Tuscany 2026

Main Destination Tuscany from $3,599.00 USD per person

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Welcome! I’m Jenn Hilchey, Travel Advisor with The Travel Box International, and I specialize in wine and culture-focused experiences that go beyond the usual tourist path. May 2026, I’m hosting a women’s trip to Tuscany that’s centered around one of my favorite wineries—an incredible family-owned property where we’ll stay, sip, and settle into the rhythm of Italian life. It’s a small group experience designed for women who appreciate good wine, authentic food, and thoughtful travel. We’ll explore local traditions, share long, relaxed meals, and take in the beauty of the countryside—together. If you’re craving something enriching, welcoming, and grounded in culture, this is for you.

🔗 Click here to view full trip details, pricing, terms & conditions, and how to secure your spot!

 

Overview of Our Tuscan Adventure: A Day-by-Day Journey

Day 1: Welcome to Wine Country!

Our adventure begins at 3:00 PM at the Florence train station, where a luxurious Mercedes Sprinter awaits to whisk us away to the enchanting Tenuta Torciano Hotel in San Gimignano. After checking into our beautiful accommodations and a brief tour of the hotel, we'll take a scenic 5-minute drive down to the winery for a delightful Welcome Dinner and a quintessential Tuscan wine tasting. Get ready to raise your first glass to new friendships and incredible experiences!

Day 2: The Art of Truffles & Tuscan Flavors

Immerse yourself in the world of Tuscany's most coveted delicacies with our Private Truffle Hunt & Cooking Class at Tenuta Torciano. Our bespoke culinary journey combines the thrill of truffle hunting with the artistry of truffle-based cooking. Begin your adventure with a private truffle hunt guided by an expert, learning about these prized fungi and gaining hands-on experience in locating them. Following your hunt, join our expert chef in a private cooking class dedicated to truffles, discovering how to handle, clean, and cook them to enhance their unique flavors. Conclude your day with a personalized lunch, showcasing the truffle dishes you've prepared, paired with fine local wines. Enjoy some leisure time to follow before dinner later at the winery with another exquisite wine tasting.

Day 3: Yachting the Tuscan Archipelago to Elba Island!

Get ready for an extraordinary day on the water! We'll journey approximately 1.5-2 hours to Livorno, departing from Porto di San Vincenzo for our San Lorenzo Cruise Expedition – an adventure through one of Italy's most exceptional marine areas. Renowned for its biodiversity, the Tuscan Archipelago encompasses over 61,000 km² of sea and is Europe's largest marine park.

Our qualified staff (Captain, Chef, and Wine Expert) will guide us to the stunning Golfo della Biodola on Elba Island. Here, we'll indulge in a spectacular four-course fish lunch on board, featuring the catch of the day, lobster, and octopus, all perfectly paired with a vertical wine tasting and wine school experience of 10 selected wines, including private reserves from 1995-1997! Enjoy time for relaxation before we sail back to Porto di San Vincenzo and return to the winery for a relaxed evening. A casual pizza night with wine in the hotel courtyard/patio area will be the perfect way to unwind after our magnificent day at sea.

Day 4: 4x4 Vineyard Exploration & Masterclass in Wine

Discover the wonderful vineyards of Tenuta Torciano in an adventurous way! Upon arrival, you'll be greeted by a family member and embark on a thrilling "safari" adventure in our 4x4 Jeep. We'll explore the vineyards where Vernaccia di San Gimignano and Chianti are produced, and visit the ancient olive groves. Learn all the secrets of this territory with our winemaker, from where the vines grow to the intricate processes of pruning, vinification, and aging, from the vineyard to the bottle. For the entire duration of lunch, our Wine Sommelier will teach you all the secrets of pairing wine with food by conducting a vertical tasting of 10 selected wines and prestigious reserves. This is a crucial opportunity to understand the difference between various blends and the production secrets of products still made in the traditional way. Enjoy a leisurely evening with dinner and another delightful wine tasting at the winery.

Day 5: Iconic Tuscan Towns & Farewell Dinner

Today, we'll embark on a captivating day trip to the iconic Tuscan towns of San Gimignano and Siena. Enjoy free time to explore, shop, and have lunch at your leisure (not included) amidst the charm of these historic villages. Transportation is included, allowing you to simply soak in the beauty. Return to the hotel for some relaxation time before our special Farewell Dinner at the winery, a perfect culmination of our Tuscan journey.

Day 6: Departure

Enjoy a final breakfast before checking out. Group transportation will be provided to the Florence train station, bringing our incredible Tuscan Girls' Trip to a close.

 

Terms, conditions and restrictions apply; pricing, availability, and other details subject to change and/ or apply to US or Canadian residents. Please confirm details and booking information with your travel advisor.

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