“In Tel Aviv you play, in Jerusalem you pray.”

It’s around noon (I think) on a Tuesday (I’m pretty sure), and I’ve just landed at Ben Gurion International Airport after a grueling 27-hour, two-flight journey from Toronto. I’m in Israel, crammed in a van with a bunch of semi-conscious travel writers about to embark on a weeklong journey through the country’s biggest (and purported) badass town, Tel Aviv. It’s blistering hot. As our car bumps its way through rutted streets, I’m trying in vain to pay attention to our tour guide Rivka, as she chats about the days and itinerary ahead. “Tel Aviv is the dream of everyone,” she says breezily. “There is no city like this in the country…in fact, the world.”

At first glance, I balk at the remark. Sure, I’ve heard that Tel Aviv is the stuff of legend: a hedonic playground for young, pretty little things that like to party. (A lot.) 40% of the city’s population is 35-years-old and under so, by virtue, the attitude here is liberal, unhinged. Trendy boutique hotels with Michelin-worthy cuisine are sprouting everywhere, and the club scene is rumoured to rival the best DJ sets in Ibiza.

But, as the scenery buzzes past by my window, I’m met with a different story. Ancient graffiti-covered buildings look gutted and inhabitable; drooping power lines are precariously close to street level and all around there’s this sense of calm, as if to say the entire city is in siesta. I notice a group of about 10 Orthodox men walk in unison, silent as they dip into an alleyway; adjacent to them a young mother shrouded in headscarf pushes her baby carriage of three across the crumbled sidewalks. This is no Cannes, I think. Certainly not Miami. What is everyone talking about?

We take a sharp turn south and our car ambles a small hill where it slows, by deliberate measure, in front of the Mediterranean. Ah-ha. I gasp audibly and Rivka winks. “See,” she says. From left to right 10 miles of crisp white sand, ahead the most spectacular azure waters with waves that twinkle against the sun’s rays. The beachfront is dotted with coloured umbrellas and deeply dark locals playing paddleboard, volleyball and working diligently on their tans. I hear the faint thump of house music in the distance, and catch the glint of a beer bottle as it’s passed from one friend to the other. Despite my looming jet lag I start to feel anxious — excited, even. So this is it, I think. Considering I’m on the cusp of turning 36-years-old and close to the party cut-off point, I better get to it. And so it begins.

DAY ONE:

The first luxury hotel of its kind in Tel Aviv, The Dan is as dichotomous as the city itself. Built in 1953, this beachfront respite has hosted everyone from Presidents to Kings, Madonna to Barbara Streisand. The exterior is where the property begins to assert its split personality: a massive rainbow-coloured façade created by Israeli artist Yaacov Agam embraces the entire seaside wall. At once it’s alarming and awe-inspiring, and I make a mental note that it will serve as a great reference point for when I’m bobbing in the ocean a bit later on.

Climbing the stone stairs into the space, however, is an entirely different experience. Doormen, both clad in white tuxedos (with cool demeanors to match) open floor-to-ceiling glass doors into a foyer that is decidedly more toned down. The aesthetic riffs of its 1960s-era roots with gold brocade chaises, hardwood, dim lighting and potted white orchids scattered throughout. My feet cool on the marbled floors, as I’m greeted with the most charming concierge and an offer of champagne and fresh figs. Don’t mind if I do.

Of the 286 recently renovated rooms, my seafront suite with a private balcony offers the ultimate in luxury. The king bed is decadent and welcoming, the unfettered views of the beach and sea is how I wish to wake every morning. Before I pop the Proseco from the mini-bar, I hear a chime at my door: One of the bellhops has a freshly baked lemon cake in hand to celebrate my arrival. How lovely.

DAY TWO:

Design and delectables aside, The Dan’s location is prime — a small jaunt brings you to Sheinkin Street, Tel Aviv’s self-appointed “Yuppie Area,” which is much akin to New York’s SoHo with designer boutiques (and the prices to prove it). Or, guests can wander over to Rothschild Boulevard, known as the “White City”; a sprawling expanse of Bauhaus buildings and architecture touted as the biggest collection in the world.

I opt out of the planned walking tour (yawn), and decide it has to be Happy Hour somewhere (yay!), and so off I head a mile or two towards the artsy neighbourhood of Neve Tzedek. South of the Yemenite Quarter, this quaint suburb was once the home of many artists and writers like Brenner and Agnon and, admittedly, walking amidst the lush Fica trees and tropical flora, I can’t help but feel inspired to put pen to paper myself. I spend time around the dozen or so streets, popping in and out of pottery shops, local jewelers and end up stumbling across the most magical terrace, Suzanna. I order a frothy GoldStar beer (ok, maybe two) with a small plate of Jerusalem artichokes, hummus with olives and settle in to people-watch. Spoiler alert: Everyone is fantastically gorgeous. I’ve never felt so North American.

DAY THREE:

“Tel Aviv is a dynamic place, and its people even more so,” says Dr. Moshe Morad, head of Israel’s biggest radio station 88FM. We are in the Old Port City of Jaffa; an ancient seaside port on the southern tip that has existed for nearly 4,000 years. Once called “Jerusalem by the Sea,” thanks to a take-over of art galleries, bistros and theatre houses, Jaffa is where a modern cool bohemia resides. The seafront boasts an epic 7 km bike path and old warehouses – once the homes to Jaffa oranges – are now converted bars and nightclubs. “Jerusalem is hours away and yet world’s apart from what this place is. People say it’s a 24/7 party and there’s truth to that. But it’s also very chill, very cerebral. Just look at it,” says Morad.

I can’t argue with the man. We’re sitting down to dinner at Kalimera, a restaurant right on the harbour, where our feast has come but mere hours from the sea: rump Carpaccio with oregano; blue mussels in coconut ginger broth and octopus arms with chestnuts and yogurt. A warm sunset works as my artful backdrop, while an Israeli rock band playing live tunes acts as the soundtrack. People look happy.

It feels… idyllic. “People come to Tel Aviv because you have everything at your fingertips: Sun, beach, music, food, friends,” says Morad. “People have a hard time leaving and, often, they don’t.”

DAY FOUR:

My day starts with a run down Gordon Beach. It’s flush with like-minded joggers, surfers and cyclists; I’m surprised by the volume of people out this early, considering how much dancing happens before dawn. Apparently, the Israeli morning meal is an exercise in stamina itself, and when I finally sit down to breakfast at the Dan, I see why. Tables are laden with dozens of small plates – hummus, tehina, baba ghanoush, freshly baked challah and a bounty of fresh vegetables and cheeses. I can’t help but be reminded of my own Italian Sunday lunches, where hours with the family are wiled away at the table. I opt for the Middle Eastern dish called “Shakshouka;” eggs poached in a tomato and vegetable sauce with a savory potato Bourekas pastry.

This day requires sustenance because I’m about to hit the infamous Old Jaffa Port Flea Market. Within walking distance from the Tel Aviv Promenade, this popular market first took its form around the end of 19th century where it served as the grounds for the local community to buy their produce, housewares and farm equipment. Now, a new Jaffa style has emerged thanks to resources being invested towards renovation and improvement of the area’s infrastructure. My afternoon is a languid adventure through the old cobbled streets, during which I periodically dart in and out of trinket shops, antique furniture stores and gourmet Middle Eastern cafes. I bargain my way through the different stalls and leave with a bevy of unique finds: Bedouin arm bangles for me, a Hamsa amulet for my twin and raw silk kaftan dresses perfect for the humid days that lay ahead.

Before I leave Old Jaffa, I’m told it’s imperative I visit the Ilana Gur Museum. The building – dating back 280 years – served as the first Jewish Inn for pilgrims on their way to the Holy City, and houses not only over 500 works from well-known Israeli and international artists, but also acts as the homestead of Ilana Gur, the museum’s curator herself. It’s a comfortable and eclectic environment; very a-typical from the sterile art galleries I’m accustomed to visiting. Meant to be immersive, you are strongly encouraged to wander from living room to dining room touching and handling the art, antiquities and sculptures that abound in the space. “It is only if one touches, feels and uses art that one can understand what it really is,” says Gur.

Touring can make a girl thirsty, so I head to Brown TLV Hotel, as the afternoon slides into early evening. This former bank from the 1970s has been retrofitted into a popular boutique hotel with a strong vintage vibe. Playboy’s cover the walls, the old-school library is well stocked with fashion tomes and martinis are quick to order and just as fast to drink. I immediately head to the rooftop bar – still a rarity in Tel Aviv — to catch the ever-rising skyline, while guests splash in the nearby Jacuzzi hot tub. A DJ sets up his tables in the corner, while the young and fashionable start rolling in at a dizzying speed. My night passes in one contented, buzzy blur.

DAY FIVE:

A word of advice: Fresh fruit is the savior for those mornings when you wake feeling all of your almost-36-years-of-age. It’s way early and I’m at the Shuk Carmel — Tel Aviv’s largest open-air food market — arriving before the locals descend to pick up their weekly groceries. For whatever reason, I need watermelon and I need it now, so I careen through the different fish stalls, butcher tables and spice counters in pursuit of it. Vendors are yelling to passerby about their just-caught pickerel, and I almost tackle a Halva stand, much to the chagrin of the Safta who is proffering it. It is a maddeningly loud place — with a stench to match — but it’s also full of energy, spirit and hospitality that seems right on point with the city itself. I find my watermelon in the middle of market, along with the juiciest pomegranates, apricots and mangos. Sanity officially restored.

Fast forward to a dip in the ocean, a glorious massage at the Dan Hotel Spa and a nap (please – I’ve earned it), I’m now in front of my last night in Tel Aviv. I figure I have to go big before I have to go home, so I sign on to hit the club circuit with Ross Belfer, a 26-year old ex-pat and creator of Eager Tourist, an insider travel network, which creates tailor-made hyper-local experiences for travelers to Tel Aviv — ideal for those who prefer their vacation not be filtered through the eyes of a Fodor’s. I’m curious though: of all the great cities in the world, of which there are many, why start in Tel Aviv? “It’s just so open-minded,” says Belfar. “It has this fervent mish-mash of nightlife from dive bars to A-lister clubs to the best indie music venues. Whatever you want, you can find it here.” It’s around 11 p.m. and we’re starting at Port Sa’id; a laid back bar with a tiny little patio behind Tel Aviv’s Grand Synagogue.

Opened by Israeli celebrity chef Eyal Shani, you can expect all the fixings of a trendy hotspot: Exposed brick walls, sexy staff, small tables and plates of tapas are shared ,while the DJ samples vinyl taken from the bar’s overflowing bookshelves. We mix and mingle in the chaos until it’s time to move on to the Montefiore; a swish heritage building just off Rothschild Blvd that’s been restored to all its 1920s glory. Think: salmon-hued exteriors, wrought iron banisters and tall green palms throughout. We head to the ground floor where the restaurant-cum-bar is minimalist and sleek, just like the patrons fraternizing it. I order a Mint Julep, which seems very apropos while we catch glimpses of the best see-and-be-seen people. Moving on, we head to Allenby Street, which Belfer compares to Canal Street in New York City. “This place was once a desolate strip with nothin’ going on,” he says “But now its streets have some of the city’s top local hangouts, including this place: Har Sinai.” Hipster hangout is the first thing that comes to mind, mostly because everyone is in their uniform: Rolled denims, black-rimmed glasses, plenty ‘o plaid. The DJ spins some indie with a dose of rock, while we happily roll with our pints of local beer.

Our eve has, surprise, turned to early morning, but we are on deck for “just one more”; an underground club back in Jaffa called Anna LouLou. Evidently we saved the best for the last as this trippy, left-leaning bar, co-owned by a Jewish Israeli and Arab Christian — is exactly the eccentricity I want to end my trip on. It’s dark, cavernous and full of strung-up lights and strung-out people. The electro beats are pumping, but I opt to deek out to the street where public drinking is not only legal, but strongly encouraged. I want one more look at the Mediterranean with a chilled cocktail in hand. What a place, what a trip, what a party. L’Chaim.

Published September 6th, 2013