Wine and dine your way like a local through this beguiling, magical Tuscan region, with its medieval hillside villages and beautifully restored ancient farmhouses.
Oct 2-5, 2025
MONTALCINO
Escape
We will introduce you to the insider’s Montalcino and its regal Brunello wines. You’ll gain direct access to the wealth of knowledge contained in the minds of our Montalcino partners, true Tuscan wine expert Roberto Cipresso and Brunello master Andrea Polidoro of Cupano, as well as several other brilliant winemakers we will visit and taste with. We will soak up the unique Tuscan culture through the eyes of locals, altogether avoiding the tourist’s Tuscany.
THE ITINERARY
DAY 1 - THURSDAY, OCTOBER 2
BENVENUTI A MONTALCINO!
Welcome to the rolling hills of Tuscany, where history, wine, and beauty blend effortlessly. Upon arrival at either Florence or Rome airport, you’ll transfer to the charming town of Pienza, where you’ll check into the elegant La Bandita Townhouse – a stylish retreat perfect for unwinding before our unforgettable adventure begins.
Terroir Tasting: Introduction to the wines of Montalcino
Kick off our experience with an in-depth introduction to the renowned wines of Montalcino. With local expert John Voigtmann as our guide, we’ll explore the region’s history, unique terroir, and the magic behind its world-class wines.
Dinner at La Bandita Townhouse
Chef David Mangan will craft a seasonal feast of Tuscan delicacies, paired with a perfect selection of wines. We’ll be joined by special guest winemakers who will share their passion and insights over an evening of delicious food, exceptional wine and great conversation.
DAY 2 - FRIDAY, OCTOBER 3
LEGENDS OF MONTALCINO
A Super Tuscan library tasting with Roberto Cipresso
Start the day with a rare tasting led by legendary winemaker Roberto Cipresso. Known for his deep knowledge and love for his region, Roberto will guide us through a selection of his exclusive library wines – a unique chance to taste the evolution of some of Tuscany’s most extraordinary vintages.
Lunch and tasting at Casanova di Neri
We’ll make our way to the stunning Casanova di Neri estate, where Giacomo Neri will take us on a private tour of his family’s historic winery. In a beautiful private dining room, we’ll enjoy a traditional Tuscan lunch paired with an extraordinary selection of wines, including rare family library vintages not available anywhere else.
Rest and relaxation at the hotel or optional walking tour of Pienza
Take time to unwind at the hotel or join us for a leisurely stroll through Pienza, exploring its Renaissance architecture, charming streets, and breathtaking views of the Val d’Orcia.
Sunset Negronis on the Pienza center wall
Italians take apero very seriously, and the Negroni is a crucial part of the ritual. Join us as we do as the locals do and enjoy freshly mixed Negronis as we watch the picturesque sunset over the magical town of Pienza.
Dinner at local favorite Il Rossellino
We’ll walk into town for a magical meal of Tuscan specialties and fabulous wines from all over the region. We’ll be joined by a special guest winemaker who will share his wines and stories with us.
DAY 3 - SATURDAY, OCTOBER 4
THE BEST OF BRUNELLO
Brunello tasting with Andrea Polidoro at Cupano
Begin the day with an exclusive tasting at Cupano, led by Andrea Polidoro, winemaker and general manager of this iconic estate. Andrea will share his expertise on Brunello di Montalcino DOCG, guiding us through a selection of stunning estate Sangiovese wines and rare vintage treasures.
Private wine tasting and lunch at Castello Sesti
The Sesti family, one of Montalcino’s most esteemed winemaking dynasties, will graciously open their historic estate to us for an exclusive private tasting of their exceptional Brunellos. Following the tasting, we’ll savor a once-in-a-lifetime lunch prepared by Michelin-starred chef Roberto Rossi of Il Silene. Known for his inventive approach to regional cuisine, Chef Rossi’s specially curated menu promises to be an extraordinary culinary experience.
Rest and relaxation
Unwind at your own pace – whether that means enjoying a quiet afternoon at La Bandita, taking in the Tuscan scenery, or exploring more of Pienza.
Dinner in Pienza at Buca delle Fate
Our final dinner together will be a celebration of food, wine and adventure, hosted by a beloved chef and friend of The Vines. Expect an evening filled with unforgettable flavors, laughter, and a few surprises – all capped off with a farewell cocktail at La Bandita’s bar, where we’ll raise one last toast to an incredible journey.
DAY 4 - SUNDAY, OCTOBER 5
ARRIVADERCI!
Departures, or continue on for further exploration.
THE DETAILS
How to arrive
Guests should ideally fly into Florence’s Amerigo Vespucci Airport (FLR) and either rent a car or The Vines will arrange transfers (not included in trip cost) for the 1.5-hour drive to Pienza. The alternative airport is Rome’s Fiumicino Airport (FCO), and then a 2.5-hour drive to Pienza.
Accommodations
La Bandita Townhouse, a chic and luxurious 12-room hotel right in the historic center of the jewel box village of Pienza – the perfect stylish base from which to explore the region. The building is a rambling renaissance-era palazzo where nuns have lived for over 500 years, and the hotel’s restaurant is renowned for its fresh seasonal food.
Maximum number of guests
14


SOME of the EXCLUSIVE WINES YOU
WILL DRINK
WILL DRINK
San Lorenzo Brunello di Montalcino 2019
Sesti Brunello di Montalcino Riserva “Phenomena” 2018
Salicutti Brunello di Montalcino “Teatro” 2017
Castello Tricerchi Rosso di Montalcino 2022
Castello di Ama Chianti Classico Vigneto Bellavista 2006 in mag
Castello di Ama Chianti Classico Vigneto La Casuccia 2004 in mag
Castello di Ama Toscano IGT L’Apparita 2010
Roberto Cipresso ORIA IGT Toscana Rosso 2020
Casanova di Neri “Irrose” Rosato 2022
Casanova di Neri Brunello Tenuta Nuova 2019
Casanova di Neri Brunello Giovanni Neri 2019
Casanova di Neri Brunello Cerretalto 2018
Bakkanali Rosa 2023
Bakkanali Fiorenzo 2022
Les Oiseaux d’Oulan-Bator IGT Toscana Bianco 2022
Cupano Brunello di Montalcino 2019
TASTING AND LUNCH AT SESTI
Sesti Sauvignon 2023
Sesti Rosato 2023
Sesti Brunello 2019
Sesti Brunello Riserva “Phenomena” 2018
Mastrojanni Brunello 2018
Mastrojanni “La Schiena” 1999
Mastrojanni Brunello 1980
Poggio Di Sotto Brunello 2014
Poggio Di Sotto Brunello 2018
PRICING INFORMATION
The trip cost includes all accommodations, meals, wines, local transportation and group activities. Guests are responsible for the cost of their flights and airport transfers to the hotel.
Please note that Vines itineraries are highly unique and customized, and the overall schedule, events and timing are subject to change due to unforeseen circumstances beyond our control.
Cancellation Policy
We understand that sometimes life requires changes or cancellations. We have created cancellation policies that take this into account while also accounting for the realities of our non-refundable event costs and prepayments. You can see our cancellation policy at www.vinesevents.com/terms