If you’re thinking of going on holiday with a few good friends, we couldn’t think of a better destination to bring everyone together than Tuscany. The beautiful weather, stunning hilly landscapes and an abundance of cuisine and culture in the region make it the perfect place for friends to unwind, reconnect and go on adventures. There’s always something new to do, and enough variety to keep everyone happy.

But since we know that planning activities for big groups can be a bit of a hassle sometimes, we decided to do some of the groundwork for you to make sure you get the most out of your holiday. We’ve listed some of the best things to do in Tuscany below, all perfect for a group of friends or a big family!

1. Take a tour with Walks of Italy

Elderly couple watching the view from the village of Pitigliano, Tuscany  | best group activities in Tuscany

Why go: When you only have limited time in Tuscany, it can be difficult to know what to prioritise. Finding the best course of action on behalf of your group will require a lot of research and a designated driver or two should you want to try some of the region’s wine while you’re at it. Our advice? Absolve yourself of all responsibility and hand over the reins to Walks of Italy. Their capable guides know these undulating hills like the back of their hands. They’ll take your gang on a private tour to Siena, bring you and your pals up to a Chianti vineyard-cum-farmhouse for a wine tasting and show you around the soul-stirringly beautiful walled village of San Gimignano. You’ll be kept well entertained throughout your tour with fascinating stories and commentary.

Location: Tuscany

Book: Online here!

2. Hit the road with Tuscany Bike Tours

best group activities in Tuscany

Why go: With the wind in your hair, the Italian sun on your face and spectacular views of picturesque vines and olive groves all around you, it’s hard to imagine anything that beats a bike ride with friends in the Tuscan hills. Tuscany Bike Tours make the whole experience a pleasure with their cycling tours. After departing in the morning, your posse will be transferred to an achingly pretty hilltop village, where you’ll begin pedalling. Over the course of the day, you’ll cover around 23 kilometres on the bike (with frequent breaks from the saddle preventing bruised bottoms). In between bouts of cycling down country lanes you’ll stop at a 12th-century castle for a wine and olive oil tasting, breaking for a leisurely lunch at a family-run ristorante, as well as resting your legs at a village café.

Location: Via Ghibellina, 34-red, 50122 Florence, Italy

Book: Online here!

3. Zoom around with Tuscany Vespa Tours

best group activities in Tuscany

Why go: Bikes too slow for your taste? Try a quicker and much more quintessentially Italian mode of transport instead. The word ‘scooter’ alone conjures up images of improbably stylish young men and women zipping down the web-like lanes of an Italian city past ancient ruins and stunning churches. Rather than tackling those narrow and tricky urban routes, your biker crew will be lacing their way around the Tuscan hills and stopping en route to tour a family-owned castle where you can taste local wine and olive oil. You’ll also be pausing for lunch in a typical Tuscan eatery. Everyone in the group needn’t drive (unless they want to, of course) as each scooter has the capacity to hold a passenger.

Location: Via Ghibellina, 34-red, 50122 Florence, Italy

Book: Online here!

4. Get cultural with ArtViva

best group activities in Tuscany | Florence, Italy - April 25, 2016. Uffizi gallery in Florence, Italy. It is one of the oldest and most famous art museums of Europe.

Does someone among your group fancy themselves an amateur art critic? Or do you just want to find out more about art while you’re in the birthplace of the Renaissance? Call on the cultured folks at ArtViva, who will take your group on a private tour to see Florence’s greatest masterpieces. You can hone in on the Uffizi Gallery or go see David at the Accademia as well as other Florentine highlights. ArtViva is an intelligent tour company with its roots in theatre, so your tour guide will understand the importance of keeping things entertaining as well as informative. If you’d rather go lowbrow than highbrow, they also offer a Dan Brown-inspired ‘Inferno’ tour, which may raise a few eyebrows among your friends (but we won’t judge, we promise).

Location: Via Sassetti, 1 (2nd floor) – cnr Piazza Davanzati – 50123 Florence Italy

Book: Online here!

5. Explore Lucca with Lucca Tours

best group activities in Tuscany | Lucca, Italy - September 28, 2017: Tourists admire the view from the Torre Guinigi tower in Tuscany in Lucca, Italy on September 28, 2017

For reasons we can’t quite fathom, the lovely little town of Lucca just doesn’t seem to get the same tourist footfall as some of its neighbouring Tuscan towns and cities. Which, as anyone who has ever found themselves at the end of the Uffizi queue in the height of tourist season can attest, may well be a blessing in disguise. This handsome town is all cobbles, medieval towers and Romanesque churches – basically the stuff of postcards. During a private adventure with Lucca Tours, you and your friends will be shown around by local who will not only highlight the famous attractions but will also show you the hidden shops, restaurants and sights of their hometown.

Location: Via delle Ville 598/A, 55018, Lucca, Italy

Book: Call 39 583 927 391

6. Take the wheel with Tuscany Adventure

best group activities in Tuscany

As the cradle of the Renaissance, Tuscany has long been praised for its art and culture, but groups travelling here needn’t be restricted to purely genteel pursuits. It’s just as possible to let loose and a satisfy your clique’s thirst for adventure with an adrenaline-fuelled buzz, such as a quad tour through the countryside with Tuscany Adventure. Spend an hour or two speeding around, or opt for a longer quad trip, which will include a stop-off at a castle where you can fortify yourself for the return journey with wine, salami, cheese and olive oil.

Location: Via della Cave 12, 53040 Serre di Rapolano SI, Italy

Book:  Call +39 339 461 9216

7. Speed downhill with Bike in Florence

best group activities in Tuscany

For cyclists who are relatively comfortable in the saddle and aren’t afraid of building up a little downhill speed, there is lots of fun to be had in the Tuscan hills. Take the ‘Downhill to Florence’ tour with Bike in Florence, and you’ll be transferred up to the quiet, hidden-away hilltop Sanctuary of Monte Senario. Here, you can taste a little of the liquor produced by the local monks. Just a little mind you, because soon after you’ll be back on the saddle, freewheeling down a sloping stretch of road with views of Florence and Fiesole spreading out before you. Roll on past woods and castles toward the village of Settignano, where – after a brief rest – it’s back on your bike for a ride across the hills above the Arno Valley. The final stretch is along a riverside route that leads all the way to the iconic Ponte Vecchio, Florence’s oldest and most beautiful bridge.

Location: Via Faentina 310  50133 Firenze (Italy)

Book: Book online here!

If you check our selection of villas in Tuscany, you’ll see that our portfolio is full of the kind of properties you’ve always dreamed of staying in – your very own villa on a hill, stunning views, swimming pools and all. If you need some help finding the perfect one, get in touch with our concierge team and they’ll help you with your search. 

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