A 14-Day Scotland Itinerary

Travel plans and musings tend to go into overdrive at this time of year. It’s really very funny to watch. Suddenly there’s a whole bunch of stuff that shoot up the priority charts when it’s pishing down. Gaps in life need filled, memories are aching for the making and the heart starts to completely overrule the head. I want to see X, I must experience Y, my life is incomplete because I’ve never had Z. Helps make it one of my favourite times of year in a dreamer’s sense. Anticipation is king. Which brings me to the question that’s been coming my way a lot in recent weeks in the context of Scotland travel planning – what would I do? Never mind all that done-to-death stuff, away with you and your tourist traps. With a 14-day itinerary, how would a local truly do Scotland?

First of all, I completely understand this mindset. The desire to tap into local knowledge and preferences in the search for originality. You’ll not catch me wandering the Royal Mile in the height of summer unless it’s unavoidable. The Fairy Pools have been ruined for me. I couldn’t give a flying fish about a fictional monster not living in an underwhelming loch. Queuing at Eilean Donan and joining the procession up Ben Nevis’ tourist route…..not this guy. So originality and authenticity weigh heavily for me too….but I do still want to be wowed. Solitude is important, I want to feel the real Scotland in my bones. But it can’t be at the expense of quality.

Alright then. Let’s assume loosely that I’m now advising a once-or-twice-in-a-lifetime visitor who is looking for a comprehensive appreciation of what this land is all about. It’s Scotland so the outdoors and history are the priority. Hikes, ruins, beaches, a dram or three and first-hand experience of our famous romantic melancholy must feature. Give me a hypothetical 14 day Scotland itinerary to play with, a mid-range budget and total freedom to choose without obstruction. I’d visit in spring or autumn and it would look something like this…..


Itinerary Days 1 and 2 – Glasgow

I’m a Glasgow boy, you’ve probably noticed. So I start in Scotland’s largest city, where culture dominates. Kelvingrove Art Gallery, Glasgow Cathedral, the Mackintosh attractions and the Gallery of Modern Art will fill your two days easily. Whisky aficionados can head to the shiny new Clydeside Distillery, music lovers to King Tut’s and street art admirers have a ready-made trail.

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Glasgow University.
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Glasgow Cathedral.


Seafood fans book well in advance to get into Crabshak. For something fancy try Cail Bruich or the Ubiquitous Chip. Curry fans head to Mother India Café outside Kelvingrove. Pizza doesn’t get better outside Italy than Paesano. Hipsters look no further than Hanoi Bike Shop. Glasgow does food well.



Day 3 – Loch Lomond and Argyll

Adjusted and fattened up nicely, it’s time to leave the bright lights behind and head into the Highlands. Loch Lomond’s bonnie banks will be your introduction and outdoors lovers may want to get their boots on early with a straightforward wander in the Luss Hills. Luss village itself is far too busy in peak season. For something bigger, Ben Vorlich or Arrochar’s Ben Arthur (also a busy one) are options along your road.

Non-hikers can skip all that and can continue straight on to Inveraray, stopping where it feels right. The famous Rest and Be Thankful is one of many that will unashamedly snatch your breath out from you. Inveraray’s castle is one of our most visual and you can close the day in or around the coastal town.

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Rest and be Thankful, Argyll.
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Inveraray Castle and Gardens.

A complete alternative to all of that (for hikers and non-hikers) is to head straight to Glen Coe from Glasgow. Peaks like the Lost Valley, Buachaille Etive Beag and the Pap of Glencoe are ideal half-day options while others will be happy at ground level, listening to the decipherable wail of woes past in the most famous Glen of them all. There’s paddleboarding, gentle walking at Glencoe Lochan and the full story of the infamous massacre at the Visitor Centre. Stay overnight in Glencoe or Ballachulish.

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Buachaille Etive Beag ridge.
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14 Day Scotland Itinerary – Glen Coe.


Seafood lovers will not be able to stop themselves from pausing at Loch Fyne Oysters (if going the Inveraray route) and Loch Leven Seafood Café is even better (for those going via Glen Coe).



Day 4 – Central Argyll and Oban

Your first morning drinking in Highland air is special, so enjoy that at Loch Awe (or Glen Coe depending on yesterday’s decision). Admire how Kilchurn Castle manages to effortlessly watch over, sentinel-like, our longest loch. Hikers can fuel their fire with a moderately challenging battle with Ben Cruachan; non-hikers just head to Oban where castles at Dunstaffnage or Dunollie are on offer. If coming from Glen Coe, pause at Castle Stalker on your way down to Oban.

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Kilchurn Castle, Loch Awe.
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….vs Castle Stalker.

A late afternoon/evening ferry to the Isles will whisk you past Duart Castle on Mull, the remote Ardnamurchan Peninsula and eventually into open waters for the crossing to the Outer Hebrides. It’s a four or five-hour ferry journey so you’ll arrive late into Castlebay.


Seafood again in Oban, it’s not the Gateway to the Isles for nothing. A classic fish supper can do battle with something fancier at the wonderful Etive Restaurant in your ponderances.



Day 5 – Southern Outer Hebrides

You’ve arrived. I’m genuinely jealous of you, the anonymous person on this hypothetical journey. Feels good I bet. You’ll have heard the faint whisper of Gaelic on the water, somehow penetrating the din of the Calmac kitchens, on the crossing. It’s like a solemn security perimeter to these islands, the first line of defence. It will let you enter easily enough, just don’t be surprised if it’s much harder to escape.

You’re starting towards the southern end of the island chain so take the morning to admire Kisimul Castle, maybe scrambling up Heaval for whopping views or to Vatersay Bay for sands that’ll bury themselves in your soul. In the late afternoon, jump on the short ferry to Eriskay, relive the moment Bonnie Prince Charlie first set foot on Scottish soil at the neighbouring beach and then drive north onto South Uist, where accommodation is generally more plentiful (AirBnB may be the best bet).

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Kisimul Castle, Castlebay.
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Vatersay Bay.


Café Kisimul does an extraordinary job of delivering good Indian food, something I’ve otherwise yet to experience outside of Glasgow and Edinburgh in Scotland.



Day 6 – The Uists

While the extremely rugged peaks of South Uist will tempt walkers, coast fanatics are about to be spoiled rotten. I can’t get enough of North Uist’s west and north facing sands and that whole corner of the island is arguably Scotland at its raw, beautiful and mesmerising best. Hat-holdingly gusty, you’re a mere pawn in nature’s game up here as the Atlantic dances with a landmass that humankind seems to have almost forgotten about. The very occasional fellow gobsmacked soul aside, you can drift solo around the Udal Peninsula in a dream-like state for as many hours as daylight will allow. Capture a sunset if you can, safe in the knowledge it’ll be a moment never forgotten.

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Sunset at Traigh Iar.
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Hosta Beach, North Uist.

Itinerary Days 7, 8 and 9 – Harris

The theme continues on Harris, our most celebrated beach mecca and coastal playground. A morning ferry into Leverburgh leaves you time to play with as the countless beaches of South Harris contest with the rough, unwandered terrain of North Harris for your attention. I’ve listed what may seem a generous 3 days here, I feel it needs it and you should never rush Harris.

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14 Day Scotland Itinerary, Isle of Harris.

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Lost in the North Harris hills.


The Anchorage in South Harris is one of our best island restaurants and not to be missed. Stock up on Scotland’s current favourite gin at the Harris Distillery in Tarbert too.



Day 10 – Lewis and Ullapool

I’m doing Lewis a bit of a disservice in giving it less than a full day, I’m just besotted by Harris and can’t help myself. I apologise, sort of. But definitely take the time (ideally for a sunrise) to understand Callanish, the most emotionally-charged standing stone site in the world. Dun Carloway is an historic marvel and the west coastline does have yet more glorious sands, Bosta on Great Bernera is another favourite. For a bit of local culture, visit Stornoway’s Lews Castle to see a lovely tribute to island life that includes the celebrated Lewis Chessmen.

An evening crossing to Ullapool will take you back to the mainland.

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Callanish, 14 days in Scotland.
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Lewis Chessmen.


The Digby Chick in Stornoway is my go-to.



Itinerary Days 11 and 12 – Assynt, Sutherland

Assynt battles with Skye and the Cairngorms as our most serious hiking terrain. For me it actually comes out tops given the digestibility of it – there are a handful of spectacular peaks that need seeing to and it’s easy to get your head around how to go about them. They are remote. They are popular. And they will astonish you.

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Stac Polliadh.
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Novices could not ask for better than Stac Polliadh, a fearsome-looking shard that is in truth one of the easiest hills of this scale that you’ll likely ever climb. Bucket list enthusiasts will be drawn to lonely Suilven, the sugar-loaf masterpiece that requires a full day.

Even if hiking is of no interest however, the scenery from ground level will suffice. Ardvreck Castle is an eerily isolated wreck on the banks of Loch Assynt, the Bone Caves give a chilling reminder of life here before human interruption and the beaches at Achmelvich, Clachtoll and Clashnessie are some of the mainland’s finest.

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Clachtoll Beach.


Day 13 – The Drive South

There will be a pang of sadness at turning your back on these other-worldly lands and heading back to civilisation, you have been warned. The road south is a long one, but full of welcome interruption. Pause at one last distillery en route, with both Tomatin and Dalwhinnie helpfully set alongside the A9. Ruthven Barracks and Culloden (with a slight detour at Inverness) are both warmly advised too.

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The Hermitage.

A stretch of the legs at The Hermitage or Killiecrankie will throw you right into the deep end of Perthshire’s Big Tree Country before the final retreat to Edinburgh.


Day 14 – Edinburgh

I’m generously assuming you’ve got a full day to play with here and, while the Castle is too touristy for me these days, I’d brave the crowds for the excellent Mary King’s Close, the view from Calton Hill and the ascent of the iconic Scott Monument. Dean Village is one of the few, relatively, serene spots (forget it in August mind you) and cultural attractions don’t come much finer than the National Museum of Scotland.

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Dean Village, Edinburgh.
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Edinburgh Castle.


Head to Leith and either Fishers or The Kitchin, both top drawer. Ondine is a long-standing culinary powerhouse in the Old Town for something more central.


Notes – 14 day Scotland Itinerary

I’ve omitted huge swathes of Scotland here, I’m all too aware. Some really good stuff too which doesn’t sit well I promise you. But the North East needs to be taken on alone and is too difficult to fit into a nationwide fortnight like this, similar story for Southern Scotland. You’ll need another week at least for them. Skye I’d only ever recommend outside of peak season, for the time being at least. I missed so many islands…..

I like our cities a lot, but they’re not where Scotland’s true magic lies (for most visitors anyway) and you’re going to need to be brutally selective with just 14 days. This is just one man’s opinion and do tweak it, expand on it and overhaul it at your pleasure.

Accommodation should be booked months in advance to avoid it dictating your itinerary. Your own wheels are essential. Food recommendations have assumed that local produce is your leaning and that you have at least a partial soft spot for world-class seafood.

All that considered, the above 14 days will be a trip you’ll never forget. You’ll have gathered an understanding of our pace – from big city buzz to Outer Hebridean tranquillity. You’ll get that we are unique, and almost impossibly diverse for such a small nation. Mournful glens, stoic ruins and beaming beaches will be ceilidh’ing around in your mind’s eye, encouragingly coerced by the taste memory of fresh-from-the-oven single malts.

This is Scotland, spread the word.