Tuscany villa holidays,
your questions answered

It depends on where your villa is. Florence (FLR) is closest to Chianti and the villas around San Casciano, 18 km from Casa Bachicche, but it has few flights from the US. Pisa (PSA) is best for Lucca and the coast. For Cortona and southern Tuscany, Perugia airport is about 45 minutes from Villa Laura and Villa Ivana, and Rome Fiumicino (FCO), where most US flights land, is about two hours away. Tell us your villa and we will tell you the easiest way in.

Cortona is about two hours by car from Rome Fiumicino, and Sarteano, home of Villa Benessere, is close to the A1 motorway exit at Chiusi. Florence is 1 hour 30 minutes from Rome by high-speed train. From Florence, the northern edge of Chianti is 15 minutes away, Siena about 1 hour 15 minutes, and Cortona about 1 hour 35 minutes.

To the nearest town, yes, but not to the door. Certaldo station, about 10 minutes from La Poggiolaia, is on the line to Florence, and Chiusi station is 8 km from Villa Benessere. A countryside villa still needs a car or a driver for the last stretch, which is often a white gravel road. We book private transfers for most of our guests.

Usually from 4 p.m., and check-out by 10 a.m. Some villas set a window: Villa Morea checks guests in between 3:30 and 5:30 p.m., and Villa Colli up to 9 p.m. Most rentals run Saturday to Saturday with a seven-night minimum. We send directions and the keyholder's number with your trip documents.

Make the gap part of the trip. Have your driver stop for a long lunch on the way, with the luggage safe in the car: from Florence airport, the Antinori nel Chianti Classico winery near San Casciano is an easy detour, and from Rome, Orvieto or Montepulciano break up the drive. On departure day, do the same in reverse. Tell us your flight times and we plan it.

Yes, if you stay in a countryside villa, or a driver. The roads are good and distances are short, but the villas sit at the end of country lanes, and Villa Trionfante is half a mile down its own dirt road. Drivers with a US license need an International Driving Permit too. If nobody wants to drive, we arrange private drivers for airport runs, dinners and wine days.

A limited traffic zone. Most historic centers, including Florence, Siena, Lucca and Cortona, are closed to unauthorized cars, and cameras issue fines automatically, often months after you get home. Park outside the walls and walk in. Your villa's keyholder can tell you the closest parking lot.

Yes, if you base yourself in a town. Our Florence apartments start at €2,975 a week, Villa Benvista is a 25-minute walk from the Duomo, and Villa Tullia is a 15-minute walk from the piazza in Cortona. From Florence, trains reach Siena, Lucca and Pisa, and our concierge books drivers for days in the country.

For a first trip, Chianti: it sits between Florence and Siena, so both are day trips. For the cypress roads and hill towns of the photographs, the Val d'Orcia near Pienza and Montepulciano. For Under the Tuscan Sun, Cortona. For historic villas near a walkable city and the beach, Lucca. And if you want Florence for dinner, the hills of San Casciano, 15 minutes from the city. Read more in our guide to Tuscany villa rentals.

Chianti for convenience, the Val d'Orcia for scenery. In Chianti, Florence and Siena are both within an hour, and the wine villages of Greve, Radda, Castellina and Gaiole are minutes apart. The Val d'Orcia is quieter and farther south, with Montalcino, Pienza and Montepulciano close together, but Florence becomes a long day. Our villas there include Villa Araldica near Montepulciano and Villa Cardinale near Pienza.

Villa Benvista is within walking distance of the center, about 25 minutes to the Duomo. In the hills, Casa Bachicche is 9 km away (about 15 minutes), Villa Tavernaccia about 5 miles, with a view of the Duomo from its tower, and Villa Fontanella is 15 minutes south.

Yes, especially for a week split between Tuscany and Umbria. Cortona is a hill town above the Val di Chiana, with Montepulciano, Lake Trasimeno, Assisi and Perugia all within an hour. Villa Tullia is a 15-minute walk from the piazza, Villa Ivana sits at the foot of the town, and Villa Laura is 7 minutes away by car. See our day trips from Cortona.

Villa Hortus is 10 minutes from Siena's walls, with an elevator to all three floors and a private wellness floor. Villa Collina, 20 minutes from the city, sleeps 36.

Our Tuscan villas start at €5,005 a week for Villa Tullia in Cortona (sleeps 12), €7,060 for La Novellina in Chianti (sleeps 10) and €8,855 for Villa Morea (sleeps 12). Most villas for 14 to 20 guests are €15,000 to €32,000 a week: Villa Montosca from €15,000 (sleeps 20), Villa Colli from €19,895, Villa Benessere from €25,000 and Villa Tavernaccia from €32,000. These are starting rates; July and August cost more.

Less than you might think when the cost is shared. Villa Ivana, a 1600s villa in Cortona with frescoed ceilings and its own chapel, sleeps 18 from €9,450 a week, about €75 per person per night. Villa Chiara in Castellina in Chianti sleeps 16 from €11,460, with an infinity pool and a private spa.

It varies by villa, and we confirm it in writing before you book. Electricity, water and Wi-Fi are usually included, and so are pool and garden care. Some villas include much more: daily breakfast at Villa Hortus, Villa Cardinale, Villa Benessere and Villa Laura; a welcome dinner at Villa Amarika; and a manager and four waiters for groups of up to 25 at Villa Collina. Final cleaning, heating and air conditioning are sometimes charged separately.

Every villa in our collection has air conditioning. At a few it is charged as an extra, for example €300 a week at Villa Morea, so we tell you up front.

Yes. Italian towns charge a visitor tax of about €1.50 to €6 per person per night, usually for the first 7 to 10 nights. It is paid locally in euro cash, and the amount depends on the town.

For July and August, eight to twelve months ahead, because returning guests rebook the best villas before the season ends. For May, June and September, four to six months. We are already taking 2027 bookings, and we sometimes have late availability, so it never hurts to ask.

Villa Collina near Siena sleeps 36. La Poggiolaia above Certaldo sleeps 22 in five apartments around one pool. Villa Laura, Villa Benessere and Villa Montosca, near the village of Radicondoli, each sleep 20. Or book Villa Tavernaccia and Casa Bachicche together: they are 500 meters apart and sleep 32, 15 minutes from Florence. For bigger groups, the Coselli Estate near Lucca sleeps 101.

Yes, at almost any of our villas. At Villa Araldica, a cook and waiter serve breakfast and lunch every day (you pay for the food). Villa Aiola has a Tuscan cook who cooks the food of the region. At Villa Laura, Chef Francesco cooks breakfast each morning, included in the rent, and organizes dinners to remember. Near Lucca, the Coselli villas include a chef for breakfast and one meal a day; see our Lucca FAQ.

It depends on the villa, the chef and the menu. As an example, last season our guests at Villa Montosca paid €90 to €100 per adult and €55 per child for a chef's dinner at the villa, with menus like gnocchi with fresh tomato and stracciatella, and peposo, the Tuscan beef stew. You choose the menu ahead of time so the chef can shop, and we send you a quote for your own dates.

Yes, and it is one of the best evenings of the week. At Villa Laura, the class with Chef Francesco includes Villa Laura aprons and recipe books to take home. Casa Bachicche has a cooking-school kitchen built for a group class, and La Novellina runs seasonal workshops on wild herbs and preserves. You cook, then you sit down and eat it.

Many offer to stock the kitchen before you arrive: you send a list and pay for the food. Some do it for free: Villa Trionfante delivers your groceries at no charge (you pay for the food), and at Villa Laura you find a cake baked that morning, coffee, tea, milk and a bowl of fruit when you arrive.

Most include light daily housekeeping. Villa Araldica has five hours a day, seven days a week; Villa Montosca five hours a day except Sunday; Villa Hortus and Villa Cardinale four hours a day. At Villa Hortus two staff live on the property year-round.

In Chianti for Chianti Classico, near Montalcino for Brunello, or near Montepulciano for Vino Nobile. Villa Amarika is a 1684 estate near Castellina in Chianti, Villa Colli is outside Gaiole, and Villa Araldica is just outside Montepulciano. At La Poggiolaia, tastings at the family's own cellar are included for every guest. Book a driver for tasting days.

Antinori nel Chianti Classico, the winery built into the hillside near San Casciano, for the architecture; Castello di Ama near Gaiole for wine with contemporary art in the vineyards; and from our Tuscany wine guide, Badia a Coltibuono, Castello di Volpaia, Castello di Fonterutoli, Rocca delle Macìe and Vignamaggio, where Much Ado About Nothing was filmed. Most Chianti estates are small family operations, so book tastings ahead and check opening hours. They will sell you a bottle for the villa.

A few from our Tuscany restaurant guide: Dario Cecchini, the butcher of Panzano, for a meat feast at one long table; Osteria di Passignano, the Michelin-starred restaurant beside the abbey of Badia a Passignano; Arnolfo in Colle di Val d'Elsa, with two Michelin stars, for a special night; Osteria Le Logge, a few steps from the Campo in Siena; lunch at Taverna dei Barbi, inside a Brunello estate outside Montalcino; and La Loggetta, in an old palazzo cellar on the main square in Cortona (closed Wednesdays). Book ahead in summer. We book your tables before you arrive.

Yes. In Florence, Enoteca Pinchiorri (three stars) and Il Palagio at the Four Seasons. Between Florence and Siena, Arnolfo in Colle di Val d'Elsa (two stars), Osteria di Passignano beside the abbey, and La Torre at Castello del Nero in Tavarnelle Val di Pesa, the nearest town to Villa Morea and Villa Trionfante. Tables go weeks ahead in summer, so tell us early and we book them.

Bistecca alla fiorentina, ribollita (bread and bean soup), pappardelle with wild boar, pici pasta around Montepulciano, pecorino cheese from Pienza, and new olive oil in November, poured over warm bread. In the fall, white truffles: La Novellina arranges truffle hunts from March to December, best in October and November, and brings the truffles back to the villa kitchen.

See Florence's Duomo and Michelangelo's David, stand in Siena's Piazza del Campo, drive the Chianti wine road between Greve and Castellina, climb a tower in San Gimignano, taste Brunello in Montalcino and pecorino in Pienza, and soak in a hot spring. Leave whole days for the pool. See our day trips from Chianti.

The best known are at Saturnia, where the Cascate del Mulino are free and open all day, every day, at about 99.5°F year-round. Bagni San Filippo, in the woods of the Val d'Orcia, is also free. In Bagno Vignoni the hot spring fills the town square, but you cannot bathe in it. Our hot springs guide has directions.

You can stay in it. Villa Laura in Cortona is the villa where Under the Tuscan Sun was filmed, and it sleeps 20 across the main villa, a farmhouse and a lemon house. Our rule is that whoever books it gets the Diane Lane bedroom. For 2027 it is €25,000 a week, or €30,000 from June to October. Read the story of Villa Laura.

Twice a year, on July 2 and August 16, in the Piazza del Campo. Siena's neighborhoods race bareback around the square. The piazza fills hours before the start, so arrive early.

Yes. Villa Danica looks over the Castelfalfi golf course, and you can be on the first tee in under fifteen minutes. Near Florence, Golf dell'Ugolino in Impruneta plays through the cypress and pine of the Chianti hills, and south of Siena, Royal Golf La Bagnaia was designed by Robert Trent Jones Jr. Book tee times ahead in summer.

For designer outlets, The Mall Firenze near Leccio and the Prada outlet at Montevarchi, both under an hour from Florence, and the Valdichiana Outlet Village near Cortona. For craftsmanship, the leather and artisan workshops of Florence's Oltrarno, ceramics and linens in Siena, and pecorino and olive oil straight from the farms around Pienza. Florence's Mercato Centrale is the place for food to bring home.

Book the Uffizi and the Accademia ahead, and remember that Michelangelo's David is at the Accademia. Both museums are closed on Mondays. The center is a ZTL, so park outside it or come by train. The view from Piazzale Michelangelo is worth the climb. See our Florence restaurant guide.

May, June and September: warm days, cool evenings and fewer crowds. April brings wildflowers, and October the grape harvest. July and August are hot and busy, but that is pool-and-long-lunch season. One thing to plan around: August 15 is Ferragosto, a national holiday, when many shops and restaurants close or keep short hours.

Most open in late April or May and close in October. Villa Tullia's pool is open April 30 to October 15, La Poggiolaia's April 30 to October 25, and Villa Trionfante's April 1 to November 1. Villa Colli has a heated pool; heating in April, early May and October costs €1,000 a week extra.

Yes, for food and quiet. October is harvest time, November brings white truffles and new olive oil, and Florence's museums have shorter lines. Some restaurants close in January and February. Villas with working fireplaces, such as Villa Chiara, are cozy into the cold months.

A week, which is also the usual minimum stay at our villas. That gives you Florence, Siena and a hill town or two, a wine day, and still a few lazy days by the pool. Two weeks lets you split between Chianti and the south, or add Lucca.

Villa Colli has a remote-controlled safety cover on its infinity pool, and we often book it for families with young swimmers. Villa Morea has swings and a treehouse. Villa Danica has a playroom annex with a pool table for the teenagers. One caution: Villa Fontanella's pool is unfenced. See all our family villas.

Climb the Leaning Tower of Pisa (children must be at least 8), visit the Pinocchio Park at Collodi, see Leonardo's machines in his hometown of Vinci, soak in the free hot springs at Saturnia, and take a pizza or pasta class at the villa. Older children love a dawn hot-air balloon flight over the vineyards, which La Novellina can arrange. Ask us about babysitters: Villa Laura and the Coselli villas near Lucca can arrange one, so the adults get a dinner out.

Villa Hortus near Siena has an elevator to all three floors, and Villa Benessere has a wheelchair-accessible cottage with its own bedroom and bathroom. Tell us exactly what you need and we will check the details with the villa before you book.

Yes. Villa Ivana in Cortona has its own restored chapel and a concierge who is one of the best wedding planners we work with. Villa Laura hosts weddings in its gardens, and Villa Collina sleeps 36, so the wedding party can stay on site. See our wedding villas.