The Idler Literary Florence Retreat, September 2024


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SOLD OUT Retreat with the Idler to Florence and the Tuscan countryside, 7-14 September 2024


The city of Florence and its surrounding countryside have inspired writers from Dante to Henry James. As Charles Dickens exclaimed when he first visited, “How much beauty of another kind is here, when, on a fair clear morning, we look, from the summit of a hill, on Florence!”

In the company of Idler editor Tom Hodgkinson and Idler Academy director Victoria Hull, you’ll follow in the footsteps of these poets and authors to find creative inspiration in the Florentine streets and Tuscan hills. We’ll spend a week idling, feasting, and learning in beautiful surroundings and in excellent company. 

It’s just the thing to give your soul a boost.

Join us for the Idler Literary Florence Retreat.  

Literary Florence Retreat

About the programme

On the Idler Literary Florence Retreat, we’ll visit the Benedictine Abbey of Vallombrosa, an 11th-century monastery set in the mountains that provided John Milton with inspiration for Paradise Lost. We’ll take a day trip to Fiesole, the hilltop town overlooking Florence where Boccaccio set his famous Decameron. We’ll wander through the streets of Florence’s Oltrarno, learning about the poets who made this bohemian neighbourhood their home. There will be walks in the Tuscan hills, trips to medieval churches and towns, and a chance to see some beautiful Renaissance art. 

Your tutors will be Idler editor Tom Hodgkinson, experienced tour guide and art historian Molly McIlwrath, and literary historian Cathleen Mair. Idler Academy Director Victoria Hull will be your host.

Tom Hodgkinson will discuss medieval values and idling in the lives and writings of Boccaccio, Dante and John Milton.

Molly McIlwrath will show us around Dante’s medieval Florence. We’ll see his house and the church where he met his love Beatrice and we’ll learn how he shaped the literary landscape of the Italian Renaissance.

Cathleen Mair will tell us about the English poets who travelled to Florence to fuel their creativity. We’ll read the works that sprung from their travels and wander the streets that inspired them.

Expect good food and wine, interesting company and plenty of time to idle in a stunning location. We’ll be staying at the lovely eco-resort Podere Castellare, around 30 mins outside Florence.

Places are extremely limited on the Idler Literary Florence Retreat so secure your place now with a £500 deposit.

“A stress-free holiday with no pressure to do anything and just be idle.” 

“The food was incredible; the Idler hosts were wonderful, knowledgeable and enthusiastic…”

“The most memorable things were the raucous conversations around the dinner table.”

“Great food, really good people, excellent hosts.” 

About Podere Castellare

The Idler Literary Florence Retreat takes place at Podere Castellare, an eco-resort located in the stunning countryside, about 30 mins from Florence. Podere Castellare is a working organic farm, producing wine, olive oil, fruit, vegetables and the first Tuscan craft gin, Peter in Florence, made using local botanicals from the estate. You’ll have access to the pool, tennis court, spa and a small gym. There are plenty of local hikes to explore. There is also an honesty bar available at the hotel. The rooms are simple but stylish, and are cleaned daily. 

Loaf by the pool overlooking the Chianti hills
The simple rooms at Podere Castellare all have ensuite bathrooms


Tom Hodgkinson is editor of the Idler and author of several books including How to be IdleHow to be Free and An Idler’s Manual. He founded the Idler in 1993.

Molly McIlwrath is a professional art history guide in Italy with 13 years of experience leading tours in and around Florence. Before becoming a guide her formal academic degrees were in Italian Literature with a focus on early modern Italy and specifically late 16th and early 17th century writers in Venice during her PhD studies at the University of Wisconsin-Madison. She now lives just outside Florence in the historic centre of Pistoia. Her tours have been recommended by the Lonely Planet, the Guardian and Independent.

Dr Cathleen Mair is an intellectual and cultural historian of eighteenth-century Europe, with special expertise in the romantic period. She teaches at Queen Mary, University of London. Alongside her academic research, she writes for the Idler, and helps run the Idler Festival and the Idler Retreats. Cathleen grew up in Florence and currently lives in Stroud.

Victoria Hull is director of the Idler Academy and founder of the Clerkenwell Literary Festival.

Boccaccio’s bright young things spent lockdown telling bawdy tales in the hills of Fiesole

More about the Programme

The Idler Literary Florence Retreat programme is designed to provide great ideas for living, lots of fun, good dining and plenty of time for idling. All activities, talks, walks and days out are optional.

Each day will start with an excursion. Afternoons are for napping, tennis, reading, swimming and local walks. An aperitivo lecture is given at 6pm. Dinner is at 8pm.

Please note the itinerary below is subject to change but gives you a good idea of what we’ll be doing. We’ll also provide reading lists and a city guide should you wish to do some exploring on your own.

Saturday 7 September

Arrivals at Podere Castellare.

Aperitivo lecture: Tom Hodgkinson on idling, medieval values and the city of Florence

Sunday 8 September

A tour of Dante’s Florence with Molly McIlwrath and discover what life was like in the medieval city

Lunch at a pizzeria

Visit to the Church of Santa Croce to see the monuments dedicated to Dante and Machiavelli, the frescoes of St Francis by Giotto, and the chapel designed by Brunelleschi

Monday 9 September 

Guided visit to the 11th-century Abbey of Vallombrosa. Follow the trail of the chapels to visit Paradisino, where John Milton stayed in the 17th century

Picnic in the gardens of the abbey

The Abbey of Vallombrosa in the snow, (photo by PROPOLI87 – Own work, CC BY-SA 4.0)

Tuesday 10 September

Optional extra: wine tasting and light lunch at Castello di Nipozzano, a 1000 year-old castle that is home to renowned Chianti wines and owned by the historic Frescobaldi family. Price around 60 euros, including transport. There is an option to hike to Castello di Nipozzano from Podere Castellare (those who are not participating in the wine tasting can join for the hike).

Aperitivo Lecture: Cathleen Mair on the romantic poets in Florence

Wednesday 11 September

A walking tour of the bohemian Oltrarno, with visits to Casa Guidi, home of Elizabeth and Robert Browning, and the Boboli gardens.

Lunch at a traditional trattoria in Santo Spirito.

Free time in Florence


Wine Tasting at Castello di Nipozzano in the Tuscan hills

Thursday 12 September

Excursion to Fiesole, the hilltop town overlooking Florence, where we’ll visit the 14th-century Franciscan monastery, the Roman amphitheatre and the villa to which the group of friends allegedly fled from the Plague in Bocaccio’s Decameron.

Lunch in Fiesole

Aperitivo Lecture: Tom Hodgkinson on idling in the works of Milton, Boccaccio, and Dante

Friday 13 September

Local hike in the Chianti countryside.

Picnic by the pool.

Optional extra: Cooking Class. Learn to cook Tuscan classics like cantucci or pasta with rabbit ragù with Castellare’s chef. The class includes a glass of wine. Price around 40 euros. 


The view of Florence from Fiesole (Photo by Rufus46 – own work, CC BY-SA 3.0)

Saturday 14 September



SOLD OUT Noce apartment comprises two separate, ensuite double bedrooms + one sitting room with a kitchen. It can be shared between 2 to 4 people (across two double bedrooms). Please contact us for more details.

SOLD OUT £1,895 per person for a single occupancy, ensuite room

SOLD OUT £1,750 per person for a shared, ensuite room

SOLD OUT £2,500 (single occupancy) or £3,600 (shared occupancy) for the Mandorlo suite (one double bedroom, one sitting room with sofa bed, one bathroom, for 1-3 people)

A deposit of £500 is payable now. The remainder will be due three months before the retreat. Please email to let us know which type of room you want or if you have any questions. Please also let us know if you have any accessibility needs so that we can ensure you get a suitable room.


View of the vineyards around Castellare

What’s Included

  • All talks, museum tickets, and trips
  • Accommodation and tourist tax
  • All dinners including wine
  • Six out of seven lunches (including a drink)
  • All breakfasts

What’s Not included

  • Flights
  • Transport between Podere Castellare and the airport. Where possible, group transport can be arranged at an extra cost
  • Wine tasting, gin tasting, and cooking class
  • Additional alcoholic and soft drinks
Florence Retreat
Brunelleschi’s famous dome on the Cattedrale di Santa Maria del Fiore. Pic by Florian Hirzinger, CC BY-SA 4.0


Please be aware that retreat participants must have a good level of fitness and mobility as there will be a fair amount of walking. We will also be standing in churches and galleries for at least an hour at a time, and walking round uneven medieval streets. If you have any questions about this, or if you’d like to enquire about possible adjustments, please email


We recommend the following flights for which we will arrange a group transfer:

7 September
Vueling flight VY6205, London Gatwick to Florence, departure at 9:00

14 September
 flight VY6206, Florence to London Gatwick, departure at 13:15

Transport between Florence and Castellare will cost around 25 euros each way per person, depending on numbers.

There are other flights to Florence that day, should the times above not suit you (including a flight from London Heathrow, departing at 8:15, which would allow you to take the group transfer). From Florence airport, you can get a cab to Podere Castellare.

Alternatively, there are flights to Pisa and Bologna, from where you could travel to Castellare (you could either hire a car or travel by train to Florence or Pontassieve and then get a cab). 

Pontassieve is the nearest train station. It is about 15 minutes by car. 

Terms & Conditions

– Please ensure you take out travel insurance.

– It is a condition of accepting your booking that you provide proof of personal travel insurance, including cancellation insurance for medical reasons, redundancy, jury service etc. for all members of your party. Please note that the use of Podere Castellare (the facilities, grounds and swimming pool) are entirely at the user’s risk.