Chianti is more than just a name on a wine label—it’s a region that speaks to the soul. Rolling green hills, medieval terracotta villages, and fragrant vineyards that stretch as far as the eye can see set the backdrop for an unforgettable Tuscan escape. Whether you’ve explored Tuscany before or this is your first time venturing beyond Florence and Siena, Chianti offers a deeply personal, yet shared experience, one perfect for gathering those closest to you.

Winding Hills and Golden Sunsets: The Group Journey Begins

Imagine this: You and your group, friends or family, hiking the hills around the fortified village of Volpaia. The sun dips low, casting its golden light across a landscape draped in vineyards, and you pause, breathless not just from the climb, but from the beauty. In a place like Chianti, even the sunsets invite tears of joy.

Here, you can slow down and savor the moment. Each step on these trails is a reminder that luxury isn’t always in what you acquire, but in what you experience—and in this corner of Tuscany, those experiences are shared with the people who matter most.

Dario Cecchini of Macellerie, a sustainable butcher — Dario Cecchini of Macellerie, practices a sustainable approach to butchering

Dining That Inspires: Sustainable Indulgence in Panzano

Chianti’s charm goes beyond its landscapes; it extends to the tables where centuries of culinary tradition meet modern sustainable practices. In the small town of Panzano, your group will find one of Tuscany’s hidden gems: Dario Cecchini’s Macelleria. Dubbed the "world’s most famous butcher," Dario’s reverence for animals shows in the way he uses every part of the beast, embracing a more sustainable approach to butchering meat.

Gather your group around the communal table to enjoy a meal that transcends expectations—each bite of perfectly prepared Tuscan cinghiale (wild boar) an ode to the land and its traditions. This is dining that doesn’t just nourish the body, but feeds the soul.

A Market Day in Gaiole: Take Tuscany Home with You

For the perfect group bonding experience, head to Gaiole’s bustling Saturday market. In the heart of the main piazza, your group will browse stalls brimming with local goods, from the finest olive oils to pungent Pecorino cheeses. Imagine the laughter shared as each person selects something to bring back—gifts for loved ones, or better yet, a memento of an unforgettable journey together.

This small town, like many others across Chianti, holds the charm of the past while celebrating the artistry of the present. Every olive oil and cheese bought here tells a story, connecting you to the land and the people who care for it.

Chianti Classico Riserva 2019 Castello di Volpaia, with notes of violet, candied blackcurrant, lavender and cherry.

Savor the Wines of Chianti: A Toast to Togetherness

Chianti’s wines are renowned the world over, but few experiences compare to tasting these celebrated vintages on the very land where they are grown. A must-visit for your group is Querceto di Castellina, a female-run, organic winery that’s as committed to sustainability as it is to crafting some of the region’s most elegant wines.

Raise a glass of the Chianti Classico Riserva 2019 Castello di Volpaia, a wine that sings with notes of violet, lavender, candied blackcurrant and ripe cherry. As the flavors dance across your palate, take a moment to appreciate the deeper connections made—not just with the wine, but with the people who share this experience beside you.

The golden light of Tuscany makes for beautiful evening parties & weddings

Group Travel Ideas: Perfect for Every Occasion

Chianti is more than just a destination; it’s a backdrop for life’s greatest celebrations. Here are a few group travel ideas for your next Tuscan escape:

Destination wedding or babymoon with close friends and family
A sweet 16 or graduation present from parents to child, bringing along their favorite friends
A 40th Wedding Anniversary, or 65th Birthday Party, provided by the couple's adult children
A yoga guru hosting a peaceful retreat immersed in nature
A photography influencer organizing a nature photography trip for top-tier followers
A chef, ready to be pampered with fine food and wine, alongside close friends for a quick getaway
A law firm’s celebration of a hard-won case with a Tuscan retreat
An independent film producer rewarding their cast and crew with a wrap party to remember

Private villa rentals from Abercrombie & Kent

Chianti’s Private Villas: The Height of Group Luxury

No journey to Chianti is complete without the perfect accommodation. Abercrombie & Kent offers a selection of private villas that blend the freedom of a private estate with the luxury of five-star service. Whether you’re looking for a romantic 18th-century villa or a grand medieval watchtower, each estate comes with a host of amenities—heated pools, yoga studios, outdoor kitchens, and tennis courts, to name just a few.

These villas come fully staffed, with options to customize your experience. Whether you prefer to be left to your own devices or want a full team of chefs and concierge at your disposal, A&K’s 24-hour service tailors the stay to your desires. All villa's include:

A case of Tuscan wine and a welcome hamper of specialty cheeses, breads and other local treats.
Welcome and farewell dinners at the villa, prepared by an esteemed local chef.
Wine tasting at the villa or in the winery on your estate, with an expert from a leading vineyard.
A cooking lesson with a local Italian chef, who tailors the class to your party’s tastes and skills.
A session at the villa with a professional photographer, who captures the best holiday photos you’ve ever had.
Exclusive goodie bags of gifts for children and adults.
A dedicated local host and concierge with round-the-clock availability.
Pre-arrival grocery shopping service.
A meet-and-greet at the airport.
Private arrival and departure airport transfers.
A lavishly presented continental breakfast every day at a time of your choosing.
Daily housekeeping.

Palazzo Bellavista

Price: From $85,000 per week

Sleeps: 16 | 8 Bedrooms

With its sun-baked ochre walls and panoramic views of the olive, vine and chestnut-clad Tuscan hills, this deeply romantic 18th-century villa works both as a secluded retreat for family and friends and a peaceful base for exploring the Chianti wine region and nearby Florence. It has eight elegantly colorful en suite bedrooms and refined reception rooms, including a converted dovecote with views to the Apennines and coast; outside, sunlight slants through cypress trees and umbrella pines onto a heated outdoor pool in 35 acres of lawns and wooded grounds.

The Villa Palazzo Bellavista is owned by an Italian sports agent who fell in love with the place long ago. It’s since been renovated by his sister, Rome-based Ilaria Miani, who mixed family antiques with swathes and stripes of color that reflect the local landscape. Comfortable sofas, black-and-white engravings, freshly cut flowers and open fireplaces in the dining and living/TV rooms enhance the effortlessly elegant feel. The bedrooms are more theatrical and come with queen- or king-size beds, en suite shower rooms and air conditioning; the ground-floor double has a four-poster bed and another double is squirrelled away on a mezzanine beneath the tower. The six first-floor bedrooms include two twins, one double with a four-poster and two doubles with separate bathtubs and showers. All look onto the poetic grounds where white canvas chairs and loungers frame a 100-year-old swimming pool lined in pietra serena, mossy statues gaze over an antique amphitheater and a kitchen garden produces vegetables for cooking classes in the all-white kitchen with its marble worktops and antique cabinets.

The Location Palazzo Bellavista is set in the countryside of northern Chianti, 10 miles from Florence with its world-beating Uffizi and Accademia art galleries, its Duomo visible from the estate. The nearest town, Chiesanuova, is two miles away; within striking distance are beautiful, fortified Lucca (55 miles), the 14 towers of San Gimignano (30 miles) and unmissable Siena, the site of the bareback Palio horse race that opened the Bond film Quantum of Solace. It’s also just off the Chiantigiana wine route and your hosts Marcella and Remus can recommend local wineries such as Antinori and Castello Sonnino, as well as walks through the wider 178-acre estate in which the villa sits, along with two acres of its own Chianti Classico vines and 1,000 olive trees.

Il Cellese

Price: From $90,000 per week

Sleeps: 19 | 10 Bedrooms

Owner Sergio Sardelli’s grandfather planted the first vines at Il Cellese in the 1960s, and his aunt was one of the first women in the region to produce Chianti Classico. A 20-year restoration has transformed the ruins of this family-run private wine estate in Castellina into a drop-dead gorgeous villa that sleeps 19, a vision of Tuscan tradition given a cool, contemporary twist, with a dreamy quality you’ll wish you could bottle and take home.

The Villa With interiors of terracotta tiles and exposed beams and bold abstract art on the stone walls, Il Cellese fuses quintessential Tuscan charm with state-of-the-art modernity. Headline acts include the indoor and outdoor pools, an open-air yoga studio and indoor wellness area with gym, sauna and steam room. The estate’s nearby winery offers a private restaurant space that invites oenophiles to sample wine produced by the villa’s own vineyard, where custom barrels are painted by artists Santiago Ydáñez and Miki Leal. (Take home your favorite bottles in the villa’s custom-made crocodile leather trunk.) In the beautifully landscaped gardens is a wood-fired pizza oven and barbecue for those who love to cook, with a terrace for under-the-stars suppers overlooking Chianti’s hills and Il Cellese’s rows of vines.

The Location The cute Tuscan town of Castellina is a 10-minute drive from Il Cellese. Those interested in architecture and history will be curious to learn about its connections to Filippo Brunelleschi, founding father of Renaissance architecture. This authentically Italian neighborhood is home to a handful of low-key, family-run trattorias serving delicious, simple, Mediterranean flavors and time-honored recipes alongside fabulous homegrown wine. Castellina’s hilltop position provides a fresh perspective on the vine-lined countryside that rolls out like a green carpet in every direction towards Siena and Florence.

Borgo Castelletto

Price: From $65,000 per week

Sleeps: 12 | 6 Bedrooms

Set on a working wine estate, a country mile from the medieval hilltop town of Radda, this six-bedroom villa has sensational views of Chianti’s olive groves and vineyards — especially from the former medieval watchtower at one end of the property. It’s ideal for families and friends travelling together, with several terraces for outdoor dining, including one overlooking the pool and children’s play area beyond.

The Villa Owned by the Austrian family behind the Tenuta di Carleone winery which has been producing Sangiovese wine for over a decade, this six-bedroom villa is surrounded by olive trees, vineyards and rolling hills. The glorious rural landscape is typically Tuscan and so too is Borgo Castelletto’s stone building, terracotta-tiled roof and medieval tower that has been turned into a billiards room and bar. Inside, contemporary furniture, bold abstract art and flashes of colour (geometric cushions, cosy rugs, painted sea-green wardrobes) are juxtaposed with exposed stone walls, beamed ceilings and wooden floors.

The accommodation is split between two buildings. The ‘Owner’s Wing’ has a kitchen and conservatory, along with a dining room, drawing room, a TV area with a fireplace, and a library; on the first floor are two lovely bedrooms. The Guest Wing has another four bedrooms, all ensuite, split between the main floor – which has a pair of sitting rooms, two dining rooms and a fully-equipped kitchen made by artisan kitchen-makers in Florence – and the lower garden level. For chilly evenings, there is underfloor heating and a fireplace; for balmy summer nights, a wood-fired pizza oven, barbecue and multiple terraces for supper outdoors. The outdoor pool and wellness spaces are the final stand-out touch.

The Location Of all Chianti’s quintessential Tuscan hilltop towns, Radda takes the top spot, with its medieval tangle of streets, charming old houses and 360-degree views over the surrounding vineyards and golden hills. It’s in the heart of the Chianti Classico DOC, a designation with a history that dates back more than 300 years, and some of the best wines in the world. The food is just as good, with local restaurants creating the most delicious dishes from the top-quality seasonal local produce, and in fabulous settings. Nearby, you’ll find charming Tuscan towns to explore, and it’s an hour’s drive to the must-see cities of Florence and Siena.

Podere La Gloria

Price: From $70,000 per week

Sleeps: 16 | 8 Bedrooms

Tranquil Podere La Gloria is like a Tuscan hilltop village in miniature. The owners have sensitively restored the traditional honey-hued sandstone buildings, retaining original features while giving the interiors a contemporary shake-up. Set high in a secluded spot between Florence and Siena, the location makes for utter privacy, peace and spirit-lifting views across Tuscany’s vine-threaded hills from verandas, garden terraces and a sensational infinity pool.

The Villa Originally built in the 11th century, Podere La Gloria has aged beautifully, like a fine Chianti wine. It’s a light-filled hilltop hideaway conjured out of a medieval tower and an old barn, and blanketed in Boston ivy, which was sensitively restored in 2023 in a top-to-toe makeover by owners Jane and Steven Collins (she is an antiques dealer, he a hotelier), who also run Henry’s Townhouse in Marylebone and Cotswold estate Temple Guiting. Their taste is exquisite. Clean, elegant interiors embody Italian quiet luxury, the earthy palette injected with fun points of focus thanks to abstract art by Peter Haigh, vintage Giotto Stopino furniture and statement seating by Pierre Paulin. Light, open living spaces foster connections, designed for eating, drinking and hanging out, from laid-back breakfasts and espressos in the well-equipped kitchen that opens up onto the garden, to chef-prepared feasts beneath the vaulted ceiling of the dining room, with its great wooden table for 16 – the perfect place to fill with your favourite people. There are eight fresh-faced, elegant bedrooms. Some have living spaces with fireplaces, some open onto gardens, two have free-standing bathtubs, and all but one have en suite bathrooms kitted out with Dyson hairdryers, Frette bathrobes and bathroom products from Florentine institution Santa Maria Novella, the world’s oldest pharmacy. A separate studio by the pool is perfect for extra guests or round-the-clock staff. At every turn – from bedroom windows, verandas, various terraces, gardens – are sensational views of the green patchwork hills stretching out below. Outside there’s an outdoor kitchen (complete with Fontana pizza oven), dining areas, seating nooks for beating a retreat from the crew, and the most beautiful hand-tiled infinity pool, lined with parasols, that feels suspended mid-air, high above the Tuscan landscape.

The Location The surrounding Val d’Elsa hills offer up pretty villages to explore, and medieval towns such as San Gimignano, whose historic centre is a UNESCO World Heritage Site; nearby Tavarnelle Val di Pesa (a 10-minute drive away), where churches are filled with elaborate frescoes; and Badia a Passignano, where tables laid with Tuscan produce are set among the vines. Strike out a little further south to Siena or north to Florence: both are brimming with Renaissance art, impressive cathedrals and osteria-lined piazzas made for an evening passeggiata.

Podere La Piana

Price: From $55,000 per week

Sleeps: 10 | 5 Bedrooms

Just a few miles from the medieval town of Radda in Chianti, this sensitively restored five-bedroom Tuscan farmhouse sits on a family-owned wine estate. Perfect for multi-generational gatherings and groups of friends, it has masses of space, from the contemporary living areas to the children’s playground and outdoor pool with panoramic views of the olive groves and vineyards. There’s also a gym and steam room, and for outdoor dining, a pizza oven, barbecue and well-stocked wine cellar.

The Villa It was while holidaying nearby that an Austrian family stumbled across a pair of ruins on the other side of the valley. Having purchased them both, they tasked a local architect with their restoration. Five-bedroom farmhouse Podere La Piana, which is surrounded by olive trees, vineyards and rolling hills, was completed in 2019 (sister property Borgo Castelletto followed a year later). Rustic-modern interiors marry exposed stone walls, vaulted ceilings and vintage wooden furniture with bold artwork, velvet sofas and shimmering statement lighting. The ground floor living room, kitchen and dining room all open out onto the garden where there’s a shady loggia for eating outside; upstairs, the bedrooms are all en suite (the largest have walk-in wardrobes). The lower ground floor houses the gym, steam room and wine cellar, which is stocked with buyable bottles from the winery. Games for all ages, such as table tennis, boules and table football, provide fun entertainment during downtime.

These exclusive estates offer more than just a place to stay—they provide a backdrop for unforgettable experiences shared with the people who matter most. Whether your group is after a quiet retreat or an active exploration of Chianti’s best, these villas offer the perfect combination of luxury, privacy, and personalized service.

Luxury Worth Every Penny

It’s true: Tuscany can come with a price tag that raises eyebrows. But consider this—what’s more valuable than spending a week in Italy, surrounded by the people you love, in complete luxury?

When you do the math, staying in a villa like Podere La Gloria is not just a trip, but an investment in life’s most cherished moments. At $70,000 per week, it may sound extravagant, but break it down by number of guests and you’ll see the value: just $4,375 per person for 7 nights and 8 days, inclusive of welcome & farewell dinners prepared by a local chef, expert-led wine tastings, a customized cooking lesson, gifts for all of your guests, private airport transfers, a photography session to capture every memory, and a full staff available. When you evaluate it like this, the price seems rather extrodinary!

Make It Your Own: Plan Your Group Escape

Whether it’s celebrating a milestone or simply reuniting with the people who matter most, Chianti offers a transformative group experience. Let Bespoke Legacy Luxury Travel help you create a journey that’s as unique as the bonds you share. From sustainable, organic wine tastings to private villas fit for royalty, we’re here to bring your Italian dreams to life.