Route: I ride a route of about 12 miles each way - mainly downhill in the morning (net elevation diff is 700 feet, not sure of total climbing, as there are many 20-50 foot ups and downs). The route is mixed with about half of the ride through charming older hilly neighborhoods on designated bike lanes, and the other half in the urban/semi-urban core (flat valley floor), also on designated bike lanes. My building is not in the heart of downtown, so my route skirts around the center of the city.
My morning ride in is 35-45 minutes depending on lights. The ride home is 50 min to 1 hour - the last 3-4 miles home is a steady uphill grade with a few steeps.
I resumed riding my bicycle this Spring after a few years off, and am quickly getting back into shape. Woohoo! I'm currently commuting 3-4 days a week, but intend to bump it to a steady 5 days by Summer's end, and am planning to commute through the winter. I love riding in the rain, too.
Bike: I sold my stable of road and mountain bikes some years back and am now riding a 120th anniversary Bianchi Milano (charcoal/silver paint, Nexus 8 IGH drivetrain) that I've modified for commutability: Flat bar, topeak explorer rack with trunk bag (ottleib pannier soon), clipless pedals, the usual assortment of lights, hutchison top slick HP tires, and planet bike cascadia fenders. I am planning to buy/build a cross bike to be my main commuting steed, and set up the milano for exclusive rain/snow duty (further mod: replace the front fork/wheel with disc-compatible, and get set up with a disc brake instead of the cheesy shimano V-brake). No pics yet, but it's a very handsome bike. I love the IGH - my only gripe is the "steps" between gears make it difficult to fine tune my pace, but who cares? I no longer race, and am content to spin in a slightly lower gear than I COULD be cranking.
I pack a spare tube, patch kit, Topeak Alien multi-tool, tire levers, mini-pump (never got into CO2 - I'm too old school, I guess), 15mm wrench for the rear (nexus) wheel, clothes for the office, and toiletries. I keep a towel at the office and am shortlisted for a locker at work. I shower and change at work, then switch back to my riding clothes before my ride home. I can't stand riding my bike for more than a few blocks in regular clothes - too restrictive and hot.