An Escape to Tuscan Wine Country

Spring 2026

May 18-23, 2026 | 6 days, 5 nights

From $8,150

Introduction

Step into the heart of Tuscany this May a tremendous Wine Enthusiast’s Cork & Compass Travel escape, where the springtime Tuscan landscape is the perfect backdrop for an unforgettable wine journey. Guests will experience Tuscany at its most vibrant, staying at the four-star Borgo San Luigi, a luxe 17th-century property set in elegant gardens surrounded by rolling vineyards and olive groves. 

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 world-class Brunello di Montalcino and Super Tuscans. With visits to charming medieval towns like Siena and Montepulciano, this immersive journey offers the ultimate Tuscan experience.

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. 

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 roughly 25,000 wines and spirits from across the globe. Its reviews are widely recognized in the industry as reputable and from trusted experts.

Dr. Callegari is also 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 guidebook can replicate.

What Travelers Say



Each winery was so unique and special in their own way.


Paul and Sharlean G.
Tuscany 2025 Travelers



The Tuscany Cork & Compass wine tour was amazing! The wine tastings and wine education were fantastic! I was initially hesitant to book as a solo traveler but everything worked out perfect! Everyone on the tour was warm welcoming and inclusive. Our group became fast wine friends and we are still sharing our experiences and memories of the trip


Carol V.
Tuscany 2025 Travelers

Image



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.


Image

Matteo Giustiniani
CEO
Avignonesi

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 proprietors, personally introduced by your expert host, Danielle Callegari, for an insider look at Tuscan winemaking.

Authentic Cuisine

Savor rustic, wine-paired feasts with exquisitely authentic Tuscan flavor.

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.

Bindi Sergardi



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

Alessandra Casini Bindi Sergardi
Co-Owner
Bindi-Sergardi-Tenuta Mocenni

Itinerary

Tuscany Path with Trees by Simone Daino

Day 1

Tuscany

Benvenuti in Toscana!

Upon arrival in Florence, transfer independently to the enchanting Borgo San Luigi, 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, the tour begins with a curated welcome tasting at the hotel. Here, the first sips of Tuscany reveal themselves—elegant, expressive wines showcasing the region’s depth and artistry. Enjoy dinner at a local restaurant this evening to showcase the Tuscan flavors. Cork + Compass host Danielle Callegari will talk about the wines poured with dinner and how they pair with the dishes on the menu.

Included Meal: Dinner

Accommodations: Borgo San Luigi

Alexander henke chq2rc42vbo unsplash1

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. 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, poured alongside their exquisite olive oil.

Continue to 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. Return to the hotel for some time at leisure. Gather in the early evening for a cooking class followed by dinner on the hotel grounds.

Included Meals: Breakfast, Lunch, Dinner

Accommodations: Borgo San Luigi

Wineries: Il Borro, Tenuta Sette Ponti

Day 3

Tuscany

The Majesty of Montalcino: Brunello & Beyond

Today, we venture into Montalcino, home to some of Italy’s most revered wines. Our exploration begins at Col d’Orcia, one of the region’s pioneers in organic viticulture. As we visit the estate’s historic cellars, we uncover the philosophy behind their exceptional Brunello di Montalcino, tasting the elegant Brunello Vigna Nastagio and the bold, age-worthy Poggio al Vento Riserva. A curated tasting of six wines is complemented by a traditional Tuscan lunch, highlighting the harmony of wine and regional cuisine. The afternoon brings a visit to Siena for an independent dinner, with time to wander the medieval streets and admire the beautiful central square.

Included Meals: Breakfast, Lunch

Accommodations: Borgo San Luigi

Wineries: Col d’Orcia

Day 4

Tuscany


The Essence of Chianti Classico

After a relaxed 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 authentic Tuscan fare. After a light lunch, continue onto the magnificent 900-hectare estate of Castello di Albola, once home to some of the most famous noble families of Tuscany and now producing exceptional high-altitude Chianti. After some free time at the hotel, set out for dinner nearby.

Included Meals: Breakfast, Lunch, Dinner

Accommodations: Borgo San Luigi

Wineries:  Bindi Sergardi Estate, Castello di Albola

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, take some free time at the hotel or 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 the hotel to gather for a farewell dinner, where Danielle will share some of her best-kept secrets from the world of Tuscan wine. Toast to an unforgettable journey celebrating Tuscany’s finest food, wine, and hospitality.

Included Meals: Breakfast, Lunch, Dinner

Accommodations: Borgo San Luigi

Wineries:   Avignonesi Estate

Day 6

Tuscany

Alla prossima!

Depart hotel for individual flights home.

Included Meals: Breakfast

ColDorcia



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

Piermichele Capulli
Communications Manager
Col d’Orcia

Accommodations

Gallery borgo14

Borgo San Luigi

Tuscany

Set in a restored 17th-century Tuscan hamlet in Monteriggioni, this four-star resort blends rustic elegance with modern comfort. Rooms feature terracotta floors, wooden beams, and antique furnishings, evoking authentic countryside charm. The property offers lush gardens, a large outdoor pool, tennis courts, and scenic walking paths. Guests can enjoy regional cuisine and horseback riding, all within easy reach of Siena, Florence, and Chianti—an idyllic retreat steeped in history and style. Classic Terrace rooms have been reserved for Cork + Compass Travel guests; there is the option to upgrade to larger Deluxe Terrace rooms at $250/person in a double occupancy room or $400 in a single occupancy room.

ColDorcia



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.


Image

Eleonora Piomboni
Wine Marketing & Communication
Il Borro

Inside the Experience

Tuscany Photo and Video Credits: Lucy Plato Clark

Explore More Trips

Let us take you there.

Wine Enthusiast’s Cork+Compass Travel is the magazine’s gateway to 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.