Food and Wine of
Val D’Orcia
Taste, sip & explore Tuscany like a local on our exclusive Tuscany food and wine tour
DATE
Oct 31 - Nov 7, 2026
COST
$5 490 per person,
no single supplement
GROUP SIZE
Maximum 8 guests
Overview
In our enchanting October tour, we artfully weave together the irresistible flavors of Tuscany's cuisine and the sublime richness of its wines, creating a harmonious experience set against the backdrop of the region's harvest season, history, and culture. Immerse yourself in a journey through time as you meander along narrow cobblestone streets in centuries-old villages, where the echoes of history resonate in every step.
Our accommodation is a private luxury Villa embedded in Val D’Orcia, Tuscany, where golden vineyards kiss the rolling hills, cypress sentinels stand tall against the azure sky and sun-drenched olive groves whisper secrets to the breeze..
Indulge your senses in the breathtaking panoramas of Tuscany's most picturesque landscapes, allowing the beauty of the surroundings to transport you to a world of timeless charm. Every day is crafted to be a delightful revelation, promising a seamless blend of culinary excellence, world-renowned wines and historical immersion, and the sheer joy of Tuscany's cultural tapestry.
Embark on a captivating journey through wineries of all sizes, where wine professionals will unveil the secrets behind the renowned Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano wines. Elevate your palate to new heights as you expertly blend local culinary delights with some of Italy's finest wines, creating a harmonious symphony of flavors that will linger in your memory.
Your host, boasting over two decades of frequent visits to Val D'Orcia, possesses an intimate familiarity with the region's concealed treasures. Filled with this extensive knowledge, she is dedicated to crafting an unparalleled, authentic, and unforgettable experience that goes beyond the ordinary.
Experience a leisurely pace that strikes the perfect balance between engaging activities and ample opportunities for relaxation.
Some of the highlights you can expect are:
Spend a week in a private luxury villa with 360 ° views over Val D’Orcia
Visit Siena with a local guide and expert, including a visit to the famed Duomo
Visit hilltop towns such as Pienza, Montalcino, Montepulcano, Bagno Vignoni and more
Authentic Cooking Experience of traditional Tuscan dishes
Savor the diverse array of local culinary specialties
Food and wine pairing lunch at a winery
Art history presentation by Florence insider
Take a selfie outside the legendary villa from the movie “Under the Tuscan Sun” in Cortona
Visit a 15th century Villa and its world famous gardens
Chianti, Brunello Di Montalcino and Vino Nobile di Montepulciano wine tasting
Gelato sampling
Put on your chef’s hat and prepare your own pizza
Embark on a captivating journey where each moment is meticulously crafted to enchant and delight, guaranteeing a tour that mirrors the authenticity and uniqueness of the area. This extraordinary and magical adventure is destined to linger in your memory, creating an indelible mark on your travel experiences.
Daily Itinerary
Day 1 - Saturday, October 31, 2026
Kick off in Florence and travel to our Private Villa in Val D’Orcia
Your journey begins at 9 am in the center of Florence at our preferred pre stay hotel, where a guest speaker introduces us to Tuscany, its rich history, world renowned artists and timeless art.
Leaving the Cradle of the Renaissance behind, we drive through the Chianti Wine Region and stop at a winery for a wine tasting and lunch.
Settle in at our Private Villa, your home for the next 8 days and enjoy 360° views over Val D’Orcia. Join your fellow travelers for a delightful Welcome Dinner at the Villa.
Meals: L, D
Day 2 - Sunday, November 1, 2026
A historic Villa and a charming hilltop town
Our drive this morning meanders across the beautiful countryside and hilltop towns to Villa La Foce, a residence dating back to the late 15th century. In 1924 it became the property of Antonio and Iris Origo who created its now world-famous gardens. Iris Origo made a name for herself with books such as “War in Val d'Orcia” and “An Italian War Diary 1943-1944”. A guided tour around the property and garden provides insight into the life of times past.
On our way to Pienza we drive through breathtaking landscapes along the rolling hills often depicted on postcards and calendars.
Enjoy lunch at a local restaurant.
Back at the villa, immerse yourself in the art of Italian wine. Learn the nuances of tasting, how to select the perfect bottle at a restaurant and pair wine with food. This intimate tasting is guided by your host, a certified sommelier and devoted wine enthusiast, ensuring an experience that is fun, educational and indulgent.
Meals: B, L
Day 4 - Tuesday, November 3, 2026
Local tastes, flavors and food
Today we indulge our senses in a gastronomic symphony that transcends the ordinary and elevates your taste buds to new heights as we explore the rich culinary delicacies of Val D' Orcia. As you take your first bite of the best local products, the vibrant explosion of flavors dances on your palate and awakens your taste buds to a sensory delight.
Dinner will be entirely created by you during an authentic cooking experience with only the freshest local and seasonal ingredients.
Meals: B, L, D
Day 3 - Monday, November 2, 2026
Vino Nobile Di Montepulciano, Cortona & Hollywood movies
This morning we explore the Vino Nobile di Montepulciano named after the nearby town and learn all about the famous Tuscan Vin Santo dessert wine.
We continue our morning drive to Cortona, the picturesque setting of the 2003 blockbuster “Under the Tuscan Sun” with Diane Lane. After a stroll through town or a cappuccino on the piazza, lunch awaits at a family run trattoria where seasonal ingredients and family recipes dictate the menu.
No visit to Cortona would be complete without a selfie stop by Villa Bramasole where “Under the Tuscan Sun” was filmed. We drive by some of the iconic filming locations from the 2000 Academy Award winning “Gladiator” with Russel Crowe on our way back to the Villa.
For dinner we drive to the nearby town of Bagno Vignoni, where the public square is a pool filled with water from a natural hot spring. Imagine that the Romans already discovered and enjoyed these waters. Our dinner restaurant is located right along this Renaissance Square.
Meals: B, L, D
Day 5 - Wednesday, November 4, 2026
Siena
No Tuscan sojourn is complete without experiencing the timeless charm of Siena – a quintessential town adorned with a majestic Cathedral and the fervor of the Palio Horse Race, a spectacle that echoes through its medieval streets. The "Burnt Siena" hue, derived from iron-rich red bricks, paints the medieval cityscape. Wander through the narrow back alleys guided by a local expert, savoring the authenticity of the city. Indulge in the simple pleasure of gelato on the Campo, the beating heart of Siena's main square, while unravelling tales of the Palio, city neighborhoods, and the legendary Florence-Siena rivalry. A visit to the famed Duomo becomes the final brushstroke to the masterpiece that is Siena.
Lunch at a Country Inn near Siena.
A light dinner is included at the Villa
Meals: B, L, D
Day 6 - Thursday, November 5, 2026
Visit Iconic Montalcino and savor some Brunello Wines
Every Italian meal is elevated by the richness of Extra Virgin Olive Oil, and this morning we discover the secrets behind this liquid gold at a charming, family‑owned estate. Through a sensory journey of tasting, aroma, and tradition, olive oil will never be the same.
Lunch is served at the estate, featuring the family’s own wines and a unique treat: homemade olive oil gelato—a deliciously unexpected indulgence that embodies the essence of Tuscany.
Discover the charm of Montalcino as you stroll through the streets of a place that has changed little since the 16th century. Soak in the spectacular views of Val D’Orcia where the rolling hills seem to go on forever.
Montalcino is celebrated worldwide for its iconic Brunello di Montalcino, a red wine of extraordinary elegance, depth, and aging potential. At one of the region’s rare biodynamic estates, we experience Brunello like never before: walking the sun-drenched vineyards, exploring the art of winemaking, and savoring each nuanced sip in an intimate, guided tasting. Here, tradition, terroir, and sustainability come together, creating a truly unforgettable encounter with one of Italy’s most distinguished wines.
What would a visit to Italy be without Pizza? Tonight we are having a Pizza Party. What are your favorite toppings?
Meals: B, L, D
Day 7 - Friday, November 6, 2026
Local, Local, Local
Montalcino is also renowned for its prestigious Brunello di Montalcino, a red wine celebrated for its exceptional quality, rich flavors, and exceptional ageing potential. Today, we explore everything about one of Italy's most distinguished and sought-after red wines.
Enjoy a food and wine pairing lunch at a local winery.
What would a visit to Italy be without Pizza? Tonight we are having a Pizza Party. What are your favorite toppings?
Meals: B, L, D
Day 7 - Saturday, 1 November, 2024
Arrivederci - Until we meet again
After breakfast, we bid farewell to Val D’Orcia as our adventure comes to an end. We transfer you to the Rome Fiumicino airport with a drop off time of 2 pm. The week may be over, but we sincerely hope the memories and friendships made this week will last a lifetime. This is not goodbye, but rather, until next time - or as the Italians say: ARRIVEDERCI.
Meals: B
Optional pre-stay in Florence
Book an extra night in Florence through Travel Visions and enjoy a complimentary walking tour and visit to the Academia Gallery, the home of Michelangelo’s David on Friday afternoon.
Meals: None
Included
Accommodation in a private luxury Villa in Val’d’Orcia for 6 nights
Excursions, Sightseeing and Admissions to all included activities
Knowledgable local experts and speakers
A Professional host
Transportation throughout the tour in an air conditioned vehicle starting in the center of Florence on Day 1 and ending at Rome’s Fiumicino airport on day 7
Meals as listed in the itinerary
Wine, water and coffee with all included lunches and dinners
Wine and food tastings as outlined in the itinerary
Authentic Cooking and Pizza experience as outlined in the itinerary
Gelato sampling
All gratuities and local taxes
Guaranteed small group size of maximum 8 guests
Not Included
Airfare
Visas (If applicable)
Travel Insurance (highly recommended)
Transportation to the starting point and from the finishing point of the tour
Meals not listed in the itinerary
Items of a personal matter
Prestay hotel in Florence
Anything not mentioned in the “Included“ paragraph
Accommodation
A little bit of Tuscany in every detail
Welcome to our enchanting villa boasting 360° views of Val D’Orcia. A haven of comfort and sophistication, this Tuscan style retreat offers 5 distinct bedrooms, each equipped with a private bathroom, air-conditioning and wifi.
