When you’re thinking of going on holiday with a few good friends, it’s difficult of think of a better destination than Tuscany. The beautiful weather, stunning hilly landscapes and abundance of cuisine and culture makes it the perfect place for friends to unwind – there’s always something new to do, and enough variety to keep everyone happy. We’ve listed some of the best groups activities in Tuscany below, and 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.

1. Take a tour with Walks of Italy 

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 – should you want to try some of the region’s wine while you’re at it – a designated driver or two. 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. They’ll keep you entertained throughout with stories and commentary.

Location: Tuscany

Book: Online at Walks of Italy 

Walks of Italy - Tuscany

Walks of Italy – Tuscany

2. Hit the road with Tuscany Bike Tours

Why go: With wind in your hair, the Italian sun on your face and spectacular views, picturesque vines and olive groves, it’s hard to beat a bike ride with friends in the Tuscan hills. Tuscany Bike Tours cycling tours make the whole experience a pleasure. After departing in the morning, your posse will be transferred to an achingly pretty hilltop village, where you’ll begin the pedalling portion of the tour. 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, as well as breaking for a leisurely lunch at a family-run ristorante and resting your legs at a café.

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

Book: Online at Tuscany Bike Tours

Tuscany Bike Tours - Tuscany

Tuscany Bike Tours – Tuscany

 3. Zoom around with Tuscany Vespa Tours

Why go: Bikes too slow for your taste? Try a quicker and much more quintessentially Italian mode of transport instead. Just 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, stopping en route to tour a family-owned castle where you can taste local wine and olive oil. You’ll also pause 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 at Tuscany Vespa Tours

Tuscany Vespa Tours - Tuscany

Tuscany Vespa Tours – Tuscany

4. Get cultural with ArtViva

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, which has its roots in theatre and therefore understands 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 at Artviva

Florence Cathedral

Florence Cathedral

5. Explore Lucca with Lucca Tours

For reasons we can’t quite fathom, lovely little 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 – all cobbles, medieval towers and Romanesque churches – is the stuff of postcards. During this private tour, you and your friends will be shown around by a Lucca 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

Lucca Tours  - Tuscany

Lucca Tours – Tuscany

 6. Take the wheel with Tuscany Adventure

As the cradle of the Renaissance, Tuscany has long been exalted for its art and culture. But groups travelling here needn’t be restricted to pureply genteel pursuits. It’s also possible to let loose in Tuscany and to satisfy you 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

Tuscany Adventure - Tuscany

Tuscany Adventure – Tuscany

7. Speed downhill with Bike in Florence

For cyclists who are relatively comfortable in the saddle and not 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 there by monks. Just a little mind you, because soon after you’ll be 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, most famous and many would argue, most beautiful bridge.

Location: Via Faentina 310  50133 Firenze (Italy)

Book: Book online at Bike in Florence

Bike in Florence - Tuscany

Bike in Florence – Tuscany

Whatever size, style or setting you want from your Tuscan villa, our friendly concierge team is on hand to help you whittle down your selection. Just get in touch and let them know what you’re looking for. We’ve got loads of info on Tuscany on our blog too. We’ve found the best ways to explore Tuscany, have put together our top 10 favourite pools with views (they’re seriously swish!) or you can read how to get an authentic experience in Tuscany with the help of our local guide. Better yet, if you and your friends want to indulge in a little retail therapy we’ve already found the best places for fashion shopping in Tuscany.

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