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Tuscany is justifiably famous for scenery and 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.

We have enjoyed our small groups so much that we will continue to keep numbers low and personal attention high. This tour will have a maximum of 8 guests.

Tour Leader: Roberto Bechi

Day One

Overnight: Casalciccia

Welcome to Off the Beaten Path Tuscany

After pick up at the Rome (FCO) airport we will drive north. Taking the coastal Aurelia highway we will 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. Lunch with a sea view followed by rest at restored Tuscan farmhouse, Podere Casalciccia, your home for the next six nights. Welcome home-cooked dinner at the farmhouse.

Day Two

Overnight: Casalciccia


Tour of the Etruscan museum located inside a former granary near the historic center of Chianciano. 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.

Day Three

Overnight: Casalciccia

Siena and Farm-to-Table Dining Experience

Walking Tour of Siena and its Cathedral followed by a visit to Madonna Bella Farm. Lunch will consist of a delightful farm-to-table food and wine pairing with local dishes and our own wines. Optional drawing class for those interested available at our return to our Casalciccia. Light dinner in Asciano.

Day Four

Overnight: Casalciccia


Walking tour of Florence, enjoying the back streets and lesser-known masterpieces with a local guide. Lunch on your own in Florence and a free afternoon to enjoy the city’s delights. Light dinner in Arbia en route to home.

Day Five

Overnight: Casalciccia

Village Tour of the Clay Hills

Morning dedicated to a chosen extra activity (art, yoga, walking). Light lunch at Casalciccia. Clay Hills tour in the afternoon, visit of Monteoliveto Abby and its amazing art followed by the village of Lucignano D’Asso. We end with a visit of the medieval village of Chiusure, followed with a pizza dinner on a terrace with an amazing view of the Clay Hills at sunset.

Day Six

Overnight: Casalciccia

Cooking class and Chianti wines

Chianti + cooking class. Visit of the off-the-beaten-path medieval hamlets like Vertine and San Donato in Poggio followed by a visit of the Villa Geggiano and Utd Gardens. This is a national treasure, and is owned by a good friend of Roberto’s, a noble Count! Light lunch with the Count. Cooking class followed by dinner at Casalciccia.

Day Seven

Overnight: n/a

Farewell lunch and wine tasting in Val D’Orcia

We’ll tour the Val D’Orcia, including visits to the famous hilltowns of Pienza and Montalcino, Farewell Lunch will be at a family run BRUNELLO winery followed by a visit to the cellars. Late afternoon transfer to Rome.

Price: $2850 (Air not included). Due to lack of rooms at the farmhouse, single supplement may not be available. We are happy to pair solo travelers to share a room.

What’s included: 6 dinners (wine included) and 7 lunches, 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 airport.

Deposit Policy: we require a $600 non-refundable deposit at the time of booking. If your plans change, you may transfer this deposit to any of our other tours.

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

If you would like to book this tour just for your own group of friends or family (6-8 people), we can offer a private tour with dates to suit your travel needs.

Fantastic experience. The tour was exceptionally well organized and expertly led by Anna Piperato. Her knowledge of Italy, Florence, and art history and her engaging personality made the tour extremely enjoyable and enriching. She looked after the needs of the tour participants exceptionally well. The hotel was comfortable and well-located. The mix of activities was just right. The food tour of Florence markets was a distinct highlight. We highly recommend this tour.

Michael Carlsonfor StayCation Florence SEPTEMBER on Sep 29, 2022

Sicily is a culturally complex and geographically large and diverse place. It can easily fill 3 weeks. However, for many of us, 3 weeks is not possible. For a great way to get to know the three millennia of history that shaped this place, see the ancient remains of past cultures and how they are incorporated into modern day life, and experience the variety of foods brought by its many invaders, Adventures with Sarah's Sicily Highlights tour is the way to go. Sarah is passionate about Sicily and knows it intimately. In addition to her vast knowledge and experiences, she incorporates local guides who add their personal flare and love for the island. And the small tour group size helps single travelers, like me, feel part of the tour and not a third wheel.

Janet Suttonfor StayCation Florence on Sep 24, 2022

Anna is a prize! She knows and shares so much about the local events, culture, and art. She and Sarah led us to fantastic viewing sites for the practices, the race itself, and other related events. The group were all good travelers and fine companions, and it was delightfully small. We have heard about (and seen videos of) the Palio for decades and it was a bucket list experience for us to be there. Even the weather stayed cool for us. Food and hotels were excellent. Thank you Sarah and Anna for making this trip possible and for teaching us so much about the local culture. Sarah, please keep finding special and unusual trips and events for us to enjoy! Regards, Ben and Linda Shuler.

Richard Corbinfor Palio and Tuscany Deluxe on Jul 17, 2023