In a portside city bursting with history, see ten of the best sights (with a little help from your host!), like the incomprehensibly big fortress the San Felipe Castle, with a monument on its outskirts honoring a Spanish admiral. Behind the Old Town's mighty walls, see the loud-and-proud city's watchful eye the yellow Clock Tower, and take your pick of surrounding landmarks, like the lively Plaza de Los Coches with vendors selling everything from sweets to a phone call, to the busy Plaza de la Paz and its El Camellón de Los Mártires statue, honoring independence soldiers. Brighten your day with a peek at the candy-pink theatre Teatro Heredia, and feel the bustle in Plaza Santo Domingo, sprinkled with Botero sculptures and foot-stamping buskers.

Jump right into your adventure on top of the San Lázaro Hill, where the colossal San Felipe fortress is strategically located with breathtaking panoramic harbor views. Wander along intertwined paths of the barricaded Old Town, along a palm tree-lined plaza to the city's main gate, flanked by Tuscan columns overshadowed by the beaming Clock Tower. Pass an array of landmarks to El Camellón de Los Mártires, which honors revolutionary martyrs, with an emblematic view of surrounding must-see spots. Dart through narrow alleyways lined with charismatic fruit sellers from a nearby village, and hidden hues of yellow and blue Spanish colonial buildings, towards a dusty pink convent turned theatre, before darting to the bright balconied Plaza Santo Domingo.