views will melt even the most traveled hearts, and the traditional rustic decor will make anyone fall in love with the region. All the major attractions of Tuscany are within easy driving distance, and the train station in Figline Valdarno makes a jaunt to Florence a breeze. Don’t forget to visit San Gimignano, the UNESCO world heritage site with 14 towers that hosts open air concerts throughout the fall season.
Tuscany has so much to offer, and the Panorama Villa near Montecatini Terme is the perfect example of the idyllic retreats for which the area is so well known. Overlooking the Val di Nievole, or Valley of the Mists, this villa sleeps up to 12 people and offers add-ons like a personal chef, cooking classes and wine tastings. If you manage to peel your eyes from the panoramic views, you can practice your pizza making skills with the stone oven or cozy up by the fireplace in one of the villa’s living rooms. The rustic character of the property is an ideal place to watch the leaves change around the countryside, and once you return from visiting nearby Pistoia and Lucca, you’ll sleep peacefully under the frescoed ceilings and historic wood beams in the bedrooms. Don’t forget to visit the stone chapel on site, and keep your eyes open for the monument to Victor Emmanuel II, the first King of United Italy who once stayed at the villa.
Southern Tuscany remains one of the most under explored areas in the region, and intrepid travelers are rewarded with authentic cuisine and unspoiled views of the majestic Val d’Orcia. Riposo Verde near San Casciano dei Bagni is a restored farmhouse overflowing with the charm and classic beauty of Tuscan living. Plus, its position in between Rome and Florence makes it the ideal place to discover the hidden sights that will surprise even the most seasoned traveler. The fall season is absolutely unmissable in this corner of Tuscany, as you’ll be able to take advantage of the many spas and thermal baths that dot the countryside. The town of San Casciano dei Bagni is named for the baths that date from Roman times, and there are numerous thermal parks to choose from for natural spa treatments or an extended soak. The famed Cascate dei Mulini are one of the most recognizable sights in Italy, and they’re within an hour’s drive of the villa, perfect for a day trip to the southern corner of Tuscany. Spend the day relaxing in the natural pools that the Romans loved and then duck into any of the authentic trattorias around the area, where you’ll find truffles that hunters deliver from their morning walks. There’s no better way to celebrate the fine art of dolce far niente.
Tuscany is one of the world’s most desirable destinations, but it is so much more than a spot for a summer holiday. The fall months, when the weather starts to cool and the seasons change, is perhaps the most glorious time to visit the area. Enjoy the scenery and cuisine that make it so famous, and explore the cities that hold the key to Italian history without the rush of crowds and the heat of the summer. For those in the know, autumn in Tuscany is the place to be!