Organize the Perfect Family Holidays in Tuscany

Organize the Perfect Family Holidays in Tuscany

Tuscany, with its rolling hills, vineyards, and centuries-old cities, is the perfect backdrop for an unforgettable family holiday. The region offers a unique blend of cultural richness, serene landscapes, and exquisite cuisine. Whether you’re exploring the art and history of Florence or enjoying the tranquil beauty of the Tuscan countryside, a well-planned trip can cater to the interests of every family member. Here’s how to organize the perfect family holidays in Tuscany, from finding the perfect villa to planning your itinerary and activities.

Finding the Perfect Villa

The first step to a memorable family holidays in Tuscany is finding the right accommodation. Websites like Airbnb and will be your go to for this process. There is a wide range of villas in Tuscany that cater to all needs and budgets. When searching for a villa, consider factors such as location, size, and amenities. A villa with a swimming pool, for instance, can be a delightful retreat during the warm Tuscan summers. Opt for properties that are centrally located to minimize travel time between destinations. Read the reviews and check the proximity to local attractions. It will help ensure that you find the perfect home base for your Tuscan adventure.

I found the most amazing villa for our perfect family holidays in Tuscany on AirBnb- Il Fitto 10. It had 5 bedrooms and 5 bathrooms, a swimming pool, a viniard and the most spectacular view of the Tuscan hills. It was located next to Cortona. Our family includes 9 adults and 3 kids (including 1 infant). And the total cost of the villa ended up being roughy 32 EUR per person per night (2252 EUR for a 7 day stay). For a place like that I’d call it a bargain!

Example Itinerary

Of course you will spend some relaxing days just chilling by the pool of your beautiful villa. But you can still explore some of the marvellous locations close by. A well-planned itinerary can help you make the most of your time in Tuscany. Here’s a suggested route that covers some of the region’s most iconic destinations:

  • Florence: Visit the city of art and architectural marvels. Don’t miss the Uffizi Gallery, the Duomo, and Ponte Vecchio.
  • Cortona: Perfect for an afternoon stroll, this charming hilltop town offers stunning views and ancient streets to explore.
  • Montepulciano: Famous for its wine, Montepulciano is a must-visit for any oenophile.
  • Siena: Known for its spectacular Piazza del Campo and the Duomo, Siena is a Tuscan gem. Spend a day wandering through its historic streets.
  • San Gimignano: San Gimignano offers a unique skyline and medieval architecture that will enchant any visitor.
  • Pisa: No trip to Tuscany is complete without seeing the Leaning Tower of Pisa. Although a tourist hotspot, the tower and adjacent cathedral are worth the visit.

 Tip : When visiting Siena, don’t forget to pass by the Agriturismo Baccoleno. This famous location was a movie set the Gladiator and has of the most beautiful views in Tuscany.


  • Wine Tasting: Tuscany is synonymous with wine, and a tasting tour is a great way to explore the region’s vineyards. Many villas offer wine tasting experiences or can arrange visits to nearby wineries. The bonus of staying at Il Fitto villa, was the wine tasting included in the stay!
  • Pizza Making Night: Participate in a pizza-making class right at your villa. It’s a fun activity for all ages and a great way to indulge in authentic Italian cuisine.
  • Dinner by a Private Chef: For a truly special evening, hire a private chef to prepare a traditional Tuscan meal at your villa. It’s a luxurious and intimate way to enjoy the local flavors.

 Tip : Look for a private chef at Take a Chef. It’s a great website that allows you to contact different chefs in the area that will cook a special menu just for you and your family.

Best Time to Visit

The best time to visit Tuscany is during the spring (April to June) or fall (September to October) when the weather is pleasant, and the crowds are thinner. During this months you can also get a pretty good deals on the rental villas.

If you are from Europe, we consider the long weekends in May an ideal time for to organize the perfect family holiday in Tuscany. With many official holidays in May, it often happens that the adult family members can get a 9 day holidays, by taking only 3 days off.

Getting to Tuscany

There are 2 main airports in Tuscany serving international flights- Florence and Pisa. However an extra hour drive away lies Bologna and even Rome. Use skyscanner to find the best flight deals.

My family was flying from Warsaw, Poland with Ryanair to Bologna, Italy. Each return ticket costed apx 150 EUR (with checked in luggage and large hand luggage).

 Read : How to save money on your travel bookings

Getting around

Renting a car is the most flexible and convenient way to explore Tuscany, especially if you’re staying in a rural villa. It allows you to discover off-the-beaten-path villages and scenic landscapes at your own pace.

We rented a 9 sitter van from a local company in Bologna Dai Gas Noleggio for 700 EUR for 7 days, plus a small car from Morini Rent in Pisa for 220 EUR for 7 days.

 Tip : When looking for the best car rental, we highly advise you to check the local companies. They have very competitive prices and high quality service.

When to book

The earlier- the better. For the villa and the car rental. The nicest villas in the area are usually sold out months in advance. I booked our villa in January for a trip at the beginning of May. I would also advise you to book the van early- since it’s a specific car, there is a limited amount of them.

However for the cheap airline flights, you can wait till apx 3 months before the trip. The ticket prices tend to be higher a lot in advance.

Cost of the perfect family holidays in Tuscany

Naturally the final cost of your holiday will vary depending on many factors. How luxurious the rental villa is, how many people will travel, will you mostly eat out, or decide to cook for yourself, where will you fly from etc. However since you are splitting the costs of everything between many family members, this amazing holiday shouldn’t be a big strain on your budget.

I believe that our trip costed apx 850 EUR per person (for 10 people) for 7 days (including everything: accomodation, flights, cars, fuel, restaurants, groceries, private chef, pizza night, museum entrances etc).

Organizing the perfect family holidays in Tuscany requires a bit of planning, but the rewards are immeasurable. The memories that you will get to create together with your family are priceless. And all of you will cherish them for years to come.

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