4-Nights Val d'Orcia and Val di Chiana

2026 Dates

April 24-28
May 1-5

Price

$4,000

All Inclusive package including accommodation, transportation, food, wine tastings, expert led tours and a photographer capturing the experience.

*Price per person
*Flights not included
*Itinerary subject to change

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Itinerary

Day 1: Under the Cortona Sun 8:30am: Meeting and Pickup in Florence 10:30am: Cooking Class with chef Giada Mattioli 2:00pm: Winery tasting and vineyard walk @ Colle Acacia 4:30pm: Winery tasting @ Colle Acacia 7:00pm: Check in and Aperitivo at Agriturismo Pescaia 8:30pm: Dinner at Ristorante L'Oliveto

Day 2: Historic Dive Into Montepulciano 9:00am: Breakfast at Agriturismo Pescaia 9:30am: Visit to Tempio San Biagio or free time 12:00pm: Lunch at a local winery 3:00pm: Winery tasting and tour at Contucci 5:00pm: Free time Montepulciano/Aperitivo at Agriturismo Pescaia 8:00pm: Dinner at a local restaurant

Day 3: Hidden Gems of Val d'Orcia 8:00am: Breakfast Agriturismo Pescaia 9:00am: Visit to Montichiello, a small medieval village 11:00am: Winery tasting and tour at La Nascosta 2:00pm: Cheesemaking, wine tasting, Lunch, and Pecorino farm tour at Caseficio Piu 6:00pm: Free time 8:00pm: Dinner at Ristorante L'Oliveto

Day 4: Breathtaking Val d’Orcia and Montalcino’s Identity 8:00am: Breakfast Agriturismo Pescaia 9:00am: Visit to Pienza 11:30am: Winery tasting and tour at Colle Mattoni 1:30pm: Winery Lunch at Le Ripi 3:30pm: Winery tasting and tour at La Fornace 6:00pm: Golden hour drive and aperitivo in Val d'Orcia 8:30pm: Dinner at Ristorante L'Oliveto

Day 5: Arrivederci. Departure from Florence Sadly, our time together has come to an end, but the memories will last forever! We will make our way back to Florence after one final breakfast together. We will arrive back in Florence around 11 am. We can help you organize any transfers or plans that you need to make. Thank you for an unforgettable adventure!

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Highlights:

8 Winery Visits - tastings/tours with the producers

Experience the ever changing Terroir of Tuscany like never before. Indulge in different expressions of numerous grape varietals as we travel across multiple microclimates and Italian wine denominations of Cortona, Montalcino, and Montepulciano. Learn about the stories and history of 7 different families of the Chiana and Val d'Orcia valleys while you quench your wine thirst.

Cheese Making Classes and Cozy, Authentic Dinners

Enjoy Italian food like never before. Satisfy your need for cheese as we explore Val d'Orcia and Val di Chiana, two valleys famous for pecorino. Get your hands dirty and stain your apron as we learn how to make cheeses in an authentic Tuscan style. In the evening, we will be eating the true Italian way, local and seasonal. Cuisine in Val d'Orcia is every sense of the word, rustic.

Visits to 5 towns across Val d'Orcia and Val di Chiana

On a ride through Tuscany, you will quickly discover that straight lines hardly exist. Roads whip back and forth, up and down, whilst passing through farmland, forests, medieval towns, olive groves and of course, vines. It is so easy to fall deeply in love with Tuscany, as this stunning landscape is not only one of the most romantic destinations on Earth, but one of the most diverse.

Professional Photographers Capturing your experience

We are professional photographers and love to capture the moment, so we want you to live in it. Don't worry about spending too much time taking a selfie, we would rather do it for you. Our tours include professional photographers following along to help best capture your experience and provide you with your very own memory book to show off to friends and family.

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Book the Val D'Orcia Tour

Click below to reserve your spot(s) on our Nobile Wines, Organic Vines, And
Val d'Orcia's Quintessential Taste Tour. You will be required to pay a deposit of $1,000 per person upon reservation (If you are reserving for a group of 2, you will select 2 deposits totaling $2,000). We will send an invoice with the remaining amount ($3,000 per person), due six weeks before the tour.

SPRING 2026 TOUR DATES:

April 24-28 & May 1-5

Our small group tours require at least 4 people to run (with a maximum of 8). If the tour gets canceled due to insufficient group size, you will receive your deposit back

Must be 21 or older to purchase:
This tour includes wine tastings and experiences that involve alcohol.

What's Included

Accommodation in a gorgeous Tuscan agriturismo, with breakfast each morning to start your day right.
All private transportation throughout the tour in a comfortable van with a professional driver.
Eight exclusive winery visits and tastings, featuring small-production, artisanal wines.
All meals as detailed in the itinerary, showcasing authentic Tuscan flavors and local specialties.
Hands-on experiences, including a cheesemaking class and other immersive activities.
Professional photography capturing your journey, with a curated collection of memories to take home.
Expert local guidance and storytelling at every stop, giving you a true taste of Tuscan culture.

Not Included

Flights or transportation to and from the starting/ending point of the tour.
Travel insurance.
Free time activities or experiences not listed in the itinerary.
Additional drinks or wine outside what’s included in tastings and meals.
Personal expenses such as souvenirs, laundry, phone calls, Internet, or gratuities for guides, drivers, and winery staff.