Founded in Florence in 1990, Tuscany Now & More started out with just one villa and a simple idea: to connect our guests with local owners and places we know and love. We chose to keep a deliberately small portfolio, growing it carefully — partner by partner, house by house — to give guests a level of support that only comes from living and working in Italy.
35 years later, our roots may have spread beyond Tuscany to Umbria, Northern Italy, Amalfi and near Rome, but our approach hasn’t changed. We still hand select every villa. We still work directly with owners on restorations, design decisions and long-term care. And when a guest asks a question, the answer comes from someone who genuinely knows the property, the landscape and the people behind it.
To mark 35 years, we look back at the original core of our collection in Tuscany, and a few of the longstanding partnerships that have shaped who we are and how we work.
The Estate of Petroio: partnership since 2003
Our relationship with The Estate of Petroio began in 2003 with a single villa. Today, after more than two decades of partnership, we represent the entire 650-acre wine estate. It has evolved into nothing short of a flagship escape: three beautifully restored residences, two private pools, sports and spa facilities, and a dedicated team of in-house staff.
Resident chef, Francesco — whose résumé includes stints in Florence, London, and working with Michelin greats — leads in-house cooking classes that feel like a masterclass in Tuscan tradition. Wine tasting, meanwhile, happens on-site, with estate-produced Chianti, olive oil, and Vin Santo available to sample while overlooking the vines.
The Estate of Petroio shows what long-term collaboration can achieve; a historic estate that improves with each generation of guests. It’s where our clients return year after year for family reunions, weddings, or simply to experience again the special sense of belonging they have discovered here.
Tizzano: partnership since 2014
We first partnered with Tizzano in 2014, drawn to its commanding views over Chianti and its easy proximity to the Tuscan greats: Florence, San Gimignano, and Siena. The villa is set within a 300-hectare organic estate with a 12-metre private pool overlooking the hills. Interiors reflect its history as a country home of an aristocratic family, filled with antiques, art, and rare books.
Perfect for hosting larger groups without losing the feel of a private home, it’s a villa we know intimately. We know how the house flows, which outdoor spaces catch the best light at different times of day, and we also know the dedicated staff who provide seamless, warm care for every stay. Tizzano has worked so well for over a decade because it is everything our guests could dream of when they picture Tuscany. And over those years, our connection to the villa has shaped how we help guests experience the surrounding countryside at its best — from local producers to the small places worth detouring for.
Villa di Masseto: partnership since 2015
Just north of Fiesole and a short drive from Florence, Villa di Masseto is one of our longest-standing grand dames. Everything about this Renaissance villa feels lifted from a fairytale, from the Italian terraced gardens to the loggias and stately living spaces.
Service is included for six breakfasts and three dinners, a thoughtful rhythm to the week that frames days spent wandering Florence’s streets. And, as a Florentine family, no one knows the Renaissance city quite like we do. We also love this corner of the countryside for another reason: you don’t always need to venture into the city centre to find some of the region’s best restaurants.
Villa di Masseto has set the bar high for Tuscan getaways that balance relaxation and culture. It has also taught us a great deal about what our guests consistently value in a villa stay.
La Badiole: partnership since 2015
Added to our collection in 2015, La Badiole represents a decade of knowing Montepulciano and the calming rhythms of the Val di Chiana as only locals can. The hilltop villa shows just how elegantly a farmhouse restoration can work for the modern traveller. Vaulted interiors open onto cypress-lined lawns with a solar-heated infinity pool and panoramic views of one of Tuscany's most breathtaking corners.
La Badiole is one of those villas that radiates serenity. And when we select our villas, we aren’t just thinking about the destinations you can spend days exploring, but the hours that slip by almost unnoticed once you arrive. The loggia invites alfresco dinners, the boules court lulls you into lazy afternoons, and every room feels calm. Not to mention the famed wineries right on the doorstep. We’re Italians, after all, so the measure of a perfect villa is how naturally it invites you to embrace “il dolce far niente.”
Palazzo Cheto: partnership since 2015
Rounding out our signature Tuscan five is Palazzo Cheto, another villa we welcomed in 2015, just moments from Siena. There are several qualities that make this the perfect home for our collection: the attentive staff, their emphasis on seasonal farm-to-table cuisine, and the deep respect that has gone into its restoration. Now managed by the owner’s son, Palazzo Cheto is in its second generation of family care.
Originally a 13th-century monastery, this fully staffed escape honours its past with wood-fired ovens, wood-beamed ceilings, and a stunning central courtyard. Yet the estate continues to impress with a private tennis court and 5-a-side football pitch, a private cantina for wine tastings, gym and sauna. Views from the private heated pool stretch endlessly over the Crete Senesi, while walking paths wind through the wooded estate.
For us, Palazzo Cheto perfectly captures the essence of Tuscany: a distinct historical pedigree, generous hospitality, and a deeply welcoming atmosphere.
Explore the full collection of handpicked Tuscan villas, or get in touch with our dedicated Villa Specialists to start crafting your own unforgettable Italian escape. No request is too big or too small for our local Italian team.