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Tuscany is justifiably famous for its epic scenery and sumptuous food, but also for tourist crowds. In this tour, we will find unknown villages and sample local specialties that few travelers come across. You’ll get to be a temporary part of a Tuscan/American family, staying at the home of our local guide, Roberto Bechi.

By keeping our numbers low, we can keep personal attention high. This tour is boutique and will have a maximum of 7 guests. Book now by emailing us or completing the Provisional Registration form (select “Travelphile Tuscany“).

For more details about Provisional Registrations, please click here.

If you would like to book this tour just for your own group of friends or family (6-7 people), we can offer a private tour with dates to suit your travel needs.

Itinerary details subject to change
• *tour operated in partnership with Tours by Roberto and Roads Less Traveled LLC

Day One

Welcome to Off-the-Beaten Path Tuscany

After the pick-up at the airport (Rome, Fiumicino), we will drive to Podere Casalciccia. Taking the coastal Aurelia highway, we stop in the picturesque fishing village of Talamone, once the medieval port of the Republic of Siena and still dominated by an ancient Sienese fortress. We’ll lunch with a sea view and follow that with some rest at the restored Tuscan farmhouse, Podere Casalciccia, your home for the next six nights. Enjoy a home-cooked welcome dinner at the farmhouse.
Overnight: Casalciccia

Day Two


In the morning, we’ll take a tour of the Etruscan museum located inside a former granary near the historic center of Chianciano. We’ll enjoy lunch in the medieval village of Monticchiello, located in the heart of Val d’Orcia, followed by a guided visit around this charming place.

Optional Yoga class at Casalciciccia available at our return. Dinner at a local farm.
Overnight: Casalciccia

Day Three

Siena and Farm-to-Table Dining Experience

Roberto leads us on a walking tour of Siena and its Cathedral followed by a visit to his own Madonna Bella Farm. Lunch will consist of a delightful farm-to-table food and wine pairing of local dishes with Roberto’s own wines.

Optional drawing class for those interested available at our return to our Casalciccia. Light dinner in Asciano.
Overnight: Casalciccia

Day Four


Let’s go on a walking tour of Florence, epicenter of the Italian Renaissance. We’ll enjoy the less-touristic back streets and lesser-known masterpieces with a local guide.

Lunch leisurely on your own in Florence and a take advantage of a free afternoon to enjoy the city’s delights or perhaps discover your favorite gelateria.

Light dinner in Arbia en route to home.
Overnight: Casalciccia

Day Five

Village Tour of the Clay Hills

Dedicate your morning to a chosen extra activity (art, yoga, walking, photo safari). Following a light lunch at Casalciccia, we’ll tour the clay hills, explore Monteoliveto Abby and its amazing art, and continue to the village of Lucignano D’Asso. We end with a visit of the medieval village of Chiusure.

Tonight we’ll feast on a pizza dinner on a terrace with an amazing view of the clay hills at sunset.
Overnight: Casalciccia

Day Six

Hamlets, Villas, Cooking and Chianti

We’ll visit off-the-beaten path medieval hamlets like Vertine and San Donato in Poggio, followed by a visit to the home of a good friend of Roberto who happens to be a noble count! We’ll explore his Villa di Geggiano and its gardens—considered a national treasure—and enjoy a light lunch with the count.

We’ll partake in a cooking class followed by farewell dinner at Casalciccia.
Overnight: Casalciccia

Day Seven

Farewell breakfast and transfer to Rome

Enjoy our final breakfast at our countryside bed & breakfast, and then we’ll head out for our transfer to Rome’s Fiumicino Airport.

Overnight: N/A

Tour Dates:

July 24-30, 2021

[Second July tour (July 18-24) pending. Please email us if you’re interested.]

[November dates TBD]

Price: $2550 (Air not included). Due to lack of rooms at the farmhouse, we cannot welcome solo travelers who require their own room.

What’s included: 6 dinners (wine included) and 6 lunches, 6 breakfasts, 6 nights lodging in a clean, comfortable and family-run farmhouse in the gorgeous Tuscan countryside. All tastings and entrance fees per itinerary above. Local guide, driver, ground transport and transfer to/from Rome Fiumicino airport.

You can reserve a spot on this tour without deposit. Simply complete the Provisional Registration form (select “Travelphile Tuscany”). A non-refundable deposit of $600 will be due in early 2021.

Tour begins and ends in Rome. International airport there is FCO.

If you would like to reserve a spot on this tour, please complete the online Provisional Reservation form (select “Travelphile Tuscany“). For more information about Provisional Reservations, please click here.

If you have additional questions please email us at:

*Tour operated in partnership with Tours by Roberto and Roads Less Traveled LLC.

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