10 best things to do in Tuscany on your villa holiday
Looking for the best things to do in Tuscany? From exploring Florence and Siena to wine tasting in Chianti, discovering medieval hilltop towns and enjoying long lunches overlooking the vineyards, Tuscany is a destination made for memorable holidays.
And staying in a private villa gives you the freedom to experience it at your own pace.
Spend one day discovering Renaissance masterpieces and the next beside your private pool. Visit a vineyard in the morning, stop for lunch in a tiny hilltop village and return to your villa in time for sunset drinks on the terrace.
If you're planning a Tuscan villa holiday, here are ten experiences that deserve a place on your itinerary - plus some of our favourite Sun-hat villas to stay in along the way.
- Explore Florence
Florence is unquestionably one of the best places to visit in Tuscany and somewhere we recommend experiencing at least once during your stay.
The birthplace of the Renaissance is home to some of Italy's most celebrated art and architecture. See the magnificent Cathedral of Santa Maria del Fiore and its famous dome, admire masterpieces in the Uffizi Gallery and cross the medieval Ponte Vecchio spanning the River Arno.
But don't feel you need to rush from one attraction to another.
Some of Florence's greatest pleasures are found simply wandering through its historic streets, stopping for an espresso in a beautiful piazza or settling in for a long Italian lunch.
Stay into the early evening if you can, when the streets begin to quieten and Florence takes on a completely different atmosphere.
Where to stay: A Sun-hat villa in the Chianti countryside allows you to combine days exploring Florence with the peace, space and privacy of rural Tuscany.
- Go wine tasting in Chianti
If there's one experience synonymous with a holiday in Tuscany, it's surely wine tasting in Chianti.
The beautiful countryside between Florence and Siena is filled with vineyards, historic estates and wineries producing the region's famous Chianti Classico.
Spend an afternoon touring a wine cellar, learning about the winemaking process and tasting wines produced from the surrounding vineyards. Many estates also produce their own olive oil and offer tastings accompanied by local cheeses, meats and other Tuscan specialities.
For wine lovers, Villa Claudia offers a particularly special place to stay.
Sleeping up to ten guests amongst the vineyards of Panzano in Chianti, the villa belongs to a prestigious local winery. Guests can enjoy a complimentary vineyard tour and wine tasting during their stay with one of Tuscany's quintessential experiences right on your doorstep.
- Visit Siena, one of Tuscany's most beautiful cities
Smaller than Florence but every bit as captivating, Siena is another of the must-see places in Tuscany.
The city's historic centre is a maze of narrow medieval streets leading towards the magnificent Piazza del Campo, one of Europe's most distinctive public squares and home to Siena's famous Palio horse race.
Visit the spectacular striped-marble Siena Cathedral, explore the little shops hidden amongst the historic streets and find a table overlooking the piazza for lunch or an early evening aperitivo.
Where to stay: Villa Floriana, near Radda in Chianti, overlooks vineyards and olive groves and puts you within easy reach of Siena while allowing you to retreat to the Tuscan countryside afterwards.
- Take a Tuscan cooking class
Eating incredible Italian food is one thing. Learning how to make it yourself is even better.
A Tuscan cooking class is a wonderful way to discover more about the region's food and traditions, whether you're learning to make fresh pasta, preparing a traditional Tuscan sauce or discovering how simple local ingredients are transformed into some of Italy's most celebrated dishes.
It's also a fantastic activity for families and groups of friends travelling together.
Then take your new skills back to your villa and recreate the experience around your own dining table.
Or, if cooking sounds suspiciously like hard work while you're on holiday, ask our team about arranging a private chef and let somebody else take care of dinner.
- Discover Tuscany's medieval hilltop towns
You don't have to visit Tuscany's major cities to experience some of its most beautiful places.
The countryside is scattered with medieval villages and hilltop towns where cobbled streets, ancient stone buildings and little piazzas seem almost untouched by time.
In Chianti, visit Greve, Panzano, Radda and Castellina, stopping at local markets, independent shops, cafés and wine bars along the way.
Don't try to fit too many into one day. Tuscany is much better enjoyed slowly.
Choose one or two places, stop somewhere wonderful for lunch and enjoy the journey through the countryside between them.
Where to stay: Villa Tuscan 6 is around a 15-minute walk from Greve in Chianti, putting the town's shops, cafés, restaurants and wine bars within easy reach.
- Take a road trip through the Tuscan countryside
Hiring a car gives you the freedom to discover a completely different side of Tuscany.
Cypress-lined lanes wind through vineyards, olive groves and sunflower fields, connecting tiny villages, historic estates and family-run trattorias.
And unlike many destinations, here the journey can be every bit as memorable as where you're going.
Pack a picnic, choose a couple of towns you'd like to visit and leave enough time to stop whenever somewhere catches your eye.
Perhaps you'll discover a vineyard you hadn't planned to visit, a tiny village with an irresistible restaurant or simply a view that demands you pull over and take it all in.
Some of the best moments of a Tuscan villa holiday are the ones you never put on the itinerary.
- Visit Lucca and Pisa
If you're staying in northern Tuscany, two very different cities deserve a place on your holiday itinerary.
Pisa is home to one of Italy's most instantly recognisable landmarks. Seeing the Leaning Tower standing in the Piazza dei Miracoli is one of those classic Italian experiences that's worth doing at least once.
Nearby Lucca offers something completely different.
Its beautifully preserved Renaissance walls encircle an atmospheric historic centre filled with cobbled streets, churches, elegant squares and cafés. Hire bikes and cycle along the top of the walls for a particularly enjoyable way to see the city.
Where to stay: Villa Alberto is set in the Lucca countryside and combines a large private swimming pool with easy access to Lucca, Pisa and the Versilia coast.
- Explore Tuscany on foot or by bike
For a completely different perspective on the Tuscan countryside, swap four wheels for two or simply put on your walking shoes.
Chianti's quiet country roads weave between vineyards, olive groves and villages, making cycling a wonderful way to explore the region. Keen cyclists will find plenty of challenging climbs amongst Tuscany's famous rolling hills, while e-bikes make the countryside considerably more accessible if you're looking for something gentler.
Walking can be just as rewarding.
Head out early before the heat of the day, explore the countryside surrounding your villa and reward yourself afterwards with lunch in a local trattoria.
It's a wonderfully simple way to experience Tuscany.
- Discover the Maremma countryside and coast
If you're wondering where to stay in Tuscany away from its most famous cities, look south towards Maremma.
This beautiful part of southern Tuscany feels wilder and wonderfully unspoilt, with rolling countryside, vineyards and historic towns stretching towards the Mediterranean coast.
It's an excellent choice for guests who want to combine countryside living with days beside the sea.
For somewhere particularly special, consider Villa Maremma 1.
Set within a vast private estate, this seven-bedroom villa sleeps up to 14 guests and is around 25 minutes' drive from the beach. The estate has its own 18-hole golf course, while the villa itself offers a tennis court and Turkish bath. Daily breakfast preparation and a welcome dinner are also included.
With that much on your doorstep, you might find your sightseeing plans becoming rather less ambitious.
- Spend a day doing absolutely nothing
With Florence, Siena, vineyards and medieval villages waiting to be discovered, it's tempting to fill every day of a Tuscany holiday.
Don't.
One of the greatest pleasures of choosing a private villa in Tuscany is having somewhere you'll genuinely want to spend time.
Wake up without an alarm. Take breakfast onto the terrace. Read beside your private pool. Wander into the nearest village for lunch before returning for an afternoon swim.
Then open a bottle of local wine and gather everyone around the table as the sun disappears behind the Tuscan hills.
Villa Albola, near Radda in Chianti, takes the villa experience to another level. Its medieval origins include an antique watchtower that's now home to a private wine bar with panoramic vineyard views. There's also a private swimming pool, gym and spa with a Turkish bath and sauna, while a former chapel has been transformed into a yoga room.
Sometimes where you stay becomes one of the best things you do in Tuscany.
Where is the best place to stay in Tuscany?
Choosing where to stay in Tuscany depends on the kind of holiday you want to have.
Chianti
Choose Chianti if the Tuscany in your imagination is all rolling vineyards, olive groves, wine estates and medieval villages.
Its location between Florence and Siena makes it particularly appealing for first-time visitors who want to combine beautiful countryside with some of Tuscany's most famous sights.
Lucca and Northern Tuscany
The countryside around Lucca is ideal if you want easy access to historic cities while also being able to explore Tuscany's northern landscapes and coast.
You can visit Lucca and Pisa, spend days discovering local towns and head towards the beaches of Versilia when you fancy a change of scenery.
Maremma and Southern Tuscany
Maremma offers space, countryside and a slower pace of life.
Choose this part of Tuscany if you're looking for a peaceful rural retreat, beautiful scenery and the opportunity to combine countryside days with trips to the coast.
Sun-hat Villas & Resorts offers a hand-picked collection of villas across these different areas, so our Villa Specialists can help you choose not only the right villa, but the right part of Tuscany for the holiday you have in mind.
Frequently Asked Questions about Tuscany
What are the best things to do in Tuscany?
Some of the best things to do in Tuscany include exploring Florence and Siena, wine tasting in Chianti, visiting medieval hilltop towns, taking a Tuscan cooking class, cycling through the countryside and discovering cities such as Lucca and Pisa.
Just as importantly, leave time to enjoy the slower side of Tuscany - long lunches, local markets and relaxing beside the pool at your villa can be every bit as memorable as the sightseeing.
How many days do you need in Tuscany?
A week is an excellent amount of time for a Tuscany villa holiday, giving you the opportunity to combine several days of sightseeing with time to relax.
If you're staying for two weeks, you can explore at a much slower pace and venture further afield without feeling as though every day needs to be planned.
What is the best month to visit Tuscany?
Tuscany offers something different throughout the year.
Late spring and early summer bring beautiful countryside and long days for exploring, while July and August are ideal if your priority is enjoying the sunshine and your villa's private pool.
September is another wonderful time to visit, with warm weather and the grape harvest bringing a special atmosphere to Tuscany's wine-growing regions.
Do you need a car for a Tuscany villa holiday?
For most countryside villa holidays in Tuscany, we'd recommend hiring a car.
Many of Tuscany's greatest pleasures are found away from its major cities, and having your own car gives you the freedom to discover vineyards, villages, restaurants and local markets at your own pace.
Is Tuscany good for a family holiday?
Absolutely. A private villa gives families the space and flexibility to create a holiday that works for everyone.
Days exploring Florence, Pisa or medieval villages can be balanced with plenty of downtime around your private pool. Cooking classes, cycling, local markets and gelato stops also make exploring Tuscany surprisingly family-friendly.
Which part of Tuscany should I stay in?
For vineyards, wine tasting and easy access to Florence and Siena, consider Chianti. For Lucca, Pisa and access to the northern Tuscan coast, look towards northern Tuscany. For a quieter countryside escape with access to the coast, Maremma is a wonderful choice.
Our Villa Specialists can also help you choose the area that best suits how you like to holiday.
Find your perfect villa in Tuscany
Tuscany isn't somewhere that needs to be rushed.
Fill your days with Renaissance art, medieval cities, wine tastings and countryside adventures – then balance them with long lunches, lazy afternoons around the pool and evenings spent together at your villa.
At Sun-hat Villas & Resorts, we've hand-picked a collection of beautiful Tuscany villas, from character-filled properties amongst the vineyards of Chianti to impressive countryside estates in Maremma and villas ideally positioned for exploring Lucca and Pisa.
Whether you're planning a family summer holiday, an escape with friends or a special celebration in the Italian countryside, our experienced Villa Specialists can help you find the right property.
Explore our villas in Tuscany and start planning your Italian escape.
