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.
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
Frequently Asked Questions
Trip Details
How do I reserve my spot?
A deposit of $500.00 (unless otherwise specified) is due to secure your space on the tour. Deposits are refundable up to 50% until 120 days prior to departure (unless otherwise specified).
When do I need to pay for my trip?
Your deposit is due upon reservation. Your final balance is due upon receipt of your invoice, 90 days prior to departure. If you are making a reservation within 90 days of the trip’s departure, full payment will be required upon confirmation.
How big will the group be?
Our trips have a maximum group size of 25 people. They are large enough to meet new people with diverse backgrounds, but small enough to be on a first-name basis with everyone.
Are solo travelers welcome?
Of course! There is always a good number of solo travelers on our trips, and they are welcomed with open arms. Group meals generally take place at medium to large tables, and our Travel Directors ensure that everyone is included in conversation. Because our trips are priced for doubles sharing a room, there is a supplemental cost for those who choose not to share.
How much free time should I expect to have?
Our trips are designed to give our travelers special insight and understanding of the places we visit. The talks and commentary by our hosts and local guides, in addition to time set aside for writing and reflection, are what make our itineraries special, and this kind of curated experience cannot be obtained on one’s own. For this reason, our trips generally do not incorporate long periods of free time during the day, although evenings and some meals will be at leisure.
Can I arrive early, or stay on after the tour ends?
Yes, absolutely! If you wish to arrive early at the first hotel on the itinerary or stay on at the last hotel, our Guest Services Advisors will be happy to advise you on the best way to make arrangements.
What do I need to bring on my trip?
We’ll send you a detailed clothing and equipment list well before departure so you know what you’ll need to pack. We provide the rest: comfortable accommodations, an engaging daily itinerary, expert trip management, and access to people and places that will thrill and delight you.
Once I reserve my trip, what happens next?
After you reserve your trip and pay your deposit, you will be sent a confirmation email with our Terms and Conditions, insurance information, and a Traveler Information Form from our Travel Management Company, Academic Travel Abroad. Your Guest Services Advisor will reach out when it’s time to book airfare after a minimum of 10 travelers have enrolled on your departure. Final trip details will be sent roughly 2-3 weeks before departure.
Rates and Cancellation Information
Are tips included?
Yes! Tips to local guides, restaurant staff, bell staff, and drivers are all included in the trip price. Your Trip Leader and Travel Director are taken care of and will not accept tips. The only time tips are not included is during free time and meals on your own, as well as for any personal services.
Are drinks included?
In addition to the tastings included in the itinerary, a couple glasses of wine are included for all group dinners. Any additional alcoholic beverages are not included in the program price. Non-alcoholic beverages are included in all meals.
Is airfare included?
Airfare to and from the starting and ending point of the program is not included in the price in order to give you maximum flexibility in choosing your preferences for air travel. This way you can use frequent flier upgrades, depart from your airport of choice, or add pre- and post- trip extensions with no constraints. Please refrain from booking your airfare until your Guest Services Advisor reaches out to confirm your departure.
What is your cancellation policy?
Deposits will be 50% refundable 120 days prior to departure. Cancellation between 119-91 days before departure: 100% of deposit is forfeited. Cancellation between 90-61 days, 50% of the Trip price is forfeited. Cancellation within 60 days of departure: no refund. You always have the option to transfer your deposit to a future Post and Courier Travel departure up until 90 days prior to departure with no penalty.
Health & Safety
Are you able to accommodate dietary restrictions and allergies?
Every effort will be made to try to accommodate any special dietary requests you may have (e.g., low salt, vegetarian or vegan). Please discuss your requests with us when signing up for a trip.
What are the physical requirements of this trip?
Travelers should be in good health and able to walk up to 2 miles (with stops) over uneven terrain and be able to navigate stairs unassisted. In city centers, we do try to walk from place to place due to traffic restrictions and also in keeping with our commitment to environmental sustainability.
Do I need trip insurance?
We strongly suggest purchasing travel insurance to help protect your investment and provide you with financial recourse in the event of trip cancellation or interruption due to sickness or quarantine. When purchasing a policy, please consult with a trip insurance agent to review what COVID-19- related contingencies are covered. While we will do our best to recover any unused portion of your trip due to sickness, it is often the case that payments cannot be refunded. We recommend using our partner insurance provider, Travel Insurance Services, which offers three different policies for you to choose from.
What happens if I get sick on tour?
Our top priority is to keep our travelers, staff, and the communities we visit as healthy and safe as possible. Not only do we care about your well-being, but illness on tour alters the group dynamic, diverts staff attention, and interrupts the smooth functioning of the trip. For this reason, we recommend that all travelers to stay up to date with recommended vaccinations. Additionally, we encourage traveling with a mask and notifying your Tour Director immediately should you feel any symptoms of illness.
Let us take you there.
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.