When I'm visiting a city for the first time, I love prowling around narrow alleyways and roaming in and out of groceries and other shops sometimes with no agenda in mind. But, I'm also very keen on signing up for a small, specialized guided tour that will provide some interesting insights that I might otherwise either not be aware of or that would require toting along books on history, archeology and religion in order to truly feel like I have a handle on the local culture.
In the case of Istanbul, an expansive city bustling with more than 12 million people, an expert tour guide is even more important. Not someone who will take you along to see the usual tourist haunts, telling you what you'd find in any guidebook. No. I wanted someone who is specialized and will point out sights that are flying under the radar. And, I wanted a walking tour because that's the only way you will truly see the life of the city.
That's why I took a walking tour with Context Travel, a company with well-educated docents. My guide, Claire, was a historian specializing in medieval history who'd been living in Istanbul for quite some time. Our ultra-small group roamed Istanbul's Balat neighborhood -- and the adjacent Fener neighborhood -- which is very much working class and more on the conservative side, where we saw many women dressed traditionally in long skirts and wearing head scarfs.
Our first stop: the Kariye Museum, a church-cum-mosque-turned museum. Though Kariye sees many tour groups, most race around shooting photos of the 14th century mosaics and frescoes. Too bad, because almost every surface of the ceilings and walls are covered with the ornate works that tell the story of Mary and Jesus. Instead, we spent more than an hour with Claire explaining the personalities in many of the images, what miracles were depicted in the frescoes and the reason for some curious works -- like why Jesus is shown as having been born in a cave, something that's common in the Greek Orthodox religion.
Then we climbed atop the remains of the old fifth century city walls that afforded us with panoramic views of the city. Interestingly, Claire told us that at that time, Istanbul was referred to simply as "the city" -- kinda like Manhattan -- or the "red apple" because of its beauty. We inspect a cylindrical guard town and the remains of where Constantine lived atop the walls because it was the safest place in the city. (He died fighting.) Interestingly, it wasn't until the 15th century that a canon was invented that was able to penetrate these travertine stone and brick walls.
As we wandered along the streets, we passed a woman sitting on a rug outside her house with a mass of sheep's wool beside her. Claire explained the woman is restuffing her mattress with polyester fill and wool that she recently washed, a very common practice. Nearby, a man selling fresh fish, pulled a wagon piled high with tubs of ice and various fish species and a large scale.
We were in luck when we found the tiny Church of the Dagger open -- it's only open when the woman caretaker is available. She unlocked the doors and we found out how its curious name came to be. Claire told us that long ago someone stabbed an icon of Mary and blood poured out. This may be a small church but it's quite ornate with the silverwork image of Mary and baby Jesus -- a dagger protrudes from her robes. And plenty of other silver laden images.
As we strolled the streets, Claire pointed out a series of three-story wood frame houses that date to the 19th century. These are the last remaining ones of this type that were the norm in this part of the city.
Though so many of our wandering were along windy streets, now we found ourselves in a more regimented grid system. This is the old Jewish quarter where we stopped at Ahrida, the oldest synagogue in the city. Claire told us that inside sits the reading platform in the shape of a ship's prow. One interpretation is that it represents how the Jews once traveled here. However, we could only admire the synagogue from the outside -- it requires special permission to enter.
Our final stop is considered the holiest spot in the Greek Orthodox Church. That because the 19th century Church of St. George is the worldwide headquarters of the Orthodox Patriarchate. A lunette depicting St. George can be found inside as well as a gilded altar and a fifth century throne. On our way out, we passed a black-garbed abbot with a cylindrical black hat. Claire whispered to us that it's most likely an abbot and not the Patriarch because his hat would've been much taller.
Yes, you never know what you'll learn on a walking tour.
• Don't just spend your time on the European side of 
