04/06/2012 07:15 am ET Updated Jun 06, 2012

Our Girl In Havana: First Impressions Of Cuba (PHOTOS)

I arrive to the soundtrack of Charlie Parker's jazz crackling out of a rigged up car stereo. The music is punctuated by the syncopated shake, rattle and roll of a beat up old Chevrolet hurtling along beside my taxi. All I needed was to be handed a cigar and a mojito and my stereotype of Cuba would be complete.

I have come here to work on a new Havana city guide for GuidePal. We make travel apps for smart phones, which feels somewhat ironic in a country in which Wi-Fi is still the stuff of the future. Luckily the app functions offline, but the country's out-of-date technology highlights what is a frequent complication here: the needs of the present, impeded by the problems of the past.

I am staying in a casa particular; these are private homes with rooms to rent for tourists. Cubans must be granted a license in order to run a casa, and while it is getting easier to start a private business, the red tape and fees associated with it are enormous and deter many from attempting it. Nonetheless, there are thousands all over the city; mine is in Vedado, the more modern heart of local nightlife and dining.

With a heavy old wooden front door and grand towering rooms, this is the home of a wonderful little old lady, Jessie, who has probably smoked a million cigarettes in her life and now only talks in a whisper. Like everything here, time has stood still even within the walls of the apartment. No books on the shelves are dated past the '50s, and all have turned a dusty shade of brown. The bathroom is that fabulously vintage color combination of coral and mint, and the walls are adorned with kitsch decorative plates.

I spend my first day on foot. I walk along the Malecon -- the seafront boulevard that runs parallel to Miami's Ocean Drive just over the water -- but there the similarities end. The street life here is of a very different order. Pelicans dive into the dark waters, as wizened old men sit fishing on the rocks. Waves crash over the wall splashing couples promenading arm-in-arm. A group of teenagers gather around a stereo and dancing erupts on the street. The pavements may be pockmarked, the once magnificent neoclassical buildings battered by the sea and the walkway cut off from the water by a highway that is more likely to kill you than anything else in this city, but it is the heart of Havana: an open-air theatre of Cuban life.

I stop for my first mojito at the infamous Hotel Nacional, to prop up the bar where Winston Churchill, Frank Sinatra and naturally Ernest Hemingway all once drank -- not to mention every 1950s U.S. mobster. Elevated on a great rock, the Nacional looms imposingly over the vista. Tourists drink their cocktails looking out to sea as peacocks strut around their tables, insulated from the chaos below. It costs $4 -- twice as much as a local bar -- but its worth it to follow in the wobbly footsteps of great drinkers before me.

Moving on, I walk inland. The buildings around me are a not only a study in Old World colonial architecture but also in the logistics of keeping a structure upright using precariously balanced sticks and stones. Everywhere you walk, balconies threaten to collapse above you and below, the pavement could cave in beneath your feet. The facades have chipped away and the glass in the windows is shattered, but there is a faded beauty both melancholy and alluring in the desolation.

I know I'm reaching Havana Vieja, the old town, as the houses start standing-up straight and the colors brighten. The Office of the City Historian has done incredible work in restoration. Celebrated the world over and with ongoing projects city-wide, they are well on their way to saving what was a crumbling slice of history. It is sensational.

It isn't just the buildings that make it so; they form the backdrop to the cacophony of street life here. Salsa streams from the windows of the tumbledown houses, slickly dressed boys catcall every passing girl, bicycle taxis hurtle down the cobbled roads and the cries of street sellers hawking their wares echo between the buildings. There is color and noise and sensation at every turn, all ramped up to full volume. And then there are the men sat forever on their step with a bottle of rum just watching the world pass by.