Chapter One: Edinburgh, Whimsy, and the Beginning of It All
Shannon and I had worked together for years before this trip, navigating deadlines, meetings, conference calls, and the ordinary rhythms of professional life. But this was different. This was our first real “holiday” together. No work calendars. No interruptions. Just two longtime colleagues stepping fully into friendship somewhere between Washington Dulles and Edinburgh, Scotland.
We met at the airport for our 10 p.m. flight like two college roommates reuniting after years apart. The second we saw each other, we jumped up and down in the middle of the terminal with pure excitement and absolutely no concern for how ridiculous we looked.
And honestly, it felt right.
I took the window seat. Shannon took the middle.
As the plane lifted into the night sky, I watched Shannon laugh out loud at a Brett Goldstein comedy special while the cabin lights dimmed around us. Somewhere over the Atlantic, she ordered a little bottle of sparkling wine, and that became the official beginning of our Scotland adventure.
That was also when I learned several important things about my new travel companion: she cracks her knuckles regularly, is impressively health conscious, applies hand lotion constantly, and somehow manages to keep the softest, daintiest hands imaginable while moving through airports like a seasoned adventurer.
At some point during the flight, we made a pact:
no dilly-dallying,
no sarcasm,
and complete commitment to the spirit of adventure.
That promise would become the unofficial theme of the entire trip.
When we landed in Edinburgh, we were met at the gate by Paul from BRAW Tours holding a handwritten sign with our names. He greeted us with the kind of warm, weathered smile that felt quintessentially Scottish, complete with a few charmingly spaced teeth, a five-day shadow, and the calm confidence of someone who had likely driven thousands of excited tourists into the city before us.
We were officially on our way.
Paul loaded Shannon’s expertly packed medium-sized suitcase into the van with ease. Then he turned toward my luggage situation.
My oversized suitcase had suffered catastrophic and irreconcilable damage somewhere during the flight. One wheel pointed permanently sideways, and the zipper looked emotionally exhausted. Thankfully, my smaller bag survived, which somehow made the dramatic collapse of the larger suitcase feel even more theatrical.
Paul handled it all without blinking.
We climbed into his Mercedes van and drove into Edinburgh beneath dramatic gray skies and intermittent rain that somehow made the city even more beautiful. Ancient stone buildings rose around us like they had been waiting centuries for our arrival.
We checked into the Tiger Lily Hotel, a swanky little boutique hotel right in the heart of Edinburgh, filled with bold wallpaper, velvet chairs, glowing lights, and just enough glamour to make us feel immediately sophisticated.
After dropping our bags, we grabbed a quick bite at Victor Hugo Café. Gluten-free options were somewhat limited, but Shannon took it in stride, already embracing the reality that travel required flexibility, humor, and occasionally french fries.
Then we headed out for our first walk through Edinburgh.
The rain came and went in soft little bursts, misting the streets and darkening the cobblestones. I loved it instantly. Shannon struggled with the cold at first, but within minutes she seemed completely mesmerized by the city itself:
the towering stone architecture,
the winding alleyways,
the ancient energy,
the feeling that history was somehow still breathing beneath your feet.
At one point we stopped so I could buy two medium suitcases to replace my fallen comrade of a large bag, and then we continued deeper into the city for our walking tour.
Our guide, Ben, looked exactly how a Scottish tour guide should look:
properly dressed,
slightly scholarly,
completely unbothered by the rain,
and fully committed to storytelling.
We wandered along the Royal Mile listening to stories about Edinburgh’s layered history while slowly climbing toward Edinburgh Castle. Our tour group consisted mostly of older travelers, including one grandmother who walked carefully with a cane as her daughter and granddaughter walked patiently alongside her. The pace was slow, but Shannon and I did not mind at all. There was something lovely about letting the city unfold gradually.
Ben spoke with the kind of Scottish cadence that made every sentence sound important, even when he was pointing out drainage systems or discussing medieval sanitation.
At some point, Shannon and I quietly peeled away from the tour and headed toward our next adventure: pocketbook making.
We jumped into a cab and, about five minutes later, realized we were going completely the wrong direction.
Naturally.
Eventually we found our way back into Edinburgh proper and arrived at a long workshop table surrounded by travelers from all over the world, all building their own little Harris Tweed pocketbooks.
The setup looked charming and organized in theory.
In practice, the instructor stood at the opposite end of an impossibly long table, speaking softly while demonstrating tiny details I absolutely could not see with my aging eyesight. My frustration started bubbling up almost immediately.
Meanwhile, Shannon was laughing through the entire experience.
I kept asking the instructor for help while squinting dramatically across the table trying to understand what tiny strap or clasp we were supposed to be attaching next. A few women nearby started laughing along with us, and eventually I surrendered to the absurdity of the moment.
And somehow, despite my theatrical struggle, our pocketbooks turned out beautifully.
One was soft pink plaid with warm brown leather.
The other was blue tartan with pale gray trim.
Tiny Scottish masterpieces.
That evening, after our pocketbook-making adventure and our accidental detour through Edinburgh, Shannon and I wandered back through the damp, glowing streets toward Tiger Lily completely exhausted and completely happy.
The city looked even more magical at night. Rain reflected the lights from storefront windows onto the sidewalks, and every narrow stone alleyway felt like the entrance to another secret.
By the time we got back to our room, we were tired in the satisfying way that only happens after a truly full day. We changed for dinner and headed downstairs to the restaurant inside Tiger Lily, which somehow managed to feel elegant, cozy, lively, and full of charm all at once.
The menu was enormous, and Shannon was thrilled to discover plenty of gluten-free options. Honestly, one of the nicest surprises of the trip was realizing how thoughtfully Scotland seemed to accommodate food sensitivities without making it feel complicated or limiting.
We settled into dinner and one of those conversations that somehow skips past small talk entirely. Maybe it was exhaustion. Maybe it was Scotland. Maybe it was simply finally stepping outside our work lives together for the first time. Whatever it was, we talked for hours.
And then something unexpected happened.
I had my first real alcohol in almost 23 years.
Over time, I had developed an intolerance that caused a stubborn rash whenever I drank. Leading up to the trip, I had tried everything I reasonably could under my doctor’s guidance, hoping maybe I could participate just a little during our Scotland adventure.
So that night, cautiously and somewhat ceremoniously, I ordered a playful little gin cocktail topped with cotton candy and a touch of raspberry liqueur.
Meanwhile, Shannon happily explored the cocktail menu with an espresso martini made with Licor 43, followed later by a French 75 that felt perfectly suited to the glamour and charm of Tiger Lily itself.
What surprised me most was not how delicious my drink was, though it truly was, but that for the first time in almost 23 years, I had no reaction to it at all.
So naturally, I allowed myself another.
At some point in the evening, I realized I felt delightfully relaxed for the first time in decades. Not wildly drunk. Just warm, happy, slightly floaty, and deeply grateful to be sitting across from someone who had become not only a trusted colleague, but a true friend.
We laughed.
We shared stories.
We shared secrets.
We talked about life, health, aging, family, fear, hope, reinvention, and all the strange turns life takes when you least expect them.
The whole day had unfolded with an almost suspicious level of ease.
Even the rain felt charming.
Even getting lost became part of the story.
By the time we finally headed upstairs for the night, both of us were already excited for whatever Scotland had waiting for us next.
