Retreat in Tuscany

A 6-Night Journey into the Heart of Tuscany

Your 7-Day Journey: The Soul of Tuscany

Day 1: Meeting & Check-in

Arrival: Private luxury pickup at Florence Airport (FLR). Skip the city traffic and head straight into the heart of the Chianti hills.
The Villa: Check into your Private Luxury Villa where every room features a private en-suite bathroom, premium linens, welcome gift and kit.
Afternoon: Unwind by the pool, enjoy a glass of local sparkling wine on the terrace and relax.
Dinner: A "Welcome Home" feast in the villa garden. Traditional Bistecca alla Fiorentina grilled over local oak wood, paired with bold Chianti Classico red wines.

Day 2: The Liquid Gold & The Black Rooster

Morning: A masterclass in Extra Virgin Olive Oil. Visit an award-winning organic mill to learn the "frantoio" process. Taste the spicy, polyphenolic kick of fresh oil on toasted bread, as locals.
Lunch: Al fresco at a panoramic focusing on seasonal ingredients and farm-to-table vegetables.
Afternoon: The "Poetry of the Pour" at a boutique Chianti Classico winery. Walk the vineyards and enter the cellar for a private vertical tasting of the Gallo Nero’s finest vintages.
Dinner: Explore the medieval streets of Castellina in Chianti with a reservation at a refined Ristorante built into the ancient city walls.

Day 3: Flour, Water, and Stone

Morning: The Flour-Dusted Morning. Roll up your sleeves in the villa’s professional kitchen. A local Sfoglina (pasta master) will teach you the secrets of Pici Senesi and silk-thin Pappardelle.
Lunch: Enjoy the fruits of your labor on the villa terrace, served with local sourced sauces.
Afternoon: A visit to the walled crown of Tuscany: Monteriggioni. Walk the ancient ramparts that Dante Alighieri once wrote about.
Dinner: A relaxed "Merenda" in the villa featuring Cinta Senese charcuterie and artisanal honey tasting.

Day 4: The Black Diamond & The City of Towers

Morning: Truffle Hunting. Join a professional Trifolao and his dogs in the secret woods of the estate. Experience the thrill of unearthing the "Black Diamond" of the forest.
Lunch: A dedicated Truffle Degustation lunch, where your finds are shaved over fresh tagliolini and organic eggs.
Afternoon: Visit San Gimignano, the "Manhattan of the Middle Ages." We’ve arranged a private stop at the world’s most famous gelateria.
Dinner: In San Gimignano to explore the local artisan boutiques of the village before a late-night return to the villa.

Day 5: Val d’Orcia: The Landscape of Peace

Morning: Journey south to the UNESCO World Heritage site of Val d’Orcia. Stop for iconic photos at the Vitaleta Chapel and the famous cypress groves.
Lunch: Visit a family-run dairy farm in Pienza. A guided tasting of Pecorino di Pienza, evolving from the creamy fresco to the sharp, walnut-leaf wrapped stagionato.
Afternoon: Wander the "Ideal City" of Pienza, known for its Renaissance architecture and stunning balcony views over the valley and discover secrets spots...
Dinner: Dine in the tiny village of Bagno Vignoni, seated right at the edge of the ancient thermal pool that sits in the center of the square.

Day 6: The Prestige of Montalcino

Morning: Arrive in Montalcino, the land of kings. Explore the "underground cathedrals" of a historic estate where Brunello di Montalcino ages for years in Slavonian oak.
Lunch: A gourmet vineyard picnic or a private table in the cellar, pairing library vintages with local wild boar ragu.
Dinner: The Grand Farewell Feast. A gala dinner at the villa with a private chef, celebrating the connections made and the flavors discovered throughout the week.

Day 7: A Gentle Arrivederci

Morning: One last leisurely breakfast as the mist rises over the Chianti vineyards.
Transfer: Private luxury transfer back to Florence (Airport or SMN Station). You leave not just with memories, but with the soul of Tuscany in your heart.

What’s Included

7 Nights of Luxury: Accommodations in a private, hand-picked heritage villa.
Daily Farm-to-Table Dining: All breakfasts, lunches, and curated dinners featuring seasonal local ingredients.
Private Wine Tastings: Exclusive access to boutique vineyards and historic cellars.
Artisan Workshops: Hands-on experiences with local craftsmen and chefs.
Curated Explorations: Guided visits to hidden medieval villages and iconic cities of art.
Seamless Logistics: All ground transportation during the retreat and airport transfers.

What’s Not Included

Airfare: International or domestic flights to and from Italy.
Travel Insurance: purchasing comprehensive travel insurance (including medical and trip cancellation) is mandatory.
Personal Expenses: Souvenirs, additional snacks, or laundry services.
Extra Beverages: Premium spirits or vintage wines ordered outside of our curated tastings and hosted meals.
Optional Activities: Any spa treatments or independent excursions not listed in the final itinerary.

The Details

Group Size: Small, intimate groups (Max 20 guests).
Vibe: Intentional, relaxed, and deeply authentic.

"This is the Italy you don't find in guidebooks. It's the Italy you feel."

Booking Information

Our seat at our Tuscan table is waiting. Whether you have specific intolerances or wish to customize your itinerary, we are here to listen. Tell us your needs, and we will make sure your only worry is which wine to sip next.

Please note: Regardless of your chosen installment plan, the total remaining balance must be paid in full at least 30 days prior to the retreat start date.

Your Hosts:

Bailey

Meet Bailey, the founder of Health Journey Through Food, a Georgia native who spends six months a year living in Italy. After struggling with severe food allergies, she discovered how the purity, quality, and traditional processing of authentic Italian ingredients completely transformed her health. Now, her mission is to share these incredible healing benefits with a global audience, showing how real Italian food can truly nourish the body.

Tommaso

Meet Tommaso, a 100% Tuscan local who has spent the last 13 years deeply immersed in the world of regional food, wine, and tourism. Born and raised among these hills, he has turned his lifelong passion into a mission to share the most authentic, hidden corners of his homeland. His retreats are designed to take you off the beaten path, offering an exclusive insider's look into the true Tuscan lifestyle.

Book a Call with us!

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FAQ

Read our FAQ or simply email us!

Yes. We offer a flexible payment plan so you can secure your spot with a deposit and pay the remainder in installments (3-4-6 months) ahead of departure. Details and options are available in this page, or reach out to us directly and we'll walk you through it.
Your retreat includes accommodation, all meals as outlined in the itinerary, wine tastings, cooking classes, guided excursions, and ground transportation during the retreat. Not included: international flights, travel insurance, and personal expenses. You'll find a detailed inclusions list on this page — if anything's unclear, just ask.
We offer both. Solo travelers can choose our Shared Double (paired with another solo guest of the same gender in a twin bed room) or book an Exclusive Double for private use with a supplement. Many of our guests come solo and leave with new friends — but the choice is entirely yours.
Our retreats are designed for curious travelers, not athletes. Expect leisurely walks through vineyards, markets, and hill towns, plus hands-on cooking classes — nothing strenuous. If a specific itinerary includes a more active excursion (hiking, biking), we'll flag it clearly in the day-by-day schedule.
Most of our guests book solo or in pairs, not as part of an existing friend group. What brings people together is a shared love of food, wine, and Italy — by day two, you're usually cooking side by side and sharing a table like old friends. Small group size is intentional: it's what makes that possible.
Absolutely. Dietary needs are handled with real attention, not a generic substitute plate. Just let us know when you book, and we'll make sure every meal works for you.
Each day has a clear rhythm — usually a morning activity (a market visit, a cooking class, a vineyard tour) followed by a relaxed afternoon and an evening meal together. We've built in breathing room so you can rest by the pool, explore on your own, or simply enjoy the villa — this is a retreat, not a race through a checklist.
Of course. Many guests choose to arrive a few days early or stay on afterward to explore on their own. We're happy to share recommendations for extending your trip in Italy, though logistics outside the retreat dates are arranged independently.