Arts
Williams: A lecture from a well renowned art historian, where only half the class is actually paying attention. Maybe a minute long walk to the WCMA for a full-museum tour in 15 minutes.
London: The National Gallery, the Tate Modern, the British Museum, and impromptu performance art demonstrations involving hundreds of people in Liverpool Street Station or Trafalgar Square.
Entertainment
W: Mostly YouTube in the library
L: Shows, movies for 10 pounds, a trip to the BAFTA red carpet to see all the celebs (true story! Saw Brad Pitt, Meryl Streep, Kate Winslet and more).
Sports
W: A strenuous 10 minute hike to Cole Field in the middle of the cow pastures for a soccer game. Two bleachers. No rowdy behavior or the big bad Campus Security might bust you.
L: A transportation mess (my bus was overtaken by Italians and consequently shut down) to arrive at a crowded 60,000 person stadium to see the Brazil vs. Italy football match. Unlike the American international friendlies, all the good players are actually present for the games. Excessive chanting and separated seating areas to prevent belligerent violence. Metropolitan Police enforcement at every Tube station within a mile or two of the stadium.
Leisurely Lunch
W: Sandwiches at Papa Charlie's. See everyone you know walking up and down Spring Street.
L: Tea at the Dorchester. Finger sandwiches, scones, and delicate pastries. See no one under age 45.
Go Out to Dinner
W: A selection of a few restaurants--Sushi/Thai (yes that is one place), Indian, or bad American food. There is always the dining hall I guess.
L: A million places to go. The hardest thing to do is choose.
Weekend Getaway
W: A 2 hour drive up to Middlebury, Vermont to visit friends and watch a basketball game. See cows, trees, snow, and if I have time, make a quick stop at the Apple Barn in Bennington to get my farm culture fix.
L: A 2 hour plane ride for 2 nights in Stockholm, the Swiss Alps, or any other European destination. See museums, tourist attractions, and eat amazing international food. Get a new stamp on my passport. It doesn't expire for another 7 years but I think I already need new pages.
Long Walk:
W: Anything more than 5 minutes.
L: Anything more than 45 minutes.
Shopping
There's no point in even writing this comparison.
Nightlife
See shopping