Destination Management Company - Tuscany

Wake up in Tuscany.

30+ hand-picked villas and agriturismi – we’ve slept in every one.

Land. Your driver is already there.

Private transfers from Florence, Pisa and Rome to your door.

No crowds. Just your guide and Tuscany.

Private excursions to Siena, Florence, the Val d’Orcia and beyond.

Tonight, the chef comes to you.

A private chef cooks dinner in your villa kitchen.

Tell us your dates. We’ll do the rest.

One local team, from the first villa key to the last dinner.

What we arrange

Our services

Three ways we get involved – from the first villa key to the last skip-the-line ticket.

Line drawing of a Tuscan stone house

Stay.

More than a place to sleep.

Villas with pools, farmhouse agriturismi, apartments in Cortona’s old town, hand-picked hotels and resorts. But staying here means more: coffee in the piazza, neighbours who wave, the Saturday market. We put you inside Tuscan life, not next to it.

Line drawing of a tomato

Taste.

Tuscany, one plate at a time.

Tomatoes and basil picked from the villa garden an hour before lunch. Pecorino from the farm down the road, wine poured straight from the barrel, a gin tonic with local herbs at sunset. Cooking classes, private chefs and the tables where locals eat.

Line drawing of Michelangelo’s David

Explore.

Don’t just see it. Live it.

Join the olive harvest and taste oil minutes after it is pressed. Sip Syrah in a family cellar, walk the paths of St Francis, touch stones the Etruscans laid 2,500 years ago. Private guides, no crowds, at your own pace.

Eighteen ways to spend an afternoon.

A running list of the experiences we curate – filter by what you're in the mood for.

Stone terrace with lounge sofa and armchairs overlooking the Valdichiana valley from Villa Santa Maria Nuova, CortonaStay

Villa Santa Maria Nuova

From €4,500 / week

Saltwater infinity pool, sauna and a terrace over the Valdichiana – an uphill walk to Cortona's old town.

  • Up to 10 Persons
Discover
Aerial view of the stone villa with garden, cypresses and private poolStay

Villa Tiberini Wine Relais

From €180 / night · min. 3 nights

Sleep at a family winery near Montepulciano: breakfast included, pool, and the cellar a few steps away.

  • 2–8 Persons
Discover
Two armchairs on the terrace of Villa Monte Bianco looking over pines and cypresses to the Tyrrhenian SeaStay

Villa Monte Bianco

From €2,800 / week

Sea-view villa in Castiglione della Pescaia, 1 km from the beach, with a terrace along the whole house.

  • Up to 6 Persons
Discover
Historic stone farmhouse villa with arched loggia and gravel courtyard near MonteriggioniStay

Villa & Organic Farm

From €7,500 / week

Eight bedrooms on a working organic farm near Monteriggioni – dinner for eighteen under the pergola.

  • Up to 18 Persons
Discover
Covered terrace with deckchairs and panoramic view over the Tuscan countryside at Cortona Charme apartment, CortonaStay

Cortona Charme

From €160 / night · min. 3 nights

A two-bedroom flat on Via Nazionale with a private rooftop terrace over Cortona and the valley.

  • Up to 4 Persons
Discover
Large stone terrace with parasols, lounge seating and potted plants overlooking the Tuscan hills at Villa ErbolinoStay

Villa Erbolino

From €3,200 / week

Stone villa among Chianti vineyards: panoramic terrace, hot tub in the garden, and pets welcome.

  • Up to 8 Persons
Discover
Guest tasting a glass of white wine at a wineryTaste

Vino Nobile tasting

From €110 pp · half day

Private visit and tasting at a family winery in Montepulciano – cellar, vineyard and five wines.

  • 2–8 Persons
Discover
Woman preparing fresh pasta at a table under a garden pergolaTaste

Fresh pasta class

From €56 pp · half day

Roll pici and tagliatelle with a local cook, then sit down to eat what you made, with wine.

  • 2–10 Persons
Discover
Guests sharing dinner at a long table under a green pergolaTaste

Private chef at your villa

From €85 pp · evening

The chef shops at the market, cooks in your kitchen and serves a four-course Tuscan dinner.

  • 2–18 Persons
Discover
Truffle dog with the hands of a truffle hunter in the Tuscan woodsTaste

Truffle hunt & lunch

From €120 pp · half day

Walk the woods with a truffle hunter and his dog, then taste the finds over a farmhouse lunch.

  • 2–8 Persons
Discover
New olive oil poured into a bowl beside toasted bread and lemonsTaste

Frantoio & new olive oil

From €45 pp · 2 hours

October to December: watch the olives pressed and taste the new oil on warm bruschetta.

  • 2–10 Persons
Discover
Woman sliding a pizza out of a wood-fired oven at a Tuscan villaTaste

Pizza night at the villa

From €55 pp · evening

A wood-fired pizza evening in your garden – dough, toppings and a pizzaiolo who does the work.

  • 6–18 Persons
Discover
The Chapel of Madonna di Vitaleta with cypresses in the Val d'OrciaExplore

Val d'Orcia by private driver

From €280 pp · full day

Pienza, Montalcino and the Vitaleta chapel in one day, with lunch and a tasting along the way.

  • 2+ Persons
Discover
View over the terracotta rooftops and towers of Siena towards the Tuscan hillsExplore

Siena & Chianti

From €275 pp · full day

The Campo and the Duomo with a licensed guide, then a Chianti Classico estate on the way home.

  • 2+ Persons
Discover
Florence rooftops and domes in golden evening lightExplore

Florence with a private guide

From €295 pp · full day

Skip-the-line Uffizi and the Duomo with a licensed guide, door-to-door from your villa.

  • 2+ Persons
Discover
Thermal cascades of the Saturnia hot springs beside an old stone mill in southern TuscanyExplore

Saturnia hot springs

From €225 pp · full day

Warm thermal cascades in the Maremma, a slow lunch in a hill town, and back by sunset.

  • 2+ Persons
Discover
Calm lake with a wooded island and hills in the distanceExplore

Lake Trasimeno & islands

From €175 pp · half day

Ferry to Isola Maggiore, lakeside walk and a fish lunch – twenty minutes from Cortona.

  • 2+ Persons
Discover
People sitting on the steps of a medieval town hall in a Tuscan piazzaExplore

Cortona walking tour

From €180 / group · 2–3 hours

Etruscan walls, hidden lanes and the best view in town with a guide who lives here.

  • Up to 6 Persons
Discover

What we believe

Premium doesn't mean polished flat. We keep the imperfect edges - because that's where a place actually lives.

We work with a handful of families, growers and hosts across Tuscany - people who were already living this life before it had a name. Our job is to open the door, not to stage the room.

Every stay, tasting and walk is chosen for what it feels like at 6pm, not how it photographs at noon. The warmth of old stone, the weight of good olive oil, the slow light before dinner - that's the Once Italy standard.

Get in touch.

Contact or visit us
Contact us by email, phone or through our web form below.





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    A small, careful map of Tuscany – hosted, tasted and walked by people who live here.

    Visit

    Once Italy SRL
    Tour Operator & Property Management Company

    info@onceitaly.com

    Address

    Piazza Signorelli 7
    52044 Cortona
    Italy

    www.onceitaly.com