Fall is my favorite time of year and when I prefer to travel. Most places are cooling down after summer and offer some of the best prices of the year. And, living now in San Francisco where seasons don’t really exist, it gives me a chance to experience the fall weather I grew to love as a child.

Whatever time of year I travel, though, I struggle with the same question: Do I go somewhere new or back to a favorite? The latter holds me with a nearly unshakeable grip promising to feed my desire to move beyond the shallow familiarity of the tourist into a deeper understanding of a place and its culture. Short of living somewhere long term, deep connections are slow and arduous requiring many visits coupled with a sincere effort to glimpse the locale behind the pretty facade.

But what of the allure of the new? What if a previously unknown city is the one? I’m not ashamed to admit that I’m still looking for that. I’ve come close with a couple of cities where the connection has been nothing short of spiritual tempting a belief in past lives with unfinished business.

And my journey continues.