By: Alicia Peacock Writer & Journalist Specialist Arts & European travel

From the cultural landmarks of Florence and Siena to the gastronomic delights of Chianti, crafting bespoke luxury travel experiences in Tuscany is a sure way to scratch beneath the surface of the region and ensure your interests are well-catered for. They will take you off the beaten path and encourage you to see places and people from a new perspective. 

Tuscans are incredibly proud of their culinary traditions, artistic legacy and locally sourced, seasonal attitudes towards food and wine. Upholding family legacies through local business is quite literally in their blood. Tuscany Now & More was born with this same spirit in mind. We have over 30 years of experience as a family business, building up a meaningful portfolio of luxury villa rentals in Italy and customisable experiences in Italy, working with local villa owners and suppliers that we know, respect and trust. 

Whether you adore the art and culture of Florence or your dream day out is a hike along the Tuscan coast, get inspired with our guide to crafting the perfect bespoke luxury experience in Tuscany. All of our experiences are tried and tested, and entirely designed to inspire lasting connections with the places you visit and the people you cherish most.

Adventure: Our top exclusive experiences for thrill-seekers and nature lovers in Tuscany

Hot air balloon ride over your favourite Tuscan hilltown

Hot air balloon ride

Whether you are travelling as a family or are looking for a romantic Tuscan villa getaway for two, a hot air balloon ride guarantees the best countryside views and total privacy. It doesn’t matter if you are staying in one of our luxury villas near San Gimignano or a hilltop villa near Montepulciano, we will tailor the experience to you and your interests. If you want to see the Crete Senesi at sunrise or have a champagne toast in the sky high above the rolling hills of Chianti, our luxury concierge can make it happen. 


Charter a boat and sail the wild Argentario coast

If you are staying in one of our luxury villas on the Tuscany Coast, sail away from the summer beach crowds and spend your days island hopping between untouched coves. Monte Argentario and the Maremma coast offer endless possibilities for hiking and exploring the prettiest, wildest, and rugged beaches in Tuscany. A private charter is one of the best ways to reach those out-of-the-way unspoilt coves that you’ll have all to yourself. And if an exclusive beach club is more your vibe, hiring a yacht for the day guarantees plenty of sunbathing, swimming and stunning sea views in total privacy. 


Bespoke vintage and supercar tours in Tuscany

Bespoke vintage and supercar tours in Tuscany

One of the best ways to make the most of Tuscany’s breathtaking natural scenery is from the comfort of your very own classic or supercar. From Umbria to Lombardy, we offer vintage car tours that follow the most scenic routes in Italy. Whether your style is more Alfa Romeo Duetto Spider or classic blue Fiat 500, we can also tailor itineraries to you and your party. You’ll feel like you have stepped off the film set of a classic Italian Hollywood film as you hop between Chianti vineyards tasting 0km wines, or follow the stunning lakeside routes from Sirmione. 


If that doesn’t quite get your engine revving, then a luxury Italian supercar will. Take your pick from a fleet of super-sleek Ferrari and Lamborghini supercars that we can deliver to your luxury villa. Those Val d’Orcia views are sounding even better already!


Truffle hunting on your private luxury Italian villa estate

Truffle hunting on your private luxury Italian villa estate

Truffle hunting with a local guide is the ultimate luxury experience for lovers of both the great outdoors and haute cuisine. With a trusty Lagotto Romagnolo truffle hunting dog in tow, combine a gentle walk through Tuscany’s tranquil woodland with some of the region’s finest flavours. A great option for families — follow your foraging adventure with a cooking class or in-villa lunch, truffle-themed and served up by a local chef. 

We have a whole collection of villas set on vast private estates in Tuscany with private tartufaia (“truffle grounds”). The villa owners and managers are local experts when it comes to this prized fungi and offer bespoke experiences. Here are a few of our favourite villas for truffle hunting in Tuscany:

Palazzo Cheto — a fully-staffed converted monastery in the Crete Senesi with all the service of a luxury hotel on a purely exclusive level. 

Palazzo Cheto


La Palazza nel Cielo — grand stone farmhouse right in the heart of Tuscan truffle country.

La Palazzo nel Cielo


Poggio ai Grilli —- 1000-acre Medici estate, fully staffed with a large private pool and tennis court near San Miniato, world-famous for white truffles.

Poggio ai Grilli


Arts & Culture: Our favourite luxury experiences for art lovers and history buffs in Tuscany

Bespoke art retreat with Tanvi Pathare from your luxury villa in Tuscany

Bespoke art retreat with Tanvi Pathare from your luxury villa in TuscanyNo destination on earth will inspire the art lover in you quite like a trip to Italy. One of the best ways to immerse yourself in the country’s cultural heritage is with a bespoke in-villa art retreat led by award-winning artist, Tanvi Pathare. Opt for an in-villa painting workshop in the privacy of your luxury villa grounds, or combine it with a day of sightseeing in Venice, Orvieto, Siena or Florence with a professional Florentine artist.   


Private paper marbling workshop in Florence with a local artisan 

Private paper marbling workshop in Florence with a local artisan Florence isn’t just the birthplace of the Renaissance, it is the city of artisans and still a thriving hub for Tuscan artists. Whether you are a seasoned artist or are just looking for some creative therapy, Florence is the ultimate destination for creating your bespoke itinerary of arty experiences. 

Florentine paper marbling is among the city’s most iconic crafts, dating back to the 15th century, and will ensure that you aren’t just getting a quality memento to take home, but something unique to you. It’ll take you off the beaten path and offer a glimpse behind the scenes of this buzzing, creative city. 


Behind-the-scenes experience of the Palio di Siena with a Sienese guide

This fully customisable experience is such a special way to get behind-the-scenes access to Siena’s iconic sites with a Sienese family. Their magnificent palazzo home overlooks the Siena Duomo and has been in their family for generations. You can choose from a private rooftop lunch in an idyllic garden overlooking the cathedral or throw yourself fully into the excitement of the iconic Palio di Siena horse race. 

The family will be your guides (and chef!) offering fascinating insights into the history of the horse race and exclusive access to the city’s participating contrade (“districts”). Ranging from a one to four-day experience, tailor your time in Siena and at the Palio to your interests and luxury travel itinerary. 


Discover Italian coffee culture with a professional barista in Florence

Discover Italian coffee culture with a professional barista in FlorenceCoffee is a central part of everyday life in Italy — it isn’t just about quality and flavour either, it’s an important social event. No doubt, you’ll be just as excited about the coffee in Italy as the food and the wine!

The Scuola del Caffè is housed in a converted monastery in the centre of Florence committed to total transparency, eco-sustainability and of course, only the highest quality coffee. They offer several private coffee workshops that will open your eyes to the flavours and aromas of speciality Italian coffee, while also offering a unique perspective of Florence. 


Food & Wine: Private gastronomic experiences in Tuscany for foodies and wine lovers

Private farmer’s market tour and Tuscan cooking class with a local cook 

One of the most authentic ways to experience another culture is through taste, and the Italian emphasis on local, seasonal produce and traditional cuisine is second to none. They invented the ‘slow food’ movement after all! From small Tuscan hill towns like San Gimignano and Montepulciano to larger cities like Florence or Arezzo, experience Tuscan farmer’s markets on a local level. Immerse yourself in the scents, colours and flavours with a local expert, followed by an authentic cookery class using the produce you’ve hand-selected. 


Bespoke wine and cheese tastings, tours and lunch at our favourite Tuscan wineries

Bespoke wine and cheese tastings, tours and lunch at our favourite Tuscan wineries At Tuscany Now & More, we work with a range of local suppliers and family businesses to offer our guests truly meaningful and exclusive gastronomic experiences. There is nothing quite like experiencing world-class grapevines up close or talking over your favourite Chianti Classico reds with a Tuscan oenologist. We can arrange fascinating winery tours, tastings and hidden lunch spots at your favourite wine destinations and wine regions in Tuscany.

  • Colle Bereto — an organic, 60-hectare wine estate in Radda-in-Chianti. Tour the wine cellars and vineyard, taste all nine of their red, white and rosé wines and stay for a Bistecca lunch or cooking class surrounded by vine-clad hills. 
  • Corzano e Paterno — a 200-hectare family-run farm situated in the hills surrounding San Casciano Val di Pesa. Tour the estate and enjoy a seated tasting of four wines, four kinds of cheese, bread, the estate’s olive oil and local honey. You can even stay for a four-course farm-to-table dinner. 
  • Podere Le Ripi — a boutique biodynamic winery positioned on the slopes of Montalcino. Tour the different biodynamic and Bonsai vineyards, taste 5 wines and enjoy a light lunch surrounded by panoramic views. 


An intimate three-course dinner to mark a special occasion with an in-villa chef

With luxury holiday rentals as beautiful as ours, we understand that sometimes the best experiences are shared at your villa. From aperitivo served by your private pool to sunset dinners with 360° views of the Tuscan countryside, why go out when you can stay in?! 

Hiring a private in-villa chef and wait staff is an exclusive way to celebrate special occasions, like a birthday or anniversary, or something more intimate, like a romantic proposal. Work with our concierge to plan bespoke menus according to your tastes and have all your favourite Tuscan cuisine brought to your villa doorstep. When you book one of our fully-staffed villas in Italy, in-villa meals prepared by a local chef are included in the rental price. Wake up to breakfast served each morning and seasonal dishes freshly prepared and served each evening.  


Exclusive tasting and tour of a family-run Tuscan olive oil farm

Exclusive tasting and tour of a family-run Tuscan olive oil farmIt doesn’t get much more authentic than a private tour of a working olive farm with a local whose ancestors have worked the same soil for over 200 years. Extra virgin olive oil is intrinsic to Tuscany’s gastronomic traditions and you will struggle to find the same quality and depth of flavour outside of Italy. When you visit Villa Monteoriolo, you will get to explore the beautiful 14th-century estate, complete with around 3000 olive trees, visit the idyllic, seasonal vegetable garden and savour 0km Extra-Virgin Olive Oil produced on the very land around you. 


Contact our Italy Specialists to book your luxury villa in Tuscany

Whether you have your heart set on a specific region in Tuscany, are dreaming of your next family holiday or are planning a reunion with your friends, our Villa Specialists know each villa by heart. We are here to plan your luxury holiday in Italy around your specific interests and tastes, offering first-hand knowledge on each destination. 

In-villa and destination experiences add another bespoke layer to your vacation. Whether your travel checklist is centred solely on food or wine or covers a broad range of interests, we can create bespoke itineraries around your luxury villa stay. 

You can search our villas in Italy by region or by our thoughtfully curated villa collections, which range from villas with large pools to family-friendly retreats. Then contact our villa specialists to book your dream holiday. 


Let our Concierge Specialists do the rest!

Once you have found your dream villa in Italy, our complimentary Concierge Team is on hand to assist with all the finer details. From the everyday services like housekeeping and grocery shopping to the extra-special extras like in-villa yoga classes, wine tastings and chef services, this is where our concierges shine. 

Come to us with your interests, your ambitions and your questions and we will bring your vision to life. 


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All experiences are exclusively available to you when you book a luxury villa in Italy with Tuscany Now & More. Too add on any enriching extras, contact our local Villa Specialists to share your villa shortlist and secure your stay.

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