June 6–11, 2027 · Val d'Orcia, Tuscany

Tuscany Villa Experience

Duration

5 Nights

Accommodation

Private Villa

Group Size

Max 8

From

$5,000/person

Reserve Your Spot

5 Nights

At the Villa

Val d'Orcia

The Setting

June 6–11

2027

$5,000

From / Person

The Experience

A slower way to experience Tuscany

Why Tuscany?

There is a reason people dream about Tuscany — the hill towns, the food, the wine, the cypress trees, the stone villages, and the long golden evenings. But the version of Tuscany I love most is slower, softer, and rooted in a real sense of place.

This small-group trip is centered in the Val d'Orcia, one of the most beautiful areas of Tuscany, with a countryside property as our home base. From there, we'll explore nearby towns like Pienza, Montepulciano, Montalcino and Siena, enjoy local food and wine, gather for relaxed meals and aperitivo, and build in enough open time to sit by the pool, wander a village, shop for local products, or simply take in the landscape.

I chose this location because it allows the trip to feel both curated and relaxed. You can experience the beauty of Tuscany without packing and unpacking, changing hotels, or spending every day in transit.

This is not a packed bus tour or a checklist trip. It is a small, hosted experience for travelers who want Tuscany to feel personal, beautiful, easygoing and thoughtfully planned.

With a maximum of 8 guests, the group will be intimate by design — ideal for friends, couples, mother-daughter travelers, or solo travelers who want the ease of a group without feeling like they are on a traditional tour.

Golden hillside with cypress avenue, Val d'Orcia at sunset

Historic brick street in Siena with shops and cafes

Rolling Tuscany hills from villa grounds

The Villa

Our villa sits in the heart of the Val d'Orcia — the UNESCO World Heritage landscape of rolling golden hills, cypress avenues, and medieval hilltowns that has defined the idea of Tuscany for centuries.

The estate is exclusively yours for five nights. Private pool, outdoor dining terrace, an on-site caretaker, and the kind of views that make you understand why people have been painting this landscape for 600 years.

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Private infinity pool

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Outdoor terrace dining

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On-site caretaker

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Exclusive use — no other guests

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En-suite rooms for all guests

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Val d'Orcia UNESCO views

Food & Wine

The Table

Three dinners at the villa. Three lunches. A private wine tasting with a family that has been growing Sangiovese on this hillside for four generations. And 2–3 aperitivo receptions by the pool — salumi, aged pecorino, and the first glass of something cold.

The meals are mostly at the villa, on the terrace or under the pergola. Pienza is ten minutes away when you want the market. Montepulciano is twenty when you want Vino Nobile at the source.

Tuscan charcuterie board with salumi and aged pecorino

Pricing

What's Included

Double Occupancy

$5,000

per person · $1,000 deposit

Single Occupancy

$5,750

per person · $1,000 deposit

Included

✓
5 nights exclusive use of a private villa in the Val d'Orcia
✓
5 daily Italian breakfast buffets
✓
2–3 aperitivo receptions by the pool
✓
3 dinners at the villa (traditional Tuscan menu)
✓
3 lunches at the villa
✓
Private wine tasting experience
✓
E-bike rental available upon request
✓
All ground transportation for the week
✓
Welcome gift & printed trip itinerary
✓
Erin's full planning and on-trip hosting presence
✓
Tourist tax

Not Included

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International flights to/from Italy
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Travel insurance (required — Erin recommends Faye)
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Pre/post Rome or Florence stay (Erin books at Virtuoso rates)
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Meals on your own, gratuities, souvenirs and any other personal expenses.

Talk with Erin for pre & post suggestions and accommodation ideas!

View over Val d'Orcia from villa grounds

“This trip is limited to 8 travelers.”

Day Trips

Three Towns Worth Knowing

Three of the most beautiful hilltowns in Tuscany — each a short drive from the villa.

Bagno Vignoni

Thermal Springs & Charm

Montepulciano

Vino Nobile & Views

Siena

Gothic Grandeur

The Journey

Day by Day

This is a sample itinerary and may shift slightly as final villa arrangements, transportation and local experiences are confirmed.

Arrive at Chiusi-Chianciano Terme train station, where private group transportation will bring guests to the villa. Settle in, explore the property and gather for a relaxed welcome evening.

Ease into Tuscany with a visit to Pienza, with time to wander, shop, enjoy coffee, take photos and explore at your own pace. Later, enjoy time back at the villa or a nearby stop in San Quirico d'Orcia or Bagno Vignoni.

A half-day visit to Siena with a private guided walking tour and guided visit of the Duomo, followed by time for lunch, shopping and independent exploring.

A slower morning at the villa with time to relax, walk, bike or enjoy the property, followed by a private afternoon winery experience and tasting.

A day exploring two classic Tuscan hill towns, with time to wander, shop, taste local wine and enjoy the views. If timing allows, we may include a short stop in Bagno Vignoni or San Quirico d'Orcia.

Final morning at the villa before private group transportation returns guests to Chiusi-Chianciano Terme train station for onward travel.

Questions

Common Questions

This journey is intentionally limited to 8 travelers. Small enough that every experience feels personal, large enough to share the moments that deserve to be shared.

Double occupancy (shared room): $5,000 per person. Single occupancy (private room): $5,750 per person. A $1,000 non-refundable deposit holds your spot, with the balance split into two payments in January and March 2027.

Your $1,000 deposit reserves your spot and is applied to your total. The trip requires a minimum of 8 guests to operate — if that minimum isn't met by December 1, 2026, all payments including deposits are refunded in full.

Yes — travel insurance is required. Erin strongly recommends a policy with trip cancellation, medical, evacuation, and cancel-for-any-reason (CFAR) coverage. She recommends Faye Travel Insurance and is happy to share an affiliate link at booking.

Gentle to moderate. The hilltowns involve walking on cobblestone streets and some inclines, but nothing strenuous. This trip is designed to feel unhurried.

Absolutely. Erin can arrange 1–2 nights in Rome or Florence before or after the villa stay at Virtuoso rates — often with complimentary upgrades and breakfast. Just let her know when you register.

Submit a reservation request through the form on this page and Erin will be in touch with the registration agreement and payment details.

Stone window with golden hour view of Val d'Orcia

June 6–11, 2027 · 8 Spots

Ready to reserve your spot?

This trip is limited to 8 travelers. A $1,000 deposit holds your spot.

Reserve My Spot — $1,000 Deposit I Have a Question