Under the Tuscan Spell

For men or women seeking a soul-nourishing, relaxing, and inspiring week in the Val d’Orcia region of Tuscany.

May 23-30, 2026

Join us in Tuscany!

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

  • Spend a day with a local family whose town holds decades of history and paint your own maiolica tile

  • Experience a private tour and tasting of the famous Brunello di Montalcino wine and it’s friendly competitor, the Vino Nobile di Montepulciano at two unique wineries, along with a hearty lunch

  • Enjoy tasting the nutty pecorino cheese and witness how it’s produced at a family-run farm

  • Wander through the streets of Montepulciano and Pienza, steeped in ancient history

  • 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.

Invest in Yourself! Secure Your Spot!
Chef Antonella.jpg
Casalfava dining room.jpg
Fanti group.jpeg
Casalfava kitchen.jpg
Ann's group welcome.jpg
Casalfava living room.jpg
Sharon with Tile.jpg
Casalfava outdoor eating.jpg
Group at Fighine.jpg
Casalfava summer kitchen.jpg
Casalfava outdoor group gathering.jpg
Janine with Ann and Stuart.jpg

Choose Your Room

A cozy bedroom with a four-poster bed with white curtains, a striped headboard, and beige bedding. There are two bedside tables with lamps, one with a red flower in a vase and the other with a framed picture. A breakfast tray with orange juice, coffee, and a croissant is on the bed. The room has warm lighting, terracotta tile floors, and decorative framed artwork on the walls.

Ground Floor King Room

$5,899 pp shared

$6,499 pp single

Second Floor King Room

$5,899 pp shared

$6,499 pp single

A cozy bedroom with a large bed, a nightstand with a lamp, a window with white curtains, framed floral artwork on the wall, and a wooden ceiling with exposed beams.

Ground Floor King Room

$5,899 pp shared

$6,499 pp single

A cozy bedroom with a large bed covered in a beige floral bedspread, topped with a tray of drinks and a green pitcher. The headboard has three large green cushions with ruffles. A small wooden nightstand with a table lamp, books, and a candle is beside the bed. There's a small window with a wooden frame and shutter above the nightstand. An air conditioning unit is mounted on the wall below a vibrant framed painting of red poppies, and wooden ceiling beams are visible.

Second Floor King Room

$5,899 pp shared

$6,499 pp single

Second Floor King Room

$5,899 pp shared

$6,499 pp single

Second Floor King Room

$5,899 pp shared

$6,499 pp single

Book Now!

  • 8 days, 7 nights in a luxury villa

  • All meals including 6 breakfasts, 4 lunches and 6 dinners (with wine)

  • Chef-prepared dinners at the villa

  • Maiolica tile painting experience

  • Witness cheese-making at a family-run cheese farm

  • Shop the weekly outdoor market

  • Guided tour of Montepulciano with free time to explore on your own

  • Guided tour of Pienza with free time to explore on your own

  • 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 activities

  • Gratuities for the tour guides, drivers, cooks, housekeeping, etc.

  • Local tourist tax

What’s Included

What’s Not Included

  • Airfare

  • Travel insurance

  • Anything not specified in the travel package

  • Wine and alcohol outside of what's included in the itinerary

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).