Hidden Tuscany
29 March - 4 April 2026
registration closed
From a lovely restored villa in the countryside explore Tuscany from well-known wine producing zones to tiny, out-of-the-way villages and the city of Florence. From our base in the Valdarno we'll make day trips into Chianti Classico and into the Carmignano wine producing zone. Visit producers of Tuscany’s classic foods and wines and see works of art by masters of Italian art that are still on view in the same spots for which they were originally commissioned. Chat with artisan food producers, participate in art history tours, take time to do your own thing, hang out with Lorenzo and have a sunset aperitivo. We’ll relax over amazing meals while getting a feel for the culture of the different zones of Tuscany with a mix of casual restaurants, cooking lessons in our villa and a couple of suppers prepared by a private chef while you enjoy a cocktail poolside.
Expect an exclusive small group tour with producer visits, guided tastings, major works of art in out-of-the-way places, traditional foods and free time to explore on your own.
itinerary
day 1 arrival
Late afternoon transfers from Florence city center or train station to our villa in the countryside of Reggello to the south of Florence. First group meeting in the late afternoon for an orientation cocktail. Group supper prepared by a private chef.
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day 2 explore the neighborhood of the Valdarno
In the land of terre nuove / frontier villages see an early work by Renaissance trailblazer Masaccio and another by Fra Angelico who used Masaccio's terrestrial formulas as a base for his heavenly visions. In the charming village of San Giovanni Valdarno, founded by Florence in 1301 to stake their claim on the territory, we'll discover their intriguing urban legend, take time to explore the city center with it's pleasant proto-Renaissance urban plan and have a group lunch of sangiovannese specialties in the piazza. Back to the villa for a late afternoon cooking class and group supper.
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day 3 Chianti Classico
Visit an artisanal pasta factory for a discussion of ancient grains, good gluten and traditional pasta production methods. Winery visit at Lamole, the highest point in Chianti Classico and its own sub-denomination with a small production of excellent wines from just eight family farms. Follow the winemaker through her terraced vineyards and taste her delicately beautiful interpretation of sangiovese. Tasting lunch with the winemaker in the old castle of Lamole. Free time in Greve in Chianti. Evening cooking lesson and group supper.
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day 4 Pratomagno and Arezzo
Up into the foothills of Pratomagno for a visit to the Romanesque church at Gropina with Longobard sculptural decoration and to explore the medieval village of Loro Ciuffenna. Lunch on the mountain at a charming home restaurant with vegetable garden and in-house productions of everything from bread and pasta to jams. Afternoon in Arezzo, an historical palimpsest where the vibrant modern city exists within the old medieval structure. See Roman ruins, medieval architecture, their Romanesque pieve and the Piero della Francesca early Renaissance frescoes. The pedestrian streets and piazzas of the historic center are lively with Aretini making the passeggiata, nice shops for fabrics, clothing, leather goods and antiques plus wine bars for a late afternoon aperitivo. We’ll make two visits as a group to see medieval and renaissance art and architecture and you’ll have free time to explore and have an early supper on your own.
day 5 Carmignano
Morning visit to the village of Carmignano to see Pontormo’s ground breaking Mannerist painting of the Visitation still hanging in the church for which it was commissioned. Visit to a producer of agresto (ancient Roman worcestershire sauce). We'll eat a typical Tuscan lunch on the terrace at a countryside restaurant, amazing views, amazing food. Spend the afternoon relaxing at the villa with a cooking lesson and group supper.​
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day 6 Olive Oil and the Castle of Poppiano
Walk through Elaine's olive groves and participate in a guided tasting of olive oil, learn how high quality olive oil is made, why it's good for you, how to recognize the good stuff and how to use it in the kitchen. The artisans who live and work in the borgo of the castle of Poppiano [painter, jewelry maker, woodworker, luthier, sculptor] will show us what they are working on and and offer us a casual lunch in the garden with views out over the hills of Chianti. Group supper at the villa prepared by a private chef.
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day 7 departure
Transfers to Florence city center, Florence Amerigo Vespucci airport FLR or to Florence Santa Maria Novella train station.
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Please note that this is an initial itinerary to provide a template of what to expect.
The people and places that we will be visiting are not typical tourist destinations
so plans may be modified at the last minute. We will craft the final itinerary
to provide the experience as described above.
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details
With a group of 10 - 12 travelers we’ll stay at a beautifully renovated farmhouse on an estate in the countryside of Reggello in Tuscany for beautiful countryside views plus it's a convenient location for going out and about (bedrooms on the second floor, no elevator).
We will have a private van and driver for all ground transportation.
Your activity level should allow you to walk for 3 - 5 miles per day including up and down steps often without handrails, on uneven cobblestone streets and through vineyards and olive groves that are planted on hills and terraces.
Request the guest registration document for all information including cost, payment terms, cancellation policy, etc.​​​​
feedback
Elaine is a fabulous guide. Extremely knowledgeable and easy to listen to. Our group had a fantastic time!
This is our third trip with you and every time you never cease to surprise with something out of the ordinary. This time the trip to the highest winery in Chianti with an outdoor lunch and the outdoor lunch at the artist colony with food prepared right from their garden. Looking forward to our next trip with you.
We had an awesome trip with Elaine Trigiani. I felt like the trip was a total immersion into Italian culture, it’s highly recommended.
Elaine curated the perfect trip for our group of 12. She made the logistics so easy for us, and it was a wonderful mix of art, culture and active adventures (with fantastic food of course). Tuscany is absolutely stunning and we got to experience quaint small cities and special tucked away locations that were not touristy giving us a glimpse in to what life looks like in the region. Trip of of a lifetime!!!
This trip was phenomenal! Elaine is the best! Her in-depth knowledge and desire for us to get a glimpse of the traditional and authentic Italian life, food and culture was so interesting and educational. This was not your usual, have a list of “must see and do and check it off” type trip. It was a perfect balance of enjoying, learning, experiencing and relaxing!
We had a blast. Everything was well organized and on time. The variety of stops and experiences were well thought out. The people we met, were unique and the "real deal". I never got the feeling they were big tourist sites. This was a trip I will never forget!!


























