A Luggage of Dreams: Lisbon, Longing, and the Poetry of Departure

Lisbon isn’t a city you walk through so much as a city you drift with, like a cigarette’s curl of smoke, it doesn’t take you anywhere, it simply keeps you company. It’s cobbled in contradictions: sunlight that feels like memory, hills that lead nowhere in particular, and the constant sound of something not quite said. Fernando Pessoa knew this well. Or perhaps he invented it… Lisbon as persona, as poetry, as a lover too elusive to ever touch, but too enchanting to ever leave.

To read Pessoa is to pace the city with him. You don't need a map, only a mood — a melancholy shaped like an empty café chair, or a tram vanishing just before you arrive. His Lisbon is half-flesh, half-fantasy: a place where reality is almost always in italics. Where every street carries a shadow version of itself: one for the feet, one for the mind.

For Pessoa, Lisbon was not merely a setting. It was a character, an introverted companion wrapped in fog and fado. The city, like him, was always turning inward. Its hills were metaphors for internal ascents, its miradouros points of both perspective and profound solitude. Standing at the top of a hill in Alfama, one does not simply see the city; one feels its breath against the ribs.

And what a complicated love it was. Pessoa never truly left Lisbon, but he was always elsewhere. A man with many names (Bernardo Soares, Álvaro de Campos, Ricardo Reis), he scattered himself across personas like breadcrumbs he didn’t wish to follow back. He lived a life of imagined departures. A luggage packed with metaphysics and melancholy. Lisbon held him, but he longed for places he had never been, and perhaps never wished to go.

In The Book of Disquiet, Pessoa writes, “I am nothing. I will never be anything. I cannot wish to be anything. Aside from that, I have within me all the dreams of the world.” He says this as if he’s confessing, not complaining. As if he has found more beauty in the ache of desire than in its resolution. As if Lisbon itself were not a city, but a feeling you couldn’t translate, only suffer sweetly.

The Architecture of Absence: Saudade and the Romance of Longing

There is a particular kind of hunger that has nothing to do with food, one that gnaws more delicately, but no less persistently. In Portuguese, it is called saudade: a word that behaves like perfume — it clings, it lingers, and no two people will describe its scent in quite the same way. Saudade is not nostalgia. It’s nostalgia’s more seductive, more elusive cousin, the one who left town without a forwarding address. It is the appetite for a thing you never fully had, or perhaps never existed at all. Absence, embroidered with affection. Longing, dressed for a funeral it secretly hopes will never end.

Pessoa made saudade into a lifestyle. For him, it was more than mood or muse, it was emotional architecture. Reading Pessoa feels like overhearing a man trying to fall out of love with his own melancholy, and failing spectacularly. His sentences are stained glass: fragile, luminous, and always best admired in silence. He doesn’t write to resolve anything. He writes to stay in the ache long enough that it starts to feel like home.

His famous heteronyms — Álvaro de Campos, Bernardo Soares, Ricardo Reis, weren’t pseudonyms; they were metaphysical roommates. Each carried a piece of his metaphysical luggage, each rehearsed a different version of the same despair. Together they formed a kind of emotional council, voting daily on which kind of emptiness to wear. Campos was the one who howled. Reis, the one who rationalised. Soares simply floated. All of them longing, none of them arriving.

And perhaps this is the heart of it, saudade is the worship of almost. It’s the ache between fingers that never touched. A life measured not in moments lived, but in the precision with which they were almost reached. And we do this too, don’t we? Build entire love affairs in our heads with people we barely know. Mourn cities we’ve never visited. Collect photographs of places we haven’t been, just to ache more specifically. We cradle the ghosts of unlived lives like heirlooms.

This emotional masochism isn’t inherently tragic, it’s often quite beautiful. There’s a strange richness in missing what never was. It means your imagination is working. It means your heart is still staging theatre, even when the cast is mostly shadows.

Pessoa didn’t merely write about saudade, he engineered it. He built entire literary apartments of longing and leased them to the ghosts of imagined selves. His pages are full of unreplied letters, clocks that tick in dreams, lovers described only in hypotheticals. Each heteronym feels like a room with different lighting. Some harsh and sterile, others golden and dust-specked. But all contain a chair that has never been sat in.

And the genius of it is this: Pessoa managed to turn lack into abundance. He found endless inspiration not in what was, but in what wasn’t. Every absence became an archive. Every unfulfilled desire, a diary. In doing so, he mapped an entire inner city of yearning. Lisbon, for him, was more than home, it was the physical embodiment of his emotional state. A city of gentle sadness, soft colours, and alleyways that lead to themselves.

Lisbon becomes, under Pessoa’s pen, the perfect metaphor for saudade. A place too beautiful to leave and too quiet to fully inhabit. Its charm lies in its restraint. You’re always looking over the city, from a miradouro, a rooftop, the window of tram 28, never quite in it. Like you’re waiting for something to begin, and maybe it already did, but so softly you missed it.

There’s something oddly democratic about saudade, too. It doesn’t care for status, wealth, or age. A child missing summer has it. An exile missing home lives in it. A teenager staring out the car window, soundtracking their future heartbreak with a song they don’t understand, they’ve got it too. Saudade is deeply Portuguese, yes. But also deeply, disastrously human. It’s the echo you still hear from a hallway you’ve never walked.

And the more you try to resolve it, the more it multiplies. Saudade does not reward closure. It rewards cultivation. It isn’t cured by arrival, only deepened by it. Ask anyone who has finally gotten what they wanted, whether it be a flat, a job, or a lover, only to realise they now miss the wanting itself. The longing was the plot. Fulfilment, just the credits.

That’s the quiet trick saudade plays. It doesn’t want to be fixed. It wants to be felt. Like a familiar song you keep on repeat, not because you hope it ends differently, but because the ending makes you ache just right.

Pessoa knew this. His entire oeuvre is an homage to longing left undisturbed. A museum of feeling suspended mid-air. And that’s what makes his work feel so modern, so alive. He was never writing to explain the world, he was writing to survive the parts of it that didn’t quite make sense. That liminal space between presence and absence. That hauntingly lovely void where the almost lives.

He turned saudade into a practice. A ritual. And Lisbon became its sanctuary. A city of stairs that lead to more stairs. Where the sea feels close enough to touch, but somehow always one block away.

It is not a place to find answers. It’s a place to ask more beautiful questions. And to miss things, even while you’re standing right in front of them.

Suitcases and Ghosts: On Travelling Without Ever Leaving

Not all departures involve boarding a plane. Some are quieter, stranger, more existential than geographical. You can be halfway through brushing your teeth and suddenly realise you’ve left yourself behind somewhere. Not in a literal sense, no, the body stays put, obedient as ever. But the self? The self goes wandering. Leaves a note, sometimes, if you're lucky. Other times, it just slips out the side door. That’s what exile really is, isn’t it? Not the leaving of a country, but the losing of alignment. You’re still in your life, technically, but it doesn’t quite fit. Emotionally jet-lagged. Spiritually mislaid.

Pessoa understood this all too well. He never really left Lisbon, but his interior passport must’ve been ragged from overuse. His writing carries the weight of departures that haven’t happened yet, a kind of pre-nostalgia, like standing at the gate before the gate even exists. He wrote like someone constantly mid-pack: socks emotionally rolled, metaphysical shirts folded with anxious tenderness. It’s no wonder his words travel. They were born to. They longed for it before they even understood the destination.

And we do this, too. Some of us feel displaced even while sitting in the rooms we’ve decorated ourselves. There’s a particular alienation that doesn’t announce itself with sirens, it hums softly, like the fluorescent buzz of an airport lounge at 3am. I’ve felt it in hotel rooms where the sheets smelt too clean. In dinner conversations where my jokes landed in the wrong timezone. You don’t need a passport to feel dislocated. You just need a mind that won’t sit still and a soul that keeps rehearsing its exit, even when the door’s closed.

For the artist, this is often the baseline. To want to be elsewhere. Elsewhen. Elsewho. The impulse to create so often blooms from the refusal, or inability, to be content with one reality. We write not just to escape, but to relocate the self. Some days I write because I want to crawl back into a moment that never happened. Other days, because I want to build a room where the moment could live.

The art is the luggage. The longing is the destination.

I once arrived in Lisbon with a suitcase full of linen shirts and Pessoa’s Book of Disquiet, which, in hindsight, was like bringing a tuning fork into a city already vibrating with its own sad music. It was summer, but the city smelt like autumn — sweet rot, soft decay, the perfume of endings. My friend’s flat overlooked a street so unremarkable it circled back into abstraction. And yet, I sat on that little balcony for hours, watching the blank wall opposite as if it were a canvas that might blink. I was convinced, utterly and foolishly convinced, that it was trying to tell me something.

That’s the thing about cities like Lisbon. They don’t shout. They haunt. They lodge themselves in the small, unassuming parts of you. They become the feeling that lingers in your chest two weeks after you return, when you catch the scent of roasted chestnuts in an unexpected place. Lisbon isn’t loud like New York, or theatrically seductive like Paris. It doesn’t perform for you. It invites you to overhear it. To linger long enough for the whispers to sound like words.

You don’t really photograph it. You scribble nervously in your journal, as though the city might read over your shoulder. You stare at the cobbled streets like they might rearrange themselves into a poem. You buy a coffee and sit with it too long, hoping the condensation on the glass will drip into a symbol you can interpret.

Pessoa didn’t need to travel because he was already in transit, perpetually in emotional motion. He moved through selves instead of countries. His desk was a ticket counter for lives he might’ve lived, his poems a long layover in the land of what-ifs. He traversed the continents of the soul with nothing but a notebook and an ache sharp enough to cut through the page.

And perhaps that’s the greater irony, or maybe not irony at all, but a deeper truth: that the most significant journeys don’t always announce themselves with a passport stamp. They begin with a glance out the window, a line of verse, a silence that doesn’t feel empty. They happen when you realise you’ve outgrown a version of yourself and the only thing left to do is write your way out of it.

The greatest odysseys are often internal. Pessoa never left Lisbon, but he mapped the entire terrain of absence. He knew that exile isn’t a place you go, it’s a feeling that moves in and hangs its coat.

And sometimes, when I’m packing for a trip, folding clothes I may not wear and books I won’t finish, I think of him not as a man of mystery, but as a fellow traveller of the in-between. The ghost at my shoulder as I zip the suitcase. The quiet voice that says, “You’re not going there, you’re going away.”

We are all, in our way, travellers. Some carry cameras, others carry wounds. Some collect stamps. Others, shadows. And some of us… the foolish ones perhaps, carry poems, unread letters, the names of cities we’ve never seen.

Because even when we never leave, something in us is always departing.

Dreams Deferred: Exile as a Creative Practice

There’s something wildly fertile about longing. Not pleasant, fertile. Art doesn’t bloom from comfort; it claws its way through cracks in the pavement, blooming defiantly where it shouldn't. Like a poppy on a construction site. Pessoa knew this. His work was never the fruit of fullness. It was the flowering of absence. A slow, deliberate blooming in soil made of sighs.

When you’re removed from what you want, not gently distanced, but exiled with ceremony, your mind has no choice but to reimagine the object of your desire in impossible detail. It becomes more than it ever was. Sharper. Lovelier. Untouchable in the best and worst way. That’s why longing makes for such beautiful work: it isn’t tethered to the heavy gravity of reality. It floats. It gleams. It gets away with grandeur. Exile offers this strange alchemy, it doesn’t just distance you from what you want, it dramatises the distance until it becomes art.

Pessoa's poetry is so potent precisely because he never got what he wanted, and he didn’t trust reality to give it to him anyway. Why settle for the actual when the imagined can be embroidered to perfection? His writing doesn’t quench thirst. It perfumes it. And that perfume lingers long after the poem ends.

There’s a kind of aesthetic heroism in choosing longing over satisfaction. It’s impractical, yes, but also deeply romantic. Look at any great piece of art and you’ll find, stitched into its lining, a little packet of heartbreak. The best songs are written at the airport gate. The best films end on the precipice of “what if.” The best poems hold their questions tenderly, like a letter you re-read but never reply to.

And perhaps this is why exile, self-imposed or otherwise, has produced some of the world’s most haunting art. James Baldwin’s Paris was not a backdrop, but a balm. Nina Simone’s Switzerland was not sanctuary, but stage. They didn’t escape home; they wrote from the perimeter of it, peering in with eyes sharpened by distance. Exile doesn’t dilute creativity, it distils it. Removes the excess. What’s left is pure ache.

Pessoa, curiously, lived in Lisbon his whole life, but make no mistake, he was emotionally expatriated. Lisbon wasn’t his comfort zone; it was his haunting. He wandered its streets like a tourist in his own story. There’s a line in The Book of Disquiet that goes something like, “I wasn’t meant for reality but life came and found me.” That’s the Pessoa condition in one breath: a man caught red-handed in existence, dreaming of abstraction.

Because exile doesn’t always come wrapped in geopolitics or tragedy. Sometimes it’s subtler than that. It arrives as a sense of not quite fitting. Of pressing your life against your skin and feeling it bunch awkwardly at the seams. You’re present, technically. But emotionally, spiritually, you’re elsewhere. Floating just above the room like steam from your own cup of tea.

And yet, this discomfort is not just a curse. It’s a furnace. Artists thrive in the threshold, between languages, between identities, between selves. That’s where Pessoa camped out. He wasn’t just one man; he was several. Álvaro de Campos with his sharp rage. Ricardo Reis, the classicist. Bernardo Soares, the melancholic clerk with too many thoughts and too little will. Pessoa split himself not to hide, but to feel more fully. Each heteronym was a vessel for a different exile. A different flavour of distance.

I’ve felt versions of this myself. That haunting sense of being elsewhere, even while sitting in your own flat, wearing your softest socks. Missing people who are still in your life. Missing a version of yourself you can’t seem to find, the one who was bold, the one who believed, the one who sat down to write and didn’t stop halfway to scroll. That self is often somewhere else. Lisbon, maybe. Or Kyoto. Or a quiet train between nowhere in particular.

There’s a quiet grief to it, this internal homelessness. But also a flicker of power. Because when you’re not fully here, you’re also a little bit there — in the dream, in the future, in the page. The work we make from that space is charged. It carries voltage. That’s why some of the greatest art is, at heart, a failed arrival. A suitcase packed with emotions that never quite clear customs.

And so, the artist becomes a kind of perpetual migrant. Not of countries, but of selves. A romantic fugitive, moving through imagined conversations and alternate timelines. Carrying not just notebooks, but whole continents of feeling. The friction between desire and destination becomes the spark. The poem is a flare thrown up from the border. A souvenir from a place that doesn’t exist, but somehow still feels like home.

Pessoa didn’t wait for satisfaction to find him. He wrote from within the ache. He used longing like ink. He stitched absence into rhythm and made a symphony of shadows. And maybe that’s what we’re all doing, in our own way, composing lullabies for our lost selves. Packing for places we may never see. Writing letters to the parts of us still in transit.

Because at the end of the day, every piece of art is a luggage of dreams. Deferred, yes. But never discarded.

The City That Writes You Back

There are cities that merely house you — they give you a roof, a bed, a street to walk down. Then there are cities that write you. Lisbon, for all its faded beauty and stubborn soul, is the latter. It doesn’t let you pass through. It makes you stop. It makes you listen to the rustle of the trams, the murmur of the river, the whisper of cobblestones beneath your feet as if they’re telling you secrets. It doesn’t ask for your attention; it takes it. Without permission, without apology.

The thing about Lisbon is that it’s a city in constant dialogue with its own melancholy. And when you step into that conversation, when you walk those narrow streets where time feels both suspended and infinitely slow, you can’t help but feel it, too. There’s a sensation that lingers, like a conversation half-heard, words hanging in the air with the promise of something deeper, something almost understood. You leave the city with more questions than answers, your heart full of words you never quite wrote down.

Pessoa understood this. He wrote not just for the city, but from it. Lisbon isn’t a place on a map for him; it’s a living, breathing character. A lover, a mother, a phantom. The city is an extension of his own longing, each street a line in his poetry, each building a verse unfinished. And in return, the city doesn’t let him rest. It refuses to be resolved, just as he refused to resolve himself. Lisbon, in its quiet way, holds him captive. It makes him its own.

I remember walking through the Baixa district one late afternoon, feeling the heavy warmth of the sun stretch across the pavement. The city felt different that day, not the gentle tourist’s Lisbon, but the one that insists on being understood. I found myself in front of a small, unremarkable bookstore, the kind that doesn’t make a fuss, but somehow knows more than it lets on. As I stepped inside, the faint scent of paper and old leather greeted me. The shelves were stacked with books that looked like they hadn’t been opened in decades. I wandered through, feeling like a ghost myself, until I stumbled upon a faded copy of Mensagem.

It was a small moment, unremarkable to anyone who hadn’t read Pessoa, but for me, it felt like a quiet surrender. The book, worn and folded by the years, seemed to be waiting for me. In that moment, the city wrote me back. It whispered its name through the pages of Pessoa’s words. Lisbon had found me, just as it found him.

There is a sadness in Lisbon, but it’s not a tragic sadness. It’s the kind of sadness that exists when beauty is no longer fresh but still burning. It’s the soft ache of something that has been loved and left, something irretrievably lost, but cherished in the absence. It is a city that mirrors the human condition. It asks you not to forget it, not to romanticise it into something perfect, but to hold it as it is — imperfect, struggling, but alive.

Perhaps it is this tension, this persistent ache, that makes Lisbon the creative furnace it is. Pessoa didn’t just walk through Lisbon, he wandered it. His words, like so many others, are infused with the city's disquiet. And it’s here, amidst the sun-drenched alleys and the cracked facades, that writers are born, or reborn. Lisbon refuses to let them go home unchanged. It insists that they leave with something more than they came with, a deeper sense of loss, but also a kind of quiet revelation. A promise that what is lost is never entirely gone.

Lisbon doesn’t just house your stories. It offers them to you, over and over again, in new shapes, new layers. It writes itself into you, the way a lover’s scent clings to your skin, refusing to be scrubbed away. And like Pessoa, you begin to understand that you were never meant to leave. Not completely. Because Lisbon doesn’t want you to. It wants you to stay a little longer, to wrestle with its ghosts and to carry them with you, wherever you go.

And isn’t that the ultimate gift of exile, that the city never really lets you leave, even when your body is long gone? The city writes you into its pulse, and you remain, etched into its pavement, lingering in the spaces between its narrow streets.

Because Lisbon, like all great cities, doesn’t just live in the past. It exists in the people who walk it. The artists who can’t help but be reshaped by it. The poets who drink their coffee slowly, in silence, wondering if they’ll ever be able to capture it all. It’s not just a place. It’s a dream, one that never really leaves you, even when you leave it.

The View from Elsewhere: Why We’re Always Just About to Arrive

I often wonder: are we ever really in the moment? Or are we always packing for the next one, emotionally at least? Maybe that’s why Pessoa still resonates. Because he doesn’t pretend to have arrived anywhere. He just keeps writing from the departure lounge of his soul.

There’s a reason we romanticise train stations and airports, they’re liminal. Not here, not there. They hold the poetry of almost. And that’s where most of us live, emotionally speaking. We’re always just about to fall in love. Just about to move. Just about to write the thing, be the person, change the life. Almost.

But maybe the beauty isn’t in arrival. Maybe it’s in the luggage, in the dreams we pack and re-pack, never quite knowing where we’re going, only that we’re still in motion. Still searching. Still aching beautifully.

Pessoa would have understood. He spent his life writing postcards from a place he never fully reached — Lisbon, but also something deeper. A home inside the self. A place where language might finally hold the ache. Where longing wouldn’t be a symptom, but a style.

But perhaps we never truly arrive. Not in cities, not in love, not even in our own lives. We are perpetually in the airport lounge of ourselves, staring at departure boards and wondering why our flight never gets called. Pessoa understood that. He built an entire literary canon around the layover.

Maybe that’s the point. That longing is not a flaw, but a feature. That saudade is not a wound, but a womb. The birthplace of poems, of paintings, of midnight confessions and unposted letters. We long, therefore we create. We ache, therefore we matter.

Lisbon doesn’t offer answers. It offers ambiance. Foggy clarity. Streets that spiral rather than lead. And Pessoa is still there, in the corners of cafés and the curves of tiled walls. Not walking beside you, but ahead. Always just ahead. Always just about to turn the corner.

And maybe that’s where we belong too — on the edge of elsewhere, suitcase in hand, dreaming not of arrival but of the poetry made possible by delay.

S xoxo

Written in Miami, Florida

23th March 2025