About the Renaissance Retreat at Castello di Postignano

Join me for an enchanting eight-day getaway at the Castello di Postignano, a medieval borgo (hamlet) originally built back in the…

All of our time painting from the model is spent inside our studio, the old church, while several afternoons will be spent painting en plein air under the awning of the Rose Garden.

If you are enthusiastic about portraiture and landscape as a subject, and are a beginner or advanced painter in pursuit of adventure and community, this is an experience for you!

Time not painting is dedicated to special activities enjoyed by all painters and accompanying family/companions: learning to cook, tasting wines,  swimming in the glorious outdoor pool, touring the beautiful city of Spoleto or horse-back riding on the plains near Casteluccio.

About Castello di Postignano

Castello di Postignano is an historic medieval fortified hamlet, located in Valnerina in the heart of Umbria, that had languished abandoned for decades.

A passionate and dedicated team has given it a new lease of life, as multi-building hotel, implementing this remarkable restoration project paying meticulous attention to every single detail.

The Food & Wine

La Casa Rosa is the real heart of the Postignano castle. Its cuisine is simple, and its philosophy is based on great care, respect for local traditions and excellent quality of the fresh ingredients. The welcoming staff will make you feel at home even if you just drop in for a coffee.

Our Chef Maria Massimiani, will tickle your taste buds with original combinations of traditional Umbrian dishes and from other parts of Italy too; there will be biscuits, cakes and many delicate details; Maria’s cuisine is primarily made of local seasonal ingredients.

Sign Up for the Next Retreat

The next Renaissance Retreat at Castello di Postignano will be:

October 16th to October 23rd, 2022

The minimum number of Painting Participants is 4.

The maximum number of Painting Participants is 8 per retreat.

The maximum number total–Painting Participants + Non-Painting Companions–is 24 per retreat.

Register below

Should none of the above dates work for you and your group, Custom Retreats are possible.  Please contact me using the Questions form for details.

For any and all questions that you don’t find an answer to on this web page, please use the Questions form to contact me or send a message via WhatsApp: +39 347 263 1033.

—Timothy Joseph Allen
Your Painting Teacher and Renaissance Retreat Organizer

Video Highlights from Past Retreats

2019 – October

2018 – October

Location of Castello di Postignano

The 8-Day Renaissance Retreat Schedule and Painting Program

We strongly recommend that you arrive in Rome at least the day before the scheduled pick-up and transfer from Rome to Castello di Postignano… and schedule your return flight for at least the day after the transfer from Castello di Postignano to Rome.

Day 1


9:00 am: Meet in Rome.  Exact location TBA.

  • Transfer to Castello di Postignano. Estimated time of arrival: 13:00


13:00 – 14:00: Lunch

14:00 – 15:30: Free Time

  • Swim / Spa / Relax / Rest

15:30 – 18:30:

  • Tour of Castello di Postignano
  • Introduction to the Painting Course


19:00 – 20:00: Activity for all

  • Wine Tasting

20:00 – 21:30: Dinner at Castello di Postignano

Day 2


8:00 – 9:30: Breakfast

9:30 – 12:30: Painting the Portait

  • Blocking in the Portrait


13:00 – 14:00: Lunch at Castello di Postignano

14:00 – 15:15: Free Time

  • Swim / Spa* / Massage* / Yoga* / Rest / Other

15:30 – 18:00: Painting the landscape


19:00 – 20:00: Aperitivo / Slide Show

  • Renaissance Portraits and the Tuscan Landscape

20:00 to 21:30: Dinner

  • Dinner at Castello di Postignano

Day 3


8:00 – 9:00: Breakfast

9:30 – 12:30: Painting the Portrait

  • Developing the lights and shadows


13:00 – 14:00: Lunch

14:00 – 15:15: Free Time

  • Swim / Spa* / Massage* / Yoga* / Rest / Other

15:30 – 18:00: Painting the landscape


19:00 – 20:00: Aperitivo / Slide show

  • Technical examination of famous portraits

20:00 – 21:30: Dinner at Castello di Postignano

Day 4


7:00 – 8:00: Breakfast

8:15 – 9:00: Transfer to Monteluco

9:15 – 15:30: Visit the sacred woods of Monteluco, then travel to Piatrico to hunt for truffles and enjoy a robust lunch.


15:30 – 16:15: Transfer to Spoleto

16:15 – 18:30: Tour of Spoleto, including the museum of archaeology, the ancient Roman theatre, museo del tessuto e del costume


19:30 – 21:00: Light Dinner in Spoleto

Day 5


8:00 – 9:00: Breakfast

9:30 – 12:30: Painting the Portrait:

  • First round of glazing…
  • What does it mean to paint a “skin tone”?

13:00 – 14:00: Lunch

14:00 – 15:15: Free Time

  • Swim / Spa* / Massage* / Yoga* / Rest / Other

15:30 – 18:00: Cooking lesson


19:00 – 20:00: Aperitivo / Relax

20:00 – 21:30: Dinner at Castello di Postignano

Day 6


8:00 – 9:00: Breakfast

Travel to Assisi*
– Guided visit of the Hermitage (1 hour)
– Visit the city, free time (1 hour)
– Lunch in Assisi
– Guided visit of the Basilica (1.5 hours)

This excursion is OPTIONAL and has an additional cost


Return to the Castello

17:00 – 18:00

  • Wine Tasting 


20:00 – 21:30: Dinner at Castello di Postignano

Day 7


8:00 – 9:00: Breakfast

9:30 – 12:30: Painting the Portrait

  • Final touches & Final Critique


13:00 – 14:00: Lunch

14:00 – 15:15: Free Time

  • Swim / Spa* / Massage* / Yoga* / Rest / Other

15:30 – 18:00: Pack up paintings


18:30 – 21:30: Farewell party and dinner

Day 8


7:00 – 9:00: Breakfast

9:30: Departure – Transfer to Rome. Estimated time of arrival in Rome: 13:00

Note: activities indicated with an asterisk (*) are extracurricular activities and are not included in the package price of the Retreat and must be booked in advance.  If you are interested in these activities, please let us know in the Registration Form below.

What Does it Cost?

The Renaissance Retreat at the Castello di Postignano is….  The total cost varies according to room choice and the number of people in the room.

The total cost for a single Painting Participant starts at €6,513.

If you add a companion who is not participating in the painting experience, the price starts at €10,000.

The final price is calculated once we know:

  • How many in the group are Painting Participants and how many are Non-Painting Particpants
  • Which excursion you prefer on Day 6: the trip to Assisi is more expensive than the horseback riding in Casteluccio di Norcia
  • How many want single apartments vs. how many want to share an apartment

The cost does NOT include all the extra-curricular activities (marked with an asterisk *) like yoga or massage that you can book while you are there, nor does it include airfare and/or travel to Rome.

We strongly recommend that you arrive in Rome at least the day before the scheduled pick-up and transfer from Rome to Castello di Postignano… and schedule your return flight for at least the day after the transfer from Castello di Postignano.

We also strongly recommend you buy travel insurance in the event you have to cancel.  Please read carefully our Terms and Conditions prior to booking.

Transfer to and from custom locations is possible at an additional charge.

How Do I Register?

Registration is a 3-step process.  Using the Registration form below, you can:

  1. Indicate the total number of people and the room category.
  2. Provide your Contact Information
  3. Confirm your Registration Information

Very important:

  • Payment is NOT due at the time of Registration.
  • After we have received and reviewed your information, we will send you a Request for Payment for a Deposit of 30% of the total cost per Painting Participant and Non-Painting Companion.
  • Once we have received the Deposit, your reservation and participation is secure.
  • The Deposit is non-refundable.
  • The remaining amount is due 60 days prior to the start of the Retreat.
  • Please read carefully our Terms and Conditions.

Questions Before You Register?

Please send us any questions you may have using the Questions form below and we’ll be happy to reply as soon as possible.

Meet the Painter and Organizer, Timothy Joseph Allen

Tim working on a recent portrait in his studio in Rome.

Greetings! My name is Tim.  I’ve been a figurative painter since 1992, I’ve lived in Italy since 1998, I’ve taught at The American University of Rome since 2006, and I have managed and directed my own painting school in Rome–The Painting and Drawing Art Studio of Rome–since 2010.

I’ve been doing the Renaissance Retreats now for over two years.  There is nothing quite like it: the locations, the landscapes, the people, the food, the wine and the painting all combine for an extraordinary experience.

I hope you’ll join me in Tuscany at La Moscadella!


For more about Tim and his paintings, please visit his website.

Oil Painting: The Portrait in a Landscape – What Can You Expect to Learn?

7 days work on a painting really isn’t that long, especially for a workshop intent on leveraging the full scope of oil painting: an oil sketch, underpainting, glazes, scumbles, etc..  However, there are ways to move things along in order to accommodate such a robust and ambitious endeavor, while also making it possible for you to have a sense of what steps could be taken in the future.

Working from a live model, our primary considerations will be:

  • Composition – setting the placement and scale of the subject within the landscape
  • Likeness – what does it mean to achieve a likeness in a portrait and what are the best strategies to do so?
  • Light –  management of light in connection to the specific subjects vs. management of light of the whole (the light pattern).
  • Glazes and Scumbles – how to use them and how each affects volume, space and atmosphere.


Testimonials from Previous Retreats at Other Locations

… the Retreat and the renaissance portrait painting course, well… it totally exceeded expectations. The ‘devils in the detail’ they say. Tim went to outstanding lengths to ensure the ‘studio’ was equipped with everything we would need and with every comfort. Each morning two gorgeous life models, Sara and Erika greeted us in the most impressive authentic renaissance costumes and Tim would begin the session with a demonstration and continue with help to each and all.

Regarding Castello di Potentino (and its wonderful and awe-inspiring host Charlotte Horton) it was inspirational… as were the wine tastings, stories, histories, lodgings, meals, lovely-young-volunteers and surrounding vistas. Tim chose exceedingly well with this beautiful place on earth. All the extras were such a treat and yes we all fell in love with the Michelin Chef Roberto Rossi and his 5 star restaurant in Seggiano.
Honestly I could go on and on, I’m afraid I have already, but I cannot thank Tim enough for this life-changing experience

An experience I will never forget and a trip of a lifetime. It was wonderful to be able to take a week out of my busy life to reconnect with nature and my creativity. I learnt so much from Tim in a short time improving my painting skills dramatically. As I never had the opportunity to study art at a university level I feel that after what Tim has taught me I have confidence to produce more professional paintings. I couldn’t think of a more perfect atmosphere to paint in. From painting in a studio room of a medieval Tuscan castle with live models to landscape painting on a warm autumn afternoon in an olive grove looking over vineyards, forests and ancient villages. I am so grateful for this amazing opportunity.

Timothy Allen knows Renaissance art. With intelligence and humour he inspires his students to paint from life, fortified by the fabulous food and wine of the Castello. Under Tim’s guidance I actually produced a portrait, while living in a castle in Tuscany. It’s hard to convince myself that this really happened! But it did and I’ll never forget it.

The Renaissance Retreat was an experience of a lifetime. The castle setting was perfectly conducive to learning the techniques of the Masters under Tim’s excellent instruction and inimitable flair. It was immensely satisfying to see the quality of work achieved in such a short time. Tim put together a programme of intense study more than balanced with unique and memorable extra-curricular activities. I recommend the Renaissance Retreat highly.

Painting in Tuscany, in a Castle, with a live model, what more can be said! I’m still in awe that I had this experience of a life time. If you have the opportunity to take advantage and make it a reality, I can highly recommend it.

The Renaissance Retreat didn’t just meet my expectations, but exceeded them.  Tim went above and beyond to be accommodating, friendly, helpful and a great chauffeur as well.

Tim offers a week of learning to paint from a model and en plein air in a Renaissance style. That is the focus of the week, and it is an intense learning experience. I went to sleep at night thinking about what I would do next with my painting, and woke to thumb through photos of paintings by the Italian masters. Tim is a great instructor, and led us through the process of slowly building a painting. We had an excellent, lovely model and a beautiful setting for the backdrop to our developing portraits. Staying at the castle was like finding a little piece of heaven, and the food, wine and conversation were of the highest quality. Our restaurant outings were top notch. It was a week I will never forget.

The Renaissance Retreat was one of the highlights of my life, especially for two of my passions: painting and food. The castle and the landscape were beautiful. The food and wine plentiful and delicious. Tim provided a once-in-a-lifetime opportunity to learn and apply renaissance oil painting techniques with inspiring subjects (live, costumed model and beautiful Tuscan landscapes). The opportunity to learn from a Michelin chef and from artisan local cheese-makers added so much to the experience. Thank you Tim!

I highly recommend this amazing trip to Potentino, with delicious food, divine wine and inspirational art classes!
Tim is an excellent and passionate art teacher who gently encourages his students to push forward! We received all the art supplies we needed, worked with a beautiful and professional model and painted plein air too! The time I spent at the castle with him and the amazing group of friends I made there, inspired me grew as an artist and also got me motivated to carry on with all of what I’ve learned.
I will never forget this magical experience. Thank you!

This painting retreat exceeded my expectations. There was an intense focus on painting and Tim was patient and instructive and always willing to answer questions and demonstrate techniques. The castle was the perfect setting … beautiful and inspirational…enhanced by its hostess, Charlotte, who created unbelievable meals with an emphasis on fresh, local products. All meals were shared at large community tables that provided an opportunity for us to meet other guests and a charming group of young volunteers.