A Little Photoessay… Scottish Highlands, Glens and Day Trips near Dundee

Last updated on August 2, 2025 by Shannon

After a week of uncommon hospitality given to me in Scotland, I surly owe a debt of kindness to other travelers—one to be repaid at some point in the future.

On an icy-cold evening in Northern India, I met two sisters, fellow backpackers, who were nestled into a tiny restaurant in McLeod Ganj. We shared a table—there was not a seat to spare in the warm and cozy one-room restaurant—and backpacking stories during our hot meal.

When we parted ways several hours later, they casually mentioned that if I headed to Scotland that I should stay at their mom’s house for a few days.

Now, although the offer was genuine, all parties admitted that they didn’t think I would actually take them up it. Four months later, I did. I wasn’t even sure why, except that the chance for a local perspective, and a warm, quiet place to crash, sounded great.

So, I spent a lovely four days touring the Scottish highlands and glens with Jeannie, mom of two other RTW backpackers on year-long journeys. Jeannie graciously opened her home to me and made it her task to show me Eastern Scotland’s highlights.

Things to Do Near Dundee, Scotland

We toured the highlands and glens around Dundee, Scotland, and these are my favorite photos and stories from my explorations!

We hiked to the top of the gently rounded mountains afforded views of the River Tay, the North Sea and all of the low-lying farmland.

Have a Spot of Tea at Crail Harbour

The small fishing village of Crail is quiet and quaint and dates back to 800 AD, when it was first settled. This place was utterly charming. Small pottery shops hide in the small side-streets and the perfect cuppa tea awaited us overlooking the sea at Crail Harbour Gallery.

Big cities have a lot of interesting museums and a fast pace of life, but its villages that hold the heartbeat of culture and history, these hold the traditions of an older way of life.

And even better, it’s just 10 miles from Crail Harbour to St. Andrews, which makes it very accessible as a quick stop. We parked in the village and then walked down to the Habour, had our tea, enjoyed the sunshine and perfect weather.

Crail Harbor is a poetic palette of maritime charm, set along the rugged coastline of Scotland’s Fife. It’s as though the town has been preserved in amber, capturing the essence of a bygone era.

While the rain-smeared skies of Scotland often add to the mystique of its landscapes, Crail seems to bask in its own microclimate of nostalgia, presenting you with an experience that’s as heartwarming as it is visually stunning.

Why visit? For starters, there’s a tangible sense of history at Crail Harbor. This isn’t just another dock where boats come and go; it’s a narrative set in stone and wood, built over centuries of fishing traditions. The harbor itself, with its cobblestone pathways and quaint fishing boats, appears like a scene plucked straight out of an old maritime painting.

Now, imagine walking along the harbor front, the air tinged with the briny aroma of the sea. Lobster traps are neatly stacked by the edge, and local fishermen, steeped in generations of knowledge, go about their day with an understated expertise that only comes from years of battling the elements. Their boats, often weather-beaten yet defiant, bob gently in the water—each a character in its own salty tale.

Then, there’s the intimate interaction with the village itself. Crail is a respite from the touristic hustle. Here, you can wander through narrow streets, flanked by historic buildings and inviting little shops that prompt you to explore more.

Take a moment to visit the local market, if it’s on, where you can sample local produce, freshly caught seafood, and artisanal crafts. Perhaps you’ll indulge in a warm bowl of Cullen skink or feast on a lobster roll, sourced directly from the harbor’s catch.

As evening falls, find your way to a local pub or a quiet spot overlooking the harbor. The setting sun casts a golden hue over the water, and for a moment, time stands still. You’re enveloped in a tranquil reverie that only a place like Crail Harbor can offer. Here, you don’t just witness life as it unfolds; you become part of the tapestry—woven into the sea, the sky, and the soul of this enchanted harbor.

Tour Glamis Castle for a Bit of British History

When we left Crail, which truly is the prettiest of these East Neuk of Fife,  we took a quick drive by Glamis Castle, which is where the Queen Mother spent her childhood.

Visiting Glamis Castle is like stepping into a living fairy tale, complete with turreted towers, hidden rooms, and a history steeped in legends. It’s perhaps most famous for being the childhood home of the Queen Mother and the setting for Shakespeare’s “Macbeth,” but it offers much more.

Beyond its architectural grandeur, Glamis Castle presents stunning gardens, guided tours that unveil its intriguing history, and family-friendly activities. Whether you’re a history buff, a fan of Shakespeare, or simply someone who appreciates beauty, Glamis Castle offers a rich, multi-layered experience that promises to captivate your imagination.

Sip Hot Chocolate in Kenmore

Nestled at the northeastern tip of Loch Tay, this charming village is a lesser-known gem that captures the very essence of Scottish tranquility. Take a moment to escape the everyday rush, and find a seat by the window in a bright and roomy restaurant overlooking the loch—a body of water that stretches 14 miles long and is imbued with myth and legend.

Here, order a hot chocolate, maybe with a dollop of whipped cream or a sprinkle of cinnamon if you’re feeling decadent.

As you sip your cocoa, the views of Loch Tay unfurl before you like a tableau painted in tones of blue and green. This isn’t just a backdrop; it’s an invitation to contemplate the deep-seated natural beauty that makes Scotland so endearing to its visitors.

Imagine a landscape carved by ancient glaciers and filled with lore of mythical creatures; a living, breathing canvas that has inspired countless poets and adventurers.

But this isn’t just a place for idle observation. Kenmore invites you to take the peace you’ve found here and carry it with you as you explore the surrounding areas—perhaps to a hike in the nearby Drummond Hill, or a visit to the Scottish Crannog Centre, where you can delve into ancient history.

The key is that in Kenmore, you recharge and recenter, fortified by the quiet strength of the landscape and the warming hot chocolate. Onward to the next stop.

Visit the Fortingall Yew and the Church

The Fortingall Yew is a humbling marvel whispering stories older than written history itself. After our cozy reprieve in Kenmore, savoring hot chocolate by a hearth overlooking the Loch Tay, the journey to Fortingall is like a pilgrimage into deep time.

The yew tree is a living monument, estimated to be between 3,000 to 5,000 years old. While modern dendrochronology leans towards the more conservative 3,000-year estimate, the tree’s age is still a subject of awe and speculation.

The tree’s girth was once a staggering 56 feet in diameter, a testament to its ancient resilience and grandeur. Yet it has been whittled down over the years—not just by the relentless hands of time and natural erosion, but also by human interference.

Souvenir hunters in bygone centuries, unaware of the tree’s historical and biological significance, hacked away at its wood, forever altering its original structure. Most of the space you see today within its surrounding stone wall was once a robust, living trunk, embodying thousands of years of natural history.

To contextualize the Fortingall Yew’s age, consider that when it first sprouted from the earth, human civilizations were in their infancy. The Egyptian pyramids had not yet been built, and Stonehenge was a future endeavor.

Standing before this yew, you are quite literally touching a living link to a distant past, an organic archive that has silently observed the unfolding saga of human civilization.

Therefore, when you visit this venerable tree, you’re not just witnessing a botanical wonder; you are connecting with a story that transcends millennia, one that holds the secrets of time in its gnarled branches.

Get Out in Nature at Angus Glens

Hike through this series of five stunning glens in Angus, each offering its own unique landscape and level of difficulty for a picturesque Scottish outdoor experience.

We hiked in between the towns on our day trip to Crail and St. Andrews, and the Scottish hillside was abloom in gorgeous heather. I’m a fan of folk music, and I couldn’t stop singing Wild Mountain Thyme in my head while we hiked to vistas and viewpoints of the Scottish highlands and glens.

Spend Half a Day Enjoying St. Andrews

St. Andrews is beautiful and worth a visit. I would have loved to spend a day or two poking around—you could easily visit just St. Andrews on a day drip from Dundee.

The small city is best known for golf and for Prince William attending college there, but it’s so much more than either of those two claims to fame. I have a fondness for small cities (like my days poking around Stirling, Scotland).

St. Andrews is charming and I thoroughly enjoyed this pretty little town. With just a half-day to spend in St. Andrews, you’ll want to make every moment count.

Start your exploration at the University of St. Andrews, one of the oldest in the world, to absorb the academic atmosphere that has shaped this town for centuries. Wander through the cobblestone streets, maybe stopping at a local café for a quick, authentic Scottish scone.

But don’t miss the true gem of the town: St. Andrew’s Cathedral. The cathedral, now mostly in ruins, was once the largest church in Scotland. A visit here isn’t just a stroll through an ancient stone structure; it’s an evocative journey back in time.

You’ll get a visceral sense of Scotland’s religious history, its centuries-old conflicts and hopes. Even in its ruined state, the cathedral stands as a symbol of Scotland’s enduring spirit and complex heritage.

Climbing to the top of St. Rule’s Tower within the cathedral complex offers a breathtaking panoramic view of the town and the sea, a vista that stitches together the tapestry of past and present. So, while time may be limited, a half-day in St. Andrews can provide enriching experiences that offer both a glimpse into Scotland’s past and the vibrant life of its present.

Additional Things to Do in and Near Dundee

Discovery Point: Learn about the Antarctic expedition of the RSS Discovery, housed in Dundee, through interactive exhibits.

V&A Dundee: This design museum offers an in-depth look at Scotland’s design history, from architecture to fashion, and is a marvel of modern design itself. It’s a good rainy day activity in Dundee.

Broughty Ferry Beach: This charming seaside suburb is perfect for a leisurely day at the beach, complete with views of Broughty Castle.

Verdant Works: Experience Dundee’s rich industrial past through the lens of its jute industry, with exhibits on factory life, machinery, and textiles.

Cairngorms National Park: For those keen on extending their range a bit, a visit to the largest national park in the British Isles offers activities like hiking, wildlife-watching, and cycling.

Arbroath Abbey: Known for the “Declaration of Arbroath,” this abbey is an important historical site detailing Scotland’s fight for independence.

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Driving through eastern Scotland, through the country’s famous Scottish glens and highlands, has been an absolute highlight from my round the world trip. I can only extend an enormous thank you to Jeannie, because of her gracious hospitality I was able to explore the nooks and crannies of this area of Scotland.

I owe one to the Universe now, and will repay it when I finally find a place to settle down. I have loved this insider’s take on the best hikes and towns, the stories of how Jeannie and her children enjoyed living this region as locals.

Planning Your Trip to Dundee

Where to Stay

Scotland is full of hostels and budget-friendly accommodations, as well as mid and high-range hotels. One of the best ways to find Scotland hotel deals is through Booking.com, where you can accrue status and save on future bookings.

Onward Travel

Think about buying the Scotland Lonely Planet before backpacking the region— I found the transportation advice to be invaluable when I was backpacking in Scotland on a budget. From Dundee, I was bound for Edinburgh!