Wine Travel by Jenn Hilchey
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Tuscany Girls' Trip:
Your Dream Italian Escape Awaits!
Curated & Hosted by Jenn Hilchey, The Travel Box International
A Tuscan Escape Rooted in Wine, Culture, and Connection
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.
Your 5-Night Tuscan Escape: May 20-25, 2026
Get ready for an intimate and personalized experience! This exclusive girls' trip is designed for a maximum of 10-12 women, ensuring a truly connected journey. Here's a taste of the magic that awaits:
Tucked into the heart of Italy’s wine and food capital, the Torciano Boutique Hotel is a warm and inviting retreat surrounded by the vineyards of San Gimignano. With Tuscan-style bedrooms featuring iron beds, wooden beam ceilings, and terracotta floors, it offers the perfect blend of charm and comfort. Enjoy peaceful views from the terrace, wander the garden, or sip wine as you relax after a day of exploring. It’s the perfect home base for our group—laid-back, beautiful, and full of character as we dive into Tuscany together.
Your Tuscan Adventure: A Day-by-Day Journey
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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!
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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.
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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.
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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.
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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.
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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.
Pricing & What's Included
$3,599
Double Occupancy
Per person
$4,099
Single Occupancy
Per person
What’s Included in Your Tuscany Girls’ Trip:
  • All meals included daily—breakfast, plus multi-course lunches and dinners expertly paired with regional wines and served in elegant, authentic settings. One lunch during free time in Siena and San Gimignano is not included and is at your own expense.
  • Private luxury transportation for all scheduled experiences and group activities
  • 5 nights at Torciano Boutique Hotel, an elegant countryside stay nestled among vineyards and olive groves
  • A private yacht experience on the Tuscan coast — sun, sea, and serious celebration
  • All curated excursions and cultural experiences listed in the itinerary — no surprise costs, just seamless enjoyment
  • On-site host and dedicated concierge — I’ll be with you every step of the way to ensure seamless coordination, personalized support, and an unforgettable experience
Relax and fully savor the magic of Tuscany.
Payment Details:
Non-refundable deposit:
  • $750 due at registration.
Final Payment Due:
90 days before trip start date February 19, 2026
  • $2,849 for double occupancy
  • $3,349 for single occupancy
What's Not Included:
  • International flights
    We’re happy to assist with flight recommendations based on your arrival and departure.
  • Travel insurance (required)
    We can help you secure a policy tailored to your trip.
  • Visa fees (if applicable)
  • Lunch during free time in San Gimignano and Siena
    Additional meals or alcohol outside the itinerary during free time are not included.
  • Taxis or transportation for personal leisure
  • Optional add-on activities and excursions
  • Tips for drivers, guides, and servers
  • Personal items such as souvenirs
Cancellation Policy:
Cancellations will be evaluated individually in accordance with the terms of your mandatory travel insurance policy, (which The Travel Box International can assist you in obtaining). For cancellations outside of insurance coverage, please review the standard cancellation policy HERE. Travelers seeking the flexibility to cancel for any reason are strongly encouraged to purchase additional travel insurance.
Travel insurance is required for all travelers. It helps protect your investment and gives you peace of mind in case of unexpected changes or emergencies.
Enhance Your Tuscan Experience
During your leisure time throughout the itinerary, you have the option to indulge in these exciting activities (at your own expense – these cannot replace an activity already listed but can be done instead if preferred):
Horseback Riding
€200 per person
Archery
€150 per person
Helicopter Ride
Please inquire for pricing.
The Heart of Our Stay: Tenuta Torciano
Our journey is intimately connected with Tenuta Torciano, a historic estate founded in 1720 by Bartolomeo Giachi. For 13 generations, the Giachi family has passionately cultivated grapes and olives in the heart of Tuscany, upholding traditions passed down from father to son. Located on lands bathed by the ancient "Borro di Torciano" torrent, the estate has grown from its humble beginnings to become a beacon of quality, glamour, and the art of hospitality in the international wine tourism scene.
Today, Tenuta Torciano is renowned for its exceptional wines, including Vernaccia di San Gimignano and Chianti, produced from its own vineyards and olive groves. Beyond the exquisite products, the estate offers a wide array of authentic wine experiences, from cellar tours to tastings in their beautiful gardens and at the Chigi Tower in San Gimignano. It's a place where you can truly immerse yourself in Tuscan life, discover the region's beauties, and appreciate the commitment to promoting Italian food and wine culture worldwide.
Is This Your Next Adventure?
This trip is crafted for women ready to embrace the magic of Tuscany and connect with like-minded women. Read on to see if this incredible journey resonates with your travel style:
You're a Curious Explorer
You love diving deep into new cultures, eager to learn and experience a destination firsthand, no matter how different it is from home.
You Embrace the Unexpected
Even the best plans can shift. You’re open-minded and ready to adapt, making the most of every moment along the way.
You're Ready for Sisterhood
Whether you're traveling solo or with a friend, you're excited to connect with fellow travel-loving women, share laughs, and build lasting friendships.
You're Comfortable Exploring on Foot
This trip involves easy to moderate walking and standing to fully immerse ourselves in the beautiful Tuscan landscapes and charming towns.
This trip is built on mutual respect, curiosity, and connection. As a group, we'll be interacting with incredible people across the service and hospitality industries. We ask that all travelers treat staff, guides, and locals with kindness, patience, and cultural sensitivity. By registering, you're acknowledging that you're on board with creating a positive, respectful experience for everyone we encounter.
We reserve the right to decline any requests for this Girls' Trip with Jenn Hilchey.
Questions about whether this trip is the perfect fit? Please feel free to email us: [email protected]
Solo Travelers: Welcome to Your Community!
Embrace the freedom of solo travel and join a supportive, vibrant community! This trip is designed to warmly welcome and embrace solo adventurers. We believe traveling solo on a group trip is an incredible way to build confidence, make new friends, and create truly personal memories.
If you're interested in sharing a room and wish to be paired with another solo traveler at the double occupancy rate, we strongly encourage it! Please note that while we'll do our best to find a compatible match, pairing is not automatically guaranteed until confirmed. We'll provide a separate questionnaire to help us make the best possible match for you. Get ready to forge incredible bonds and experience Tuscany with new amazing friends!
Getting There & Extending Your Stay
Nearby Airports:
FLR (Florence), FCO (Rome Fiumicino), MXP (Milan Malpensa).
Please note that FCO and MXP will require some train travel to reach Florence, and Jenn can assist you with all the details for a seamless journey.
Extend Your Italian Adventure (On Your Own):
Consider extending your time in Italy to explore more of its iconic cities:
Florence
Wander through the Uffizi Gallery, marvel at the Duomo, cross the Ponte Vecchio, and discover hidden wine windows.
Rome
Immerse yourself in ancient history at the Colosseum, Palatine Hill, and Roman Forum. Visit the Vatican City and toss a coin in the Trevi Fountain.
Milan
A fashionista's dream! Indulge in world-class shopping.
Day Trips
From Milan, easily day trip to the stunning Lake Como. From our Tuscan base, consider a visit to Santa Margherita Ligure – Jenn's personal recommendation for coastal elegance without the crowds.
Jenn can seamlessly arrange your pre and post-trip travel, assisting with hotel and flight packages, train travel, and all coordination. Her deep love and expertise for Italy ensure unparalleled support for your entire journey.
About Your Host: Jenn Hilchey
Hi, I'm Jenn! I'm a travel advisor, and I absolutely love helping people explore the world – especially through the lens of wine tourism. As an avid traveler myself, I've seen firsthand how travel can be the most powerful form of education, opening our minds and connecting us to new cultures. While I love planning all kinds of trips, I wanted to create something more personal. This girls' trip is a chance to share a region that completely captured my heart—Tuscany—alongside a small group of women who love meaningful travel and good conversation over a glass (or two) of something local.
When I'm not organizing memorable getaways, you'll find me enjoying life in Tampa, Florida, with my husband and our two dogs, who are truly a huge part of my world. My background in food, wine, and hospitality fuels my passion for designing personal, fun, and truly memorable experiences. I can't wait to share the magic of Tuscany with you!

What Our Travelers Are Saying:

What Our Travelers Are Saying:

I just returned from the most unforgettable experience in Tuscany, and it's all thanks to the incredible Jenn Hilchey. She curated an absolute dream of a wine retreat—so thoughtfully planned, flawlessly executed, and overflowing with charm, elegance, and authentic Italian magic. Jenn's level of organization and attention to the guest experience was truly next level. We enjoyed unlimited wine (yes, unlimited!), delicious meals, breathtaking views, and even better company. The warm, welcoming family that hosted us made the entire experience feel personal and heartfelt—like we were truly part of their home and traditions. Honestly, this was more than a 5-star experience. Jenn has an incredible gift for creating meaningful, luxurious, and memorable retreats. Anyone lucky enough to attend one of her events will be absolutely blown away. I'm already counting down the days until the next one!
— Maryanne S.
I just got back from the trip of a lifetime! Jenn curated the most amazing 5-day girls wine getaway in Tuscany. When I saw it posted on Instagram, I reached out…only one spot open…and I went for it! I had never been to Europe, I had never solo traveled, and Jenn made it feel easy. Not only did she plan fun-filled and interesting experiences, but when I wanted to extend my trip to see Florence and Rome, she helped me book rooms, train tickets, and more. She recommended amazing restaurants and sites to see. She even checked in on me during my solo adventures!! If you book with Jenn, you will be in very good hands. She is exceptional!!
— Vickey D.
Five stars isn't enough! Our Tuscany wine trip was an absolute dream — and it's all thanks to the incredible planning and care from Jenn. From start to finish, every detail was seamless: charming vineyard tours, perfect food and wine pairings, and the most scenic accommodations that felt straight out of a movie. She didn't just plan a trip; she curated an experience we'll never forget. The itinerary balanced fun, relaxation, and adventure flawlessly — and the personal touches made it feel so special. If you're dreaming of Tuscany (or anywhere, honestly), don't even think twice — this is the travel wizard you want on your side. Grazie mille for the memories of a lifetime!
— Cindy B.
Ready to Uncork Your Tuscan Dream?
Join us for an unforgettable journey of wine, culture, and connection! Spaces are limited to ensure an intimate and personalized experience.
Have questions or want to discuss if this trip is for you? We'd love to chat! Request a complimentary phone consultation with Jenn.
Contact Jenn Hilchey directly at: [email protected]