5-Nights Val d'Orcia and Val di Chiana

Available

Spring, Summer & Autumn

Price

$4,800

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 timeline subject to change

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Itinerary

Day 1: Arrival in Tuscany • Pickup in Florence • Scenic drive into Val d’Orcia • Check-in at Agriturismo Nobile or Pescaia • Welcome aperitivo overlooking the countryside • Group dinner to celebrate the beginning of our week together

Day 2: Montepulciano & Renaissance Beauty • Breakfast at the agriturismo • Visit to Tempio di San Biagio • Winery lunch in Montepulciano • Private tasting/tour at Contucci • Guided walk and free time in Montepulciano • Evening aperitivo and group dinner

Day 3: Under the Cortona Sun • Breakfast at the agriturismo • Hands-on cooking class and lunch with Chef Giada • Vineyard walk and tasting at Colle Acacia • Guided wine tasting and tour with Iviti • Free time in Cortona • Group dinner at a local restaurant

Day 4: Hidden Gems of Val d’Orcia • Breakfast at the agriturismo • Visit to the medieval village of Monticchiello • Tasting at La Nascosta • Cheesemaking experience, farm tour, wine tasting, and lunch at Caseificio Più • Relaxed afternoon • Group dinner in Val d’Orcia

Day 5: Montalcino & Brunello Country • Breakfast at the agriturismo • Visit to Pienza • Brunello tasting at Colle Mattoni • Winery lunch at Le Ripi • Tasting at La Fornace • Golden hour drive through Val d’Orcia • Farewell dinner together

Day 6: Departure Day • Final breakfast together • Scenic drive back to Florence • Arrival in Florence around early afternoon Transfers or extended travel arrangements can be organized upon request.

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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 ($3,800 per person), due 4 weeks before the tour.

Available:

Spring, Summer & Autumn
April - October
This experience is offered on custom dates between April and October.
Choose your preferred season and we’ll curate the perfect week around you!

Ready to Choose Your Dates?

Email us at info@grapestained.com with your ideal travel window and group size.
We will personally confirm availability and curate your week before you submit your deposit.

Once confirmed, your $1,000 per person deposit secures your dates.

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.
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.
Daily breakfast and lunch detailed in the itinerary, showcasing authentic Tuscan flavors and local specialties.
Hands-on experiences, including cheesemaking and cooking classes, 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.
Dinners at local restaurants
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.