Small Group Journey
Through the Val d’Orcia Region
It’s time you knocked this dream Tuscany villa vacation off your bucket list!
Date: May 2- 9, 2026
Location: Sarteano in the Province of Siena
Group size: 12-14 guests
Designed For: Men and Women (couples, groups & solo travelers)
Fitness Level: Ability to walk on uneven surfaces and climb hills and steps
Discover the heart of Tuscany on this immersive Val d’Orcia journey, where rolling vineyards, medieval villages, and age-old traditions create the perfect setting for an unforgettable journey. Guests will learn to prepare classic Italian dishes in a hands-on cooking class, visit renowned Brunello and Nobile di Montepulciano wineries, explore a traditional cheese farm, and stroll through medieval villages steeped in history.
8 days, 7 nights in a luxury villa
Chef-prepared breakfasts and dinners
Planned activities just for your group
Private transportation to activities
Tour guides
Wine with dinners at the villa
Local tourist tax
Cooking class
Transportation at designated times to and from the Florence train station and the villa upon arrival and departure
Gratuities for the tour guides, drivers, cooks, housekeeping, etc.
What’s Included
What’s Not Included
Anything not specified in the travel package
Wine and alcohol outside of what's included in the itinerary
This 7-bedroom villa is located in the very pretty and tranquil town of Sarteano, a town that is rich in archaeological history with some of the most important Etruscan tombs surrounding its village. There are many shops, restaurants and bars in Sarteano, from boutique groceries to larger supermarkets, as well as an outdoor market every Friday morning.
Why we love this villa: its charm and close proximity to the beautiful medieval hamlet of Sarteano and the historical villages of Pienza and Montepulciano. The villa has incredible views of the Val d’Orcia, modern updates, lots of spaces to gather, indoor well-equipped chef’s kitchen, outdoor kitchen with grill, and gorgeous pool. This villa has all the charm of a 1700s home with all the modern amenities due to the careful restoration by its current owners.
Sarteano
Here’s What You’ll Experience
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Culture
Step back in time as you wander through hidden hamlets. Explore iconic landmarks and soak in the rich cultural heritage.
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Cuisine
Use your hands to create delicious Italian dishes in cooking classes with experienced chefs. Savor the meals prepared by other culinary artisans, including your very own in-villa chef.
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Tastings
Sample select wines, cheeses, and olive oil from both world-famous, as well as small, organic, family-run venues. Learn how to pair the wine, cheese, and olive oil with each other and with local cuisine.
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Experiences
Observe the beauty that surrounds you. Visit the village markets as if you were a local. Watch how olive oil, cheese, and wine are made. Appreciate a local artisan’s creative talents.
Room Accommodations
Ground Floor King Room
Second Floor King Room
Exterior King Room
Photo Gallery
Terms & Conditions
Cancellation Policy
A non-refundable deposit of $500 is required within 3 days of booking your Together in Tuscany trip. Half of your trip balance is due 150 days prior to the trip start date. The remaining balance is due 120 days prior to the trip start date. All bookings made within 120 days of the trip start date require full payment.
Should an installment payment not be received seven (7) days of its due date, we will consider your space on the trip as cancelled and no refunds will be provided for any payments received. You understand the unique services Together in Tuscany provides. Deposits and payments are applied to third party vendors providing itinerary activities very shortly after payments are received. As such, once payments are made to Together in Tuscany, we cannot issue any refunds.
Travel Insurance
We HIGHLY recommend that you obtain travel insurance. If you must cancel your participation in a Together in Tuscany trip for any reason whatsoever, including health conditions, death of a family member, travel difficulties, personal reasons, or any other reason whatsoever, the travel insurance can cover some or all of these expenses.
Service Agreement
All guests are required to review and accept the Terms and Conditions outlined in the Service Agreement which will be provided upon booking your room. The Service Agreement addresses risks and liabilities for the Provider (Together in Tuscany) and the Purchaser (Guest).