What’s the Perfect Tuscan Villa for You?

Photo: Marco Awerbuch

I get tingly when talking about Tuscany. Over the years, I have luxuriated at spots like Castello di Casole and hibernated at hidden, hilltop Airbnbs like this one owned by two lovers named Francesco and an old man who made meat sauce in his sleep — and I must say, both were equally stellar. Why? Because it’s Tuscany — where beauty is king, Chianti is queen, and olive oil, ribollita, lavender, and sophistication comprise a very specific religion that I wholeheartedly embrace. In Tuscany, the Italians are tall, the beef is tender, and all roads lead to an authentic countryside experience that is accessible (and Instagrammable) without ever feeling too lost, or too found. In fact, the only stressful thing about Tuscany is selecting the right place to hang your hat (a custom-made Fedora, of course). There are thousands of hotels, villas, Airbnbs, and private rentals choose from, and while we encourage you to embrace the art of aimless and random Tuscan travel (that’s how we found half these gems), here are a few places we recommend to create your very own Italian utopia.

If you want a drool-worthy pool overlooking endless olive trees and sunflower fields: Castello di Casole, Località Querceto Casole d'Elsa; Siena, SI 53031 +39.0577.961508

This all-suite, ultra-luxe property is located in a restored castle on a 4,200-acre estate. Expect the best of everything: service, food, wine, architecture, and views — and likely an under-the-radar celebrity doing morning laps.

If you want to visit the most beloved eighth-generation butcher in the world: Villa Le Barone, Panzano in Chianti
50022, Greve in Chianti, Florence +39 055 85 26 21

Guests make pilgrimages again and again to this boutique villa in Chianti that includes the renowned butchery and restaurant Officina della Bistecca from Dario Cecchini.

If you want to customize your trip and hop around to villas, chateaus, cottages, tents, castles, and houseboats all over Tuscany: Wyndam Vacation Rentals

The American company manages tons of (relatively) affordable options in the area, specifically this one, this one, and this one.  

If you want to drop dead from beauty and butlers and butterflies in a converted monastery: Villa San Michele, Via Doccia 4, 50014 Fiesole, Florence +39 055 5678 200

If you don’t mind that Kimye might have honeymooned in your bed, this place is over-the-top stunning and just a ten-minute drive from Florence.

If you want to plant yourself and your family inside a breathtaking, revived ancient village with the works: Castelfalfi, Loc. Castelfalfi, 50050 Montaione, Florence +39 0571 891000

This place has everything from horseback riding to a cooking school to a killer golf course to a Michelin starred restaurant — and is as authentic as a scene from Under the Tuscan Sun. (By the way, a short drive away is the best local Tuscan peasant food I have ever tasted at the super-cozy La Cerbana.)

If you're craving rolling hills, without the frills: Borgo di Cortefreda, Via Roma 191, 50028, Tavarnelle Val di Pesa, Florence +39 055 80.73.333

This affordable spot makes a great jumping-off point to explore the region.

If you're going on a couples' vacay and want to stay in a private home: Palazzo GiustiPescaglia, Tuscany

This place with room for four has 200-year-old palm trees and medieval fireplaces, and is just a few miles away from one of the most exquisite towns in Tuscany, Lucca.

If you are a raging olive-oil freak:  Villa Mulinmaria, Localita' S. Andrea A Pigli, 44 52100 Arezzo +328 6810424

This super-affordable, family-run villa is an Eataly-approved spot for participating in the harvest, or for simply basking in unbelievable olive-oil bliss.

If you want to choose from several chic and stunning private villas owned by an expat: Monteverdi Villas +39 0578 268 146

These villas were laboriously revived by a famously stylish and industrious Italian couple who also installed an art gallery and foodie-approved farm-to-table restaurant.

If you're throwing the wedding of the year: Castello Di Castagneto, Via della Sassetta 1, 57022, Castagneto Carducci, Livorno, +39 0565.763626

Here your guests can gaze out on the nearby isles of Elba and Corsica as you walk down the aisle.

If you want to be as close as possible to Siena and its striking Piazza del Campo: Hotel Certo Di Maggiano, Strada di Certosa, 82/86, 53100, Siena +39 0577 28 81 80

This former monastery built in the 14th century is well-located for nearby attractions but still a great place to soak in some serious luxury-countryside at the end of tedious touring.

If you want to stay somewhere with the Relais & Chateaux vote of confidence: Baglioni Hotel Cala Del Porto, Via del Pozzo – 58040 Punta Ala Grosseto

After your visit, you may want to check out Baglioni's famously elegant Rome and London offshoots.

If you're visiting Florence but need an escape from the crowds: The Francesco Rental

This bohemian Airbnb is just a short bus ride from the city in the stunning cliffside town of Fiesole.

If you want old-world, dolce vita glamour: Il Pellicano, Località Sbarcatello 58019 Porto Ercole, Grosseto +39 0564 858111

Here is the best perch on the Tuscan seaside to smoke a cigarette with your new lover and sunbathe topless with a Missoni sister.

If you're a wine snob: Castello Del Nero, Strada Spicciano n. 7, 50028, Tavarnelle Val di Pesa +39 055 80 64 70

This villa gives you easy access to all people, places, and things Chianti, San Gimignano, Brunello, Tignanello, Sassicaia, and Ornellaia, just to name a few.

If you want to mingle with painters, poets, song writers, and fashion designers: Villa LenaVia comunale di Toiano, 42 56036, Palaia PI +39 0587 083112

After your stay here in the Tuscan wilderness, you'll probably want to apply for the two-month artists' residency on site that all the culturati are swooning over.