Compared to the rest of Chile, Valparaiso is more everything: More alive, more raw, more bohemian and more photogenic. It also has more street dogs (which equals more poo per square metre) and enough history to fill its entire sprawling harbor.

'Valpo' is a UNESCO World Heritage Site and the feeling of former glory is everywhere. In the grand decaying mansions stacked high on picturesque hills, the old bars filled with photos of yesteryear and the stately downtown buildings, including Latin America's first ever stock exchange.

During the 19th Century the port city was a bustling hive of activity and the number one stopover for trade ships between the Atlantic and Pacific Oceans. Their cargo included precious metals, spices, slaves and stones used to weigh down the ships and later formed the skinny, character-filled cobbled streets still in existence today.

Valparaiso is a city of people watching from windows, a town observing itself, as fascinated by what it sees as we were of it. We watched an old lady peer out from behind white shutters high up in a sky blue building. There were pink flowers in the window box. After drinking in her fill from the street below she quietly closed the shutters, only to open a window on a new street ready to observe a different set of stories.

Searching for a place to stay after 14 hours of wearying travel from Chile's icy toes to its bustling waist we happened upon an intriguing Hospedeja door. Painted upon its yellow face was a pair of knobbly zebra striped legs atop a spinning bicycle wheel. Gilles, a bald Frenchman in paint splattered overalls unlocked the door with a cheeky grin and a wild twinkle in his eye. Each thickly accented sentence was animated by frenetic hand gestures and punctuated with "It's OK, it's the same. Relax. We're not a bank."

La Bicyclette was a winding squash of tiny rooms, all with oddly angled walls to fit inside the mustard yellow building's turreted frame. Torn books lined the wall by the door and postcards featuring wide legged women sat perched for sale. Our room was painted sky blue, off white, and a loud yellow in random panels; our bed sheets varying shades of orange petelled flowers. Our stay of one night became two, our love for Gilles justifying the extra expense of a double room in Valparaiso.

Our first full day in Valpo we embarked on a mammoth 8 hour exploration and spent the entire time gasping with delight at each new snap-able angle. We began at the old end of town and climbed the steep streets of Cerro Conception with cool cafes and boutique stores popping out of every available crevice. From there we traipsed the high winding roads of Cerro Alegre complete with striking street art and stooped old people enjoying their twilight years. Valparaiso is by far the best city we have ever photographed.

One such eye-catching establishment was Color Café. It's run by a cute girl in a brightly woven hat with earflaps and a studious looking boy with long dark hair and thick bottle-top glasses. The walls are a jumble of love notes on napkins, worn religious cards with smiling saints, black and white photographs of stern families, woolen toys, naked dolls, wooden masks and startled faces ripped recklessly from magazines. We ordered a selection of food (having no idea of what it was) and received a fresh array of savory treats (all nothing like what we had expected). We returned one night later to order the immense desert platter, and rolled our way home stuffed with "panqueque" and cake.

Besotted with Valparaiso, we decided to stay an extra three nights. In search of a residence cheaper than Bicyclette ("It's OK, it's the same!") we found Casa Kreyenberg, a buttercup yellow house propped high amongst the street murals of Cerro Alegre. Kreyenberg has five cats; one with one eye and one stalking ginger kitten named Dexter (after the serial killer on the TV show of the same name). With a blissfully sunny deck to lounge upon with views of the harbor it was the perfect place to explore the surrounding neighborhoods; close to great restaurants, the open air art museum and the Pablo Neruda's old house La Sebastiana. Over breakfast with the owners we discussed the long standing rivalry between Chile and Bolivia, the Chileans scornfully reproaching their neighboring countries for being unable to forget past victories and losses with general bad taste.

One night we wandered into the dimly lit Cinzano bar and restaurant. Old men in mottled beige cardigans sat hunched over pints of Chilean cerveza watching The Godfather 3 corrupt away on an overhead television. We watched fascinated as a stout barman with a permanent grimace concocted a delicious medley of wine, strawberries and sprinkly heaps of icing sugar (called Marona). Lining the curling brown wallpaper was a museum of black and white photos of Valparaiso through the ages; horses battling swirling floods, earthquake flattened streets and proud floating ships, yet more material for two shutter-happy travelers.

But, as we have since discovered to our dismay, the photogenic city isn't everyone's cup of tea, probably due to the exceedingly high levels of filth. Unfortunately in South America dirtiness goes hand in hand with culture, character and good experiences - even the refugios (huts) at Torres Del Paine National Park were mildly repulsive thanks to a general lack of human waste management. But so far Valpo takes the filth cake… and discards the wrapper. Most streets feature great piles of rubbish, century old dust and - public enemy number one - dog s***.

Valparaiso is littered (so to speak) with stray dogs of all kinds, colours and creeds. The main park, where you can play cards late into the night, buy antiques and massive mouth-watering shish kebabs for $500 pesos (NZ$1.50), is home to 30+ dogs. They sleep in the sun, drool after food and narrowly avoid being run over by reckless drivers. It's also not uncommon to see a group of 10 males chasing down a female on heat and having their way with her.

However, the result is oodles of cute puppies usually bizarre looking and, sadly, homeless. Not surprisingly we fell in love with many such littlies but beware the wily old campaigners who proffer up best-buddy-ship on every street corner. One such mutt we named Herman. With one brown eye and one blue, he crossed busy roads behind us and followed unshakeable for close to an hour. We eventually lost him at a supermarket where he joined the crowd of dogs gathered around a loitering band of Valpo punks. It was a match made in rag-tag heaven.

For those with a keen artistic eye, we couldn't recommend Valparaiso more.