It has now been over a year since my move to Boston from Palo Alto, which seems like a fitting time to take a retrospective look at the two places. My sampling will be far from unbiased, having lived close to 20 years in the Bay Area. As a result this will be more like “Boston through the eyes of a Northern Californian”. There is no specific order to the comparisons below; I will vacillate between the substantive and the frivolous. And there will be no declared winner; both places are far too different and offer far too much for one to dominate the other in the Pareto optimal sense. At times, this will be more about Stanford vs. Harvard than the Bay Area vs. Boston, as much of my experience is ultimately grounded by my local environment.