An Escape to Tuscan Wine Country

In partnership with Wine Enthusiast
October 16-21, 2025 | 6 Days, 5 Nights

from $7,295

Introduction

Step into the heart of Tuscany this October for one of Wine Enthusiast’s inaugural Cork+Compass Travel escapes, where harvest season sets the perfect backdrop for an unforgettable wine journey. Staying at the luxurious Castello di Gabbiano, a historic 12th-century estate surrounded by rolling vineyards and olive groves, guests will experience Tuscany at its most vibrant.

Led by Wine Enthusiast Writer-at-Large Dr. Danielle Callegari, this exclusive trip offers access to renowned wineries such as Avignonesi and Col d’Orcia, where you’ll taste some world-class Brunello di Montalcino and Super Tuscans. As the vineyards come alive with the harvest, explore the rich terroir of Tuscany through private tastings, behind-the-scenes tours, wine-paired dinners at local culinary gems and plenty of wine conversation with expert Dr. Callegari and fellow wine enthusiasts.

With visits to charming medieval towns like Siena, Arezzo and Montepulciano, this immersive journey offers the ultimate Tuscan experience.

Danielle Callegari, our guide in Tuscany

Your Expert

Danielle Callegari is a Writer-at-Large and Reviewer on the Wine Enthusiast Tasting Panel. She reviews wines from Italy, including Tuscany, Lazio, Abruzzo, Campania, Basilicata, Molise, Puglia, Calabria, Sardinia and Sicily. 

Every year, the Wine Enthusiast Tasting Panel blind tastes and rates 25,000 wines and spirits from across the globe and provides reviews that are recognized in the industry as reputable and from trusted experts.

Dr. Callegari is an Associate Professor in the Department of French and Italian at Dartmouth College and Communications Director of the Dante Society of America. Her teaching and research focus on premodern Italian literature and food and beverage studies. 

In addition to her many articles and contributions to academic and trade presses, she is author of “Dante’s Gluttons: Food and Society from the Convivio to the Comedy” (Amsterdam University Press, 2022) and the forthcoming “A Bite-Sized History of Italy” (New Press, 2026). She is also the co-host of Gola, a podcast on Italian food and beverage culture.

Dr. Callegari splits her time between New York City and Italy, and is fluent in both English and Italian. Wandering through the picturesque towns of Panzano, Valdarno, Arezzo, Il Borro, Montalcino, Siena and Montepulciano while tasting wine and learning about the region’s rich culture and history from Dr. Callegari will be a first-hand experience that no guide book can replicate.

“As fellow B Corporations, Avignonesi and Wine Enthusiast share a commitment to sustainability, transparency, and lasting impact. We’re honored to offer this exclusive journey through Tuscany with Cork+Compass Travel. Guided by Danielle Callegari and our team, guests will be invited to discover our organic and biodynamic wines, and sincerely welcomed to experience the beauty of Tuscan hospitality—rooted in purpose, tradition, and a deep respect for the land.” 

-Matteo Giustiniani, CEO

Highlights

Exclusive Tastings

Enjoy private visits to legendary estates where iconic wines like Brunello di Montalcino and Super Tuscans take center stage

Timeless Terroir

Explore historic wineries committed to tradition and innovation, from organic viticulture at Col d’Orcia to the elegant Bordeaux-style blends of Tenuta Sette Ponti

Personal Connections

Meet esteemed winemakers and estate hosts, personally introduced by your expert host, Danielle Callegari, for an insider’s look at Tuscan winemaking

Authentic Cuisine

Savor rustic, wine-paired feasts at Dario Cecchini’s famed butcher shop, Il Borro, and Castello di Gabbiano, where Tuscan flavors shine

Scenic Splendor

Journey through Tuscany’s breathtaking landscapes, from the rolling vineyards of Chianti to its medieval hill-towns, creating a picture-perfect wine country escape

“With 23 generations of tradition rooted in Bindi Sergardi-Tenuta Mocenni, guests will be surrounded by unspoiled nature and panoramic views of Siena and San Gimignano. The Cork+Compass Travel private tour will offer an intimate journey through centuries-old cellars and the authentic flavors of Chianti Classico. Our family is looking forward to warmly welcoming you to Tuscan heritage, passion and conviviality as Wine Enthusiast guarantees the very best experience, especially with Danielle Callegari as your guide.” 

-Alessandra Casini Bindi Sergardi, Co-Owner

Itinerary

Day 1

Tuscany

Benvenuti in Toscana!

Upon arrival in Florence, transfer independently to the enchanting Castello di Gabbiano, a historic estate nestled among rolling vineyards and cypress-lined hills. The afternoon invites relaxation—time to unwind, soak in the serene surroundings, and anticipate the journey ahead. As evening falls, drive to the charming village of Panzano, where the tour begins with a curated welcome tasting at Enoteca Baldi. Here, the first sips of Tuscany reveal themselves—elegant, expressive wines showcasing the region’s depth and artistry. A short stroll leads to an unforgettable dinner at Dario Cecchini’s renowned restaurant, where convivial energy sets the tone for the Tuscan wine retreat ahead. Cork+Compass Travel host Danielle Callegari will talk about the wines poured with dinner and how they pair with the sumptuous steaks and meat-focused dishes on the menu tonight.

Included Meal: Dinner

Accommodations: Castello di Gabbiano

Wineries: Castello di Gabbiano, Enoteca Baldi

Day 2

Tuscany

Discovering Valdarno: Elegance & Tradition

Today’s journey leads us to Valdarno, a region of rolling hills, ancient villages and wines of remarkable depth. Our first stop is Tenuta Sette Ponti, a prestigious estate known for its masterful Super Tuscans. Here, we explore the estate’s cellars and savor wines like the refined Oreno, a bold Bordeaux-style blend, and the expressive Crognolo, a Sangiovese-driven delight. After time in the historic city of Arezzo, we arrive at Il Borro, an enchanting medieval village meticulously restored by the Ferragamo family. A guided tasting unveils the estate’s elegant Lamelle Chardonnay and the rich, full-bodied Il Borro Toscana IGT, alongside their exquisite olive oil. The evening culminates in a memorable dinner, immersed in the rustic luxury of this timeless estate.

Included Meals: Breakfast, Dinner

Accommodations: Castello di Gabbiano

Wineries: Tenuta Sette Ponti, Il Borro

Day 3

Tuscany

The Majesty of Montalcino: Brunello & Beyond

Today, we venture into Montalcino, home to some of Italy’s most revered wines. Our journey begins at Col d’Orcia, one of the region’s pioneers in organic viticulture. As we explore the estate’s historic cellars, we uncover the philosophy behind their exceptional Brunello di Montalcino, tasting the elegant Brunello Vigna Nastagio and the bold, ageworthy Poggio al Vento Riserva. A curated tasting of six wines is complemented by a rustic Tuscan lunch, highlighting the harmony of wine and regional cuisine. The afternoon brings a visit to Argiano, where their Solengo Super Tuscan and refined Brunello di Montalcino showcase the estate’s finesse. The day concludes with dinner in a local restaurant.

Included Meals: Breakfast, Lunch

Accommodations: Castello di Gabbiano

Wineries: Col d’Orcia, Argiano

Day 4

Tuscany


The Essence of Chianti Classico

After a leisurely breakfast, journey into the heart of Chianti Classico, where history, innovation and terroir-driven wines take center stage. Our first stop is the historic Bindi Sergardi estate, where generations of winemaking tradition come alive. A tasting of five wines—including the elegant Chianti Classico La Ghirlanda and the opulent Calidonia Gran Selezione—is paired with rustic Tuscan fare. This evening, arrive in Siena for an independent dinner and time to wander the medieval streets and admire the beautiful central square.

Included Meals: Breakfast, Lunch

Accommodations: Castello di Gabbiano

Wineries: Bindi Sergardi

Day 5

Tuscany

Montepulciano

Today, we explore the renowned Avignonesi estate, celebrated for its Vino Nobile di Montepulciano and commitment to organic winemaking. Our visit includes a tour of the vineyards and historic cellars, followed by a wine-paired lunch featuring elegant selections like the bold Vino Nobile, the velvety Desiderio Merlot, and the luscious Occhio di Pernice Vin Santo. In the afternoon, enjoy free time in Montepulciano, one of Tuscany’s most charming medieval villages. Wander its cobbled streets, visit wine shops or soak in the stunning countryside views. Return to Castello di Gabbiano to gather for a farewell dinner, raising a glass of Gabbiano’s Chianti Classico Riserva to toast an unforgettable journey celebrating Tuscany’s finest food, wine and hospitality.

Included Meals: Breakfast, Lunch, Dinner

Accommodations: Castello di Gabbiano

Wineries: Avignonesi

Day 6

Tuscany

Alla prossima!

Depart hotel for individual flights home.

“We’re very happy about the collaboration with Wine Enthusiast and the extraordinary Danielle Callegari, who, like few others, has been able to bring together wine and Italian culture in an original and engaging way. Guests will enter an oasis at Col d’Orcia and see the timeless beauty of the Tuscan landscape. The winery is located in the heart of the Val d’Orcia Park, a UNESCO World Heritage Site where wine comes into communion with history and culture. Our rich library holds over 50,000 bottles of vintages that represent the liquid memory of the estate and of Brunello itself. Taking care of this legacy, Count Francesco Marone Cinzano and his son Santiago will accompany Danielle as she guides guests through this special insider Cork+Compass Travel tour.”

-Piermichele Capulli, Communications Manager

Accommodations

Castello di Gabbiano

Tuscany

Nestled among rolling vineyards in the heart of Chianti Classico, Castello di Gabbiano is a timeless Tuscan retreat. This historic 12th-century castle offers a blend of medieval charm and modern luxury. Surrounded by olive groves and cypress-lined hills, the estate boasts elegantly appointed rooms, a serene swimming pool and breathtaking countryside views. Guests can indulge in estate-produced wines, explore the historic wine cellars and dine at the renowned Il Cavaliere restaurant, which highlights traditional Tuscan flavors. With its rich history, tranquil ambiance and world-class hospitality, Castello di Gabbiano provides an unforgettable escape.

“Nestled in the Valdarno di Sopra, Il Borro is a hidden gem where you can feel our deep love for the land and commitment to sustainability. From the medieval workshops that celebrate artisanal heritage to the scenic trails perfect for horseback riding, our winery tour is a multisensory journey that pursues the harmony between nature and people. We’re excited to partner with Wine Enthusiast to share Tuscany’s richness and welcome guests to an unforgettable Cork+Compass Travel experience with the dear Danielle Callegari.” 

-Eleonora Piomboni, Wine Marketing & Communication

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Wine Enthusiast’s Cork+Compass Travel is the magazine’s first endeavor into exceptional wine travel and tourism. Our philosophy is rooted in the mission of our parent company, Wine Enthusiast—to enhance the wine experience for all.