Uri Jeremiah, the celebrity restauranteur and hotelier credited with bringing a new level of sophistication to the living museum that is the city of Akko, says this when asked about the secret of his success:

“In order to think outside of the box, you still need to have the box. I have done away with the box and I am doing my own thing. For me, that is what it really means to be an Israeli. There’s no box.”

I think about this while I dine on a late lunch of rustic bread, and plate upon plate of deliciously cooked fish at his restaurant in Akko. At the end of a long day of exploring, I’m enjoying his famous and rhythmically named eatery ‘Uri Buri’ meaning ‘Uri’s mullet’ – not the hairstyle, but the fish – although if you meet Uri, or see a picture of him on the cover of the new cook-book he’s peddling, you will soon realise that he’s not one to conform to conventional style. So I wouldn’t put a mullet (in the coiffured sense) past him. Being somewhat unconventional has put him in good stead however, and the restaurant is packed with locals and tourists alike and I’m told that you’d have to make reservations weeks in advance to come and dine here, or be travelling with the right company to get you in.

The company I chose for this particular trip is none other than Touring Israel, the brainchild of award-winning guide and tour operator Joe Yudin. They’re one of the go-tos for luxury and leisure adventures across Israel. But instead of taking them up on their tourist-trail packages of Tel Aviv, or Jerusalem, I asked that they surprise me with something a little different. My exact words to them were that I wanted something, “outside of the box.”

Cue one Tamar Loyfer, my Touring Israel companion for the day, armed with a surprise, personalised itinerary. I sense that this is not going to be any ordinary day the minute I see her – big hair, big van and even bigger personality, a loyal friend of friends of Dorothy and teller of great stories and anecdotes to last a whole day or more. Like the time when she nearly got her head shot off while learning to fire a rifle in the army, or how her family narrowly escaped Germany in the Holocaust, or how she decided to be a single mother by choice while trying not to offend her gay best friend who wanted to donate his sperm, or about the time she survived a terrorist attack. Tamar surely has a knack for bringing a story to life, humorous and jolly, a consummate guide and host. Passionately Israeli, there are times when her politics crosses the line for me, but it’s all part of the experience. I learned a long time ago to take people as they come.

Tamar was born and raised in the Galilee village of Yesod Hama’ala, so it’s fitting that we spend the day with her in the surrounding area. At first, I think – Galilee – a little bit of history, some Israeli wine, sounds easy enough, but is it outside the box? Maybe we’d walk in the steps of Jesus and feed crowds with five loaves.

The next thing I know, I’m strapped onto the back of a contraption with an enormous propeller, connected to a large parachute laid flat on the ground of the field Tamar has driven me into. A Druze (unique religious and ethnic minority of Arab descent, but non-muslim) breakfast – a cheesy wrap – does very little to calm my nerves.

“Don’t you worry about a thing,” assures Tamar. “You’re flying with the best.”

Segev Baram is my pilot, an ex-military man, turned teacher, turned flying machine pilot and instructor. He buckles me in and does a short safety check. Around him, other ‘powered parachutists’ are packing up. I ask why no one else is flying with us. The answer was short and sweet – too windy apparently. I hold on tight to the pilot’s seat in front of me and grit my teeth.

It’s quite amazing how little a powered parachute needs to get up in the air. We speed along the field for no more than 50 metres and we take off, almost vertically. Screams and rushes of adrenalin fill me as we cruise around the field and when I calm, Segev starts to explain what we’re seeing. “Over there, the sea of Galilee, a lake actually – where Jesus allegedly walked on water. Up there, Golan Heights, where you can see all the way to Syria. And all around us, agriculture, the fruit-basket of Israel.”

It’s a bumpy but somewhat exhilarating ride and from up here, the view is spectacular. I start to learn what it is that Israelis love so much about their country. Back on terra-firma, I help Segev pack up the parachute and find out what motivates him to make a living by taking tourists around in an expensive, flying go-kart. Turns out, he has been a hobbyist pilot and trainer for a while. The idea just came to him one day. And true to the spirit of Israeli entrepreneurship, he went out, procured a craft with a passenger seat, made friends and business links with travel companies he knew nothing about and created a unique product.

“Blue sky thinking,” he calls it, waiting eagerly to see if I would notice the pun.

Back in the van, we’re heading towards Akko, a place I know nothing about. We drive up past a long stretch of beach and see the bastions and sea walls in the distance, on a peninsula jutting into the Mediterranean. Tamar tells me that this is the very same sight that first greeted the Crusaders, Marco Polo and even Napoleon throughout its 4,500 years of history. As we park up, I notice something different about the place. First, the huge mosques with their colourful domes and minarets. Then, the Arabic call to prayer. Children are playing in the streets, conversing playfully with each other in Arabic and Hebrew. It’s rough around the edges, but bewitching never-the-less, a UNESCO World Heritage site, a cacophony of sounds, sights and smells wafting down warren-like alleys, designed as if purely to disorientate non-locals. And from the city, looking back out, lies a deep blue sea, stretching across the Bay of Haifa to the Carmel Range, with the Galilee mountains to the north. It’s a stunning vista, but Akko’s real beauty lies in a secret all about secrets.

Tamar jumps into full tour guide mode and tells the story.

“500 years ago, Akko was a backwater fishing village. It had an illustrious past before that, as a strategic Muslim-empire port. It is they who built the city you see today, with its significant buildings. The history of the city before that was buried in legend, quite literally. That is until your people showed up.”

By ‘your people’ she meant the Brits. It turns out, in the British Mandate, the Army took over the city, turning its fort into a prison to hold Arab offenders and Jewish political dissidents. All prisons have a story about an audacious escape. True to form, this one had one, a significant one.

At the end of the WWII, a gang of prisoners planned to break out by digging a tunnel under the fortress. What they uncovered was spellbinding, a labyrinth of subterranean passages, leading to and from intricate architecture dating back to Crusader times. The story didn’t end well for the escapees, but prompted the excavations that unearthed a majestic complex of perfectly preserved Crusader buildings, the Knight’s Halls. These massive, cavernous structures, spanned by imposing arches, are feats of construction. A wander through these echoing chambers is awe-inducing and what’s more fascinating is that they were originally built for religious tourism. A monastic, but military order known as the Hospitalers, were early-day travel entrepreneurs. They ‘code-shared’ with the Knight Templars to welcome pilgrims coming to the Holy Land. This was essentially a giant ‘resort’; dormitories, dining rooms and prayer rooms. But it is also a feat of engineering; arched tunnels stretch for miles under the city, at different levels. In some of them are streams of fresh water. The Ottomans who later seized the city wanted nothing to do with their Christian precursors, and so they buried the whole lot, building the city we see today on top of it. But we know that they didn’t even care to excavate what was there on their arrival, because they built an aqueduct to bring fresh water in from the mountains. If only they knew that they were sitting on a very sophisticated irrigation system.

The tunnels pop up into a Turkish market at street level. The contrast between the gargantuan underworld – what remains of the ancient city – and life in today’s Akko is striking. People are munching on toasted paninis, while puffing on Hookahs. A young girl on a hoverboard tries to roll along an ancient cobbled street. A covered, old market opens up into a car park where young Arab men are sat in pick-up trucks blaring out American rap on their stereo. All this with a scent of tobacco, salty air and the gentle sound of water lapping against the seawalls. If I could block out all the modern stuff, it would be like travelling back in time. Until of course, lo and behold, a hip restaurant that wouldn’t be out of place in London or New York appears in front of me, the famous Uri Buri.

Uwern’s out-of-the-box day-trip from Tel Aviv, including flying adventure, delicious lunch at Uri Buri, tour of Akko and all-day accompanying guide and vehicle was put together by Touring Israel, touted as Israel’s leading tour-operator.