Southern Tuscany Retreat: Under the Tuscan Spell
Feel your senses come alive while falling in love with the Tuscan region of the Val d’Orcia.
May 23-30, 2026
Beyond the well-trodden path of Northern Tuscany lies the Val d’Orcia, where vineyards are enhanced by wheat fields (think scenes from the Gladiator movie and the Netflix Medici series). Each day is filled with a sensory discovery: wandering through nearby Pienza and Montepulciano, witnessing how cheese is made on a family-run farm, and meeting the owner of an olive grove while sampling their olive oil along with a home-cooked meal. This is the Tuscany most travelers never find, but we’ll take you there.
Your home for the week is a luxurious villa (pictured on the right) in the tranquil town of Sarteano, rich in Etruscan history, and only 20km from Montepulciano. Here you’ll be pampered by chef-prepared meals, the ease of walking into Sarteano, expansive areas to gather with other guests, and an in-villa cooking class. You’ll experience the perfect blend of relaxation, exploration, and connection.
Tuscany is calling!
Retreat Details
When:
May 23-30, 2026
Where:
Sarteano, in the Province of Siena, near Montepulciano
Group size:
8-14
Fitness Level:
Ability to walk on uneven surfaces, climb hills and steps
Retreat Highlights
Wander through the streets of Montepulciano and Pienza, steeped in ancient history
Experience a private tour and tasting of the famous Vino Nobile di Montepulciano at a winery, along with a hearty lunch
Walk from the villa to the town of Sarteano and shop the outdoor market, meet the local artisans and enjoy the creamiest gelato
Learn how olive oil is made at family-owned olive grove
Enjoy the thrill of hand-rolling pasta dough to make fresh ravioli with your villa chef
Share stories, meals, and connection in an ancient villa surrounded by nature with farm-to-table Tuscan cuisine and local wines
Don’t miss this chance to experience authentic Tuscany in a supportive community.
Choose Your Room
Ground Floor King Room
$3,800 pp shared
$4,400 pp single
Second Floor King Room
$3,800 pp shared
$4,400 pp single
Ground Floor King Room
$3,800 pp shared
$4,400 pp single
Second Floor King Room
$3,800 pp shared
$4,400 pp single
Second Floor King Room
$3,800 pp shared
$4,400 pp single
Second Floor King Room
$3,800 pp shared
$4,400 pp single
8 days, 7 nights in a luxury villa
Self-catered breakfast at the villa
3 chef-prepared dinners at the villa
Shop the weekly outdoor market
Self-guided tour of Montepulciano including a tour, tasting and lunch at a Montepulciano winery
Self-guided tour of Pienza
In-villa cooking class
Olive oil tasting at a family-run farm
Transportation to and from the Chiusi train station and the villa upon arrival and departure
Private transportation to Pienza, Montepulciano and the olive oil tasting
What’s Included
What’s Not Included
Airfare
Travel insurance
Gratuities
Local tax
Anything not specified in the travel package
Meals outside of the itinerary
Wine and alcohol
Payments
$500 non-refundable deposit due at time of booking
Interest-free, non-refundable payments due 150 days and 120 days before tour start date
Accepted payments: Credit Card (fees apply), Zelle, Venmo, or ACH transfer
Custom payment plans available
Cancellation Policy
A non-refundable deposit of $500 is required to secure your booking. Half of your trip balance is due 150 days prior to the trip start date and 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.
We understand that plans can change and emergencies come up. However, due to the nature of our business, deposits and payments are applied to third party vendors very shortly after payments are received. As such, we have a strict no-refund policy with the following exception: if the trip is cancelled by Together in Tuscany, the guest will receive a full refund for all payments made.
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).