Pilates, wine, and a long table in TuscanySeptember 20 to 27, 2027. Terzo di Danciano, outside Cortona.
A typical day
MorningFifty minutes on the mat, in the studio or out on the lawn. Then breakfast.
Late MorningOn excursion days, the group heads out after breakfast. On villa days, the pool is yours until lunch.
AfternoonA winery tour, a long lunch in a hill town, a wander through Montepulciano or Pienza. Or back at the villa, a spa appointment, a chair in the shade, or a nap.
EveningDinner together at one long table, with wine poured. Expect conversation to carry on outside well after the plates are cleared.
The week at a glance
ArrivalWe meet you in Rome and drive north together, stopping in Orvieto for lunch. The town sits on a cliff of volcanic rock with cellars carved into it, and it breaks the drive neatly in half. That evening, a welcome cocktail reception at the villa.
The wine classOn the second day, a local sommelier sits the group down with a flight of wines and walks through the region: what grows where, why it tastes the way it does, and what you’ll see on the drives ahead. By the time you reach the cellars, you’ll know what you’re tasting.
Days outMontepulciano and Pienza. Vino Nobile in cellars cut beneath the town, then the small Renaissance town down the road, known for its pecorino.
Umbria. Over the border to a hill town and a working winery for Sagrantino, a red that rarely makes it outside Italy.
Cortona. A half day in the hill town twenty five minutes from the villa.
Cellar lunches and winery visits along the way.
Days inCooking class. With the villa’s chef, running straight into dinner.
Olive oil dinner. A local expert who has spent his working life in Italian olive oil pairs a different extra virgin oil with each course and explains each one as you eat.
Brunello dinner. Brunello di Montalcino, poured and talked through at the table.
Practice workshop. Ninety minutes with Jenna and Susan for anyone who wants to go deeper than a morning class allows.
Room to breatheA pool, a spa, and hours with nothing planned. Massages and facials can be booked at the villa.
Last nightDinner outside under lights, with flowers and live music.
DepartureBreakfast, then the drive back to Rome together.
The final order of the week will be shared closer to the retreat.
Why September?September is harvest season in Tuscany. Depending on the year, you may see grapes coming in, cellars getting busy, and the valley smelling of fresh fruit. The summer heat has passed, the evenings are warm enough to eat outside, and the whole region is getting ready for the year’s wine.
What's includedWhat’s included
Seven nights at Terzo di Danciano, with the whole villa to ourselves
Pilates every morning, plus a ninety minute workshop with Jenna and Susan
Every meal, with wine at dinner and drinks throughout the week
A welcome cocktail reception
A wine class with a local sommelier
An olive oil paired dinner and class
A Brunello dinner
A cooking class with the villa’s chef
Three excursions, with winery visits and cellar lunches
Lunch in Orvieto on arrival day
Group transfers to and from Rome
Spa access, including the whirlpool, infrared sauna, and Turkish bath
The pool, olive grove, and gardens
A final night dinner with live music
Local taxes
Not included
Flights, travel insurance, and spa treatments such as massages and facials.
Getting thereFly into Rome Fiumicino
There are nonstop flights from many major US cities, including Atlanta, New York, Boston, Chicago, Washington, Miami, and Los Angeles.
Plan to arrive in Rome by September 19. A night in the city takes the edge off the flight and means a delay never costs you the start of the week. Once you book, we’ll send a short list of favorite Rome hotels.
On September 20, we meet the group in Rome and drive north together, with lunch in Orvieto on the way. On September 27, we drive everyone back to Rome. Book a flight home for that evening or the following day.
Exact pickup and drop off details will be sent before the trip.
Mornings on the mat, evenings at the table.Seven nights of Pilates, vineyards, and long Italian dinners, beginning in Rome on September 20, 2027. With only fourteen spots, Jenna reviews every application personally.
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