Embark on the Absurdly Sacred Quest: A Monty Python-Inspired Pilgrimage

August 1 –

Arrival Day

Arrive in Edinburgh, welcome coconut cocktail reception & dinner at The Scotsman Hotel. Group viewing of Monty Python and the Holy Grail.

August 2 – Day 1

Visit White Castle Fort, a surviving round, stepped earthwork dating back over 3,000 years. Thought to be a ritual or council site, it likely hosted gatherings of warrior kings or tribal leaders. In some traditions, Grail castles shine with unnatural brightness—this site may symbolically echo such a realm. Consider it a proto-Camelot or ancient druidic high place.

In the distance rises Traprain Law, once the stronghold of the Votadini—later known as the Gododdin, a powerful Brythonic kingdom. In use since around 1500 BCE, it served not only as a fort but also as a ceremonial site. Its height and isolation made it ideal for rituals tied to kingship, solar movements, and seasonal rites—much like Tara in Ireland. In the late 4th or early 5th century, the famous Traprain Treasure, a hoard of chopped Roman silver, was buried here—possibly as tribute, plunder, or sacred offering.

August 3 – Day 2

Check out of The Scotsman, just over an hour drive. Make a quick stop at the iconic Kelpies statues. We’ll journey next to the majestic Stirling Castle, one of Scotland’s most significant royal strongholds and a center of power for centuries. Overlooking the River Forth, its commanding position earned it the nickname “the key to the kingdom.” Here, kings and queens were crowned—including Mary, Queen of Scots—and great battles were waged nearby.

Lunch at the Portcullis Pub just beneath the castle.

Just below the castle lies the enigmatic King’s Knot, a perfectly geometric earthwork with a square mound and circular features—long believed to be a royal garden. Yet for centuries, local lore and antiquarian writings have whispered a bolder claim: that this is the site of King Arthur’s Round Table.

Even 14th-century Scottish chronicles suggest that Arthur held court in the shadow of this very hill. More recently, ground-penetrating radar revealed previously undiscovered structures beneath the Knot—further fueling speculation.

Rising above the landscape like a stone sentinel, the Wallace Monument honors one of Scotland’s greatest heroes—Sir William Wallace. This dramatic Gothic tower stands on Abbey Craig, where Wallace is said to have watched the English army before the Battle of Stirling Bridge in 1297. Inside, you’ll find artifacts including Wallace’s massive sword, and breathtaking views from the crown of the tower. It’s a place of defiance, legacy, and national pride—a fitting stop on a quest where myth, history, and rebellion intertwine.

We’ll stop at the haunting ruins of Arnhall Castle, a crumbling 17th-century tower hidden among the trees of the Keir Estate. While time and nature have reclaimed much of the structure, its mossy stones and skeletal walls still whisper of forgotten lords and lost causes.

But for fans of Monty Python and the Holy Grail, this site is pure legend: it’s here that a pompous modern historian is abruptly cut down by a charging knight while explaining how King Arthur searched for the Grail. The absurdity of the scene, set against the somber grandeur of the ruins, captures the film’s genius blend of history, parody, and utter chaos.

We’ll admire the exterior of the ruins and step into the strange liminal space where cinematic farce meets ancient stone—no guarantees you won’t be photobombed by an imaginary knight.

Check into our hotel for the next two nights, The 5 star Gleneagles Hotel. Dinner here in their restaurant The Birnam.

August 4 – Day 3

No Monty Python tour would be complete without a stop at Doune Castle—one of the film’s most iconic locations. It served as the backdrop for several scenes in Monty Python and the Holy Grail, standing in for Castle Anthrax, Camelot, and the French Taunter’s fortress. More recently, it found fame as Castle Leoch in Outlander, home of Clan MacKenzie. A beautifully preserved medieval stronghold with ties to the Stewart dynasty, Doune is a dream for film buffs, history lovers, and holy grail seekers alike.

Sheriffmuir also holds a lesser-known place in pop culture lore—it served as one of the filming locations for Monty Python and the Holy Grail, with wide open terrain perfect for epic (and absurd) quests. Whether you hear the gallop of coconuts or the drumbeat of history, this stop invites both reverence and mischief.

Enjoy some free time before we regroup for dinner at the 2 Michelin star restaurant Andrew Fairlie’s. Kindly don thy finest garb. Anyone arriving in chainmail, coconuts, or shrubbery will be turned into a newt (don’t worry, you’ll get better)

August 5 – Day 4

Check out of The Scotsman, just over an hour drive. Make a quick stop at the iconic Kelpies statues. We’ll journey next to the majestic Stirling Castle, one of Scotland’s most significant royal strongholds and a center of power for centuries. Overlooking the River Forth, its commanding position earned it the nickname “the key to the kingdom.” Here, kings and queens were crowned—including Mary, Queen of Scots—and great battles were waged nearby.

Lunch at the Portcullis Pub just beneath the castle.

Just below the castle lies the enigmatic King’s Knot, a perfectly geometric earthwork with a square mound and circular features—long believed to be a royal garden. Yet for centuries, local lore and antiquarian writings have whispered a bolder claim: that this is the site of King Arthur’s Round Table.

We’ll enjoy lunch at the charming restaurant Moss, known for its locally sourced fare and cozy Highland atmosphere—an ideal place to refuel amidst the grandeur of Glencoe. Afterward, we’ll visit the Glencoe Folk Museum, where the history of the glen comes to life through intimate exhibits on Highland life, clan culture, and the infamous Glencoe Massacre. Set within 18th-century thatched cottages, this museum offers a poignant window into the lives behind the legends.

Our day ends at the striking and cinematic Castle Stalker, perched like a dream on a tidal islet in Loch Laich. Built in the 14th century by Clan MacDougall and later claimed by the Stewarts, the castle is most famously featured in Monty Python and the Holy Grail as the elusive “Castle Aaargh.” Though we won’t storm its walls, we’ll pause for photographs and reflection—standing at the threshold of history and satire, romance and rebellion.

We’ll check into the Loch Fyne Hotel & Spa, a tranquil coastal retreat where we’ll stay for two nights. Set against a backdrop of sea lochs and distant isles, it offers a restful haven to integrate all we’ve encountered—and prepare for what lies ahead. That evening, we’ll gather for dinner overlooking the sea, enjoying fresh Highland cuisine, warm hospitality, and time to reflect on the journey so far—wrapped in the quiet majesty of the west coast.

We’ll then enjoy lunch at the bistro in the Kilmartin Museum, where seasonal, locally sourced fare is served in a cozy space that reflects the glen’s atmosphere of earthy elegance. It’s a perfect moment to nourish both body and spirit before continuing our immersion into this landscape of legend.

Our final stop is the ancient hillfort of Dunadd, once the royal seat of the Gaelic kingdom of Dál Riata. As we ascend the rocky path, we’ll place our feet in the legendary carved footprint, where kings once stood in sacred union with the land during their inauguration. With sweeping views across the valley, we’ll stand in a place where sovereignty was not claimed—it was earned. Visit Kilmichael Glassary Cup and Ring Marks and finish with dinner at the The Horseshoe Inn, a proper pub.

August 7 – Day 6

Check out of Loch Melfort. Drive 2 hours, stop for lunch at Duck Bay Hotel & Restaurant. We’ll stop in Glasgow at the awe-inspiring Dumbarton Rock, a dramatic volcanic crag rising above the River Clyde where it meets the Leven. Once known as Alt Clut, or “Rock of the Clyde,” this site was the ancient capital of the Kingdom of Strathclyde—a powerful Brittonic stronghold during the early medieval period, contemporary with Arthurian legend.

From the 5th to 9th centuries, this fortress held out as a bastion of native resistance against invading forces. It has been linked by some scholars to the sub-Roman warrior culture that may have given rise to the Arthur figure, making it one of the most plausible northern candidates for a historic Camelot or allied realm.

We’ll make our way to the windswept summit of Cairnpapple Hill, one of Scotland’s most ancient and spiritually charged ceremonial sites. In continuous use since around 3500 BCE, this sacred hilltop has witnessed over five millennia of ritual, reverence, and celestial observation.

From the Neolithic through the Bronze Age and beyond, Cairnpapple served as both a seasonal gathering place and an elite burial ground. Its standing stones, henge-like earthworks, and layered cairns speak to a landscape designed not just for the living—but to connect them with the dead, the stars, and the cycles of time.

We’ll explore the concentric geometry of the site, descend into the preserved central cist grave, and take in the sweeping 360-degree views once used to mark the rising and setting of the sun. Whether as a sacred observatory or a place of kingship and renewal, Cairnpapple was and remains a temple between worlds.

After a day steeped in sacred landscapes and ancient mysteries, we’ll arrive at the stately Dalhousie Castle, Scotland’s oldest continuously inhabited fortress. Set on the banks of the River Esk and wrapped in centuries of history, this red sandstone stronghold offers both grandeur and grace.

We’ll check in and enjoy some time to rest or explore the grounds. Whether you unwind in the spa, walk among the ancient trees, or sip a quiet drink in the library, the castle’s warm hospitality invites you to relax.

Tonight’s dinner will be casual yet elegant, served in one of the castle’s cozy dining spaces—a perfect setting to unwind with good company and local Highland flavors.

August 8 – Day 7

On our final day together, we’ll journey to the heart of mystery and legend, beginning with a visit to the village of Temple—named for the Knights Templar, who established one of their earliest and most important Scottish preceptories here in the 12th century. Though only ruins remain, the land itself holds memory: carved gravestones, forgotten foundations, and an air of deep reverence linger beneath the trees and soil.

From there, we’ll continue to the world-famous Rosslyn Chapel—a place steeped in symbolism, architectural genius, and centuries of speculation. Built in the 15th century, Rosslyn is famed for its enigmatic carvings, hidden references to the Grail, and possible Templar connections. We’ll take time to explore its sacred geometry, reflect in silence, and appreciate its spiritual resonance.

A short walk will take us to the remains of Roslin Castle, nestled quietly below the chapel. We’ll enjoy a brief pause here for photos and reflection before returning to the village of Roslin for lunch at the local pub, a warm and rustic spot where we’ll share laughter and conversation over hearty fare.

After lunch, we’ll return to Dalhousie Castle for a relaxing afternoon. Enjoy free time to unwind in the spa, explore the castle grounds, or simply take in the serenity of this historic sanctuary.

In the evening, we’ll reconvene for a farewell dinner in “The Dungeon,” Dalhousie Castle’s award-winning fine dining restaurant. Set in the atmospheric stone vaults of the castle, this will be an elegant and memorable close to our journey—complete with gourmet Scottish cuisine, candlelight, and reflections on all we’ve experienced together.