The very first thing we do is break the rules. We’d embraced the challenge of spending a weekend getaway solely on one  road – the bohemian Mecca of Wellington’s Cuba Street – and, barely 20 minutes after landing, we fail. Our downfall comes served on a plate, lightly toasted and topped with tomato, basil and melted mozzarella. Our downfall is a crumpet. Our downfall is delicious.

We spy Crumpet en route to our hotel. This small art deco café is attached to the Opera House on Manners Street and its nostalgic charm instantly appeals, as does the promise of its homemade crumpets. They do not disappoint, being thick, light and scrummy. I wolf two – one savoury, one sweet – and wash them down with a frothy lime shake.

Afterwards, as we make our way uptown, we successfully argue that as we hadn’t yet arrived on Cuba, we hadn’t technically broken the rules. We determine to throw ourselves back into the challenge with renewed conviction.

A restless energy envelops Cuba Street this Friday evening. The hustle and bustle of the business-suited after-work crowd mingles with students and the strained warbling of the occasional busker. People are sipping pints in pubs or barreling towards bus stops, the weather not encouraging loitering. We join the fracas, ducking into the first bar that’s not too crammed.

The less inhibited market goers join the bongo circle, jerking awkwardly in a rough approximation of dance.

The rainbow dance floor tiles in the entrance, the disco balls and the Village People pumping on the stereo should have provided clues we’d walked straight into a gay bar. We just thought we were walking into a cosy bar that played atrocious music. By the time we realize, we’re committed to staying. We order drinks and shake our heads in disbelief that we hadn’t clicked after seeing the name of the bar: Scotty & Mal’s Cocktail Lounge. S&M for short.

In the office on Monday I will relay tales of gastronomical bravery to a colleague who is a gourmand. I’ll speak of ordering offal and she’ll be impressed and ask what I ate. With a small note of pride I’ll reply "beef cheek" and she’ll laugh while launching into an explanation of why cheek is not offal. But, that’s still a couple of days away. For now I’m nervously pushing a thin crispy sliver of a cow’s cheek around my plate at Wellington’s long-established cultural capital of hip, the Matterhorn. The menu informs me that the cheek’s been drizzled in yuzu dressing, but I don’t know what a yuzu is, so that’s little comfort. Determined to be more adventurous, I slowly raise the cheek to my mouth and take a bite...Wellington1 Inpage

Feeling full of culinary courage, we hit the neighbouring Left Bank night markets in search of a sweet treat for dessert. The damp hasn’t deterred a decent crowd from milling around and neither has the folk singer murdering Madonna’s ‘Material Girl’ near its alleyway entrance. As we wander, a growing commotion near the far exit commands our attention. Turns out it’s a bunch of bongo players whopping and a-hollering and banging their drums. The less inhibited – or possibly more intoxicated – of the market goers join the bongo circle, jerking awkwardly in a rough approximation of dance, but most just head-nod to the rhythm before chucking some coins into the group’s donation hat and continuing on.

We wake to a very wet Saturday, but the deluge does not wash away my partner’s enthusiasm for what she’s gleefully titled ‘shopping day’. I voice the usual manly protestations, but happily join her in dashing from shop to shop through Cuba’s vast array of vintage stores. The retro furniture tucked upstairs in Hunters & Collectors has us concocting increasingly ridiculous transportation plans; we try on and put back expensive winter coats in Ziggurat, but eventually succumb to purchasing a period digital watch (me) and some second-hand boots (her) in funky opshop, Emporium.

Then we drop inside the Light House Cuba, a brand spanking new boutique cinema just around the back of Cuba on Wigan Street. Inside the quaint theatre are rows of comfy two-seater couches and we plonk down, snuggle up, and forget all about the wind and rain outside.

Saturday night sees us entering into negotiations. Despite best intentions, our self-imposed rules have been flagrantly ignored. While Cuba has remained our launching pad, we’ve smuggled across its borders regularly during our stay. We decide to extend our boundaries to encompass ‘the Cuba district’; in other words, the whole central city. Satisfied with this compromise, we leave the backstreet Havana Bar, pop open the brolly and leave Cuba behind, as we venture forth into the wild night.

It’s a bleary-eyed kind of morning. Memories of exotic venues and outlandish drinks dredge themselves wearily to the surface; Jungle Birds at sophisticated lounge bar Motel, ‘Pils n Thrills’ craft beer at trendy Hashigo Zake Cult Beer Bar, Long Island Iced Teas and scrumptiously tasty tapas at El Matador. Fragments of grooving to old school hip hop in the dark of Good Luck Club and rocking out to guitar bands in the cartoonish glow of live venue Mighty Mighty flutter in and out and away.

But mostly at this late hour on this fuzzy morning there are just thoughts of scoffing breakfast and getting to the airport before our midday flight. We may have broken the limitation of holidaying in a single street, but when it comes to airline check-in times, we don’t mess about. There are some rules in this world that just aren’t meant to be broken.

Reported by Karl Puschmann for our AA Directions Winter 2013 issue

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