Where Leonardo da Vinci Studied the Valley—And You Can Too
Leonardo da Vinci knew what he was doing when he repeatedly climbed this hilltop to sketch the Chiana valley spread below. The observation point he mapped in the 15th century is still here, and the view - now stretching toward modern Arezzo - remains as breathtaking as when he studied it. From the pool, you genuinely feel on top of the world.
San Michele has occupied this privileged position since the 7th century, watching civilizations rise and fall across the valley floor. The current owners spent years meticulously restoring what wartime bombing had damaged, preserving authentic materials and architectural details while creating a home that works beautifully for modern families. Their original plan was to create four separate apartments; fortunately, they changed their minds, adding interconnecting doors to open the entire house to groups who enjoy togetherness but appreciate personal space.
The result is a villa for eight with four bedroom suites - each with its own ensuite and character - spread across ground and upper floors. Air conditioning keeps summer afternoons comfortable, while multiple kitchens, dining areas, and sitting rooms mean your group can spread out or gather as the mood strikes. A long furnished portico runs the length of the house, perfect for lingering over morning coffee or evening aperitifs with that Leonardo-approved vista.
Outside, the spectacular pool and adjacent Jacuzzi command the hilltop, with a fully equipped pool house below offering another venue for alfresco meals. The owners live next door and are excellent cooks - available if you'd like an evening of authentic Tuscan cuisine or a cooking class where you learn to prepare it yourself. Down the hillside, their small farm delights visiting children: ponies, goats, geese, chickens, and more create an impromptu petting zoo.
San Michele is listed under the following categories:
On the left at the end of the entrance drive, San Michele has a furnished portico the length of the house with four doors that access its ground floor. The door to the right leads into the main dining room with a table for 8 and a corner kitchen, while the two central doors access the sitting room, which has comfortable sofas, a corner fireplace, a galley kitchen and a nearby staircase to the upper floor.
A short corridor off this sitting room leads past a small utility room with a washing machine to the only ground floor bedroom suite - a double bedroom with independent access and an adjacent shower room. The last door off the portico opens to an additional kitchen/dining room, though here the table for 4 might well serve for an evening card game or a place to catch up on the journal. This room has a second laundry room and stairs leading up to another double bedroom suite with a view towards the pool and an ensuite shower room.
The remaining two double bedroom suites are accessed from the central staircase and on opposite sides of the landing. While that on the right consists of a spacious bedroom and rosy shower room, the suite on the left also has a large sitting/dining room furnished with a table for 6, an attractive hutch, the ubiquitous kitchen and a single sofa-bed equipped with a trundle bed. From this room there are stairs leading down to the back of the house and very near the entrance to the church, no doubt very handy for the priest of earlier days. All of the bedrooms and shower rooms in San Michele are beautifully finished with authentic materials befitting the style of the house and sparkle with the added light of small chandeliers. The handcrafted vintage beds are queen size and made up with linens from well-known artisans from Anghiari.
While the wide portico has a lovely view of the grounds and its gas barbecue and outdoor table and chairs make it a delightful place for dining al fresco, there are other options that make 'going out to dinner' an easy and very local affair. Taking the path down to the large panoramically placed pool with its adjacent Jacuzzi also brings you to the pool house whose covered terrace is furnished for outdoor meals, all made easier since the pool house has a handy kitchen as well as a WC and changing/shower facilities. The pool itself is part of the view from the glass-fronted dining hall in the owner's home, itself a venue for dinners, pizza evenings and cooking classes they can arrange for guests on request.
The road leading up to Villa San Michele goes through a small hamlet and is steep and a little narrow, but is tarmacked, with only the last section turning to gravel
Possibly. There's a bus stop at the bottom of the hill, about 1.5km away (just under a mile). The walk back up is steep, so it's not for everybody.
When one decides come down from the hilltop, the obvious destination is the famous city whose medieval towers they have spotted from on high. One of the 12 most important Etruscan cities, Arezzo remained prominent in Roman times for its fine pottery and important throughout the Middle Ages thanks to powerful bishops and its artisans who excelled in goldsmithing and textiles.
Piero della Francesca captured part of the city's history in his famous frescoes, scenes of which are easily imagined in the city's beautiful Piazza Grande. Arezzo hosts both the Saracen Joust in late June and early September as well as monthly Antiquarian Fairs that fill the streets with fascinating pickings.
Yet there are other worthwhile places to visit nearby. A short drive brings you to the charm of the Cortona of 'Under the Tuscan Sun' fame, to the shores of Tuscany's 'inland sea' Lake Trasimeno, or even to the delight of bargains at nearby outlet shopping. Excellent access to major motorways and delightful country roads also place the ancient cities of Siena and Florence within easy reach, but what a pleasure to know that a quiet terrace and a hilltop view await your return.
From € 386 to 633 per day
From € 2,700 to € 3,800 per week
Approximately
$ 3,159 to $ 4,446 in USD
For over 40 years, Invitation to Tuscany has personally selected and visited every villa we represent. Our team knows each property and its surroundings intimately - allowing us to help you choose the perfect home for your family or group, and to make your stay as memorable as the place itself.
Check availability: View pricing and availability in the calendar above. To book online, click your desired arrival date, then your departure date. The calendar will grey out dates for stay lengths that aren't accepted—most villas book Saturday to Saturday, but many also allow shorter stays or flexible dates.
We visit our properties regularly and can provide firsthand advice based on your wishlist. Contact us and we'll help you select the best villa for your holiday. Secure your dates: We can hold your preferred dates for 48 hours while you confirm flights and coordinate with your group. To confirm, simply pay the 30% deposit. Your balance will be due 10 weeks before arrival.
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Need more support? Our Concierge Plus (€300) provides dedicated planning support for guests requiring more activity bookings, larger group logistics, or special occasions. Please note that weddings and event planning do not fall under this. Request this when booking or as early as possible.
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Tourist Tax: Many local administrations charge a tourist tax for rental accommodation, which varies by town. Charges typically range from €0.50 to €5 per person per night, with a maximum of 5-7 nights. Children are sometimes exempt. These charges are collected by property owners and paid directly to them.
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