A Tuscany Vacation in Seven Days, Planned by Our Experience Director

The best way to spend a Tuscany vacation is a week in one private villa, with the days planned around it: a wine morning in Chianti, a day in Florence, an evening in Siena, a sunrise over the Val d’Orcia and at least two dinners cooked at home. This is the week as Monica Mian, our Experience Director, plans it for our guests from Florence, with the experiences, the menus and four villas from our collection of Tuscany villa rentals.

A week in Tuscany at a glance

The team who plans your week

Monica Mian is our Experience Director. Based in Florence, she knows Tuscany and Umbria extremely well, from the Val d’Orcia to Assisi and Montefalco, and works directly with our private guides, drivers, wineries, chefs and restaurants. Once your villa is booked, she becomes your contact for every experience of the trip.

Pamela Mannino works alongside her and coordinates the logistics of each stay: the drivers, the timings and the small changes a week in Italy always brings. The day before each service, they send a short WhatsApp message with the next day’s programme, including the driver’s name and number, so the details are always close at hand.

The planning starts with a call. Monica asks about the group, the children’s ages, any celebration, the flights, and whether you would rather have private drivers or a rental car; then she sends a suggested itinerary to discuss and refine together. Every experience is private, with dedicated assistance throughout, and the team coordinates with the local providers when plans change at the last minute.

“Unless a guest specifically asks for something different, I always try to avoid overly touristy places and instead focus on authentic restaurants that are genuinely appreciated and frequented by locals.”

Monica Mian, Experience Director

Her rule for the pace of the week is just as simple: alternate fuller days with lighter ones, and leave several afternoons free to enjoy the countryside.

Before you arrive

• The pantry. From your own list, Monica prepares the first shopping for about three days, from breakfast to the cheese board and the wine; the villa staff help with the shopping for the rest of the week.
• The arrival. Tell her your arrival time: she checks whether an early check-in is possible and gives you the villa manager’s number, so you can reach each other directly.
• The drivers. Booked by the day for the outings, with the timings set once you have chosen the days.
• The table. Allergies and dietary needs before the chef dinners are confirmed, so the menus are written for your group.

Your Tuscany vacation, day by day

This is the shape of the week from a villa in Chianti. Every day is a suggestion: Monica moves, swaps and lightens them around your group.

Saturday: arrive and settle in

A driver meets you at the airport, the pantry is stocked when you walk in, and the first dinner is at home. At Villa Le Masse in Panzano, the Saturday welcome dinner is part of the stay.

Sunday: Chianti Classico

Private tastings at the Chianti Classico estates around Greve and Panzano, lunch among the vineyards, an afternoon by the pool, and dinner booked in a village where the table is local, not a set menu for visitors.

Monday: Florence

A full day with a driver. A private walking tour or a food tour with a local host, away from the usual routes; for those who love wine, a private tasting in a historic family palazzo, where some of Florence’s oldest families, who also own wine estates, receive guests in their homes, often with the younger generation now running the business. Shopping appointments with dedicated staff at the fashion houses, a guided e-bike tour or a sidecar tour with tastings for the more active, and dinner where Florentines eat, ordered à la carte, or on a rooftop with views over the city.

Tuesday: a day at the villa

The lighter day. A cooking class at the house, a long lunch, nothing booked in the afternoon, and the private chef in the evening, with one of the menus below.

Wednesday: Siena

A private guide for the city and its cathedral in the morning, the afternoon free, and, for the evening, an exclusive dinner in a historic palazzo overlooking Piazza del Campo.

Thursday: the Val d’Orcia

A private hot-air balloon flight at sunrise, with breakfast afterwards. Then a Brunello day in Montalcino, with two estates and lunch, or an e-bike ride through the Val d’Orcia; for the cooks in the group, a truffle hunt followed by a cooking class and lunch.

Friday: the last evening

A private dinner in a vineyard in Chianti Classico, cooked by our chefs with a mobile kitchen. For a birthday or an anniversary, Monica pairs the vineyard dinner with a guided stargazing evening, weather permitting.

Saturday: home

The driver collects you at the villa, timed to your flight.

At the villa: four menus from this autumn

These are four menus a group chose for their week in a Tuscan villa this October, each cooked at the house by a private chef. Monica confirms the dinner times and the dietary needs before the menus are final.

For the villas where a chef comes with the house, see our Tuscany villas with a chef.

Four villas for this week

Three in Chianti and near Florence, for the week above, and one near Montepulciano for a week built around the Val d’Orcia. For more houses in the same hills, see our villas in Chianti and villas near Florence.

Villa Le Masse

Panzano in Chianti · 6 bedrooms · sleeps 12

A stone farmhouse among olive groves and cypresses, about a kilometer and a half from the village of Panzano.

Included: continental breakfast every day, a Saturday welcome dinner, a Wednesday pizza night with local wine or artisanal beer, and a chef for one meal a day, with the groceries added to the stay.

Villa I Busini

Near Florence · 7 bedrooms · sleeps 14

A Peruzzi de’ Medici estate with formal gardens, half an hour by car from Florence and an hour from Chianti.

Included: Tuscan breakfast every day, a butler and housekeeping daily, and a cook and server for one meal a day, with the groceries added to the stay.

Zietta

Castellina in Chianti · 9 bedrooms · sleeps 22

For the larger family: a hilltop villa between Florence and Siena, four kilometers from Castellina in Chianti, reached by a final stretch of unpaved road.

Included: a 24/7 concierge and a welcome basket.

Villa Teresa

Montepulciano · 6 bedrooms · sleeps 12

For a week in the south, with the Val d’Orcia close by and Siena about an hour away by car.

Included: breakfast and housekeeping every day.

With a second week: Umbria

With two weeks, keep the first in Tuscany and move the second to Umbria: Assisi with a private guide, a Sagrantino tasting in Montefalco and quieter discoveries close to the villa, with the same team planning both. See our villas in Umbria.

More for your Tuscany vacation

• Where to stay in Tuscany
  Florence, Siena, the Val d’Orcia and the Maremma, area by area.
• The best towns to stay in Tuscany
  The towns to base yourself in, from Chianti to the south.
• The best time to visit Tuscany
  The months for each kind of week, from spring to the harvest.
• Michelin-starred restaurants in Tuscany
  The tables worth booking before you fly.
• The best experiences in Tuscany
  Cooking, wine, truffles and the countryside.

Tuscany vacation: your questions answered

Updated October 2026. The villas in this guide were checked against their listings on October 12, 2026; the menus are from a stay planned by our team in October 2026.