So this wasn't much a competition, but for consistency sake, here's the low down.
Let me start by saying that my parents accentuated this trip and made it more than memorable. My mother's passion for the royal family made her an impeccable tour guide, often times knowing more than the tour guides we actually had. So with her by my side, this quickly became a favorite sight.
We took a train to Windsor from London and thanks to a colleague here back in New York, I learned that Slough, where we transferred to catch the train, is the city where the British series, The Office, takes place (equivalent to the American version's Scranton). And when we arrived, we were delighted to come across a quaint little town, full of character and good shopping. We caught a brew at a local pub, The Three Tuns, which turned out to be the oldest building in the town where I was delighted to hear a little Lou Reed while dining, "Hey babe, take a walk on the wild side" - a perfect soundtrack to my first overseas experience.
Moving onto the castle, I must state it was outstanding, but what I found of most interest was it's on site church. Buried there is Henry the VIII as well as King George VI (Colin Firth in the King's Speech) and his wife. Needless to say, my mom was freaking out.
We explored the state rooms, near where Queen Elizabeth still resides today - as you may know, Windsor is her weekend/country home to Buckingham Palace. Between the paintings, the mural and opulent wood and marble work, I was blown away by the castle's extravagance.
The Monument (picture coming soon)
The Monument was interesting, but a bit disappointing in the same fashion. It was built as a memorial to the Great Fire in which most of London was singed to pieces (although few casualties we were told). The statue was built to be exactly 202 feet tall which represents its distance from the site of the fire - a baker's shop on Pudding Lane (I know, I was excited too that a baker worked on Pudding Lane).
While it was tall and towered over many of its surrounding buildings, there really wasn't much to it, and so Windsor Castle, which its rich history and lavish nature steals this one easily.
Winner: Windsor Castle