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.
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
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Each winery was so unique and special in their own way.
Paul and Sharlean G.
Tuscany 2025 Travelers
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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
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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
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.
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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
Bindi-Sergardi-Tenuta Mocenni
Itinerary
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
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
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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
Col d’Orcia
Accommodations
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.
Please note that this property does not have elevators. All guest rooms are accessible only by stairs. For your convenience, luggage will be delivered to your room upon arrival. If you have mobility concerns or need additional assistance, please let us know in advance so we can ensure a comfortable stay.
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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
Il Borro
Get the Brochure
All details about the Bordeaux trip are available in the PDF version of our brochure.
Frequently Asked Questions
Trip Details
How do I reserve my spot?
A deposit of $1,000.00 (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 3 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 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 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.