Winchester, UK
Join Ian Fennelly for a Week-Long Urban Sketching Retreat in the Historic City of Winchester, England
- 15 - 21st August 2027
- 15 Spots
- 5 Workshops
15th - 21st August 2027
Fifteen strangers arrive on a Sunday. By Friday evening, they don’t want to leave.
Here’s what happens in between.
You’re sitting by a low stone wall outside Winchester Cathedral. Morning light catching eight centuries of Gothic stonework. Your sketchbook open. A pen in your hand. Ian Fennelly beside you showing you where to start and what to leave out.
Around you, fourteen other people doing the same thing. By the second morning, they’re swapping tips over coffee. By Wednesday, they’re saving seats for each other at dinner.
That’s the part you can’t get from a screen.
Five days. Five locations. A different part of Winchester each morning. Ian teaching at your shoulder every day.
The Urban Sketch Team – Rebecca, Kayla, and Annette – handling everything else.
And at the end of it, a sketchbook full of work you didn’t know you could do.
Where You'll Be Sketching
- Winchester Cathedral – where Ian shows you how to capture 900 years of Gothic stonework with a few confident lines, and why the shadows do half the work for you.
- The Great Hall – home to the legendary Arthurian Round Table. A masterclass in sketching scale without getting lost in detail.
- The medieval Butter Cross – sitting in the bustle of the high street, learning to sketch living scenes with people moving through them.
- Cobbled lanes and Norman archways – where every wrong turn reveals a sketch you didn’t know you needed
- The River Itchen and St Cross – willow-framed bridges, water meadows, and the riverside walk past guests consistently call their favourite, ending at a medieval almshouse that looks like it was built to be drawn
"The whole team are so professional and attentive ensuring that everyone on our retreat was confident and able to produce amazing work whatever their previous experience.
"Learning the techniques that Ian uses in his sketching of such complex subjects is broken down into logical steps with plenty of demonstration, help and encouragement along the way. By the end of a fun week individual progress is guaranteed!"
Trip Information: Sketch Winchester
We’re thrilled to present this unique opportunity to join Ian Fennelly and the Urban Sketch team for a week-long sketching retreat, in the historic City of Winchester.
DURATION: 6 nights
LOCATION: Winchester, UK
VENUE: Winchester Royal Hotel
SPACES: 15 (+ Companions)
DATES: 15th – 21st August 2027
“5th in-person retreat with Ian. Great teacher. Nice, professional, well-organized company. Learned things previously taught but couldn’t absorb before.” – Elisabeth S
Your retreat begins at the Winchester Royal Hotel on the evening of Sunday, August 15th, where you’ll meet with Ian and the team and your fellow sketchers for an informal welcome reception with drinks and snacks.
Over the next 6 days, Ian will lead you to some of Winchester’s most iconic and beautiful sketching locations. Each morning, you’ll head out to a different location in the city, spending the day sketching alongside your fellow participants with guidance and feedback from Ian.
The week concludes on Friday evening, August 21st, with a farewell dinner where you’ll be able to share your sketchbooks and celebrate a fantastic week of urban sketching in the historic City of Winchester.
What’s Included:
Your Winchester Sketching Retreat package covers everything you need for a wonderful week of art and exploration:
- Six nights’ accommodation at the Winchester Royal Hotel
- A full English or Continental buffet breakfast each morning
- A welcome evening with drinks and introductions on the first night
- Daily guided on-location sketching workshops with Ian Fennelly (Monday – Friday)
- Dedicated afternoon studio space.
- All Urban Sketch Course teaching materials and handouts
- A celebratory farewell dinner on the final evening
- Your Urban Sketch goodie bag
Not Included:
To keep the package flexible, the following are not covered:
- Travel to and from Winchester
- Transfers to/from the hotel on arrival and departure days
- Lunch and evening meals (other than the welcome drinks and farewell dinner)
- Art materials and painting supplies
- Gratuities and tips
- Luggage handling and porterage
- Travel insurance (strongly recommended)
- Personal spending and any other individual expenses
- Anything not specified in the inclusions above
Explore the Hotel tab for full details about where you’ll be staying during your time in Winchester.
For your 6-night stay we have selected the Winchester Royal Hotel which is perfectly located in the heart of Winchester. The hotel is a pleasant walk away from all of our sketching destinations.
The hotel is included within the price of this trip (double or twin rooms are available).
Room amenities include:
- Full English/Continental buffet breakfast
- Free WiFi internet
- Over 100 digital TV channels
- Tea/coffee making facilities
What happens when you book
You’ll receive immediate confirmation and a full Winchester prep guide – accommodation recommendations, travel tips, what to bring, and a direct line to the team for any questions.
I’m a beginner, is this trip for me?
Yes. Ian will assume no prior experience and will take you carefully through each of the steps in his process as he is doing it – from blank pages to the shapes and colors he uses, through to finished artwork.
What do I need to bring with me?
We recommend that you bring with you an A3 Sketchbook, your watercolour paints and brushes, a small pot for water, brush pens and fine liners, a small chair to sit on, drinking water, sunscreen, and a raincoat (it is the UK after all!) and your best sketching attitude!
For a full materials list, take a look here.
Will we be drawing and painting on location?
Yes. This is authentic urban sketching and Ian will be taking you through all of the steps while we’re there on-location; from blank page to sketching everything out, to applying the paint and fine liner detail work, there and then. There will also be lots of opportunities and a special area back at the hotel to finish and refine your work should you wish to.
What’s the difference between this Sketching Retreat and just doing an online course?
Firstly, while our online courses are a wonderful way to learn urban sketching, truthfully, nothing can replicate the experience, knowledge, and sheer pleasure you will gain from sketching live on location with Ian Fennelly.
Secondly, there is a vast difference between watching and learning from Ian through online tutorials, and actually being there on location, learning and sketching alongside him.
You see, urban sketching is not only about the lines you put on your paper, but about developing and refining the skill of thinking, working, and responding to your environment in real time. And that can’t be developed through sketching from photos. But this is where Ian excels and it’s this level of detail and expertise that you are getting through being there on-location with Ian Fennelly.
Finally, Ian is not only one of the most respected urban sketchers in the world, but he’s also a trained and highly experienced teacher who will be there each day to personally help you to improve on those areas you might be struggling with. The value of having him there to personally guide and coach you are far beyond what you can gain through any online course.
And of course, along with this, you are getting a highly enjoyable week’s experience with a group of fellow sketching enthusiasts! Not only will you make wonderful art together, but you’ll make some special friendships too.
Anything else I should consider?
We strongly recommend that you have a good travel and medical insurance policy in place to cover you in the event you must cancel your trip and any emergency medical services you might need while travelling in a foreign country. Fennelly Art Ltd and V-Learn Ltd t/a Urban Sketch Course cannot be held responsible for any accident/loss or injury incurred during the course of the trip.
Will I have to share a room?
No. Each participant will have their own private room at The Hotel. You will only share a room if you choose to bring a travel companion with you, such as a friend, partner, etc.
Can I extend my stay or upgrade my room?
Yes. If you wish to make any adjustments or upgrades to your room, please contact us at: [email protected]
Can I bring a partner or friend?
Yes. Non-sketching companions are welcome if they are sharing with a sketcher as there is plenty to see and explore on this trip.
What is your cancellation policy?
Here’s what you need to know:
- The cost of the trip is non-refundable once booked and paid for.
- In the unlikely event this trip is cancelled you will be issued with a 100% refund.
- If you are unable to attend the event after booking, we will strive to resell your place on your behalf. A refund will only be issued if we manage to successfully resell your place, minus a cancellation fee for the additional work and fees incurred in reselling your place.
Please read our full workshop terms and conditions here.
Who do I contact with any questions about the trip?
Contact our support team at any time on support@urbansketchcourse.com. We will be delighted to help you.
Click all the tabs above for full details of everything included in this Sketch Winchester retreat
"For those of you who see Ian on the screen, you know how good he is. But when you come to a workshop, you see what an amazing teacher he is.
"I worked for 39 years in education and I have to say, this is one of the best teachers I have ever met. For a beginner, I’ve come through the precipice. And I think I can take that step to become an artist."
Watch What Makes an Urban Sketch Retreat Special:
Booking Information
Places are limited to just 15 participants. Each year our retreats have sold out within 3-weeks.
To avoid disappointment secure your spot using the payment options below.
This is a rare chance to learn in-person from one of the world’s finest urban sketchers and teachers, learn new skills, build confidence, meet new people, make wonderful art, and create special memories that last a lifetime.
EARLY-BIRD PRICE - UNTIL APRIL 30
Includes:
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5 On-location Workshops
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6 Nights Accommodation
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Daily Breakfast
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Goodie Bag
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Dedicated Sketching Studio
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Welcome Reception
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Farewell Evening Meal
Just 15 spots, a city worth drawing, and the best urban sketching teacher in the world standing right beside you for a week.
"Walking into this retreat, I felt nervous. Stepping out of the comfort of photo references and into a lively square with shifting sunlight, people passing by, and a blank page waiting for me felt daunting.
"So grateful for Ian. And what made the biggest difference was having other sketchers right there beside me. Their presence, encouragement, and the simple comfort of knowing we were all facing the same challenges made the whole process feel lighter and more enjoyable. It truly helps to share the moment with people who understand the wobble and the wonder of drawing outdoors."
"If you have an in-person workshop with Ian and you have some problems, you can say ‘Ian, please help me’ and he comes directly to you and shows you. That’s something you just can’t do on an online workshop - you have to unmute and ask him to come to you with a pencil.
More Questions?
You might be a complete beginner who has never held a fineliner. Great! That’s exactly where most people start with Ian, and it’s a perfect starting point because you’ve got no bad habits to unlearn – and a week of personal guidance ahead of you.
You might be someone who’s taken Ian’s online courses and now wants to step up a level and experience what it’s like to learn directly from him, in person, in a city that practically begs to be drawn.
Or you might be someone who came on a previous retreat and already knows what impact this week has. (Some of our guests are on their fifth!)
What you don’t need to be is “talented.” You don’t need to be experienced. You don’t need to have it all figured out before you arrive.
You just need to want to spend a week doing something entirely for yourself, surrounded by people who understand exactly why that matters.
Every day follows a rhythm that our past retreat guests describe as “intense but never overwhelming.”
After a good breakfast, mornings start with Ian demonstrating at the day’s location – breaking down what looks impossibly complex into the logical steps that have made him one of the most respected urban sketching teachers in the world.
Then you sketch. Ian moves between the group, working with each person individually. This is the part you simply cannot get from a screen. The moment where he stands at your shoulder and says, “See that roofline? Forget the windows. Just catch the angle” – and suddenly something clicks.
Afternoons are typically spent back at the private studio adding later steps, refining your work, and making new breakthroughs.
Throughout the week you’ll be supported by the Urban Sketch team. Rebecca, Kayla, Neil & Annette are there for one reason: to make sure you don’t have to think about anything except your sketching. Logistics, questions, supplies, dinner recommendations – it’s all handled. One past guest described it as being like “travelling with Mum and Dad again, only more fun.”
Winchester is one of England’s oldest cities. A former capital. A place where medieval, Georgian, and modern sit layered on top of each other.
It’s a treasure trove for sketchers – Norman archways, timber-framed buildings, hidden courtyards that open up around every corner.
In a single day, you could sketch:
- The soaring nave of Winchester Cathedral – one of the longest Gothic cathedrals in Europe
- The Great Hall, home to the legendary Arthurian Round Table
- The medieval Butter Cross on the bustling high street
- Cobbled lanes and Norman archways that haven’t changed in centuries
- The gentle River Itchen, with its willow-framed bridges and water meadows
- St Cross – the medieval almshouse at the end of what may be the most picturesque riverside walk in southern England
Every location is walkable. Every angle is worth drawing. And Ian knows exactly which spots will challenge you, teach you, and – by the end of the week – make you realise you’re better than you thought.
Ultimately, Winchester is the kind of city where you could fill ten sketchbooks and still feel you’d only scratched the surface.
No – and that’s deliberate. Part of what makes Ian exceptional is his ability to read the conditions on the day and put the group in the right place at the right time.
If the light is better by the river in the morning, that’s where you go. If a street is too crowded to set up, he knows three alternatives within a five-minute walk.
If the weather changes, he adapts – a covered courtyard or the studio instead of an exposed terrace. If the group needs a simpler subject after a tough day, he adjusts.
This isn’t a fixed tour itinerary – it’s a week of teaching by someone who’s sketched in more cities than most people will visit in a lifetime.
What’s guaranteed is that every location will be chosen for a reason, you’ll be challenged, and your skills will be visibly better by Friday than they were on Monday.
If you have any more questions, don’t hesitate to contact our support team on [email protected].
A real human will get back to you within 24 hours.
More Photos!
Winchester, UK
About the Instructor
Ian Fennelly is one of the world’s most in-demand urban sketching instructors. His method –
teaching on location, breaking complex scenes into simple shapes, and building sketches in layers –
has helped over 50,000 students across 188 countries discover that they can draw.
He’s the author of three books.
He’s taught workshops from New York to Barcelona, Liverpool to Marrakech, Chester to Sicily.
His philosophy is simple: “There’s no space or time in a photograph.” He teaches in the place itself – sitting beside you, sketching the same scene, showing you what to leave out and where to start. That’s what makes his in-person teaching different from anything you’ll find on a screen.
Students call him “the Bob Ross of urban sketching” for the calm, encouraging way he makes
everything feel achievable. His retreats typically sell out 12 to 18 months in advance.
