There’s something about painting in a new place that changes everything.

I don’t mean it in a fluffy, inspirational-poster kind of way. I mean it literally. The light is different. The colors are different. The way you see and respond to what’s in front of you shifts when you’re out of your usual space.

Watercolor retreats have become one of my favorite ways to experience that shift. Not just as a teacher, but as a painter who still gets stuck sometimes. Who still needs a reset. Who still craves that feeling of being fully present with a brush in hand and nowhere else to be.

When you’re painting on location, whether it’s plein air painting in the countryside or working from a terrace overlooking water, something loosens. You stop overthinking. You respond to what you see instead of what you think you should paint. Your watercolor techniques start to feel more intuitive because you’re reacting in real time.

It’s hard to describe until you’ve done it.

That’s why I wanted to write this post. If you’ve been curious about what a watercolor travel experience actually looks like, or wondering if it’s something you’re ready for, I want to walk you through it. What to expect. How it works. And why it can be such a powerful creative reset.

I’m Jenna, and I’ve been teaching watercolor for years through courses, YouTube, and in-person experiences like retreats. If you’re newer to watercolor or want a solid foundation before diving into something like this, my free Complete Beginner's Guide to Watercolor eBook is a great place to start. It covers supplies, techniques, and all the basics in one easy download.

What Makes These Watercolor Retreats Special

I want to be really clear about something first: online courses and videos are an incredible way to learn watercolor. I’ve built my entire teaching world around them for a reason. They’re accessible, flexible, and powerful.

Watercolor retreats aren’t a replacement for that kind of learning. They’re simply a different expression of it.

My teaching approach (whether online or in person) is intuitive and personal. Everyone arrives with a different background, pace, and relationship with creativity, and the goal is always to meet you exactly where you are.

During the week, we explore a blend of structure and freedom, including:

• Core foundations like brush techniques, color theory, and simplifying scenes
• Florals and landscapes inspired by the environment around us
• Expressive, intuitive approaches that encourage experimentation
• Mindfulness and creative reset exercises
• Open conversations about the creative process—and sometimes the business of art

But what truly sets these retreats apart is the shared experience.

Evenings often turn into relaxed Q&As, long meals made with local ingredients, and conversations that wander far beyond technique. People arrive as strangers and leave with friendships that continue long after the trip ends.

These retreats aren’t about cramming in information or chasing perfection. They’re about reconnecting with why you create in the first place. All while nurturing your artistic identity in a way that feels grounded, supported, and human.

Inside a Jenna Rainey Retreat: What a Week Actually Looks Like

So what actually happens on one of these trips?

Every retreat looks a little different depending on the location, but the rhythm stays pretty consistent.

Mornings usually start slow. Coffee, good food, and time to ease into the day before we pick up brushes. No rushed starts—these places are meant to be absorbed.

Then we paint. Sometimes that means working together in a beautiful studio space. Sometimes it means heading outside for plein air painting in a courtyard, village, or along a coastline. You’re not painting from a photo on your phone, you’re painting what’s right in front of you, with all its shifting light and unexpected details.

I teach during these sessions, but not in a lecture-y way. It’s more like painting alongside you. Offering guidance when you’re stuck. Showing you how I’d approach a tricky wash or simplify a complicated scene. Watercolor landscape painting feels much less intimidating when someone’s next to you saying, “Yep, that shadow’s off. Let’s fix it together.”

Afternoons often open up for exploring. Markets. Architecture. Long walks through places that feel like paintings themselves. What you see between sessions feeds what you create during them.

Dinners are unhurried and full of conversation. Art talk, life talk, the kind that happens when you’re away from your normal routine and surrounded by people who get it.

By the end of the week, you’ve painted more than you expected. You’ve tried things you wouldn’t have attempted at home. And you’ve probably made a few friends who now text you photos of their latest florals.

It’s immersive, restorative, and built around actually painting not just talking about it.

A Look Back at Past Destinations

Each retreat brings its own kind of magic. New light. New rhythms. And new ways of seeing. And every destination we’ve painted in has left a distinct imprint on how I think about color and place.

France, 2022

Oh, France. The land of fairy tale villages, gentle light, and chateaus that practically paint themselves. We stayed at a charming 18th-century French Manoir, sipping incredible regional wines and soaking up scenes that felt pulled straight from a storybook. Our painting days were inspired by the rolling hills around Limoges, Château de Pompadour, and the medieval beauty of Ségur-le-Château. There were live watercolor demos, one-on-one coaching, and more laughter than I can count. You can peek inside that dreamy experience here:

Morocco, 2023

This retreat stretched my palette, literally and creatively. The colors of Agadir, the patterns in the Souk, the soft pinks of the Mini Sahara dunes… It all pushed me into a new realm of expression. We stayed in a stunning eco-Kasbah nestled at the base of the High Atlas Mountains, painting exotic textures and soaking in the vibrant energy of Taghazout and the desert. Warm evenings, authentic Moroccan food, and rich cultural immersion made this one unforgettable.

Spain, 2023

In Andalucía, everything felt bold and warm, from the light to the tapas. We made a private estate our creative home, tucked into Spain’s first UNESCO Biosphere Reserve. The “pueblos blancos” of El Gastor, Setenil de las Bodegas, and Ronda were a watercolor dream: bright whites, deep shadows, dramatic hills. Our days were filled with plein air painting, wine tastings, and the joy of translating sun-drenched architecture into expressive brushwork. You can check out the Morocco and Spain experience here:

Italy, 2023

Tuscany was visual overload in the best way. We painted under golden sunlight with San Gimignano in the background, sipping Chianti after art-filled afternoons. Our historic estate was full of soul, and piano music! This week was about slowing down, noticing subtle shifts in color, and remembering that imperfection is part of the process. The views, the food, the connection… chef’s kiss.

Portugal, 2023

This one was coastal bliss. We stayed at a luxurious Portuguese Quinta with 2.5 acres of Italian gardens, ocean views, and a pool for post-painting dips. After daily workshops focused on watercolor landscapes and florals, we sailed into the hidden grottoes of the Algarve and wandered the ancient streets of Lagos. The saffron beaches. The salty air. The vibrant, supportive artist community. It was everything.

France, 2024

Back to France—but a new region, and a whole new palette. This time, our base was a majestic 18th-century château in the countryside, where we dove into floral and landscape painting inspired by the medieval towns of Montpezat-de-Quercy and Saint-Antonin-Noble-Val. We sipped wines from a family-owned vineyard, explored botanical gardens, and let the peaceful rhythm of rural France guide our brushes. This retreat felt restorative, like a deep breath you didn’t know you needed.

Scotland September 2026 – Highlights from the Sold-Out Buchlyvie Experience

Scotland has been on my list for years.

Not just to visit. To paint. The rolling hills. The moody skies. The way light shifts from soft gold to silver gray in a single afternoon. It's the kind of place that practically begs for watercolor.

So when I started planning the September 2026 retreat in Buchlyvie, I knew it had to be something special. And it sold out fast. Like, blink and you missed it fast.

Here's what made this one stand out.

The landscape itself is a masterclass in value and atmosphere. Scotland doesn't hand you bright, obvious colors. It asks you to slow down. To notice the subtle shifts between greens. To embrace soft edges and let the weather become part of the painting.

We'll be staying in a restored country house with views that feel almost too good to be real. Big windows. Stone walls. The kind of place where you want to paint before breakfast just because the light is doing something interesting.

Plein air sessions will take us into the countryside. Think misty mornings, sheep dotted hills, and ancient stone structures that have weathered centuries of Scottish rain. We'll work on capturing atmosphere without overworking. On letting the paper breathe. On trusting that less can absolutely be more.

And yes, there will be cozy evenings. Good food. Long conversations about art and life and why we keep showing up with a brush in hand.

This retreat is already full, but if Scotland stirred something in you, keep reading. There's a way to make sure you don't miss the next one.

Frequently Asked Questions

Do I need to be an experienced painter to join a watercolor retreat?

Not at all. These retreats are designed to meet you where you are. If you can hold a brush and stay curious, you’re ready.

Can I join a retreat if I’ve never painted outside before?

Absolutely. I’ll guide you through simplifying scenes, mixing colors on the go, and working with changing light.

What if I’m traveling solo and don’t know anyone?

Most people come alone and leave with new friends. The small group size makes connection feel natural and easy.

What if I sign up for a watercolor retreat and don’t feel ready when the time comes?

That feeling is more common than you think—and it usually fades once you arrive. Most people leave wondering why they waited so long.

How to Join a Future Watercolor Retreat 

Here's the thing about retreats. They fill fast.

That means spots are limited. And once they're gone, they're gone.

If you're reading this and thinking maybe someday, I get it. Retreats feel like a big commitment. A new place. A full week. People you've never met. It's okay to sit with that for a while.

But if something in this post stirred a yes, even a quiet one, the best thing you can do is get on the list.

My retreat waitlist is where I share new destinations first. Before social media. Before the general announcement. The people on that list get early access, which honestly makes all the difference when spaces go quickly.

You’re not committing to anything by signing up. You’re simply making sure you hear about future retreats in time to decide.

Future locations are always in the works. I'm always dreaming up new places that would challenge and inspire the way we paint. Places with light worth chasing. Colors worth mixing. Moments worth being fully present for.

So if this feels like something you want to be part of eventually, don't wait until the next one is already full.

Get on the list. And when the right trip comes along, you'll know.