My ears woke up before my eyes at eight o’clock in the morning. The rumbling snores of the hostel dorm were slowly being replaced by the sounds of creaking bunk bed ladders, rustling backpacks, and what I imagine was some pretty unsightly scratching. I reluctantly gave up on the dream I was having and got up to make my own contributions to the morning soundtrack. I made my way downstairs with my backpack and trusty umbrella Excalibur to rendezvous with Jack and Dave, my new American friends and drinking partners from the night before. They were my ride to the Isle of Sky that day and I couldn’t have been more excited. We were all set to leave as soon as the final passenger, Chelsea the Canadian, showed up. When she finally did arrive, we were all taken aback by the sheer massiveness of her backpack—85 cubic liters of female “necessities,” which judging by the weight, consisted primarily of bricks and cannonballs.

Our quartet filed out into a rainy Inverness morning and hiked to the parking garage where Jack and Dave left their rental car. I had been forewarned that it might be a tight squeeze since the car was small, but when I saw the car I felt certain that it would in fact be an impossible squeeze. I was staring at an off white Fiat 500, a car so small that it made the Minicooper parked next to it look like a veritable tank. The trunk opened to reveal a locker-sized space just big enough for my backpack and a spare pair of boots. Everything else would have to be crammed into the tiny backseat with two unlucky passengers. As soon as I processed that fact, in a true display of chivalrous courtesy I shouted “SHOTGUN” and pushed passed Chelsea to lay claim to the coveted front seat. To be fair, I was the designated navigator, having the only 3G phone capable of GPS coverage in the Highlands. I’m fairly certain that the inside of that Fiat was bigger than the outside because after a bit of luggage Tetris, everything and everyone somehow managed to fit inside the car. Sure all of the rear windows were completely obscured by luggage and the legroom in the backseat was practically nonexistent, but it was cozy in a claustrophobic “I’m having trouble breathing” sort of way. With a sputtering cough from the Fiat’s lawnmower engine and a boisterous Red Bull belch from our driver Jack, we were off.

Our first stop on the road to the Isle of Skye was the far side of Loch Ness to see the ruins of Urquhart Castle. The rain was coming down hard when we arrived, but we weren’t deterred. Chelsea had a rain jacket, I had Excalibur, and Jack and Dave simply had no concerns about getting soaked. To access the ruins, we had to go into a little silo in the parking lot and pay a woman eight Euros before descending a long spiral staircase that brought us to an underground museum. There we found a fascinating array of Scottish artifacts from the area, but more importantly, a cafe that sold coffee. After some perusing, the four of us went into a small theater to watch a short film about local clan history and the legacy of Urquhart castle. It was very theatrical and I’m not sure how much of it was really educational. By the end, when I thought the film could not get any more dramatic, bagpipes droned over the rolling credits and the projector screen slowly retracted to reveal a panoramic window overlooking the ruins on misty Loch Ness. Touché.

Embracing the Scottish weather, we hiked out to the ruins to explore them properly. Halfway between the museum and the old castle was a full-scale replica trebuchet. Reading the sign next to it, I learned that these war machines were typically built on site, just out of arrow range from the castle it would lay siege to. I can only imagine how miserable the guards on watch must have felt every morning when they saw how far along construction had come since the day before. “Oh get it right up ye! Today’s the day, I’m tellin ye MacMillan. They don’t look to have had so much as a piss break since supper!”

Seeing Chelsea shiver under her soggy jacket, I attempted to redeem my earlier lack of chivalry by letting her huddle under my umbrella as we took the castle by storm. The cold, damp, dripping stonework had an eerie feel about it. The ground beneath my feet was saturated with the blood, sweat, and tears of four centuries of Scotsmen. The quietness was immense. But there was still lightheartedness to be found amongst our group when we found our way into the subterranean, medieval kitchen. One of those fake fireplaces consisting of an orange light and some streamers being blown by a small electric fan had been set up inside a stone circle for dramatic effect, and Dave, a man best described as ‘Neanderthalic,’ took up a hilarious caveman pose beside it and grunted his approval.

Back in the cozy confines of the Fiat, we took a series of entertaining wrong turns before finally finding the right road toward Skye. While this would normally be cause for elevated stress levels and incessant bickering on a road trip, the chemistry of the car encouraged only riotous laughter. Our group had amassed no less than fifty inside jokes before noon, mostly relating in some way or another to the ungainly array of sounds and smells experienced in a car full of vagabonds with high protein diets and questionable hygiene. There was ongoing speculation on what Chelsea had in her mountain troll of a backpack, the favored opinions being ice blocks for igloo building and severed heads of ex lovers. As we passed one Loch Ness tourist shop after another, Jack became increasingly tempted to pull over and buy a jumbo stuffed Loch Ness Monster to occupy the remaining square footage of the back seat. “I KNOW we don’t have the room for it DAVE! Blah blah blah, you already can’t breathe back there, well what about what I want, huh?” When we actually stopped at a knick-knack shop, I was convinced that Jack was going to go through with it. But to the great relief of Dave and Chelsea in the backseat, he emerged from the shop with only a palm sized Nessy. He also bought novelty bottles of scotch the size of fingernails coined as being the smallest bottles in the world. He is a man of interesting tastes to be sure. What I can say for certain is that Jack and Dave deserve their very own travel show documenting their hilarious banter and bickering through the Highlands.

Words and photos do little justice in describing the road to the Isle of Skye. You have to experience the narrow slithering route yourself; breathe the crisp misty air as your eyes feast on endless snow-capped mountains, ravines gushing with melt water, and valley-filling lochs of flawless sapphire blue. It was an absolutely overwhelming amount of unspoiled natural beauty. Coming around a corner we saw the first signs of civilization in over an hour. It was the quaint town of Dornie, the famous home of Eilean Donan (pronounced Alien Done-In). 

Eilean Donan is a tiny island floating between where three sea lochs meet, and on it, one of the most picturesque castles I have ever seen. Once we were out of the Fiat and walking across the stone footbridge to the castle, an overwhelmingly sense of déjà vu struck me. I felt certain that I had seen the castle somewhere before. In fact I had, and so have you if you’ve ever seen Braveheart, Highlander, or James Bond: The World is Not Enough. The castle is a popular filming and photography location. Annually, dozens of people even drop a cool $20,000 just to get married at the little island fortress. The inside of Eilean Donan is astonishingly well preserved and decorated. It is still technically a family home, though the current owner has kindly opened the doors to tourists. Since photography is prohibited inside the castle itself, I sadly have only one clandestine photo to share.

After exploring all the nooks and crannies of the castle, getting repeatedly startled by creepy mannequins standing in unlikely corners, and attempting to raid the armory, we retired back across the bridge to attempt a ravenous raid on the cafe instead. To our stomach’s dismay though, it was already closing up for the day. Chelsea pleaded with the guy stacking chairs to fulfill her fantasy of a hot panini and moist red velvet cake, but despite her best efforts, the kitchen remained closed. We drove to the one restaurant in the little town, but found it to be despairingly closed for the season. We tried the local pub across the road, but were let down there for sustenance as well as the little old man behind the bar had only half a lemon and a questionable mix of bar nuts to offer. Eventually, we came upon a gas station with a little shop where we spent a frankly obscene amount of money on snack foods. Jack was again tempted to make an unnecessary purchase when he saw the cases of beer branded Armchair Athlete.

Back on the road, we pressed on as the sun began to set behind us. We crossed the famous Skye Bridge, a surprisingly modern looking bridge connecting the isle to the mainland. I did a search for nearby youth hostels on my phone and came up with an address in what looked to be the middle of nowhere. We turned off of the already humble main road onto a serpentine lane that slithered its way between streams and small waterfalls. We followed the road up a small mountain until it brought us to a downhill dirt road plunged in darkness. We proceeded slowly and carefully. Almost immediately we hit a sheep. Not hard. It came gallivanting out of the night and just brushed the front end of the Fiat with its bushy bottom before carrying on its merry way. We proceeded even more slowly and soon found ourselves in the middle of an entire flock of sheep. I don’t entirely remember why we didn’t use the car horn to scare them out of the road—something about it being rude or inhumane or something—so we opted instead to lean out of the windows and shout obscenities at them.

We saw a light up ahead and felt our hopes rise. But it wasn’t the hostel. Instead, it was a funky blue and orange VW bus parked in a small roadside lot. As we were running frighteningly low on fuel, we decided to pull over and ask for directions. After a democratic vote, I was pushed out of the Fiat to go see if the owners of the VW bus were friendly or murderous. Thankfully it ended up being a nice Australian couple camping out to do a morning hike to the mythical Fairy Pools—the Scottish fountain of youth. I filed that tidbit away in my own T-Do List and got on about asking them if they knew about a hostel somewhere nearby. They said there was a building at the bottom of the hill where the road came to a dead end, but they weren’t sure if it was a hostel. I thanked them and wished them luck on their adventure.

At the bottom of the hill there was indeed a building. There was a sporty red convertible parked out front and a light burning on the second floor. We rang the doorbell and waited. Nothing. We rang again and followed up with a few eager raps on the door. Nothing. Suddenly, the light upstairs flicked out and the whole situation felt decidedly more sinister. Our foursome of weary travelers circled the building looking for secondary entrances. We congregated at the back door where we were greeted by a motion sensor floodlight and a handwritten note stating that the hostel would be closed until April 2015. There was a collective sigh of disappointment and sense of utter defeat amongst the group. We crammed back into the little Fiat like a tin of rejected sardines and puttered our way back to the main road. We were coasting on fumes by that point and I was fully anticipating a sputtering last cough from the engine at any moment. Luckily it was mostly downhill to the nearest town and we made it to a gas station without having to substitute manpower for horsepower.

We put up for the night at the Portree Hostel. It was a spacious and comfortable place that had an impressive VHS collection and a weathered old Spanish guitar, both sporting copious amounts of dust. There were a handful of other travelers at the hostel, more than I would have expected this far up north during the off-season. Great minds think alike I suppose. We made some fast friends and ended up sitting down to a poker game in the kitchen with an interesting international group from Spain, Chile, and Switzerland. Chelsea had never played poker before, so Dave and I coached her during the first few hands. We quickly stopped coaching when she began raking in the chips with her uncanny beginner’s luck. The card game eventually dissolved into a group resolve to find a pub.

Everyone bundled up to face the icy wind coming off the Atlantic and together we went in search of a good pub at 10 o’clock. I borrowed the hostel’s acoustic guitar and spontaneously composed a ballad of our search for whiskey as we walked. Portree is a quaint little fishing town that doesn’t need to add any frills or flourish to captivate visitors. Our group got carried away sightseeing and wandered into the harbor where waves rhythmically lapped against old wooden docks. A colorful fleet of small fishing boats tugged gently at their mooring lines, bobbing almost toy-like in the shimmering water. The backdrop of a cloudless sky peppered heavily with starlight and the glow of a crescent moon brought a revering silence over us all as we soaked in the simple brilliance of that moment.

Pulling ourselves away from the harbor, we continued our pub hunt until, finally, we found a hotel bar that was open until eleven. Perfect. I strode up to the bar with the guitar propped over my shoulder and asked the bartender for a bottle of Craggenmore Scotch (a superb brand I had once tasted at the Appalachian Highland Games). The bartender’s reaction to that Hemingway of a question was priceless. Her lips soundlessly parted as she raised her index finger at me, and her eyebrows reached for her hairline as she turned to scan the bar. When she spotted the gold and purple label peeking out from the top shelf, unopened and pristine, she pointed at it and looked at me without lowering her eyebrows and asked, “Will you be needing a glass?” As I squinted my eyes with a smile that said Of course I won’t be needing a glass, I realized that this was possibly the coolest moment of my life. Here I was on the Isle of Skye with a bottle of my favorite scotch in one hand and a guitar in the other; I had a band of new friends and not a care in the world. The rest of the night was filled with laughter, music, and a fair bit of flirting between the Canadian card shark and me. Good whiskey, good company, good times. It had been, in nearly every conceivable way, a perfect day.