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Wellington is a compact capital city – two kilometres in diameter, with about 180,000 people in the downtown core – that feels more like a village, yet it oozes urbane sophistication. Head down to the Cuba Quarter in the bustling Te Aro business district for a taste of kiwi cool. This is where the city's cognoscenti gravitate to enjoy an eclectic mix of eateries, nightclubs, galleries and boutiques.

Cuba Street has seen a century of good times blow in and out like the harbour breeze. Named after the Cuba – a ship of settlers that arrived in 1840 – the street prospered at the turn of the century as a commercial strip along the route of Wellington's early electric trams. As banks, businesses and shops sprouted, the elegant Edwardian and Victorian buildings reflected the newcomers' British roots. Ironically, ensuing periods of economic gloom and boom proved a blessing for Wellington's architectural heritage. Developers looked to vacant lands, and Cuba Street was spared: Its older buildings were never razed and the area became a bohemian hub for writers, artists and musicians.

Meanwhile, mid-Cuba (the nickname for the middle stretch of Cuba Street) gained notoriety as its cross streets and laneways cultivated a red-light district and a hive of Chinese opium dens. Although opium was banned in 1901, myths abound of its sordid existence to the 1960s. When the trams stopped running in 1964, the street was closed and the area was turned into a pedestrian shopping neighbourhood and renamed Cuba Mall, now known throughout the city as the place to shop. Today, Cuba Street is a designated historic district and an architectural treasure trove of Victorian and Edwardian commercial architecture. Just as important, it's a neighbourhood worth visiting if only to sense the burgeoning Kiwi vibe.

GOOD COFFEE, GREAT PEOPLE WATCHING

Floriditas: 161 Cuba St.; 04-381-2212; www.floriditas.co.nz

Scopa: 141 Cuba St.; 04-384-6020; www.scopa.co.nz

It's common to find the city's elite – from cabinet ministers and museum curators to film producers like Peter Jackson – meeting colleagues over espresso alongside university students and artists from the nearby Toi Pöneke Arts Centre. Look for them among the early risers at Floriditas. The Parisian-style café – also renowned for its extensive wine list – which offers mouthwatering breakfasts as well as seasonal Kiwi fare like Clevden buffalo mozzarella with purple and green micro basil, and pan-fried hapuku fish with sorrel and caper risotto for the lunch, dinner and late-night crowds. Another great spot for people watching is Scopa Caffé Cucina, where most celebrities eventually arrive to indulge in heady espressos, creative salads, thin-crust pizzas and savoury pastas.

A CULINARY CAPITAL

Logan Brown: 192 Cuba St.; 04-801-5114; www.loganbrown.co.nz

Consistently ranked as the nation's finest restaurant, Logan Brown Restaurant and Bar mingles tastes of Cuba Street's past and present in an opulent, 1920s bank building. The restaurant delights diners with sensuous dishes such as Paua (abalone) ravioli, and oenophiles with its cache of exclusive wines. The bar is an intimate haven to linger over cocktails while listening to live jazz.

NEW MUSIC AT THE MATTERHORN

106 Cuba St.; 00-64-4-384; www.matterhorn.co.nz

The Cuba Quarter thrives with clubs that attract international bands and musicians, but Matterhorn reigns as Wellington's incubator for new sounds. It was also the setting for the Fat Freddy's Drop album Live at the Matterhorn. Locals frequent the restaurant for seasonal cuisine, and linger in the bar over cocktails, tapas and music.

AOTEAROA STYLE

Madame Fancy Pants: 217 Cuba St.; 04-385-0830; www.madamefancypants.com

Munro: 160 Cuba St.; 04-384-1945; www.munroclothing.com

Aotearoa – New Zealand's moniker in Maori (pronounced A-o-tay-ah-roe-ah) – abounds with creative characters eager to showcase their talents on Cuba Street.

Madame Fancy Pants is the fashionista's source for funky accessories, coveted jewellery crafted by owner Claire Terry and other fave kiwi designers, quirky bags by Deadly Ponies, and curios like sweet ceramic dishes by Rachel Carley.

Munro is the source for Kiwi Caroline Munro's designer label of New Zealand merino wool sweaters in a rainbow of sassy hues for men, women and children, as well as her cheery God and Goddess underwear, all cozy souvenirs for Canadian climes.

SLOW BOAT TO CUBA ST.

183 Cuba St.; 64-4-385-1330; slowboatrecords.co.nz

Slow Boat Records is a must for music buffs. New Zealand's longest-running indie record store is the ultimate source for vintage vinyl, CDs, posters and cool T-shirts. Visited by the likes of Radiohead, the Beastie Boys, Oasis and the Smashing Pumpkins, it carries everything from jazz and rock 'n' roll to classical and electronica music.

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