Jerusalem Free Walking Tour With Romantic Twist

Walk with me in Jerusalem old town and find out why this breathless city is the perfect scenery for a cinematographic love story!

Read also Israel Ready to go: travel itinerary, cost, and tips.

Mezes (appetizer) 

Since I discovered the existence, I have been addicted to Free Walking Tours.

I know, I know, you might now think “It is a marketing trap, they are not for free, you have to tip the guide!” or “Walking after someone with a red or yellow umbrella? No thanks!”. But I still love them, even with the risk of a neverEndingUselessBoringDetails guide, I include at least one Free Walking Tour in each of my travel plans! I walked for free in Granada, New York, even here in Amsterdam where I live: hey, there is always something new to learn and an alternative way to spend Sunday morning. But nothing can beat the romantic comedy with a final twist I witnessed in Israel: not at the cinema, directly in Jerusalem’s streets!

Spoiler alert: if you are a female reader, please go ahead reading, this story will just confirm a theory that you probably already believe in.  If you are a male reader, be aware that you might reconsider many past episodes of your life! 😀


Main Dish

It is a warm afternoon of June in Jerusalem, time of the day when the sunlight turns slightly orange and inflames the old town built with stones.

We reach Jaffa Gate after a long walk around the wall and we see from far the red umbrella: ok, we are not the last… actually, we are the first! We slow down to take a deep breath and to enjoy the Medieval view in front of us. The gate is majestic, I stand still staring at it, attracted by the multitude of people with colorful traditional African clothes, followed by girls with Asian eyes and Israeli kids with the school backpack on the shoulders.

The guide moves towards us with a happy smile and he introduces himself in a rush of a warm welcome. He is young, good looking with a no intimidating beauty, black hair, white teeth and olive skin, a bit short and funny in his new wicker hat. His talk is energetic, but clear and his eyes are searching for ours: all excellent signs for an entertaining tour!

Our group grows fast and the happiness of our guide increases with the number of free maps distributed. We are almost ready to start the tour when two girls, running towards us, shake the arms to catch our attention. They are both pretty and very diverse: the tall blonde girl on the left with a pale skin looks exotic but the energy of her dark haired friend on the right is magnetic. Petit but strong body, dark long linen trousers with a popup mustard-yellow top, that enhances the color tone of the tanned skin. Her eyes are hidden behind big dark sunglasses, but the shining smile is so powerful that makes our Cicero talks loudly “Wow, what a smile!”. We wait patiently for the new fellows to reach us for a fast introduction.

“Well… I am from Jerusalem!”- says the brunette confirming her role as host and increasing the curiosity of the guide:

– “Ah… but have we met already?”

– “Yes, last Thursday at the party… we have danced together… rubbing our bodies… do you remember?” – The quick and detailed reply makes us turn the eyes to the guy, holding the breath and hoping he would remember. Long 2 seconds of silence. Damn, he doesn’t. Come on, make an effort!

-“Yes… are you the monotheist?… I never forget a smile!” – pheeeewwww, he does remember!


We finally cross the gate, an apnea dive into a time machine, back to hundreds of years ago and we reach the Tower of David and the Citadel. Every step makes us more curious and eager to know, in a whirl of questions about religion, history, traditions, and people.

We start from the Armenian quarter, with the shops of colorful hand-made pottery and we walk through the Cardo – the old Roman north-south axis and shopping street.  We move to the Jewish district, quiet and elegant and after a stop to admire the Western Wall and the golden Dome of the Rock, we deep dive into the maze of the Arabic Quarter, so chaotic and lively.

The old town has the power to carry you away, I forget my reflex with the promise to shoot the next day… you don’t know what to look, listen or smell: the guide’s stories about Abraham and the destroyed Temples, the traditional clothing of Jewish man with black suits, the smell of spices and felafel, the ancient huge stones of the Western Wall, a crazy fast and noisy carriage down to the streets of the bazar, the coffee taste of halva or the sellers’ voice?

Our guide is patient, in the impossible attempt to reply to all our doubts and partially given up to the idea to spend more time with his special guest. Sorry, no time for flirting now: we need you as a 3 years old kid with the father, just carry us by hand and reply to the hundreds of “why?”.

We finally reach the small square in front of the church of The Holy Sepulchre, at the end of Via Crucis or Via Dolorosa, where Jesus has been crucified. Like small pupils we sit down on the steps, following the narrative flow of the young guide and admiring the dense history of Jerusalem. Everything we study and we (can) believe in happened here, right here, on these stones, despite different faiths or religions. Jerusalem brings everyone together and even if the extreme police presence might remind you the status of tension, you don’t really feel it.


Two hours fly away, the small appetizer of Jerusalem leaves us with the desire of a full meal. The tour ends with the funny voice of the guide mimic Omer Simpson and an invite to a party dropped by the brunette. Everyone is happy and hungry, time for goodbyes and dinner!


The next day I receive an email from the Free Walking Tour agency, asking to write a review and to check out the group photo on their Facebook page. “True, the photo at the start of the tour! Ok, let’s see…”. I scroll fast the browser and I recognize the yellow-mustard top “Here she is… yes, there is also her blonde friend… but where are we? Wait a minute: the tour of 11:00 a.m.?! no, it should be 17:00… also, the guide is different!”.

The revelation arrives like a thunder in my head:  she went in the morning with the hope to find him, she did not and she tried again in the afternoon, taking the tour for the second time in few hours! That’s the reason for the shining smile, the quick answer about the party and the boredom of her friend… wow, girl, you really know how to reach your goals! And no worries, as long as you don’t tell him, he will probably always think it was just Destiny.

Heading to Israel and need to plan a travel itinerary? check out my travel itinerary and tips and my impressions!

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