Once Italy / Explore

EXPLORE

Experiences, not just itineraries.

Week-long packages built around a private villa, a few unforgettable days out and every transfer in between – in Tuscany and across Italy. Local hosts, one contact, no loose ends.

Stone farmhouse with lawn under a deep blue evening sky

HOW IT WORKS

Experience, stay and transfers.

Every package is private and built from the same three pieces – then shaped around your dates, your group and your pace.

Every package includes
  • A private villa or apartment for the whole stay
  • The signature experiences of the package, with local experts
  • Transfers to every excursion – airport transfers on request
  • A personal travel assistant before and during the trip
  • Mid-week cleaning, linen change and final cleaning
Good to know
  • Private for your group – no strangers, no fixed departures
  • Dates, length and accommodation can be changed
  • Flights are not included; we can add car hire or a private driver
  • Prices on request, depending on season and group size
  • Travel agencies: net rates and white-label service

IN TUSCANY, FROM CORTONA

A week in Tuscany.

Seven nights in a private villa in the hills around Cortona, with the experiences that make the week.

Under the Tuscan Sun – Villa, Chef & Wine

7 nights · up to 8 guests · villa near Cortona

A week in a four-bedroom villa in the hills around Cortona, with a private chef who cooks your breakfast every morning, a hands-on cooking class and a full day in the cellars of Cortona and Montepulciano.

Includes: villa, daily chef breakfast, cooking class with dinner, wine day at two wineries with lunch and transport.

Tuscan Experience Getaway – Dinner Every Night

7 nights · up to 10 guests · villa near Cortona

Made for families and groups of friends: a private chef cooks breakfast and dinner every day, there is a cooking class at the villa and a private winery visit with lunch in the countryside.

Includes: villa, daily chef breakfast and dinner, cooking class, private winery visit with lunch.

Truffle Hunt Week – Into the Woods with a Truffle Hunter

7 nights · up to 6 guests · villa near Cortona

Follow a local truffle hunter and his dog through the oak woods, then sit down to a truffle lunch. The rest of the week is yours – Cortona, Siena, Assisi, Montepulciano or the villa pool.

Includes: villa, daily breakfast and maid service, full-day truffle hunt with tasting, lunch and transfer.

Wine, Dine & Tee Time – Golf and Wine in Tuscany

7 nights · up to 8 guests · villa near Cortona

Three rounds on three courses – Ugolino in Chianti, Antognolla near Perugia and La Bagnaia near Siena – plus a Montepulciano wine day and a cooking class at the villa, with a private driver every day.

Includes: villa, three golf days, wine tour with lunch, cooking class, daily private driver, airport transfers.

Yoga Escape – Vineyards, Lake and Hills

7 nights · up to 8 guests · villa near Cortona

Daily vinyasa at the villa, yoga among the vines followed by a tasting, paddle-board yoga and a boat picnic on Lake Trasimeno, a countryside hike and a cooking class with dinner.

Includes: villa, daily yoga, vineyard yoga with tasting, SUP yoga and boat trip with lunch, guided hike, cooking class, transfers.

Active Tuscany – Hike, Bike and Breathe

7 nights · up to 8 guests · villa near Cortona

Walk the hills above Cortona with a guide, cycle past hill towns to Lake Trasimeno and end the week with a private yoga class at the villa – with free days for Siena, Florence or Assisi.

Includes: villa, daily breakfast and maid service, guided hike, guided bike tour, private yoga class.

BEYOND TUSCANY

Travel around Italy.

Accommodation, guided excursions and transfers in other regions – arranged with partners we know personally.

Amalfi Coast & Capri

5 nights · up to 8 guests · villa in Amalfi

A hillside villa above Amalfi with two dinners cooked by a private chef, a boat day along the coast to the grottoes and Capri, and Pompeii with a private driver and English-speaking guide.

Includes: villa, daily breakfast, two chef dinners, private boat tour, Pompeii with guide and driver.

Venice & Valpolicella

6 nights · 2–8 guests · Venice + Verona

Three nights in Venice with a cicchetti walk and a private gondola, then three in Verona with a guided city tour and a full day among the Amarone wineries of Valpolicella.

Includes: apartments in Venice and Verona, cicchetti tour, gondola, guided Verona tour, Valpolicella wine day with transfer.

Volcanic Sicily

6 nights · 2–8 guests · Catania + Syracuse

Catania and Syracuse as your bases: a jeep tour on Mount Etna with lunch at a volcano winery, a guided morning in Taormina and a walk through the Baroque streets of Noto.

Includes: apartments in Catania and Syracuse, Etna jeep tour with winery lunch, guided Taormina and Noto tours with transfers.

ADD TO ANY STAY

Day experiences & in-house services.

Book them on their own or add them to a week in one of our villas or apartments.

Day experiences
  • Truffle hunt with a local hunter and his dog
  • Wine day in Cortona and Montepulciano
  • Cooking class at your villa
  • Boat trip and picnic on Lake Trasimeno
  • Guided hike or bike tour
  • Golf day in Chianti, Perugia or Siena
  • Private driver to Siena, Florence, Assisi or the Val d'Orcia
In-house services
  • Private chef – breakfast, dinners or the whole week
  • Cooking class at the villa
  • Daily maid service and extra cleaning
  • Yoga or fitness lessons at the villa
  • Massage at the villa
  • Cot and high chair on request
  • Airport, station and excursion transfers

READY WHEN YOU ARE

Tell us who is coming – we will build the week.

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