The Hills of Tuscany

May 1 - 8, 2024

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Italy 2024

Please note that due to the number of applications we receive, we will only respond by email if you are selected to join a tour.  We regret that we cannot accept everyone who applies.

If you are applying to join the tour with another person(s) each person in your traveling party must complete an application.  Note on your application whether you are applying to be accepted together.

The 2024 walking tour in Italy took place in May.  Later this year we will be announcing the locations, dates and application process for the 2025 walking tours.

To ensure you receive notifications about the walking tours, consider joining our email list.



Italy Walking Tour - 2024

A Springtime Pilgrimage

From the first evening standing on the threshold of an ancient Etruscan tomb with the light slanting across the stone, imagining centuries of mothers, fathers and children making their lives amongst the olive groves, to the closing night’s celebration under the stars, the week in Italy is a moveable feast both literally and imaginatively; The Hills of Tuscany tour is a true celebration of the senses accompanied by David’s poetry and thought; a shaping of the mind and the body through walking, seeing, listening and tasting.

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A Springtime Pilgrimage

Tuscan culture is about standing in one’s place in the world, choosing what you do and doing it well, no matter how simple the task and no matter how many times it has been done before, finding the note you can hold in the song, and the path you can make yourself simply by walking.






Italy Tour Details




Our accommodations are in two or three beautiful agriturismos and a twelfth century convent along a road lined with vineyards. The location is 20km south of Florence in the heart of the Chianti Classico region, with a stunning view of the neighboring hills and countryside. The rooms are lovely apartment-style accommodations, each with its own
unique character, varying from studio to three bedroom configurations.

Bedrooms are shared with one other person, with a limited number of private bedrooms available for a supplemental fee. Please note that a private room does not guarantee a private bathroom or a studio accommodation.

Wifi is available throughout, however it is not strong enough to accommodate much more than checking your email. Cell phone coverage is decent.
There are no laundry services available. Hair dryers are provided.

Cost of the Tour



The total cost for the tour is $6500 USD per person for a shared room, and $7450 USD for a private room.  As noted, a private room does not guarantee a private bathroom.

The cost includes David’s services as tour leader and local guide, all accommodations for seven nights; all breakfasts, with the possibility of the occasional lunch or dinner on your own, depending on the day’s activities; all transport in country during the trip and transportation between our accommodations and the Piazzale Michelangelo in Florence.

Not included. Airfare to Italy, the occasional lunch or dinner.

Meals & Dietary Restrictions



A breakfast buffet is available in a common area at Fattoria la Loggia each morning. We provide all meals, with the exception of one dinner or the occasional lunch you will need to purchase on your own.

Meals are buffet-style feasts. There will always be a hearty vegetarian option, as well as plentiful fruit and vegetables. We do our best to cater to multiple dietary preferences; however, we are unable to offer gluten-free pasta or bread options. If you are gluten-free, vegan, or have other food intolerances, please bring along a few things to fill in the occasional gap, as there is not a market nearby.

Arrival & Departure



The closest airport is Florence (FLR); train station Santa Maria Novella. Whether arriving
by air, train, or car, you will make your way to Piazzale Michelangelo, a large car park overlooking the city, by 2:15pm on the first day of the tour. Any taxi driver will know where it is, and you should plan about 30 minutes for the trip from the airport, 10 minutes from the city center. We meet at the replica of the statue of David in the middle of the piazzale.

We determine departure logistics at the end of the trip based on everyone’s itineraries. We
will return you to the Piazzale Michelangelo in Florence in plenty of time to catch a taxi to your point of departure. We apologize that due to driving
restrictions in the city of Florence, we are not able to take people directly to their hotels or the train station. Please note that we need to be out of our accommodation by mid-morning, so we are not able to transport people in the

Walking & Hiking



Walks during the week will last from two to four hours over hilly terrain in warm to very warm weather. Most of
the walks are on seldom-used dirt roads. There may be short walks through fields and on more rugged pathways. Several of the walks have steep uphill portions.

As these walks are an important part of the tour experience, please be as realistic as possible in assessing your level of fitness before applying for the tour.

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