Scotland: Two week, Three Cities & One Brave Yes
Hey there, fellow wanderer!
Some trips begin with a perfectly organized itinerary. Others begin with a dream that refuses to go away. My Scotland trip was originally planned for 2020, but as you can probably guess, COVID had other plans. For five years, Scotland lingered in the back of my mind: its castles, misty mountains, ancient stories, cozy pubs, and landscapes that looked like they belonged in another world.
Then, in the summer of 2025, I finally stopped waiting. I booked the flight. Packed my bags, took a deep breath, and traveled to Scotland by myself. For two weeks, I made my way through Edinburgh, Glasgow, Inverness, and the Scottish Highlands; occasionally by train, frequently by tour bus, and, in one particularly brave chapter, from the opposite side of a rental car. There were castles and cathedrals. Whisky tastings and golf lessons. Rainstorms, winding Highland roads, warm bowls of soup, and more stairs than I care to count. There was also one very tall swing. But we’ll get to that.
Three Cities, Three Very Different Sides of Scotland
My Scottish adventure began in Edinburgh, where history seems to rise from every stone. I wandered along the Royal Mile, explored the Palace of Holyroodhouse and Edinburgh Castle, searched Greyfriars Kirkyard for names that helped inspire characters in Harry Potter, and stood at the Ross Fountain admiring one of the prettiest views of the castle.
I also climbed Arthur’s Seat. Calling it a “walk” feels wildly optimistic. It tested my legs, patience, endurance, and possibly my relationship with nature….but the view from the top reminded me why I kept going. If you want a beautiful Edinburgh overlook without reconsidering every decision that led you there, Calton Hill is the gentler option.
From Edinburgh, I traveled to Glasgow, a city that felt less polished and more lived-in. Glasgow gave me grand architecture, the magnificent Kelvingrove Art Gallery and Museum, and a much-needed lesson in the value of the hop-on-hop-off bus when your feet have officially filed a complaint.
Glasgow also became my gateway to Stirling Castle, Loch Lomond, Glencoe, and one of the most magical experiences of the trip: riding the Jacobite Steam Train across the Glenfinnan Viaduct. Yes, it felt like I was heading to Hogwarts. No, I did not receive my letter. I’m still holding out hope though!
My final city base was Inverness, where the pace softened and the Highlands began to feel even more present. From there, I traveled to the Isle of Skye, Eilean Donan Castle, Dunrobin Castle, John o’Groats, Culloden Battlefield, Clava Cairns, and Cawdor Castle. The weather did not always cooperate. On the Isle of Skye, the mist swallowed some of the famous views before I could see them. By the end of that day, I looked and felt a bit like a drowned rat. And yet, Scotland in the rain still had a kind of magic to it.
The Moments I’ll Remember Most
Some memories came from the places I had dreamed about seeing: standing beneath the Three Sisters of Glencoe while a man in a kilt played the bagpipes, crossing the Glenfinnan Viaduct aboard the Jacobite Steam Train, and walking through the battlefield at Culloden.
Others came from experiences I added simply because they sounded interesting.
I took a three-hour golf lesson at St Andrews, my first golf lesson ever, because when in Scotland! I spent five unforgettable hours at The Macallan Estate, enjoying a beautifully curated dining and whisky experience that made me feel like a proper VIP from the moment the doors opened. I treated myself to a stay at Dornoch Station, where a little history, a little luxury, and a very good sticky toffee pudding made the final stretch of the trip feel extra special.
Then, on my last full day, I did something that scared me enough to consider backing out: the Highland Fling Swing. Standing beneath the bridge, I was nervous. I knew that if I stood there watching everyone else take their turns, I might lose my nerve - and there was absolutely no way I was letting a bunch of little kids be braver than me. The initial drop may have inspired some colorful language, but once I was swinging above the river, I could finally look around and take it all in.
I had done it.
What Scotland Taught Me
This trip wasn’t only about seeing Scotland. It was also about learning to trust myself. I learned how to eat alone without feeling like everyone was watching me. I figured out how Scottish pubs worked, navigated trains and taxis, drove on the left side of the road, adjusted plans when the weather had ideas of its own, and kept moving through moments that felt uncomfortable or intimidating.
Traveling by yourself can feel freeing and frightening, sometimes within the same five minutes. But somewhere between Edinburgh’s stone closes, the misty mountains of Glencoe, and the wild northern coastline, I became proud of more than the places I had checked off my list.
I was proud that I had finally booked the trip.
Proud that I didn’t let fear make my decisions.
Proud that I noticed the small moments, breathed through the uncomfortable ones, and allowed myself to be fully present for all of it.
Scotland gave me castles, whisky, rain, history, Highland views, and a few stories I will probably be telling for the rest of my life. More importantly, it reminded me that courage doesn’t always arrive before the adventure. Sometimes, you find it along the way.
Coming Up in the Scotland Series
Over the next several posts, I’ll be sharing more from each part of the trip, including:
✨ What to see, eat, and experience in Edinburgh
✨ How I used Glasgow and Inverness as bases for Highland adventures
✨ The tours and experiences I would—and wouldn’t—book again
✨ Practical tips for trains, rental cars, weather, and traveling solo
✨ My favorite castles, meals, hotels, and unforgettable splurges
✨ What I would change if I planned the same trip today
Whether Scotland is already on your list or you’re simply wondering what it might feel like to take that brave first solo trip, I hope these stories help you picture an adventure that feels entirely your own.
Because sometimes the trip you keep postponing is the exact one waiting to show you what you’re capable of.
I DID THE DAMN THING. 🩵🤍🩵
And I’m so glad I did.
Let’s Wander Somewhere Magical
Dreaming of your own Scotland adventure? Whether you’re picturing castle stays, scenic train rides, whisky tastings, Highland road trips, or a thoughtfully paced journey designed around what excites you most, I’d love to help turn that whim into reality.
Come wander with me, follow along for the rest of the Scotland series, and start imagining where your own brave “yes” could take you next. ✈️✨
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