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The Total Tuscany Experience
Custom-curated journeys for couples, private clients, and small groups
The Total Tuscany experience is our signature, fully curated journey through the heart of Tuscany — designed for private clients, couples, and small groups seeking a seamless, deeply local, and unforgettable Italian experience.
Whether you’re traveling independently, as a group, or as a travel advisor bringing your own clients, this itinerary serves as the foundation for a completely customized week — thoughtfully planned, personally tailored, and executed with our trusted network of local partners.
Private hosting by Sandy & Phil may be arranged upon request, depending on availability.
How This Experience Works
• This is a sample curated itinerary, fully customizable
• Designed for private travelers, couples, or small groups
• Available as:
– Fully planned independent travel
– Advisor-supported group travel
– Privately hosted experience by Sandy & Phil
• All services are arranged directly with our trusted local partners
Highlights of the Experience
• 7-Night / 8-Day Curated Tuscany Experience
A fully designed journey from arrival to departure — including accommodations, private transportation, dining, and a thoughtfully curated selection of immersive experiences. Every detail is tailored to your pace, preferences, and style of travel.
• Boutique Accommodations in the Montepulciano Countryside
Stay in a beautifully designed boutique hotel set among the rolling hills of Montepulciano, offering refined accommodations, thoughtful service, and an intimate connection to the surrounding landscape.
• Designed by Sandy & Phil
Created by locals who live in Montepulciano and have spent years building trusted relationships with winemakers, chefs, artisans, and guides across the region.
• Optional Private Hosting
For those seeking a more personal, fully guided experience, private hosting by Sandy & Phil may be arranged based on availability.
• Hands-On Tuscan Cooking Experiences
Cook alongside local chefs and farmers using fresh, seasonal ingredients and time-honored techniques rooted in Tuscany’s slow-food culture.
• Exclusive Vineyard Visits & Wine Tastings
Experience Vino Nobile di Montepulciano and Brunello di Montalcino with the people who produce them — in historic cantina, vineyards, and private estates.
• Thermal Baths & Time to Unwind
Relax in natural hot springs, enjoy unhurried afternoons, and experience Tuscany at a rhythm that restores and inspires.
• Medieval Hill Towns & Hidden History
Discover Montepulciano, Pienza, Cortona, and beyond with expert local guides — including underground Etruscan cellars and lesser-known corners most travelers never find on their own.
• Farm Visits, Truffle Hunting & Local Artisans (seasonal)
Meet cheesemakers, olive oil producers, beekeepers, and truffle hunters who preserve Tuscany’s traditions and bring the land to life.
• Memorable Tuscan Dining Experiences
From rustic countryside lunches to long-table dinners, wood-fired pizza nights, and celebratory evenings — each meal is an experience.
• Private Transportation Throughout
Travel comfortably with a professional driver — seamless logistics, no stress, and the freedom to fully enjoy each day.
• Intimate, Personalized Experiences
Whether traveling as a couple, privately, or as part of a small group, every journey is designed to feel personal, meaningful, and deeply connected to place.
This is the Tuscany you’ve been imagining — effortlessly brought to life.
A seamless, thoughtfully designed journey through Tuscany, where every detail has been arranged for you — from where you stay, to what you experience, to the moments in between.
Follow the itinerary as designed, or move at your own pace.
Everything is in place. The experience is yours.
Day 1 — Benvenuti in Tuscany
Your Italian story begins.
Arrive in Montepulciano and settle into your private accommodations, surrounded by vineyards, olive groves, and the quiet rhythm of the countryside.
Take time to unwind after your journey — unpack, explore the property, or simply relax and take in the views.
In the early evening, begin your Tuscan experience with a classic aperitivo — a relaxed introduction to the flavors and lifestyle of the region.
Dinner is thoughtfully arranged, allowing you to enjoy a warm, welcoming first evening with local cuisine, regional wines, and the unmistakable atmosphere of Tuscany at sunset.
As the evening winds down, step outside under the stars — a quiet moment to settle in and savor the beginning of your time here.
Welcome to Tuscany.
Day 2 — Relax, Restore & Unwind
Thermal Waters & Slow Tuscan Living
Begin your day immersed in the healing waters of Tuscany’s ancient thermal baths, where natural mineral springs have soothed body and soul for centuries. Let the warmth slow everything down.
After your soak, enjoy a relaxed spa lunch featuring fresh, local ingredients and regional wines. Optional treatments, including massages and facials, are available for those who wish to indulge further.
In the afternoon, explore at your own pace. Wander a nearby village, stroll quiet cobblestone streets, or simply return to the countryside and unwind.
As evening approaches, settle in for a beautifully prepared dinner featuring seasonal Tuscan flavors, thoughtfully paired with local wines.
A day designed for complete relaxation, where time slows down and everything feels effortless.
Day 3 — Truffle Hunting, Cheese & Hilltop Beauty
Flavors of the Land & the Traditions That Bring Them to Life
A day dedicated to Tuscany’s rich food traditions and the people who keep them alive.
A day immersed in Tuscany’s most treasured flavors — guided by the land, the seasons, and the people who know them best.
Begin the morning in the woods with a private truffle hunt alongside a local expert and trained dogs, uncovering one of Tuscany’s most prized delicacies. Learn how truffles are found, why they grow here, and what makes them so special — a true behind-the-scenes experience few travelers ever have.
Following the hunt, continue to a traditional organic cheese farm where the experience unfolds into a relaxed, truffle-inspired lunch. Enjoy handcrafted local cheeses, seasonal dishes, and fresh truffle prepared simply and beautifully — all paired with regional wines and set against sweeping countryside views.
In the afternoon, continue to the Renaissance jewel of Pienza. Stroll charming streets lined with specialty food shops, artisan boutiques, and panoramic viewpoints overlooking the Val d’Orcia. A stop for gelato at a favorite local spot is, of course, part of the experience.
Return to your accommodations later in the day for time to unwind — take a swim, enjoy the gardens, or relax with a glass of wine as the sun begins to set.
Dinner is thoughtfully arranged, featuring seasonal Tuscan dishes paired with regional wines, followed by dessert.
A day of flavors, beauty, and simple pleasures — exactly as Tuscany was meant to be experienced.
Day 4 — Brunello & the Heart of Val d’Orcia
Vineyards, Landscapes & Tuscan Icons
Today takes you into the rolling hills of Montalcino, home to one of Italy’s most celebrated and sought-after wines — Brunello di Montalcino.
Begin with a private visit to a highly regarded, small-production estate, where a focus on organic and biodynamic practices reflects a deep respect for the land. Walk through the vineyards, step inside the cantina, and gain insight into what makes Brunello so distinctive — from soil to barrel to bottle.
Depending on the season, the experience may become even more immersive, with opportunities to witness or participate in moments of the harvest and winemaking process (season permitting).
The visit concludes with a beautifully prepared, wine-paired lunch, enjoyed overlooking the surrounding vineyards — a setting that captures the essence of Montalcino.
On the return journey, stop at several of the Val d’Orcia’s most iconic viewpoints, a UNESCO World Heritage landscape. Take in the famous cypress-lined roads near San Quirico, visit the chapel of Vitaleta, and pause to capture the timeless beauty of Tuscany’s most photographed scenery.
Return to your accommodations in the late afternoon with time to unwind — swim, stroll the grounds, or simply relax and take in the countryside.
Dinner is thoughtfully arranged, featuring seasonal Tuscan dishes paired with regional wines, followed by dessert.
A day of exceptional wine, extraordinary landscapes, and the true soul of Tuscany.
Day 5 — Secrets of Montepulciano
History, Wine & Rustic Charm
Begin the day in Montepulciano, a medieval hill town rich in history, character, and timeless beauty.
A private guided walk through the historic center, led by a trusted local friend, brings the town to life in a way few visitors experience. As you wander through Renaissance palazzi, hidden alleyways, and panoramic viewpoints, you’ll gain a deeper understanding of the region’s food, wine, and cultural traditions. Along the way, meet local artisans, hear stories of noble families, and discover corners of the town that remain quietly off the beaten path.
Continue beneath Piazza Grande into ancient Etruscan wine caves, carved deep into the rock below the city. Here, enjoy a tasting of Vino Nobile di Montepulciano, surrounded by centuries of history and aging barrels — an unforgettable setting to experience the true essence of this historic wine.
In the afternoon, head into the countryside for a visit to a traditional Tuscan farm. Meet local producers, enjoy regional wines and rustic specialties, and take in the peaceful beauty of the surrounding landscape.
Return to your accommodations with time to unwind before the evening.
Dinner is arranged as a wine-focused experience, featuring seasonal dishes paired with carefully selected local wines — a celebration of Montepulciano, its land, and its flavors.
A day that blends history, storytelling, wine, and authentic Tuscan life.
Day 6 — A Culinary Experience in Cortona
Cooking, Wine & Tuscan Tradition
Begin the day with a hands-on culinary experience set in the countryside near Cortona, one of Tuscany’s most charming hilltop towns.
Step into a truly unique, old-world kitchen — a stone cantina with rustic walls, a working fireplace, and a traditional gas-fired stove that feels unchanged by time. In this warm and atmospheric setting, you’ll be guided through the preparation of classic Tuscan dishes using fresh, local ingredients.
Learn time-honored techniques, from handmade pasta to perfectly balanced sauces, while gaining a deeper understanding of the region’s culinary traditions. The experience is as much about storytelling and connection as it is about cooking.
The morning flows naturally into a relaxed, wine-paired lunch, where each course reflects the simplicity and richness of Tuscan cuisine — enjoyed around the table in an intimate, welcoming setting.
In the afternoon, take time to explore Cortona at your own pace. Wander its historic streets, browse artisan shops, and take in sweeping views of the surrounding valleys. The town’s timeless beauty and atmosphere make it a favorite for those seeking an authentic Tuscan experience.
Return to your accommodations later in the day with time to unwind.
In the evening, enjoy a relaxed pizza tasting experience featuring a variety of traditional and seasonal flavors, paired with local wines and followed by dessert.
A day centered around food, tradition, and the simple joy of gathering around the table.
Day 7 — A Final Taste of Tuscany
Wine, Olive Oil & A Beautiful Farewell
Begin your day with a visit to one of Montepulciano’s most renowned organic and biodynamic estates. Walk the vineyards, explore the historic cellars, and gain insight into the philosophy and craftsmanship behind these exceptional wines.
The experience includes a tasting of their wines, along with a light, beautifully prepared lunch set among the vineyards — a final moment to take in the landscape that defines this region.
In the afternoon, continue to a family-run frantoio, where olive oil has been produced for generations. Here, you’ll be welcomed into the working mill for a guided tasting and behind-the-scenes look at the production process, gaining a deeper understanding of one of Tuscany’s most essential traditions.
Taste freshly pressed extra virgin olive oil, learn how to recognize quality, and experience the remarkable difference of truly artisanal production — a simple yet profound expression of the land.
Return to your accommodations with time to relax and prepare for the evening.
Your final dinner is thoughtfully arranged — a warm and celebratory close to the week, featuring seasonal Tuscan dishes, regional wines, and the kind of atmosphere that reflects everything this journey has been about.
A beautiful ending to a week defined by connection, flavor, and unforgettable moments.
Day 8 — Arrivederci, Tuscany Until Next Time
For those who wish, the day may begin with an optional hot air balloon experience at sunrise — an extraordinary way to take in Tuscany from above as the landscape awakens in the soft morning light. Drift silently over rolling hills, vineyards, and medieval villages, with sweeping views that capture the true scale and beauty of the region. (Optional experience; additional cost; weather permitting.)
A final breakfast is served at your accommodations, offering a quiet moment to savor the surroundings and the rhythm of the countryside one last time.
You arrive as guests, and leave as family — with the heart, the soul, and the people of Tuscany staying with you long after you’ve gone home.
Until next time. A presto, con affetto
SANDRA LAUREN FERRETTI - TOTAL TUSCANY CONCIERGE
P.IVA 01602500520 Codice Fiscale FRRSDR71E61Z404A | STRADA PER PIENZA - MONTEPULCIANO (SI) 53045 SANDY@TOTAL-TUSCANY.COM
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