Tim O’Neill
Artist, Educator, Creative Coach
Tim O’Neill began his journey in the arts as a Navy combat photographer, learning to see the world through both a technical lens and a storyteller’s eye. Over four decades later, his creative practice has grown to include oil and cold wax, resin, encaustic, acrylics, and digital media, with works now held in private collections around the world.
Beyond the studio, Tim has spent much of his career teaching, coaching, and studying the psychology and neuroscience of creativity. He draws on research in flow science and learning to help artists understand the mental traps that hold them back, perfectionism, imposter syndrome, comparison, procrastination, fear, and self-doubt. His teaching reframes these challenges not as personal failings but as predictable barriers every artist can learn to navigate.
Through his workshops, writings, and Rogue Artist Brigade community, Tim creates spaces where artists of all levels can break through resistance, reconnect with play, and rediscover the joy of making.
workshop description
A workshop for artists ready to break free from hesitation, perfectionism, and self- doubt. Together we’ll dismantle the barriers that keep you stuck, the blank canvas, the inner critic, the endless comparisons, and open space for flow, play, and fearless expression. This isn’t about making perfect art. It’s about rediscovering the joy of creating, unbound.
Step into a castle where centuries of art history echo in every stone, and let the setting itself remind you that art is more than technique, it’s transformation.
This workshop is for artists who are ready to set down hesitation, perfectionism, and self- doubt. Together, in the rolling hills of the Marche region, home to masters like Raphael of Urbino, Gentile da Fabriano, and Federico Barocci, we’ll quiet the inner critic, release the weight of comparison, and open space for flow, play, and fearless expression. Through guided exercises and reflective practice, you’ll rediscover the joy that first drew you to create.
While the real breakthrough happens inside, the experience around you nourishes that journey. Mornings of exploration and making. Evenings gathered at long tables, savoring food and conversation. Time to wander the hills, breathe the air, and feel the rhythm of a slower world. You won’t leave with just sketches or studies. You’ll leave with a renewed relationship to your practice, memories rooted in one of Italy’s most beautiful regions, and the confidence to carry creative freedom into every corner of your art and life.
Rediscover what it means to create, unbound.
$4,499 per person ($800 fully refundable deposit*)
September 13-19, 2026
Dates and pricing
BONUS COMPANION PACKAGE
Non-artist discount of $200. Piero will be your guide as you explore opportunities to see surrounding historical villages, horseback ride, golf, visit a Roman archaeological site, visit nearby festivals, visit the Church of the Dead, take a bell tower tour, discover sunflower fields or just eat and drink with the locals!
FOR PAINTERS ONLY: EARLY SIGN IN discount of $200
*Terms and Conditions, including our refund policy, are located on the Book Your Tour page.
Private transportation to and from Bologna BLQ airport to Mercatello Sul Metauro
6 night accommodation with breakfast at the charming B&B Castello della Pieve all bedrooms ensuite (NO supplement for single)
5 Lunches and 6 Dinners with full beverage service, including wine
Welcome Aperitivo
Stunning studio
Private trip to Urbino
Entrance to Raphael’s childhood home
Private wine tasting at “La Montata” with the only smoked passito wine in the world
Private trip to Fabriano and paper workshop with master Sandro Tiberi
Private bookbinding workshop in Urbino with master Carla Luminati
Visit at last charcoal artisans in Italy
Private transportation on all excursions
Entrance to the “Church of the Dead”
Private tasting and visit at the Einstein of Cheese
Exclusive week-long class with Tim, 15 hours workshop guaranteed including plein air sessions
Activities for non-painters as listed in the itinerary
Week-long private guide and international sommelier Piero
whats included
itinerary
Day 1- Sunday, September 13
- Arrival (*Bologna BLQ is the recommended airport). In our commitment to making your traveling experience to Le Marche as easy and convenient as possible, your host, Piero Pagliardini, will meet you at the airport (*see time stipulations) and escort you to the B&B. Castello della Pieve
- Take time to settle in, unpack and explore before we all meet up. Your accommodation is within walking distance of shops, markets, restaurants, and village life unspoiled by time.
- Tim, and our host and native Marchigiano, Piero Pagliardini, will welcome you over drinks and give an overview of the week to come. Then pizza time! Enjoy the best pizza in town in an authentic Italian pizzeria. End the night with a stroll, a nightcap, and a good night’s sleep.
Day 2- Monday, September 14
- Breakfast at the hotel, then we will go to a Creative paper workshop in Fabriano. We will leave for the city where the art of paper making has been alive for centuries! Fabriano is the most important paper production centre of Europe. We will learn directly from the master Sandro Tiberi! https://www.sandrotiberi.it/
- Light lunch in Fabriano
- Plein air session in Fabriano square
- Return and relax
- Dinner together.
Day 3- Tuesday, September 15
- Enjoy a local breakfast at the hotel (have you tried the chocolate pastries yet?)
- Morning excursion to Urbino, Raphael’s childhood home. In a loose yet structured manner, we'll wander the main squares and winding medieval pathways. You will be immersed in local color, texture, and flavors (while eating everything in sight) as well as examining architectural motifs, contemporary art, and design, all the while collecting ideas that will inspire your art.
- Entrance to Raphael’s childhood home.
- Please bring your sketchbook and/or materials for an amazing plein air session in the city center and at a panoramic lookout.
- Lunch near the town square.
- Ready for a bookbinding workshop in the afternoon at http://www.stamperiadartecavirginio.it/en/
Carla, an artist and printer, will lead us in this unforgettable experience where you will bind the paper made in Fabriano into your own handmade book. Participate in this ancient tradition in an inspirational location for your story in Italy.
- Dinner together.
Day 4- Wednesday, September 16
- Morning drive through the Le Marche region, trip to Cartoceto and Velltorio Belltrami, with opportunities to sketch, photograph, or reflect.
- Lunch together, followed by an afternoon of solo exploration and optional studio experiences.
- Stations set up for mark-making, journaling, intuitive art-making, or rest. Optional group collaboration activity.
- Dinner together.
Day 5- Thursday, September 17
- Morning in the studio
Non painters TRUFFLE HUNT with a professional, local guide. Our seasoned truffle hunter, along with his dog, will lead us on a walk through the forest in search of truffles. Mud boots will be provided. If hiking isn’t your thing, spend the afternoon shopping, relaxing in a café and exploring local treasures in the village.
- Break for lunch
-Dive into village life in Urbania, including a visit to the famous “Church of the Dead” and other historical sites. Learn about Urbania’s traditions, spanning centuries, including its rich ceramic art culture.
- Private wine tasting at a tiny, local winery (a secret, local gem!) that makes the only smoked Passito wine in the world!
- Dinner together
Day 6- Friday, September 18
- Morning in the studio
- Visit to the last and famous charcoal makers in Italy. We will visit the famous coal makers in the small village of Parchiule along the Auro river. Meet the last charcoal artisans carrying out this traditional practice amongst breathtaking scenery.
- Free time to pack at the hotel.
- Meet that evening for a farewell happy hour and dinner. Share your art with the group and then raise a glass (or two, or three!) to our week in Le Marche. Cin-cin! Cheers! And a warm salute until next year!
- Group dinner in town .
Day 7- Saturday, September 19
-We recommend booking a night or two in Bologna at the end/beginning of your trip to explore this beautiful city and to make your departure/arrival flights more convenient. Please contact us for recommendations.
Time Stipulations
-Pick-ups at BLQ Bologna airport and Bologna Centrale Train Station will be offered between 12:00-3:00 p.m.
-Depart the B&B at 10:00 AM. Departures at BLQ Bologna airport and Bologna Centrale Train Station will be offered from 1:00 pm onward. In order to arrive for your flight with ample time, we recommend scheduling departing flights after 3:00 p.m.
- Pick-up and Departures from other locations, or at times outside these parameters can be arranged at an additional fee.