Discover the Timeless Beauty of Puglia 

Our painting holiday in Puglia takes you to one of Italy’s most captivating regions, where whitewashed towns, centuries-old olive groves and a spectacular coastline provide endless inspiration for artists. Staying in two carefully chosen boutique properties, you’ll experience two very different sides of Puglia. Begin your journey at the peaceful Masseria Marzalossa, surrounded by ancient olive trees and rolling countryside, before moving south to the atmospheric old town of Gallipoli, where life revolves around the sea and the narrow streets echo with centuries of history. 

From elegant limestone streets and bustling fishing harbours to quiet piazzas and dramatic coastal views, every day offers a new opportunity to paint. Travelling at a relaxed pace, you’ll have time to observe, sketch and absorb the character of each location before bringing it to life in your travel journal. 

Inspiring Locations for Your Artwork

Throughout the week, we’ll visit a carefully curated selection of painting locations, each offering its own distinctive character. From the whitewashed streets of Ostuni and the elegant waterfront of Monopoli to the Baroque splendour of Lecce and the timeless beauty of Gallipoli’s historic old town, you’ll experience the remarkable diversity that makes Puglia one of Italy’s most rewarding regions to explore. Our itinerary also includes time to paint at our beautiful masseria, where ancient olive groves and traditional Puglian architecture provide a peaceful setting before continuing south to the Salento coast. 

Bringing Puglia to Life in Your Journal

This painting holiday in Puglia focuses on capturing authentic moments in your travel journal, transforming everyday scenes into lasting memories. With Simon’s expert guidance, you’ll develop techniques to simplify complex subjects, capture beautiful light and paint expressive sketches that reflect the atmosphere of southern Italy. Whether you’re an experienced painter or picking up a brush for the first time, you’ll be encouraged to paint with confidence while developing your own personal style. 

A Celebration of Puglian Food and Culture

Puglia is renowned for its warm hospitality and exceptional food, and these experiences are woven naturally into the week. Between painting sessions you’ll enjoy leisurely lunches, fresh seafood, locally produced wines and simple regional dishes prepared using outstanding local ingredients. Staying in both the countryside and Gallipoli allows you to experience two distinct sides of Puglian life, with optional cooking experiences and spa treatments available to make your stay even more memorable. 

Expert-Led Tuition for All Levels

Whether you’re a beginner or an experienced artist, our personalised guidance will help you grow in confidence and develop your skills.
Learn how to:

✔ Simplify complex scenes into strong, balanced compositions
✔ Develop confident sketching techniques while painting on location
✔ Use expressive watercolour techniques to capture the atmosphere of your travel

A Stress-Free Creative Escape

Everything is taken care of, allowing you to fully immerse yourself in the experience. From carefully selected boutique accommodation and exceptional local cuisine to transport, painting equipment and expert tuition, every detail has been thoughtfully arranged. All you need to do is relax, paint and enjoy discovering one of Italy’s most captivating regions.

Join us for an unforgettable painting holiday in Puglia, where wonderful food, inspiring locations and creative experiences combine to create memories that will stay with you long after you return home. 

Meet Simon & Monica

Having spent decades in commercial art, Simon has discovered immense pleasure in capturing moments through watercolor, deeming it the perfect medium for the traveling artist. His passion was reignited during a 7-month solo motorcycle journey from England to Kathmandu, documented meticulously in an illustrated journal, which led to the book Tea with Bin Laden’s Brother, a cult classic in the motorbiking world.

Now, on your painting holiday in Spain, he will guide you in mastering watercolor painting, imparting that elusive extra charm to your art. With a lightness, humor, and patience that makes learning feel effortless, Simon ensures that every painter – no matter their experience – feels encouraged and inspired. His commitment is not just to teaching techniques but to helping you create timeless memories, ensuring that your artistic journey lingers forever.

Monica is the heart of your painting holiday, ensuring everything runs smoothly so you can relax and immerse yourself in creativity. She first met Simon while managing a Creative Department at a marketing agency in Bath (UK), where she commissioned him for an illustration project.

Growing up in a creative community and leading a team of creatives, Monica understands that a truly inspiring holiday isn’t just about painting – it’s about creating a welcoming, supportive space where creativity can flourish. Her exceptional organizational skills mean you don’t have to worry about a thing – just enjoy the experience.