Ken is an acclaimed Australian wine writer and critic based in Brisbane, Queensland. After studying law at the University of Queensland and gaining experience in London and Washington, D.C., Ken transitioned to journalism and became a full-time freelance writer. He has contributed extensively to publications such as The Courier-Mail, World of Fine Wine, Quill & Pad, Drinks Trade, Fine Magazine, Halliday Magazine, Ocean Magazine, Tastingbook, and WinePilot.
As a former editor of Fine Wine & Champagne Australia/New Zealand, Ken has been a regular wine columnist since 1999, and is highly regarded in the wine community.
Beyond wine, Ken writes on cigars, travel, fishing, and food. His personal blog, Kenfessions, explores these interests with wit and depth. When he’s not writing, Ken is often fly-fishing for trout in New Zealand or bonefishing in the Carribean, relaxing with a fine cigar, or passionately following sports teams like the Broncos, Washington Commanders, Queensland Reds, Arsenal FC, and the Australian cricket side.
Welcome to Tuscany
Stay: Villa La Massa (2 nights)
Meals included: Dinner
✈️ Arrival
🛏️ Check-in
Settle in and unwind at the villa
🍷 Aperitivo
Welcome drinks overlooking the Arno River
🍽️ Dinner
Private Dinner in the Wine Cellar at Villa La Massa
Meet your wine enthusiasts. We will meet in central Florence and transfer to Villa La Massa for our first evening in Tuscany.
Settle into the enchanting Villa La Massa with welcome drinks and a private wine cellar dinner
Start your Tuscany Uncorked journey with a delightful welcome drink at the Medicean Bar. As you step into this elegant space, you'll be greeted with the rich aroma of local wines and artisanal cocktails. Sip on a refreshing glass of Tuscan wine or a signature cocktail, expertly crafted to reflect the region's vibrant flavors. This is the perfect opportunity to unwind and soak in the stunning surroundings as you prepare for an unforgettable adventure through the vineyards of Tuscany. Cheers to new beginnings and the exquisite experiences that await!
Thanks to the hotel’s privileged location in the heart of the Chianti Rufina wine region, the cellar treasures a collection of prestigious labels and rare vintages, ready to be unveiled through exclusive private tastings.
Villa La Massa’s Wine Dinners are exclusive occasions for wine lovers and fine dining enthusiasts. In an intimate and evocative atmosphere, on Il Verrocchio’s riverside terrace overlooking the Arno, each evening offers a sensory journey through iconic labels and haute cuisine. Every selection, curated by Group Wine Director Alex Bartoli, celebrates the finest Italian wines with themed pairings alongside menus created by the Chef. A perfect union of flavour, tradition, and creativity, enjoyed amidst the timeless beauty of the Tuscan countryside.
Stay: Villa La Massa
Meals included: Breakfast & Lunch
🍽️ Breakfast
Villa la Massa
🍷 Wine Tasting
Fattoria Selvapiana
🍷 Wine Tasting
Castello del Trebbio
🍽️ Lunch
La Sosta del Gusto (Castello del Trebbio)
🍷 Wine Tasting
Marchesi Gondi – Tenuta Bossi
🍽️ Dinner at leisure (not included)
Villa la Massa
TODAY'S WINE SPECIALTIES
The Tuscany Chianti Rufina area is renowned for its Chianti Rufina DOCG wines, which are primarily made from the Sangiovese grape. These wines are known for their elegance, bright acidity, firm tannins, and flavors of cherry, red berries, and subtle herbal notes. Chianti Rufina is considered one of the highest-quality subzones of Chianti, often producing wines with excellent aging potential and a distinctive fresh, vibrant character thanks to its cooler climate and higher altitude vineyards.
Start your day with a delightful breakfast at Villa La Massa, where you can savor a variety of fresh fruits, homemade pastries, and traditional Italian delicacies. Enjoy your meal in a picturesque setting with stunning views of the surrounding gardens and the Arno River. The warm, inviting atmosphere and attentive service make breakfast a truly memorable experience.
Experience an exclusive private tasting at Selvapiana, where you’ll savor the rich flavors of their renowned Chianti wines. Nestled in the picturesque Tuscan hills, this intimate setting allows you to engage with knowledgeable sommeliers who will guide you through each pour. Delight in a selection of vintage wines paired with local delicacies, enhancing your understanding of the region's terroir. As you sip, take in the breathtaking views of the vineyards, creating unforgettable memories in a truly enchanting atmosphere. This personalized experience is perfect for wine lovers seeking a deeper connection to Tuscany's winemaking heritage.
Indulge in a premium wine tasting experience at Castello del Trebbio, where Tuscany's rich viticultural heritage comes to life. Nestled in the breathtaking Chianti landscape, this historic castle offers a selection of exquisite wines crafted from estate-grown grapes. As a wine enthusiast, you'll appreciate the expert guidance from knowledgeable sommeliers who will share insights into the winemaking process. Savor each sip as you explore a variety of complex flavors and aromas, perfectly paired with local delicacies. The stunning views of the surrounding vineyards enhance the ambiance, making this tasting not just a drink but a memorable journey into the heart of Tuscany's wine culture.
Enjoy a delightful lunch at La Sosta del Gusto, where authentic Italian flavors come alive. Nestled in a charming setting, this restaurant emphasizes a farm-to-table philosophy, using fresh, local ingredients that highlight the region's culinary heritage. The menu features a variety of traditional dishes, each crafted with passion and care. Savor the rich aromas of handmade pasta, seasonal vegetables, and exquisite wines that complement every bite. The warm, inviting atmosphere makes it the perfect spot to relax and indulge in a memorable dining experience.
A private tasting at Tenuta Bossi offers an intimate introduction to one of Chianti Rufina’s most historic estates, where the cellars lie partly underground beneath the villa and its ancient, tree-shaded park. Guided by a philosophy inspired by Galileo Galilei’s words — “Wine is a mixture of mood and light” — the Gondi family has, for over 25 generations, balanced human passion with the life-giving Tuscan sun to craft wines of integrity and character. Remaining steadfastly traditional, the estate focuses on meticulous vineyard care, attentive winemaking, and judicious use of oak, allowing the purity of the fruit and terroir to shine through. The estate produces a refined range of wines including Chianti Rufina DOCG, Super Tuscan IGT, Vin Santo, and grappa, alongside two exceptional extra virgin olive oils, including the highly regarded Laudemio.
Suggested options:
Villa La Massa's own Il Verrocchio Restaurant
The estate’s signature restaurant, Il Verrocchio, features a romantic terrace overlooking the Arno River and Tuscan hills. Chef Stefano Ballarino presents a refined Italian menu with contemporary touches, emphasizing local ingredients and the estate’s own organic olive oil. Dinner is served from 7:00 PM to 10:30 PM
Alternate dining options
The surrounding village offers a range of dining experiences, from traditional Tuscan cuisine to delightful pastries, all within a convenient distance from Villa La Massa.
A Journey Through Chianti Arezzo to Val d’Orcia
Stay: Monteverdi Tuscany
Meals included: Breakfast & Lunch
🥐 Breakfast
Villa La Massa
🏨 Check-out
Depart Villa La Massa
🍷 Wine Tasting
Tenuta Sette Ponti
🍽️ Lunch & Wine Tasting
The Grand Experience at Avignonesi
🏡 Check-in
Monteverdi Tuscany (2-night stay)
🍸 Welcome Drinks
Terrace Bar at Monteverdi Tuscany
TODAY'S WINE VARIETIES
At Tenuta Sette Ponti, you’ll taste bold Super Tuscans crafted from Merlot, Cabernet Sauvignon, and Petit Verdot, alongside elegant expressions of old-vine Sangiovese and crisp Trebbiano Toscano.
At Avignonesi, the spotlight is on Sangiovese (Prugnolo Gentile) in their renowned Vino Nobile di Montepulciano. You’ll also enjoy rich Merlot in Desiderio and sweet Vin Santo made from Trebbiano and Malvasia.
Start your day with a delightful breakfast at Villa La Massa, featuring fresh fruits, homemade pastries, and traditional Italian delicacies. Enjoy your meal amidst stunning views of the gardens and the Arno River, making for a memorable experience before continuing your wine journey.
Venture into southern Tuscany for delightful wine tastings at Tenuta Sette Ponti, a renowned estate known for its high-quality wines, including the celebrated "Oreno" and "Crognolo." Enjoy the scenic beauty as you explore their 100% organic vineyards, expertly managed to create elegant wines with unique aromas, thanks to the region's ideal conditions. Experience the rich Tuscan history and the essence of the land in every sip!
Join us for a gourmet lunch paired with Avignonesi’s top wines, served in our restaurant with a breathtaking view over the Val D’Orcia.
Enjoy a tour with one of our knowledgeable wine experts and discover the hidden gems of Avignonesi’s approach to winemaking, and the importance of both the land and people.
Visit the most iconic vineyard plot in Italy, travel through time in the ageing cellars and the Vinsantaia.
When you have seen it all, sit down and enjoy our gourmet lunch in our elegant Foresteria. Lunch is served in our panoramic restaurant.
Created by our chef, inspired by Virginie Saverys, this menu features seasonal organic dishes. All products are sourced locally and the fresh ingredients are taken from our organic vegetable garden.
Two MICHELIN Keys Awarded 2025
A stay at Monteverdi Tuscany immerses guests in a beautifully restored medieval village in the heart of Val d’Orcia, where art, culture, and refined living converge. Named for the verdant mountains that surround it and the 16th-century composer Claudio Monteverdi, the estate offers far more than accommodation, encompassing a fine-dining restaurant and osteria, contemporary art gallery, performing arts venue, library bar, gym, terrace lounge, and thoughtfully curated cultural spaces. Founded by Michael L. Cioffi, whose connection to the region began in 2003, Monteverdi was born from a vision to preserve and reimagine Castiglioncello del Trinoro as a place of timeless beauty and quiet inspiration. Complementing its extraordinary setting, the artists and scholars-in-residence program brings leading creatives from across the world to perform, lecture, and engage with guests, creating an atmosphere where art, architecture, music, food, and wine are seamlessly woven into an experience of world-class hospitality and soulful Tuscan living.
Take a seat under endless skies on the outdoor terrace and let the landscape feed your inspiration as we pour the drinks. Our intimate bar offers a convival, sophisticated space in which to unwind throughout the day. The terrace is a spot to gather old friends, and new. Anticipate breathtaking sunsets as standard.
From refreshing aperitivos to classic cocktails and iconic regional wines, our extensive drinks menu is an outpouring of delight by the glass or the bottle.
Dining at Monteverdi Tuscany is seamlessly woven into the rhythm of your stay, balancing relaxed Tuscan flavours with moments of quiet indulgence.
Most meals are enjoyed at Zita, the resort’s welcoming osteria, where classic regional dishes — such as handmade pici pasta and seasonal local produce — are served in a warm, village-style setting. It’s an easy choice for both lunch and casual evenings.
For a special night, Oreade offers a refined fine-dining experience with seasonal tasting menus that showcase Tuscan ingredients in a more contemporary style — ideal for a memorable dinner during your stay.
Evenings often begin or end with a drink at the Lobby Lounge & Terrace Bar, perfect for sunset aperitivos with sweeping countryside views, or in the quieter Library Bar for coffee, dessert or a relaxed nightcap.
A Vino Nobile Experience
Stay: Monteverdi Tuscany
Meals included: Breakfast & Dinner
🥐 Breakfast
Monteverdi Tuscany
🍷 Wine Tasting
Cantina De’ Ricci, Montepulciano
🏛️ Leisure
Explore Montepulciano’s historic centre
🍷 Wine Tasting
Tenuta di Trinoro
🍽️ Dinner
Curated Dinner & Wine Pairing – Monteverdi Tuscany
TODAY'S WINE SPECIALTIES
Montepulciano is best known for its Vino Nobile di Montepulciano, a prestigious red wine primarily made from the Sangiovese grape (locally called Prugnolo Gentile). This wine is celebrated for its rich structure, balanced acidity, and flavors of red berries, plums, earth, and spice. It’s one of Tuscany’s classic, age-worthy wines with a DOCG classification.
As the sun rises over the Val d’Orcia, breakfast at Monteverdi Tuscany is a quiet, unhurried start to the day. Fresh pastries, local cheeses, seasonal fruit, and perfectly made espresso are served as you take in the sweeping countryside views. It’s a simple, elegant moment — lingering over coffee, soaking up the scenery, and settling into the slow rhythm of Tuscany before the day’s adventures begin..
A wine tasting at Cantina De’ Ricci is one of Tuscany’s most evocative wine experiences, set beneath the Renaissance Palazzo Ricci in the heart of Montepulciano. Descending into the vast, candlelit cellars—often described as the “Cathedral of Wine”—guests are immersed in soaring vaulted arches, ancient stone walls, and centuries of winemaking history dating back to Etruscan times. Over approximately 75 minutes, a guided journey through these atmospheric underground tunnels brings the legacy of Montepulciano vividly to life, culminating in a tasting of De’ Ricci’s elegant Vino Nobile di Montepulciano and Rosso di Montepulciano, enjoyed in the very space where these wines have been patiently aged for generations.
Stroll & Artisan Discovery
Emerging from the cool cellars into the light, you find yourself in Montepulciano’s upper town near Piazza Grande, where sweeping views stretch across the Tuscan countryside. Take time to admire the grand square or climb the Palazzo Comunale tower before wandering downhill along Via di Voltaia nel Corso, browsing quiet artisan shops offering handwoven linens, local cheeses, and olive oils as the town settles into its gentle rhythm.
Lunch at Leisure
Montepulciano reveals itself through flavour as much as scenery, with lunch enjoyed at leisure in a local trattoria or courtyard. Menus celebrate Tuscan tradition with hand-rolled pici pasta, pecorino di Pienza, rustic crostini, grilled meats, and comforting classics such as ribollita, all prepared simply and served with pride—an honest reflection of the land and its culinary heritage.
Afternoon Gelato & Gentle Descent
After lunch, pause for gelato or an espresso before continuing a relaxed descent through town, perhaps stopping in at a wine shop or simply soaking in views across vineyards and olive groves. You depart Montepulciano unhurried and content, carrying with you the unmistakable Tuscan blend of culture, flavour, and timeless beauty.
A private tasting at Tenuta di Trinoro is an unforgettable encounter with one of Tuscany’s most uncompromising estates, set deep within the raw, dramatic folds of Val d’Orcia. Founded in the early 1980s by Andrea Franchetti, the estate defied convention by planting Bordeaux varieties in high-altitude, rocky vineyards, allowing each parcel and vintage to speak for itself. By appointment only, tastings are intimate and unhurried, offering a rare insight into Trinoro’s philosophy of precision, restraint, and respect for extreme terroir. Glass by glass, the wines reveal remarkable intensity and individuality, from the ever-evolving flagship Tenuta di Trinoro to selections such as Le Cupole or the rare Bianco di Trinoro, each capturing the wild character and quiet power of this remote corner of Tuscany.
A curated dinner and wine pairing at Monteverdi Tuscany is a refined celebration of seasonality and place, led by Chef Riccardo Bacciottini’s philosophy of sustainability and thoughtful innovation. Drawing on the surrounding countryside, the menu showcases wild herbs, foraged mushrooms, edible flowers, locally sourced meats, and ancient grains, transformed into dishes that feel both contemporary and deeply Tuscan. Each course is paired with carefully selected regional wines, creating a seamless dialogue between plate and glass, where flavour, texture, and aroma are elevated in unison. As the evening unfolds, guests are taken on a sensory journey across Tuscany’s landscapes, enjoying an intimate and beautifully orchestrated dining experience that captures the soul, heritage, and quiet elegance of the region.
Brunello in Flight: A Skybound Journey Through Tuscany’s Finest
Meals included: Breakfast & Lunch
🥐 Breakfast
At Zita – Monteverdi Tuscany
🏨 Check-out
Depart Monteverdi Tuscany
🚁 Helicopter Tour
Fly over Val d’Orcia and Val di Chiana with landings at:
Podere Le Ripi – private vineyard visit and tasting
Castiglion del Bosco – vertical Brunello tasting
Castiglion del Bosco –lunch at 2 Michelin starred Ristorante Campo Del Drago
🚐 Private Transfer
Castiglion del Bosco to Castello Banfi
🏡 Check-in
Castello Banfi Hotel Il Borgo (2-night stay)
Your second morning at Monteverdi opens gently, with breakfast offering a familiar sense of calm in a spectacular setting. A thoughtfully prepared spread of pastries, fruit, local cheeses, and freshly made coffee awaits, enjoyed while gazing out over the Val d’Orcia. It’s an effortless, restorative start to the day — a chance to pause, recharge, and savour the rhythm of Tuscan life before heading out to explore.
On check-out from Monteverdi Tuscany, please have your bags ready for collection. Our luxury bus service will transport your luggage, you will be escorted to the helicopter pick-up point to begin your exclusive Brunello in Flight experience.
Take your wine passion to the skies, soar above Val d’Orcia and Val di Chiana, savouring wine, gourmet dining, and stunning landscapes on this exclusive tour.
This exclusive experience includes the private visit of two wineries, Podere Le Ripi in the morning and Castiglion del Bosco in the afternoon, as well as a lunch at the Michelin-starred Restaurant Silene. In between the winery tours and gourmet lunch, you’ll enjoy bird’s-eye views of the picturesque villages of Montalcino, Pienza and Montepulciano from your private Helicopter.
Podere Le Ripi
“Owned by Francesco Illy, of Illy coffee fame, Podere Le Ripi is one of the most elegant biodynamic vineyards in Montalcino. Be sure to visit the new cellar” (Danielle Pergament, New York Times).
A boutique winery surrounded by forest, vineyards and centenary olive trees. An uncontaminated soil and a marvellous vegetal variety encompassed by a breath-taking view. Visit the Bonsai vineyard, the densest in the world with 62.500 plants/H. Walk through the Golden Cellar, built with ancient construction techniques using over 750.000 natural clay bricks. Finally, taste an outstanding selection of its best vintages, including the Bonsai wine.
Private Wine Tasting, Castiglion del Bosco
Enjoy an intimate private tasting in an elegant setting, either within the historic cellars or on a terrace overlooking the vineyards. The experience features a carefully curated selection of estate wines, with expert guidance offering insight into the vineyards, vintages, and winemaking philosophy.
The tasting highlights refined, expressive wines with layered aromas of dark fruit, subtle spice, and savoury depth, reflecting the distinctive character of the surrounding landscape and terroir.
Lunch with wine pairing at 2 Michelin-starred Ristorante Campo del Drago, Castiglion del Bosco
Crafted vibrant dishes with fresh produce from the resort’s organic garden. Inspired by Siena’s Piazza del Campo and the estate’s single-cru Brunello, it offers terrace views of Montalcino’s lush hills and Val d’Orcia. Awarded its first MICHELIN star in 2023 and second in 2025, it’s a culinary journey celebrating the region’s beauty and flavours.
Enjoy a comfortable private minibus journey from Castiglion del Bosco to Castello Banfi, travelling through rolling vineyards, olive groves, and classic Tuscan countryside. A relaxed and scenic transfer linking two iconic wine estates.
A stay at Hotel Il Borgo, Castello Banfi places you within the historic heart of Poggio alle Mura, a beautifully restored medieval castle rising above rolling vineyards and olive groves in the Brunello di Montalcino region. Timeless in atmosphere yet refined in comfort, Il Borgo blends elegant Tuscan design with centuries of layered history, from Etruscan and Roman origins to its development as a fortified estate between the 9th and 13th centuries. First formally recorded in 1318, the castle’s strategic position between Siena and the Maremma made it a coveted stronghold for generations, a legacy still felt in its commanding views and enduring presence. Today, each individually styled room and suite offers a serene retreat, where historic stone walls, terracotta roofs, and sweeping countryside vistas create an experience that feels both deeply rooted in the past and effortlessly luxurious.
Chef Domenico Francone's first experience in the world of catering, already in secondary school, is in pastry, a discipline that has always fascinated him.
His career path leads him to travel and experience in prestigious Italian and international restaurants. A Michelin star arrives in Tuscany, at il Ristorante Beck's Banfi, a Michelin Star in 2008.
After the restaurant closed, Chef Domenico Francone moved to London where he worked at the starred restaurant Heinz Beck's Apsleys starred restaurant. A magical and exhausting moment at the same time, which gives birth to him with the desire to continue traveling, but which also triggers a strong nostalgia for returning to Tuscany, his land of adoption
And it was here that Banfi offered him a second opportunity: to become Executive Chef of La Taverna.
In addition to La Taverna, supported by a talented brigade in both the dining room and kitchen, chef Domenico Francone also reopens the other restaurant, La Sala dei Grappoli, leading him to conquest the Michelin Star in 2020.
La Sala dei Grappoli
The majestic Castello Banfi, of medieval origins, towers imposingly in front of the restaurant. The vines that fresco the rooms explain its name, making the setting elegant and refined. As soon as the season allows, dinner is offered on the terrace, for a memorable experience given by the incredible view, chef Domenico Francone's intriguing cuisine and the great Banfi wines.
La Taverna
A traditional Tuscan restaurant in the shadow of the medieval Poggio alle Mura Castle. The tavern is located beneath the vaults of the castle's old cellars, where the large wooden barrels used to age Brunello di Montalcino once rested.
Today - Elevated Brunello
Stay: Hotel Il Borgo, Castello Banfi
Meals included: Breakfast, Lunch & Dinner
🥐 Breakfast
Hotel Il Borgo, Castello Banfi
🍷 Wine Tasting
Poggio Antico
🍽️ 🍷 Vineyard Tour, Lunch & Wine Tasting
La Togata Experience including Antipasto
🍽️ Dinner
La Sala dei Grappoli, Castello Banfi
TODAY'S WINE REGION
Nestled high in the hills of Montalcino, Poggio Antico crafts elegant Brunellos that capture the essence of its unique calcareous and galestro soils. Here, tradition meets precision in every bottle, revealing the true depth of Sangiovese Grosso. Just nearby, La Togata continues this legacy, producing classic Brunellos aged to perfection with velvety tannins and refined minerality. Together, these estates offer a timeless journey through Tuscany’s most celebrated wines.
Begin your day at Hotel Il Borgo, a charming hilltop retreat at Castello Banfi, where serene vineyard views and a warm, inviting atmosphere make breakfast a truly Tuscan experience.
A Great Vintages Private Tour at Poggio Antico offers an elevated perspective on Brunello di Montalcino, both literally and philosophically. Set on the highest hills of the region at nearly 500 metres above sea level, the estate’s vineyards are shaped by ancient calcareous and galestro soils and meticulously managed through a deep understanding of micro-terroir, with each parcel harvested and vinified separately. The experience includes a guided walk through the vineyards and cellar, providing insight into precision viticulture, winemaking, and long ageing, before concluding with a tasting of Poggio Antico’s refined Brunello wines. Surrounded by sweeping views, cypress-lined avenues, and the vivid light of the Tuscan landscape, this private visit captures Brunello at its most expressive and profound.
and bruschetta with olive oil from the area, and a tasty first course.
The La Togata Experience at La Togata is a classic and warmly personal introduction to Brunello di Montalcino, born from a family passion for fine wine passed down from its founder, a Roman lawyer whose love of winemaking inspired the estate’s name and philosophy. The experience begins among vineyards over 25 years old, planted at varying elevations and sun exposures, before continuing through the winery with a welcome flute of La Togata Brut Nature Millesimé. In the tasting room, guests enjoy a guided tasting of Brunello di Montalcino La Togata, Rosso di Montalcino La Togata, and the Super Tuscan Azzureta—wines known for their structure, minerality, and velvety elegance—alongside a classic Tuscan antipasto of local ham, cheese, bruschetta with regional olive oil, and a comforting first course, offering an authentic and beautifully balanced expression of tradition, craftsmanship, and place.
The majestic Castello Banfi, of medieval origins, towers imposingly in front of the restaurant. The vines that fresco the rooms explain its name, making the setting elegant and refined. As soon as the season allows, dinner is offered on the terrace, for a memorable experience given by the incredible view, chef Domenico Francone's intriguing cuisine and the great Banfi wines.
Stay: Borgo Pignano (2 nights)
Meals included: Breakfast & Lunch
🥐 Breakfast
At leisure – Castiglion del Bosco
🏨 Check-out
Depart Castiglion del Bosco
🍷 Wine Tasting
Tasting at Panizzi paired with local cheeses and bruschetta
🍷 🍽️ Masterclass & Antipasto Lunch
Masterclass at Rocca di Montestaffoli with antipasto and wine pairing
🏡 Check-in
Borgo Pignano
🍸 Sunset Cocktails
Borgo Pignano
🍽️ Dinner
At leisure (not included)
THE SAN GIMIGNANO WINE REGION
San Gimignano, nestled in the heart of Tuscany, is renowned as the home of Vernaccia di San Gimignano DOCG — Tuscany’s most celebrated and historic white wine. Crisp, aromatic, and mineral-driven, Vernaccia thrives in the sandstone-rich soils and rolling hills surrounding the medieval town. While white wine is the star, the region also produces limited quantities of San Gimignano Rosso DOC blends, Super Tuscans, and Vin Santo, the region’s traditional dessert wine. Together, these varieties reflect both the ancient heritage and modern innovation of this unique Tuscan appellation.
Start day two with a tranquil breakfast, savouring fresh local produce, warm pastries, seasonal fruit, and traditional Tuscan specialties. Set in a charming space with sweeping views of vineyards and rolling hills, it offers a serene and delicious beginning to your day in the heart of Tuscany.
Today we check out of Hotel Il Borgo and journey into the San Gimignano wine region, celebrated for its crisp, mineral-driven Vernaccia di San Gimignano — Tuscany’s most historic white wine. Set among rolling hills and medieval towers, the region also produces elegant reds and traditional Vin Santo, offering a refined glimpse into Tuscany’s winemaking heritage before checking in at the stunning Borgo Pignano.
A visit to Panizzi offers a beautifully immersive introduction to Vernaccia di San Gimignano, as you wind through the sunlit hills beyond the town’s iconic medieval towers to reach Fattoria di Larniano, a secluded hamlet where time seems to slow. Set among stone buildings gathered around a centuries-old Lombard tower, the estate provides a serene backdrop for a guided tasting of Panizzi’s elegant Vernaccia wines, celebrated for their minerality, freshness, and sense of place. The experience is enhanced with a carefully selected local cheese tasting, allowing the bright, expressive wines to shine alongside the flavours of the surrounding countryside, creating a relaxed and authentic moment of Tuscan hospitality.
Discover the tradition, history and true flavours of Vernaccia di San Gimignano in the fascinating and evocative Rocca di Montestaffoli.
A UNIQUE EXPERIENCE
This immersive Vernaccia di San Gimignano Masterclass unfolds within the evocative setting of the Rocca di Montestaffoli, offering an exclusive and in-depth exploration of the tradition, history, and true character of this iconic white wine. More than a tasting, the experience is a guided journey through the Vernaccia territory itself, led by expert insight and comparative samples that reveal why it is known as the “White Queen in a land of red kings.” The masterclass is complemented by a classic Tuscan antipasto of local cheeses, cured meats, and seasonal accompaniments, thoughtfully selected to enhance the wines and ground the experience in the flavours of San Gimignano, creating a refined yet convivial celebration of place, heritage, and craftsmanship.
Welcome to the private world of Borgo Pignano.
On a peaceful hilltop in the heart of Tuscany you will find elegantly curated accommodations, Michelin star dining, and a variety of healthy experiences.
A soulful Tuscan retreat where timeless elegance meets the quiet richness of place. Here, you are welcomed into a way of life, embraced by tradition, nature, and the understated pleasures of daily living.
Each day is shaped by simplicity and care. Whether nestled in the countryside or sheltered within Florence’s garden walls, the same authentic spirit prevails.
An experience that unfolds in two worlds, offering a deeper and more complete way to experience Tuscany.
Expert bartenders craft bespoke drinks — from classic aperitivi to inventive cocktails featuring local ingredients. Some highlights include seasonal concoctions garnished with herbs and fruits grown in the estate gardens, and signature mixes like rum with honey, orange and amarena cherries from the property itself.
Dinner this evening is at Borgo Pignano (not included), where guests may choose from a range of dining experiences set within this beautifully restored eco-estate. From refined, seasonal cuisine in the main villa to relaxed al fresco dining under the Tuscan sky, each option showcases estate-grown and locally sourced ingredients prepared with care and creativity.
Options include:
Michelin Green Star Villa Pignano
Villa Pignano, our Michelin-starred restaurant, offers a refined, contemporary cuisine guided by Chef Stefano Cavallini—whose Michelin Green Star award recognizes his deep respect for nature and a thoughtful, sustainable approach to the land.
Al Fresco Restaurant
Simple, seasonal dishes and local ingredients come together in the ease of open-air dining. Fresh produce from the estate, traditional recipes, and a relaxed atmosphere create a dining experience naturally tied to the land. Easy, authentic, and in harmony with its surroundings
Il Camino
Tucked within the historic walls of Borgo Pignano Volterra Tuscany, the Il Camino restaurant is a gathering place where warmth, simplicity and culinary authenticity come together. Open for dinner during the spring and autumn seasons, this intimate setting offers a true taste of Tuscany in its most convivial form.
A full day to savour the estate’s beauty, flavours, and traditions
Stay: Borgo Pignano
Meals: Breakfast , Lunch & Dinner
🥐 Breakfast
At leisure – Borgo Pignano
🌿 Estate Tour
Guided visit of Borgo Pignano’s organic gardens, beehives, and sustainable farm practices
🍽️ Picnic in the vineyards
Among the quiet rows, a moment shared
🐶 Truffle Hunting
Guided truffle foraging with Lagotto Romagnolo dogs through the Tuscan woodlands
🍽️ Farewell Dinner
An exclusive celebration iwth Tuscan Wine Pairings.
🏡 Stay
Borgo Pignano
Breakfast at Borgo Pignano is a relaxed, sun-filled start to the day, enjoyed in the elegant dining room or outdoors overlooking the Tuscan countryside. Mornings unfold at an unhurried pace, surrounded by gardens, olive groves and rolling hills, with a focus on fresh, seasonal ingredients sourced from the estate and local producers. It’s a peaceful and refined setting that perfectly sets the tone for a day exploring Volterra and the surrounding countryside.
A morning farm tour at Borgo Pignano is a serene and immersive way to connect with the land that shapes every meal and experience at this Tuscan estate. You’ll stroll through the organic vegetable gardens and aromatic herb beds alongside a guide, learning about the sustainable cultivation of heirloom fruits, vegetables, olives and grains that supply the kitchens. The tour may include a visit to the beehives, offering insight into honey production and the vital role bees play in the estate’s ecosystem, along with an introduction to Borgo Pignano’s commitment to biodiversity and traditional farming practices. It’s a grounded, enriching experience that reveals the rhythms of rural life and the source of the estate’s seasonal flavours.
A seasonal picnic provides a different perspective on the estate. Enjoy a rustic relaxed picnic crafted to bring nature and gastronomy together in harmony.
Take part in an enthralling truffle hunting experience. Learn the ancient skills used to unearth these gourmet treasures along with a loyal and fetching Lagnotto Romagnolo, the traditional Italian truffle dog.
Venture deep into the forests and hidden valleys of Borgo Pignano Volterra’s country estate alongside a local truffle hunter well versed in the spots in the woodlands and fields that might conceal a truffle.
On our final evening, a private wine-paired dinner at Borgo Pignano brings the journey of Tuscany Uncorked to a beautifully considered close. Set within the estate’s serene surrounds, this intimate dining experience celebrates the week’s discoveries through a thoughtfully curated menu inspired by the Tuscan countryside and the estate’s organic gardens. Each course is paired with exceptional regional wines, reflecting the landscapes, varieties, and stories encountered throughout the journey—from historic Chianti estates to the rolling hills of Val d’Orcia and beyond. As the evening unfolds, guests gather to reflect on a week of shared moments, remarkable wines, and unforgettable places, raising a final glass in a setting that captures the quiet elegance, authenticity, and enduring spirit of Tuscany.
🥐 Breakfast
At leisure – Borgo Pignano
🚌 Private coach transfer
Borgo Pignano to Florence
After a final breakfast your private coach returns you to Florence airport or city.
Travel with Ken Gargett, offering expert commentary and insight.
Dedicated Wine Journeys Tour Director accompanying the tour
Private luxury group transfers throughout including arrival and departure
*2 nights Villa La Massa * 2 nights Monteverdi Tuscany * 2 nights Hotel Il Borgo, Castello Banfi *2 nights Borgo Pignano
at your luxury accommodation
accompanied by local wines or wine pairings
accompanied by local wines or wine pairings
Welcome drinks hosted at your luxury accommodation
An engaging, guided tasting offering deeper insight into regional wines, styles and stories, led by an expert host.
Brunello in Flight
A guided truffle hunt in the countryside, offering rare insight into one of the region’s most prized culinary traditions.
International and domestic flights
Strongly recommended
and any required travel documentation
(laundry, minibar, room service, phone calls)
for guides, drivers, winery staff, and hotel personnel at your discretion