Reflections from Scotland 2026: Castles, Connections, and the Company We Keep

We’ve just returned from this year’s Scotland trip, and I’m still savoring it. This time we traveled as a group of ten. While last year’s gathering sparked lively debates about sales and labor, this year felt different.

There was no formal agenda and no list of burning topics. Instead, there was time and space for the kind of conversations that only happen when people step away from the day-to-day and really settle in with one another.

A Rare Gift: Scottish Sunshine

Anyone who has spent time in Scotland knows the weather can turn four times before lunch. So it’s worth saying up front: we were spoiled. Day after day brought clear skies, soft light over the hills, and evenings warm enough to linger outdoors.

Several guests who had been warned to pack for rain found themselves reaching for sunglasses instead. Good weather lifts a group’s spirits, and it set the tone for the entire week.

Edinburgh Castle: Built to Endure

We began in Edinburgh, where the castle sits high on its volcanic rock, watching over the city as it has for centuries. Walking its ramparts with views stretching across the rooftops to the Firth of Forth, it’s hard not to reflect on what it takes to build something that lasts.

Edinburgh Castle has been besieged, rebuilt, and repurposed many times over, yet it endures because each generation took responsibility for it. As business owners thinking about legacy and succession, that lesson landed with more than a few of us.

An Evening at The Kitchin

That night we dined at The Kitchin, Tom Kitchin’s celebrated waterfront restaurant in Leith. The philosophy there is simple and powerful: let the finest seasonal Scottish produce speak for itself. Each course reminded me that excellence isn’t about complexity. It’s about sourcing the best, respecting the craft, and executing with precision every single time.

A room full of service business owners couldn’t help but take notes, and the conversation around that table set the tone for the week.

Cawdor Castle and Its Walled Gardens

For a group of landscape professionals, Cawdor Castle was a trip highlight. The castle is steeped in history and storytelling (Shakespeare fans will recognize the name from Macbeth), but the gardens captured us.

Stepping through the old stone walls into the walled garden felt like entering a living masterpiece, designed, planted, and tended with care across generations.

The structure of the walls, the rhythm of the beds, the thoughtful use of shelter and microclimate, and the sheer level of maintenance on display: this is horticultural craftsmanship at its finest.

More than one of us stood quietly in those gardens and remembered why we fell in love with this work in the first place. Landscapes, like businesses, thrive on intentional design, consistent care, and a long-term vision.

Speyside, The Dowans, and The Macallan

From there we headed into Speyside and made our home at The Dowans Hotel in Aberlour. It was the perfect base: warm, welcoming, and full of character, with the kind of hospitality that made a group of ten feel like old friends.

Evenings there, often by the fire with a dram in hand, produced some of the trip’s best conversations.

A short drive away, we visited The Macallan Distillery. The estate blends heritage and modern design, with the distillery set into the landscape so naturally that it seems to rise out of the hillside.

Learning about the patience behind every cask, and the attention paid to wood, time, and consistency, felt like a fitting metaphor for business. The best results aren’t rushed. They’re built through discipline, quality inputs, and a willingness to invest for the long term.

The Conversations That Matter

Without a set list of discussion topics, the conversations went deeper. People talked about their businesses, yes, but also about leadership, succession, family, what they want the next chapter to look like, and what they’ve learned the hard way. When ten experienced people spend a week together, guards come down, and that’s when the real insight begins to flow.

Some of the most memorable exchanges were with locals: gardeners, guides, hoteliers, distillery staff, and the folks we met in village pubs. Each shared their perspective on work, community, and pride in what they do. Hearing how others approach their craft in a completely different setting can reframe your thinking. The fundamentals of good business, such as care, consistency, and genuine relationships, translate across any border.

Final Thoughts

If last year’s trip taught me that great ideas surface when peers step away from daily operations, this year taught me something even simpler: the relationships themselves are the value. We didn’t come home with a list of action items. We came home with deeper friendships, fresh perspective, and a renewed sense of why we do this work.

To everyone who joined us this year, thank you for the laughs, the honesty, and the company. And to those thinking about joining a future trip, I can promise you this: the castles, gardens, and whisky are unforgettable, but you’ll remember the people most.

Sláinte!