i lived there for over a year while on work assignment. it's the best year of my life.
i posted an itinerary somewhere either here or the old sbf on this part of italy, and if i find it will post the link. for 2 weeks, that's a lot of ground to cover, but it will be worthwhile.
first off, vehicle. i recommend a small station wagon, crossover, or small suv to carry all the luggages and things you may buy on impulse. automatic transmission preferred if you can get it. it's much easier on narrow hillside roads in italian towns. italians like their manual transmission, but the new auto and semi-auto gearshifts have improved to such a point that it makes no sense going back to manual. and by the way contrary to popular belief, italians are very good and considerate drivers on the autostrade. slow vehicles keep right, fast vehicles take the middle lane, and the leftmost lane is only for overtaking. german, swiss, and american drivers hog the left lane, to the chagrin of italian drivers. very few french cross to ventimiglia from menton. french think their riviera is still the best in the world. do not leave luggages in vehicle unattended in centro of large cities.
hotels. i recommend 4 hotels or 5 the most - 1 in milano, 1 in torino, 1 in genoa or portofino (although i recommend monterosso in cinque terre) 1 in ferenzia, and 1 in venezia. use these anchor hotels to safekeep your heavy luggages, and make day trips to towns and cities around them.
itinerary. on arrival in milano, might as well stay in milano for a day and explore city. plan a day trip to lake como the next day (a must). plan to stay in torino for a day or two. check out aosta, the northernmost town before mount blanc and the alps, cervinia-breuil at the top of alps where matterhorn is. drive down to genoa, then to the levante coast (italian riviera), and spend a day or two at santa magherita, portofino, cinque terre (5 sea towns). drive south to ferenzia and stay in the heart of the city by the duomo as much as possible. there are 3-star albergo's near the duomo. you can explore piza and siena which are near ferenzia. about 2 to 3 days. and northeast to bologna on the autostrade. if you have time, may as well detour slightly and stop in parma. parma is famous for its prosciutto and regina parmeggiano cheese. you'll need at least 2 nights in venezia. venezia will cap your romantic italian tour.
enjoy!