A Guide to Cuba

Wandering backstreets in a timeworn paradise

Cuba, a destination of extremes. Havana, city we would come to love and loathe in equal measure within the space of a day, or a single hour. The very word – Cuba – conjuring for each a vivid collection of ideas and imagery, perceptions and presumptions, a blend of the accurate and inaccurate, the real and the wildly romanticised.

Hovering for as long as we could remember high on our wanderlust list, it began last year to creep with increased frequency into conversations of travel, of creative exploration and necessary adventures…afterwards, each time creeping a little higher up that list. Fuelled by a growing sense of urgency, a slightly panicked feeling of needing to experience this country before it’s irreparably altered and loses a little of its magic (a feeling which has only been validated on arrival, change innocuously creeping in at every turn), we wondered aloud over the fleeting opportunity, of in this lifetime, within the confines of a city mere kilometres off the coast of Miami, to travel very much back in time to a destination unaffected by the outside world. Streetscapes unlittered by advertising, lifestyle untouched by technology, and inhabitants unaware of the modern luxuries we take for granted every day, every hour. For our generation, the children of Baby-Boomers and one of the few to straddle memories of pre and post iPhones and internet, Cuba seemed the last destination of its kind, to experience in this lifetime.

Forever drawn to fascinating, far flung editorial locations, our journey here, while geographically not as remote as other adventures, felt somehow a little like travelling to the end of the earth. Setting off from the East coast of Australia on a Tuesday morning, a familiar 14hr flight to Los Angeles (and 18hr stop over in Santa Monica, making the most of ill-aligned flight times to shop, shower and ever so briefly nap) we rose at 3am, coffees in hand and airport bound, boarding a flight to Mexico City. Following a 4 hour stop over, which to our amusement and mild bewilderment, became the actual length of time it took to collect our baggage – and clear… or for some of us, very nearly not clear customs – we finally, deliriously, piled onto a plane, visas in hand, Havana bound.

Landing and navigating our second customs inspection that day – this time feigning tourists who simply overpacked, cameras and dresses emerging safely out the other side – our initial impressions were admittedly somewhat jaded…A driver that inexplicably never showed up and a trip to our (online, faded but elegantly beautiful) Boutique Havana accommodation – a hilarious Faulty Towers’esq saga of shortcomings and unwelcome substitutions (of the “Señoritas, our bathroom is actually broken, but don’t worry, you are staying at my sisters house instead” variety) – both driver and accommodation having been confirmed, and double confirmed mere hours before our departure, and the sisters accommodation turning out to be nothing like that we had booked, nor reasonably entertain-able as an option. We could only laugh in an exhausted, ‘oh travel!’ kind of bemusement, and form a fast plan-B.

After communicating with our hosts in a manner that more closely resembled a game of charades meets Pictionary, and gambling on finding a room at the Hotel National (a Havana institution, and at 11pm the only option our jet lagged brains could even fathom) we piled bodies and the most comical number of overstuffed bags (bulging with all the paraphernalia required to execute 3 fashion shoots) into the back of a taxi, everything crossed for a bed, a shower and an internet connection at the other end.

Pulling into the entrance of the historic grand old dame, palatial in proportion to her surrounding buildings, we felt hopeful, optimistic even…until we explained our request to the lovely man on the front desk, greeting the question of a room that night, in the midst of high season and not a reservation to speak of with a sort of nervous smile, followed by a ’wow’, followed by a longer pause, and another ‘wow’! Still smiling, but unsure exactly what to say, clearly not wanting to be the one to tell us that there was no room, it dawned on us (coupled with the knowledge of no internet or phone connection, a possibility we’d dared not entertain) that on this Tuesday evening, at midnight in Havana, we had no plan C.

And so ensued a series of questions and quick negotiations after which we miraculously secured the very last room to be found, available for that night only. Trying not to panic at learning there’s no wifi at Hotel National, until the business centre opened at 9am the following morning (our immediate concern, securing new accommodation for the week) in hindsight, after midnight, being forced off-line proved a complete blessing, finally giving ourselves permission to stop, breath, bathe, gather our thoughts and laugh (with total sleep deprivation) over the adventure thus far. Sitting outside in the hot night air, sinking into enormous lounges in the interior courtyard, we gratefully sipped our first cocktail…strong, minty and at 1:30 in the morning, deliciously welcome.

Reclining in the balmy surrounds, the air scented with cigars, the sound of the sea beyond the wall, we imagined all it must have been seventy years ago, a hedonistic Hollywood playground. Immaculately maintained (in sharp contrast to the rest of Havana), Hotel National felt remarkably unaffected by time, not preserved so much in 1959, but rather a throwback to a much earlier era. We observed how closely the white corridors and shuttered doors resemble interiors of the Titanic, only tropical. The hotel itself a curious, beautiful mix of exotic tiles, terracotta paving, chandeliers, marble, plantation accents and beautiful brass signage. We wondered over the stories that have surely unfolded here, if only these walls could talk. The rum cocktails, the manicured lawns (dotted with fountains, peacocks and swaying with palms) the scent of salty sea air mingled with the unmistakable aroma of cuban tobacco, we imagined, and appreciated, it all to be mostly unchanged for the last hundred years.

Reflecting over those cocktails on how each of our LANE issues (particularly when travelling) have a spooky, magical tendency to self manifest, we laughed at the irony of our August Issue, published only the day prior and penned in transit to LA, discussing such themes (with a healthy dose of self awareness at the double irony) the need to switch off, be present, tune our attention away from our screens, and resist the urge to document, constantly projecting moments that when experienced through a lens, aren’t really experienced at all, at least not in their fullness, not really in that moment. With no wifi and more disconcerting still, not a hint of phone coverage to be found here (for Australians anyway, there is literally no connectivity, to any phone network, no texts, no calls, nothing), we found ourselves completely, utterly, unfamiliarly, offline. We were living and breathing (unwittingly i’ll admit) each of the ideas we’d articulated an intention to explore in our August Issue, the universe almost smiling at us wryly, a kind of “be careful what you wish for girls…”.

Waking the next morning to discover an unchanged No Service message in the top left of our screens – a sight as unbelievable as it is unwelcome to a team attempting to keep a digital publication ticking whilst travelling (or unwelcome to anyone for that matter, co-ordinating production and logistics in a foreign country) the impressions of the night before, a raw, gritty city, devoid of the most basic modernities we take for granted back home, began to colour and shape our experience. As one of the few age groups to sit on memories either side of internet access and mobiles as part of the everyday (recalling primary school years of shared computers in the library, and late high school with the arrival of mobile phones, the beginning of texting rather than calling friends on their family land line) we’re better equipped than many to quickly adapt – or revert – to a low-fi environment.

But it didn’t make the realisation around the romance versus the reality of Cuba any less difficult, accepting over breakfast that this trip was going to prove challenging, really challenging, and that the allure of this city, in all its faded glory, its infamous aesthetic time warp, was not without the trade-off of a legitimate, technological time warp to match. That day (still bewildered at how much can unfold in only 24 hours here), Cuba would prove a journey of extreme problem solving, a tricky, inconvenient, disconcerting, unfamiliar, frequent test of our patience, or, an experience that my mother would succinctly describe as ‘character building’.



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For honeymooners, Cuba offers the perfect antidote to ‘busy’, the low-fi experience of this city, following the frenetic production of a wedding, an amazingly rare opportunity to completely disconnect from the world, and re-connect with one another. However the production in real time, of an editorial on the ground (or in this case three editorials) threw a whole other set of logistical balls in the air, infinitely less romantic than honeymooning, and despite rigorous research, challenges we were quite unprepared for. Because producing an editorial, anywhere, requires a slightly obsessive approach of constant communication, confirmation, double confirmations and a chameleon style adaptability to the seemingly endless changeable moving parts. It requires the kind of keep-cool flexibility that more closely resembles a gliding duck, a projection of total calm above the surface while feet paddle frantically out of sight below. With three shoots scheduled over five days, and a team of hair, makeup, photographers and four models flying in from six different cities between them (Venice, Brazil, Los Angeles, New York, Byron Bay, Sydney – all via Mexico), landing across different days, at different hours, and unable from wherever we were stay (unsure exactly where that was yet!) to even track their flights online or say ‘text me when you land’  was a daunting prospect…and one that was going to require a military like precision of the old-fashioned, communicate and completely commit, punctual variety.

However this ‘inconvenience’ (joking amongst ourselves for how brattish our concerns sounded voiced aloud) offered something much richer. An opportunity to lose ourselves in a city very much lost in time. To float freely through streets free from phone vibrations of texts, emails or instagram, to connect over coffee and dinner, to talk to one another without digital references or interruptions. Travelling back in time, not for an hour, or a day, not for the length of a tour through an old part of town, or the time it takes to lose yourself in a museum or historical building. But for the entire length of our stay. Because unlike other countries, there is no ‘Western Island’ to escape to here. Those hotels, bars and beach clubs that exist the world over, found in even the unlikeliest of places, refuges where if the local experience gets just a bit too much, offer somewhere (rightly or wrongly) to check out of the country you’re in and check-in to somewhere else, for a single cocktail or an entire week. Here in Cuba, no such place exists, and despite our frustrations, we came to secretly love that.

Later that day, after some stealthy searching from one of the handful of wifi hotspots in the entire city, we moved in to the most beautiful private residence, all pale mint greens and ornately patterned tiles (so welcomingly cool underfoot), our host projecting total calm, a Havana mentality of stop, slow down, breathe, relax. A rickety lift shaft with elaborate clanging wrought iron double gates (a nerve wracking ride, but essential for the obscene number of bags to be lugged six floors), we travelled back down to the ground floor to meet our driver, a beautiful Cuban soul who thankfully possessed enough English to compensate for our appalling lack of even basic Spanish. Climbing into his immaculately maintained Chevrolet, our 1956 wheels for the week, all white leather interior, big steering wheel and big Cuban soundtrack, the challenges of the past 24 hours began to fall away. Driving through the streets, cruising at a leisurely pace, the city began to reveal itself to us, from the back seat of a turquoise car, its true colours and character. And in that moment, it stole our hearts.

A test of patience and character, a reminder from the universe about the importance of being present, so many spooky, inexplicable sequences of serendipity playing out in our first few days, encounters suggesting that Cuba may have a grander plan for us here, if we can only switch off long enough to recognise and roll with it. Exploring and falling that afternoon, under the spell of Havana, a city in which everything, but most of all time itself, seems to move at half speed – a sensation ordinarily only found in the wilderness, but discovering it instead in a humming city, proved as magical as it is rare. Holding up a giant, pastel tinted mirror up to all our behaviour, our obsessive connectivity and carrying of our phones, the anti-social tendency to text rather than talk, the ability to exist somewhere without really being present there at all. For all our frustrations and exasperation, these past two days have felt like a series of life-changing life lessons, a sequence of sage reminders from the universe of what’s important, and what isn’t, self discoveries, a confrontation of (& vows to adjust) all our bad habits. Without knowing it before we arrived, Cuba has proven to be everything and nothing like we expected, but most of all, all that we needed.

Where We Stayed…


Casa Concordia (Old Havana)

An incredible example of a grand old Cuban residence. On the 5th floor of an apartment building (reached via narrow stairs or an old fashioned central elevator with double wrought iron doors) the tiled floors and marbled glass windows offer a cool sanctuary high above the street. Excellent people watching, views over the city, beautiful hosts, breakfast each morning and ensuite bathrooms for every room. A complete oasis in the heart of Old Havana.


Villa Maria La Gorda (South/West tip of Cuba)

A quaint little resort right on the sand. Peachy coral buildings, a dive school, a bar and restaurant overlooking the bluest water, an abundance of palms (growing right to the waters edge), a feeling of absolute ‘blue lagoon’ tranquility, the stuff of cast away island dreams. (*note – the resort is remote, and while we were there, we experienced severe water restrictions, which isn’t very romantic, if honeymooning! Best to check before you book).


Hotel National (Havana)

A majestic Havana institution. Originally not part of our itinerary but when the production side of being offline all got a bit tricky with team members flying in an out on different days, we set up camp here making use of their Wifi, their concierge and the ability to access food at unusual hours! A grand old dame, this hotel feels like stepping back in time not to the 1950’s but to an age of Art Deco opulence, infused with tropical details. Our favourite place to unwind over a drink and de-brief on the days events, their enormous outdoor lounges, looking over fountains and lawns dotted with peacocks, a Cuban band playing in the corner, the scent of cigars in the air.

Where We Ate…


La Guarida, Caribbean / Cuban (Old Havana)

An institution and site of a famous Cuban film, but somehow not touristy in vibe, this incredible building (the location for several of our shoots) retains all the eclectic charm and character from its heyday. Think incredible etched glass windows and antique dining chairs, a marble topped bar and a bowerbird eclecticism of decor, walls decorated with antique posters, religious iconography and all sorts of art. The food is incredible, as are the cocktails. There is also a newly opened rooftop bar with breathtaking views over the city (and a private cigar room), both reached via an breathtaking glass enclosed spiral staircase. Breakfast / Lunch / Dinner – all served by the most beautiful, generous of spirit, gracious staff.


5 Esquinas Trattoria, Italian (Havana / Portside)

An absolute hidden gem we stumbled across by chance, location scouting for our Women’s editorial, this hole-in-the-wall Italian eatery is tucked down a particularly beautiful part of Old Havana just back from the water, all narrow alleys and paved streets. With tables spilling onto cobblestoned walkways, we dined outside, sipping mojitos and margaritas, ordering hand made pasta, wood fired pizza and freshly caught fish. We celebrated wrapping our first editorial here (shot in the same street) and dined here embarrassingly often, befriending the super accommodating staff. Perfect for an Italian break from the customary Cuban staples of beans, rice and slow cook protein.


Ivan Chef Justo, Caribbean – (Havana / Portside)

This tiny, discreetly signed little restaurant feels a little like dining in the house of a welcoming friend, with eclectic style and incredible cocktails. Up a narrow stairway, staff greet you warmly, talking you though a long menu (written in Spanish which they translate into English), full of fresh fish, seafood and salad options – a rarity in Cuba! The same owners and chefs also have a newly opened sister restaurant, just around the corner. We drank the best mango daiquiris there, and feasted on Ceviche and perfectly cooked steak.

We Recommend…


Hiring an old Car

If theres one ‘tourist’ experience to embrace, it’s this one! There’s nothing quite like exploring Havana from a low riding vintage American car. A driver can be booked through any hotel, or directly at various points around the city, with the Cuban drivers themselves, paying per hour, half day or full day. Every driver we engaged with had the patience of a saint, repeatedly stopping and going back (so we could photograph something amazing we’d passed!), helping with bags or waiting patiently while we ran errands. Where we found drivers who spoke a little bit of English, we appreciated the longer car rides and day trips as an opportunity to pick their brains about Havana, Cuba, the changes they’ve observed in their country, their families and way of life – an experience as immersive in the people of Cuba as the cars themselves.


Experiencing the Cigars

If you appreciate a fine cigar (or like us, don’t actually smoke, but appreciate their scent and old-world packaging!) a trip to the cigar shop inside Hotel National is a must. Then take your cigar to the lounge bar outside (a favourite haunt of ours), where you can order a cocktail and listen to live salsa music. Also, if you ask the waiters very nicely, you can order dinner to be taken out here too!


Sunset Cocktails Overlooking the City

The newly opened Terrace Bar on the rooftop of La Guarida offers one of the best vantage points overlooking the pastel colours and sinking sun over Old Havana. Excellent cocktails, a contemporary soundtrack and welcoming cool breezes. We celebrating wrapping our Mens Editorial here, the perfect place to watch the sun go down on a crazy, magic day!


Wandering the Streets of Old Havana

Explored on foot, the streetscapes of Cuba offer the most incredible textures and slightly concealed details, missed from a car. Ornately patterned tiles, weather patinas revealing ten former colours of paint, marbled entrances and ornate doorways. Our favourite time of day was before 9am or after 5pm, when the light and temperatures are most welcoming. Take a big bottle of water, flat shoes and a camera, allowing yourself to get lost. (*Start at La Guarida for a very pretty part of Old Havana, walking in any direction).

We Soon Discovered…



There are two types of pesos in Cuba. The ‘National Peso’ and the ‘Convertible Peso’ (occasionally referred to as the dollar when spoken, 25 more valuable than the ‘National Peso’). Depending on where you go and what you’ll do, you’ll need both. Fruit or bottles of water from local Cuban stands or stores will probably only accept the National Peso (local currency) while hotels and most taxis deal in Convertible Pesos.



Almost every old american car is a taxi, officially or unofficially. Don’t be alarmed to get into an ‘unmarked’ taxi, it’s how many cubans make a living here and it offers a fun ride, each of them entirely different outside and inside! There are more modern (80’s style cars, marked yellow as official taxis, but we reasoned…when in Cuba!). Agree on a price with the driver before you get in, we never travelled very fare and the far was usually 5 or 10 (convertible) pesos, or 25 to the airport.


Food & Drinks

Cuba is not a foodie destination. With the embargo it’s impossible to get so many ingredients that we take for granted, even in to the country. Fresh vegetables are a little hard to find (often tinned), however tropical fruit is abundant.  Have a plan in place for breakfast as theres no such thing as cafes. A hotel can be handy here, however if staying at a Casa, hosts will often provide breakfast – eggs, fresh fruit and coffee each morning. However drinks are another story! Its not unusual at a restaurant for the drinks menu to occupy four pages, to one page of food offerings. Stick to rum based drinks, it’s delicious and abundant here. Where it’s not possible to always find something delicious to eat, it is always possible to find something amazing to drink, mojitos served with the efficiency (and price) of a cup of coffee back home!


Access & Opening Hours

We were occasionally caught short by unforeseen closures of things like banks (located inside the big hotels), or internet access we had counted on using, sometimes inexplicably, with no explanation (A handwritten note simply stating that the bank was “closed”, despite opening hours suggesting it was trading for at least another 5 hours! Or the time the printer wasn’t working to print a code for internet access, so therefore, there was no internet access that day. Such is Cuba! Plan ahead, and always have a supply of both currencies ready.


Tour Desks

Ordinarily something we would steer clear of, however in Cuba these desks, positioned at both big hotels and the airport act more as a logistical facilitator for whichever activities you would like to arrange, not necessarily part of a bigger group or traditional ‘tour’. They can arrange a driver for you, a day trip by vintage car to the cigar fields or Varadero, any ‘experience’ you’re seeking, eliminating much of the hassle and lost-in-translation nature of attempting to book yourself.


Photography by Ted Grambeau.