A seven-night private villa stay near Cortona for up to 10 guests, with rolling countryside, pool and authentic Tuscan living.
A Tuscany villa experience is one of the most memorable ways to enjoy Italy, combining countryside living, historic towns, regional food, local wine, private space and the freedom of a relaxed group escape.
This experience is especially appealing because it is designed for up to 10 people, making it ideal for family holidays, milestone celebrations, group getaways and special occasions. Instead of staying in separate hotel rooms, guests can share a private villa, relax by the pool, enjoy meals together and explore the Cortona area at their own pace.
From long lunches by the pool to exploring Cortona’s hilltop streets and gathering for a private chef dinner, this Tuscany villa escape is designed for shared memories, slower days and classic Italian charm.
A Tuscany villa experience gives guests the space and flexibility to enjoy the countryside in a more private, personal and relaxed way.
During your stay, you can expect a five-bedroom self-catered villa near Cortona, chosen to suit your group requirements and subject to availability. The villa includes a private pool, making it easy to spend unhurried days relaxing together, dining outdoors and enjoying the surrounding countryside.
Your concierge service helps support the practical side of your stay, while the included walking tour introduces you to the historic town of Cortona. Known for its character, views and cultural atmosphere, Cortona is one of Tuscany’s most charming hilltop towns and a wonderful place to explore on foot.
One evening includes a traditional dinner prepared at your villa by a private chef, allowing your group to enjoy regional flavours without needing to leave your accommodation.
This experience is ideal for guests who want the comfort of a private villa with added experiences that bring the culture and flavour of Tuscany into the trip.
Your Tuscany villa experience includes seven nights in a five-bedroom self-catered villa near Cortona for up to 10 people.
Accommodation is arranged in a villa of your choice, subject to availability, giving you the opportunity to select a property that suits your group’s style and requirements. The villa includes a private pool, making it a comfortable base for relaxed mornings, outdoor dining, sunny afternoons and evenings together.
A typical day may begin with breakfast at the villa before heading into Cortona, visiting a nearby market, exploring a vineyard or simply relaxing by the pool. Some days can be slow and restful, while others can be planned around towns such as Arezzo, Montepulciano, Pienza or Siena.
Your included walking tour gives the group a guided introduction to Cortona’s history, streets and local culture. On one evening, a private chef will prepare a traditional dinner at your villa, creating a memorable shared dining experience without the need to travel.
Before you travel:
Start slow before the day ahead.
Head out to explore Near Cortona, or enjoy the hotel grounds.
Spa, pool or cultural highlights, at your own pace.
Local flavours and relaxed evenings.
Some activities are seasonal and weather-dependent.
Comfortable walking shoes are worth packing.
Tuscany Villa is enjoyable year-round, with each season offering a different atmosphere.
Warm days, green countryside and blooming landscapes, ideal for villa life and exploring.
Harvest season, golden light and comfortable temperatures across Tuscany.
Every Tuscany villa experience can be tailored, but this sample itinerary gives an idea of how your seven-night group stay near Cortona could unfold.
Arrive in Tuscany and travel to your private villa near Cortona. Settle into the property, explore the villa, enjoy the pool and spend your first evening relaxing together in the countryside.
Enjoy a slow first full day at the villa. Have breakfast outside, relax by the private pool and use the day to settle into the rhythm of Tuscan living. In the evening, you may choose to cook together or visit a local restaurant.
Head into Cortona for your included walking tour. Explore the historic streets, learn more about the town’s culture and admire views across the surrounding countryside. Spend the afternoon browsing local shops, cafés and restaurants before returning to the villa.
Use the day to explore the wider area. You may choose to add a vineyard visit, wine tasting, olive oil experience or countryside drive through nearby villages. Return to the villa for a relaxed evening.
Spend the day at leisure, enjoying the pool or visiting a nearby market. In the evening, your private chef will prepare a traditional dinner at the villa, allowing the group to enjoy Tuscan flavours in a private and memorable setting.
Take a day trip to Arezzo, Montepulciano, Pienza or Siena, depending on your interests and travel plans. This is a good opportunity to experience more of Tuscany’s architecture, food, wine and cultural heritage.
Enjoy your final full day at a slower pace. Relax by the pool, revisit Cortona, arrange an optional activity or enjoy one last group meal together at the villa.
A private villa near Cortona gives you the flexibility to enhance your stay with food, wine, culture, wellness and countryside experiences.Depending on your group’s interests, you may be able to add vineyard visits, wine tastings, cooking classes, additional private chef evenings, grocery delivery, private transfers, spa treatments, guided tours or day trips to nearby Tuscan towns. These additions
Tuscany is one of Italy’s most loved regions for group travel, offering countryside villas, hilltop towns, vineyards, traditional food, local markets and a slower pace of life.
A villa stay near Cortona gives guests the freedom to enjoy the region in a more personal way. Days can be shaped around the pool, local towns, vineyard visits, cooking, countryside drives and long shared meals.
Some of the top Tuscany villa experiences include:
A private villa near Cortona gives guests the space, flexibility and atmosphere to enjoy Tuscany in a relaxed and memorable way.
A villa near Cortona gives your group access to some of Tuscany’s most beautiful towns, countryside routes, vineyards and food experiences.
Cortona itself is a highlight, with historic streets, local restaurants, cafés, shops and panoramic views. It is a wonderful town to explore on foot and gives guests a strong sense of Tuscan culture without needing to travel far from the villa.
The surrounding region offers excellent opportunities for wine tasting, countryside drives, cooking classes and visits to nearby towns. Arezzo, Montepulciano, Pienza and Siena are all popular options, depending on your chosen villa location and itinerary.
Nearby and complementary options include:
This makes a private villa near Cortona a strong choice for groups who want both relaxation and access to Tuscany’s food, wine and cultural highlights.
Packing well will help your group stay comfortable while enjoying the villa, pool, countryside and nearby towns.
Comfortable clothing is ideal for relaxed villa days, while smart-casual outfits are useful for dinners, restaurants and special occasions. Comfortable shoes are important for Cortona’s historic streets and any walking tours or sightseeing days.
Recommended packing list:
For group travel, it is also useful to pack any personal items needed for children, celebrations, dietary requirements or planned activities.
Historic streets and sightseeing mean plenty of walking.
Days and evenings can differ, a light layer helps.
Popular landmarks and restaurants are worth reserving early.
Your Tuscany villa experience includes a seven-night self-catered stay near Cortona for up to 10 people, with a private pool, concierge service and included local experiences.
Your experience includes:
Flights are not included unless stated. Transfers are also not included as standard unless specified, but private transfers or car hire can usually be arranged depending on your arrival airport and group requirements.
Optional extras may include additional chef services, grocery pre-stocking, private transfers, car hire, wine tastings, cooking classes, guided tours, restaurant reservations, spa or wellness experiences, special occasion arrangements and extra nights. These should be confirmed before travel, as availability and pricing may vary.
Package details are subject to availability and may vary depending on travel dates, villa availability, group requirements, tour availability, chef availability and selected optional experiences.
Your experience includes:
The experience includes seven nights in a five-bedroom self-catered villa near Cortona for up to 10 people, a private pool, concierge service, a walking tour of Cortona and a traditional dinner at the villa prepared by a private chef.
This Tuscany villa experience is designed for up to 10 people, making it ideal for families, friends, groups and special celebrations.
The villa is located near Cortona in Tuscany. Cortona is a historic hilltop town known for its charm, culture, views and access to the surrounding countryside.
Yes, the villa is self-catered. Guests have the flexibility to prepare meals, dine locally or arrange additional private chef experiences where available.
Yes, the experience includes a villa with a private pool, giving guests space to relax and enjoy the Tuscan countryside during their stay.
Yes, concierge service is included as part of the experience. This can help support the practical details of your stay and may assist with local arrangements, depending on availability and package terms.
Yes, a traditional dinner prepared by a private chef at your villa is included on one evening of your choice.
Yes, the experience includes a walking tour of Cortona, giving guests the opportunity to explore the town’s historic streets, culture and local character.
Flights may or may not be included depending on the package. This should be confirmed at the time of enquiry so travel arrangements can be planned around your preferred departure airport and dates.
Transfers are not included unless stated in your package. Private transfers or car hire can usually be arranged depending on your arrival airport and travel plans.
Car hire is often recommended for a villa stay near Cortona, especially for groups who want to explore nearby towns, vineyards, restaurants and countryside locations independently.
Yes, this experience is well suited to families. The villa format provides shared living space, multiple bedrooms, a private pool and flexibility around meals and daily plans.
Yes, a private Tuscany villa is an excellent choice for birthdays, anniversaries, family gatherings, milestone celebrations and group holidays. The included private chef dinner adds a special shared moment to the stay.
Late spring, summer and early autumn are especially popular for villa holidays because of warm weather and pool time. Spring and autumn are also excellent for sightseeing, walking, wine tasting and fewer crowds.
Speak to the team about dates, the hotel and building the trip around you.
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