The Tuscany Edition
Montalcino & Val d'Orcia, Italy — 2027
Ten spots. One villa. No public launch date — yet.
The quiet list is open now.
Come back to Tuscany with us - it's where the passion for travel and wine started, and where I've returned every April for the last twenty years. I go before the tourist season hits, when things are quieter and the region still feels like it belongs to the people who live here - the food, the wine, the farms, the scenery, all of it. Some places you only need to see once. This one, I go back to every year.
There is an hour in Tuscany you cannot book and cannot rush — when the light turns the color of the wine in your glass, the day's only remaining appointment is dinner, and the people at your table stop being people you're traveling with and start being the whole reason you came. Old friends. A partner. Someone you met that morning and already can't imagine the trip without.
That hour is the entire point of this week. Everything else is just how we get you there.
Ten guests, by design, in a villa above the vines. Long lunches in working vineyards. A farmhouse table where the cheese, the olive oil, and the wine all came from the hill you can see from where you're sitting. Evenings that start with an aperitivo and end somewhere well past the last course, still talking.
2026 took us to Cortona. 2027 goes deeper — Montalcino and the Val d'Orcia, the corner of Tuscany our guests didn't want to leave.
Come with someone, come with a few friends, or come solo — you'll leave with people you'd travel with again.
Dates and pricing aren't public yet — the list is. Here's what that gets you:
First access. You'll hear about confirmed dates before they're announced anywhere else.
Founding-guest rate. List members get first crack at pricing before this opens more broadly — and before the rate goes up.
First pick of rooms. The villa has a few rooms with the better views. List order decides who gets first choice.
Zero obligation. Joining costs nothing and locks you into nothing — it just moves you to the front of the line.
Why Join the List Now
WHY TRAVEL WITH CYNTHIA & Nina
The Itinerary — 5 Nights, 6 Days
Day 1 · Arrival Private transfer from Florence · welcome aperitivo on the terrace · opening dinner outdoors, table set long - the best part of the day!
Day 2 · Vines A guided walk through a working vineyard · Brunello tasting with a sommelier who treats every pour like a story · chef-curated dinner at the villa
Day 3 · Montalcino, Slowly Free time to wander Montalcino's old town · farmhouse cheese & olive oil tasting · casual pizza night, no agenda
Day 4 · Culture Day — Pienza & Siena Guided walk through Pienza, the Renaissance "ideal city" · choice of a cooking class or a quiet villa afternoon · chef prepared dinner under the olive trees
Day 5 · One Last Day Slow morning, no plans · free afternoon — pool, massage · farewell dinner in a nearby hill town, panoramic views
Day 6 · Departure Gentle optional mobility close-out · farewell brunch · group transfer to Florence
Cynthia Plath Founder, Sojourn & Soirée
Cynthia spent more than twenty years as a U.S. diplomat — negotiating in Geneva and New York, working across the Middle East and Europe — before trading formal tables for long dinners in private villas. Sojourn & Soirée is what came next: small-group journeys built on the same instinct for people, place, and how a room actually works that she honed over a career spent reading rooms for a living. Every edition she designs starts from one idea — that how you travel matters as much as where you go.
Nina Berube Co-Host, EMBODY by Antonina
Nina's work is about presence — helping people step out of autopilot, wherever they are. A WSET-certified wine educator and longtime host of small-group travel and gatherings, she brings a background in wine, hospitality, and connection to every edition she co-hosts, along with an instinct for turning a table of near-strangers into old friends by the second night. She and Cynthia also co-host the Next Chapter, Anywhere podcast together.
Founding-Guest Pricing
Starting from $4,500 per person, double occupancy. That number is the floor, not the final word — it moves once dates are locked, and it only moves up. List members lock in wherever it stands when they join, before the public ever sees a price.
Ten guests. Never more.
How Joining the List Works
No payment. No forms beyond your name and email. Just first word.
Join the list — thirty seconds, name and email, nothing else.
Get first word on confirmed dates and the founding-guest rate, before anyone outside this list hears a thing.
Claim your spot in the short window list members get before this opens publicly.
Full pricing, payment, and cancellation terms go out the moment dates are locked — and they go to this list first.
What’s Included
Immerse yourself in a restorative week where every detail is thoughtfully curated for ease, beauty, and renewal.
5 nights in a luxury Tuscan villa — private ensuite rooms with panoramic views, spa access, and tranquil surroundings.
Optional Daily Pilates & movement classes (all levels welcome) led by certified instructors.
All breakfasts and three chef-curated dinners, highlighting fresh Mediterranean ingredients and regional wines.
Farm & Olive Oil Tasting at local working farm.
Cultural excursion to Siena, with guided exploration and lunch among the cobblestone streets.
Group transfers from Florence (FLR) for seamless arrival and departure.
Evening in Cortona (Final Night) — enjoy dinner on your own or with hosts in town. Choose from Cynthia’s curated list of favorite local restaurants. (Dinner cost not included.)
Add a personal touch to your journey with curated experiences available à la carte:
Vineyard Escape & Sommelier Tasting – approximately €175 per guest
Enjoy an intimate vineyard tour and tasting guided by a local sommelier.Private Driver or Extended Villa Stay available upon request.
FAQs
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Airfare, travel insurance, optional enhancements (vineyard tour, olive oil tasting, personalized consultations), and one dinner in Cortona (dinner on your own or with hosts).
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Absolutely. Many guests join solo and connect quickly with the group. Rooms can be booked for single or double occupancy.
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No — joining is free, always. It costs nothing and commits you to nothing. It just puts you first in line for dates and pricing before anyone else sees them.
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Each day includes a morning Pilates session, breakfast, wellness talk or curated excursion, and plenty of downtime for rest and exploration.
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Group transfers are arranged from Florence on arrival and departure days. Guests are also welcome to rent their own car if they prefer greater independence—there is ample parking at the villa for personal vehicles.
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Yes. Private driver service or additional villa nights can be arranged upon request, subject to availability.
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Yes. Please note any allergies or dietary preferences on your intake form, and our chef will tailor meals accordingly.
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For most travelers from the U.S., Canada, and the EU, no visa is required for stays under 90 days. A valid passport with at least six months of validity beyond your travel dates is required for entry.
We’ll provide all guests with a pre-travel checklist and guidance on flights and arrival details once booking is confirmed.