The thrill of the chill

I won't name the Caribbean island in question because the fault clearly did not lie with that entirely irreproachable tropical paradise. The fault lies with me. It was a perfectly nice island and I stayed at a fine resort there, but the one time I took a "sun and sand" vacation, which I did for two weeks some years ago, I was bored out of my mind.

I found myself joining in activities posted on a whiteboard and punctuated with smiley faces. I'm certain a change is as good as a holiday, but a holiday should not be a betrayal of one's fundamental nature. Even though such activities are the kind of things I always thought sane people only did in the hopes of winning parole, I signed up and I attended.

I learned the rules to a sport and then I played that sport. I paced the perimeter of the resort like a caged animal. I won the sand-sculpting competition two weeks running with submissions that involved complex preliminary drawings and incorporated found objects. These non-traditional elements, I later explained to the bartender, challenged the confines of the medium in order to comment upon the contradiction inherent in our capitalistic relationship to idealized mythological aquatic femininity. By which I mean – my sand-mermaids had Red Stripe bottle caps for nipples.

Four days into my vacation, I was ready to volunteer to help in the kitchen.

I don't relax well doing nothing. I'll never go anywhere just to be warm. So the question my friends now put to me is "Getting away somewhere cold this winter?" because, for so many reasons, that is my preference.

This year, I chose Scotland in January, and I've nothing but good things to report. Of course, I'm sure Scotland is great in the summer, too, but then I think an awful lot of other people are sure of that as well. One of the benefits of winter travel is that one largely escapes the crowds and lines that can give so many historic and cultural attractions all the charm of a Boxing Day sale. Edinburgh Castle, the historic fortress perched on a volcanic plug that is the city's centrepiece, receives about 1.5 million visitors a year, and deservedly so, but that's a lot of people.

While it's still advisable to buy your tickets in advance online, or have your trusty concierge arrange them, visiting when there's a bit of a chill in the air certainly makes the castle feel less stormed.

However, to be in Scotland in winter isn't a "beat the crowds" compromise.

Winter is a breeding ground for comfort. A decent cold season raises indulgence to an art and the Scottish do winter well.

I like how hungry winter makes me, and since a long walk, in which a city unfolds before you like a movie, followed by a good meal is my ideal break, it's as if Edinburgh was built – with close to 2,000 years' foresight – for me.

It's possible to skip too lightly over a city as picturesque as Edinburgh. My first day I spent several hours walking through the city with Gareth Davies of Edinburgh Expert visiting both the Old Town (medieval) and New Town (Georgian) and I can't recommend booking one of these tours enough. Davies delivered a lively overview of how the city evolved and drew my attention to architectural details and infrastructure quirks I might otherwise have walked right by – a travel nerd's worst nightmare.

Everything I saw on my considerable further wanderings in that city, as fine as it all would have been on its own, was enriched by the context served up on that stroll. Then, bless you nip in the air, at the end of all these walks I ate the kind of food you want to go home and start cooking.

I want to make the red pepper and tomato soup I ate at the Devil's Advocate, bake the bread that came with it, buy a cow and churn butter like that, or at least serve those slow-braised short ribs, truffled mash, winter greens and red wine jus. This atmospheric, low-ceilinged, appropriately candlelit bar and restaurant in a former Victorian pump house is nestled, like so many great finds in Edinburgh, in one of Old Town's countless, steep, narrow back alleys. I want to make a version of their milk-chocolate and orange posset served with little shortbreads big enough for me to live in.

I also had some of the best Thai food I've ever eaten at Dusit over on the "new" side of town and enjoyed a few drinks and a burger at the Queens Arms, the kind of lively local pub you want to take home in your pocket when you visit Britain.

I can't say – stepping out of the cold and into a warm pub – that I missed sand in the equation at all. I'll always take a comfortable hotel bar with hundreds of whiskies to choose from, over a bar in a swimming pool. Has humanity ever come up with a more suboptimal beverage-serving idea? Say "resort pool bar" to me and immersion in an amalgam of 20 distasteful fluids – only one of which is sweat, one is dissolved sunblock and 17 are sickly concoctions graced with oral-sex pun names – comes to mind.

I was lucky enough to stay at the Balmoral Hotel, (see hotel whisky bar mentioned above) so I was dead in the centre of a city one very much wants to be inside. I slept snug as a bug in a swinging UNESCO World Heritage Site, surrounded by museums and galleries. Please don't miss the Surgeons' Hall Museum if you go. You may not know that your holiday needs to include David Middleton Greig's collection of extremely unusually shaped skulls, many of which belonged to people who nonetheless led perfectly reasonable, long lives, but it does.

The Balmoral is one of those elegant old hotels that seemed to moor up, like so many luxury liners, along the railway routes in many cities during the great railway boom of the mid-1800s.

The hotel, which was completely refurbished and reopened (by frequent guest Sean Connery, no less) in 1991, still has the clock on its tower set, as it's always been, three minutes early to help ensure travellers going to the trains at Waverley Station below reach their carriage on time. It's an ethos that seems to run through the entire hotel; I felt they weren't going to let me mess up my trip. I felt cared for.

I took one of those trains to Glasgow, Scotland's largest city, less than an hour away. There, again, is a great winter town, the warmth of the people being pretty much all you need, but the city having much else besides. The Kelvingrove Art Gallery and Museum, set in Kelvingrove Park, where I might add it was still, in midwinter, warm enough that not-mean parents had taken their children out to play, is the kind of building one could spend hours in even if it weren't full of beautiful and illuminating things, which it is.

There's a lively current of art and industry running through Glasgow which is blessed with a great manufacturing history and home to the famous Glasgow School of Art. The past is very much there.

Indeed, the Hunterian Art Gallery has gone so far as to recreate the interior of architect and designer Charles Rennie Mackintosh's home, which was demolished in the early 1960s. Yet while there are plenty of them, and row upon row of Victorian homes and art nouveau architectural gems, the city itself is no museum.

This brings me to another point about winter travel. I'd rather see and feel how other people live and work than plonk myself in an all-inclusive bubble for two weeks, and off-season, when heads are down and shoulders are to the wheel, is the ideal time to do that.

To that end, I met with Alistair McAuley and Paul Simmons of the design-led manufacturing firm Timorous Beasties who were kind enough to show me around their studio where all the hand printing of their wallpaper is done. The two met while studying textile design at the Glasgow School of Art and, said McAuley, the firm, founded in 1990, was basically a way of "staying in art school," and continuing to create and experiment.

This they've done, to international acclaim and with much success. They are an example of how Glasgow's design legacy still plays out; everything Timorous Beasties creates, textiles and fabrics, even the lace (linear mosquitoes, large thistles, being but two designs) is produced in Britain. Their work, while certainly in the tradition of William Morris, is distinctively Scottish, or at least distinctively northern, I as a Canadian might say.

The flowers and leaves and animals that are a large part of what Timorous Beasties is famous for have not been tamed to lie complacently on your wall or cover your windows to help keep you safe. Twee is trashed in these designs in favour of a kind of postmodern pastoralism in which nature is a force to be reckoned with, not just decorated with, stunningly as their designs do that. A Canadian can feel very much at home in their work and the milieu that created it.

I stayed at the Dakota Deluxe, a new boutique hotel that seems to have risen up in response to Glasgow's growing reputation – it was already heralded as a shopper's paradise, and an epicentre of contemporary visual design, architecture and performing arts – as the hippest city in Britain. There's a music scene to be reckoned with and the bars and restaurants are worth the visit alone. Appropriately cool lodgings were needed and the dimly lit, monotone-grey and sleek-but-soft-pillowed-with-ports-for-all-your-devices Dakota provides. The only thing that's incongruous about this place is that nowhere this hip has ever before had a staff so uniformly pleasant.

Usually the people who work at places that cool are mean and want to keep you out, but the Dakota is like an opulent Glaswegian-staffed spacecraft, shaming the rest of the hip-to-be-hostile galaxy with their friendliness and helpfulness.

The hotel's restaurant is excellent, providing me with the best oatmeal porridge I had while in Scotland, and I was on something of a quest. I also spent some very pleasant hours dining from the inventive but not ill-considered menu at Stravaigin, where a Gibson garnished with pickled onions inspired me to take home a bottle of the Caorunn gin used therein.

Caorunn, a relative newcomer to the gin market, is infused with rowan berries, heather, dandelion, bog myrtle and coul blush apples as well as the usual juniper, and is produced in the Scottish Highlands, about which I can only say their singular, mournful, rugged beauty makes bagpipes make sense. And is there a greater compliment?

So go to Scotland and go in the winter. Amortize that expensive parka of yours out over another season. Capitalize on your Canadian-ness. Just smile politely when the people of Scotland keep apologizing for the weather when it's plus-seven.

"I'm Canadian," you may say, "you can't out-cold or out-apologize me, Scotland, but what else you got?"

The answer is "Plenty."

The writer was a guest of the Balmoral and the Dakota Deluxe. They did not review or approve this article.