When one thinks of Chianti, wine naturally comes to mind. Covered in vineyards, this photogenic region is famous worldwide for its enchanting landscapes and prestigious wineries.
While that has remained true for centuries, there’s another side to Chianti that’s just as wonderful. Perhaps the best part is the variety of experiences on offer: one moment you might be sipping wine in a rustic countryside cantina, and the next, gazing at the stars under a clear Tuscan sky. While San Miniato and Crete Senesi are well-known truffle zones in Tuscany, Chianti offers a surprisingly rewarding truffle-hunting experience of its own.
These off-the-beaten path experiences reveal a different side to the region. Whether you’re a wine enthusiast with a penchant for contemporary art or a thrill seeker in search of the best hot-air ballooning spots, Chianti has it all.
Market Days
Shop like a local with a trip to Chianti’s weekly village markets. From Greve’s Saturday market to the antique treasures of Certaldo and Panzano, there’s plenty to choose from.
No matter the season, the region’s charming local market days offer an abundance of fresh produce. In the winter months, stalls are stocked with rows of winter truffles and autumn’s porcini mushrooms; when spring arrives, the market comes alive with zucchini flowers and the first fruits of the year.
To make your life easier, many of our Chianti villas are an easy cycle ride or brisk walk away from the market. Stock up on fresh ingredients for lunch or dinner, which can be prepared by your in-villa chef. In-villa cooking classes can also be organised if you’d prefer to learn a few Tuscan recipes from scratch – just speak to our complimentary concierge for more information. A full list of market times and locations can be found here.
Stargazing
With its rolling vistas, Chianti’s landscapes are ideal for daytime exploration and nightmare stargazing. The region’s clear night skies are captivating, and as soon as night falls, the sky transforms into an ethereal spectacle.
Ideally located away from urban lights, our handpicked portfolio of villas in the Chianti offers the perfect vantage point to enjoy this celestial show, glass of wine in hand. Explore the full collection and speak to our complimentary concierge for bespoke local tips.
Contemporary Art
There’s a lot to be said for Chianti’s contemporary art scene. If you know where to look, you’ll find an array of superb museums and exhibitions in unexpected places – from hidden parks to famous wineries.
In Montefiridolfi, one of many spectacular villages in Chianti, La Loggia Art Centre features an open-air museum, with works by Betty Woodman, Franz Stähler, Arnaldo Pomodoro, Roberto Barni and Karel Appel. Elsewhere, Pievasciata’s sculpture park hosts a range of contemporary installations and sculptures by international artists.
Our award-winning concierge can also help with organising gallery visits and an immersive art-focused itinerary that’s completely unique. Enjoy a moonlit tour of the region’s museums, try an immersive painting workshop surrounded by vineyards and stay in a grand country home with painterly views of Chianti’s hills.
Truffle Hunting
Truffle hunting in Tuscany is as therapeutic as it sounds, allowing guests to wander through the beautiful woodlands of Chianti. On a guided tour, you’ll get to pick and pluck this elusive delicacy alongside a Lagotto Romagnolo, a dog breed known for its exceptional truffle-hunting skills. Along the way, you’ll learn about the different truffle varieties and their fascinating history, before rounding off the experience with a traditional Tuscan lunch.
Hot Air Ballooning
Drifting above Tuscany’s rolling hills in a hot air balloon is exhilarating, to say the least – and utterly breathtaking. Float over the region’s picturesque countryside and take in Chianti’s photogenic landscapes from a spectacular aerial perspective.
Whether you’re a pro or a first-time flyer, this is bound to be an experience you’ll cherish for years to come. Arrive early to catch the sunrise and witness the beautiful morning light drape over Chianti’s undulating countryside.
Plan your perfect Chianti Itinerary
Our villas in Chianti give you easy access to the region’s unique experiences. Each villa has been handpicked for its exquisite location, character and comfort. Contact our Villa Specialists today to discover more and begin planning your perfect Chianti adventure.
Our complimentary concierge are also here to elevate your villa stay with bespoke local adventures, whether you’re staying among the vine-laden hills at Podere Celli in western Chianti or gathering the family at La Magnifica – a stunning addition to our 2026 collection. A stay at Villa Albizi, meanwhile, offers a sumptuous culinary experience to remember.