Varun,
I wouldn't call it over optimization, but perhaps, your title tags combined with your content may be a cause. Even if it's not, heeding the following will be helpful to you in the long run.
Yes, it appears that each post is unique and maybe even somewhat "researched", but the combined vocabulary on all of your pages is very homogeneous. As you get more and more of content on your site that fits pretty much the same templated paragraph headings, the overall feel of the words in those paragraphs is that they're all the same, just in different order and different amounts. For the most part your pages contain the same weather, gender, clothing vocabulary. It's the kind of content I call "fluffy"--a lot of words but not really a lot of meaning.
To get a sense of what I mean, lift three or four sentences at random from three or four pages on your site and put them together and see if they form a paragraph of about the same quality as an average paragraph on your site. My feeling is that the more content like this you put on your site, the more it looks like "spun" content and that might be tripping a filter.
I would suggest that each page for each city also contain mention of 3-4 local landmarks, a few local boutique names, 2 or 3 local street names, and a couple of activities, events, the name of the primary mass transportation system, and/or personalities that make that city unique. Going to foursquare and selecting "outdoors" or "sites" as your "I'm searching for" criteria can help your writer with with a starting place for some of these things.
The more you incorporate this additional dimension into your copy, the more effective it will be at converting your clients and the less you'll have to worry about discounting its quality.