Our criteria for this November trip was made up of a definitive list of “don’t wants”: We didn’t want to be on a plane for more than an hour or two, we didn’t want jetlag, we didn’t want to be cold, and we didn’t want to plan ahead. We were tired.
After working nonstop through spring and summer while everyone around us was vacationing and relaxing around the Mediterannean, we needed a full stop, reset and reboot. A trip to disconnect and reconnect. Not only with each other, but with our circadian rhythms. To put it nicely, we really, really, reeeeeeally needed to get lost. In every way possible.
Jeremy had just finished his first season of boat life, during which I barely saw him – he was on said boat from 7:00 am until 9:00 pm, 6/7 days a week, for 6+++ months. Which was fine by me, since I was working on my brand design projects from early mornings until late evenings, and almost every spare minute I had in between was spent building my new art website, creating new art... and working on custom art commissions. Which is all amazing, but we were very much due for a prolonged siesta away from screens, meetings, schedules....and people.
Our list of “wants” consisted of the following: great food, proximity to a beach, weather that would permit us to nap on beach (a lot), nature, quiet....and having absolutely no plans to plan for.
We decided on southern Portugal, since we both only knew the country from Lisbon up to the North. Ironically, the last time I’d travelled to Portugal was a month before Jeremy came into my life, about 8 years ago – I had gone to check out a yoga venue in central Portugal around Coimbra where I wanted to teach a yoga retreat.
Coimbra, Central Portugal:
I also took my time devouring art, design, pasteis de nata in Lisbon.
And a little too much Porto in Porto.
Jeremy had often been flying in and out of Lisbon from Toronto until he quit planes and switched to boats. Also, about a year and a half ago – Lisbon happened to be the destination of his last landing as a commercial airline pilot.
I wanted to reconnect with pen and paper and take time to draw and read during my travels, while giving my eyes a break from pixels.
The only “to-do” on my list was to to fill my travel sketchbooks with new nature landscapes, architectural drawings, shapes, patterns and ideas that inspired me along the way. And to spend time reconnecting with Jeremy, disconnected and fully present.
We wanted to discover and explore this new side of Portugal together, while working really really hard on getting lost. Too tired to pack or plan, we threw some essentials in a suitcase two hours before takeoff, rented a car in Lisbon and South we went, in search of adventure, food and rest.
Why Having No Plans Was The Best Plan: Highlights From Our Road Trip Across Southern Portugal
10 minutes after our evening touchdown in Lisbon, we picked up our rental car and hit the coast. Our only goal was to drive South from Lisbon along the Atlantic Ocean, find a hotel to pass out in, and wake up to the sea… explore our surroundings, eat, and repeat, until we reached Andalucia, Spain. At least, that was the original no-plan-plan.
When we started this road trip, we had no expectations. We couldn’t predict that we would fall in love with the Algarve, and love it so much that we would end up reaching Andalucia, Spain.... only to do a U-turn and return to Portugal for more praya, prana and Cataplana.
We couldn’t predict that getting lost in Portugal would re-connect us with EVERYTHING... or that having zero plans would make us happy as clams immersed in Cataplana (a regional seafood stew to die for). And we certainly could have never imagined that we would end up at the end of the world, watching the sun setting on another perfect day.
We couldn’t imagine any of this for the same reason we travel in the first place: travel expands us. It opens up new worlds, experiences, ideas, sights, and knowledge that wasn’t there before, and we return better, fuller and richer in experience and understanding.
To be honest, what led us to the places below were a mix of us looking for authentic, delicious food and then subsequently exploring the radius surrounding our culinary stops. If we connected with the vibe of a place, we simply stayed and dug in deeper. And if we didn't feel it, we hit the road.
Here are my top 9 Portugal destinations and new discoveries, found through a perfect blend of food, accident and adventure. Without further ado, this is the art of getting lost.
1. Sesimbra: Sea Mist & Birds of Paradise
We arrived late at night, windows down, surrounded by darkness and the smell of the Atlantic Ocean. The good thing about travelling in November is that we had no trouble finding a last minute hotel on a beach at 11 pm. I love arriving to a new destination at night because you have just enough time to form first impressions, and then the morning light fills in the blanks of your imagination. That light greeted us with a fortress perched on a hill overlooking the ocean, the blue of the sea, salty sea waves, exotic sea birds, and a beautifully designed mid-century style hotel lobby with huge sitting areas all facing floor to ceiling windows and the star of the show – the ocean.
It brought with it a strong yet comforting wall of misty ocean breeze air, warm morning winds, swaying palm trees, birds of paradise, lush green flowers and the magnificently blinding reflections of the sun hitting the little fishing ocean bay right under our noses. A nice way to wake up our first morning in Portugal. I’ll focus on the beauty and omit the cardboard eggs and coffee quality, keeping in mind that in the summer months Southern Portugal is a mecca for British tourism. And as much as we love them for their wit and other qualities, we can all agree the culinary inclination is not a strong-suit ;) Sorry, my amazing Brit-friends.
And so, we went in search of authentic Portugese food, which brought us to our next destination: Sines.
2. Sines: Chasing Churrasqueria & Stumbling On A Lot Of Blue Things
Our love of eating where the locals eat has often led us to have the most amazing culinary experiences in the least instagrammy spots. Sines was one such place. To get to it, we drove through what I can best describe as an industrial no man’s land that was both un-appetizing and uninviting, while searching for some nice, crispy, fresh, fried fish. With a side of meat.
After driving through an industrial park, we were rewarded with an unexpectedly charming fishing village perched on a cliff that’s preserved a slow and traditional way of life, whitewashed houses with bright blue detailing, a magnificent sea view, and a right maritime history that’s played an important role in Portugal’s industry and trade. Legend has it that explorer Vasco da Gama was born here (although this has never been officially confirmed).
What I can confirm, is that the food was, indeed, authentic and delicious, and that there is a magnificent medieval castle (Castelo de Sines) from the 1400’s with stunning panoramic views of the rugged Atlantic coastline, incredible ocean views with an unspeakably beautiful light, Roman influences, a lot of blue things, and not a lot of tourists.
All this, thanks to our search of good, authentic local food. Obrigado, Sines.
3. Zambujeira Do Mar: Tides & Ostrich Selfies
We continued south and stopped where our instincts told us to, in spots filled with good vibes and prana (more on this later).
One such spot was memorable for two reasons: first, the ugly town on our left that looked like a deserted shopping mall in no way prepared us for the wild, untamed, and breathtakingly beautiful hidden beaches at the bottom of vertiginous red cliffs on our right.
Nor for the sheer powerful assault on the senses by fresh salty sea-winds, tides that went out for days and cascading, endlessly long white breaking waves dancing relentlessly towards us. Warm enough to swim, no people in sight, red rock cliffs, wild lush clifftop greenery, powder soft compressed sand and wind circling us like a tumble-dryer all amounted to good Prana (a hindu term that at its core refers to “the universal life force that permeates everything in existence – the vital energy that fills and animates the universe”.
This prana was exactly what Jeremy and I needed: a good hard dose of nature's energy to kick start our journey and charge our batteries.
The second reason this place was so memorable was a roadside Ostrich drive-by.
As we were driving through the unexpectedly lush, green, and wild natural landscapes of the Beja region towards the Algarve and commenting on how strange it was to not see a single town, car or roadside stop (all good things) in this wild, windy region, we drove past two giant Ostriches having lunch in the grass.
We picked our jaws up off the car floor, looked at each other with big WTF eyes, turned the car right around, and went back to make friends with the random Ostriches. We watched them eat, wondering why, how, and where in the actual f#$k they came from.
And while scratching our heads with questions and smiling from ear to ear, took our first ever Ostrich selfies, in the middle of no man’s land. Random. And very epic.
4. Lagos: Much More Than "Just A Party Town"
Lagos wasn’t a place we expected to love as much as we did. At first glance, it’s a British party town and vacation colony peppered with sterile hotels and apartment blocks. Dig a little deeper and you’ll find a city with a rich cultural history, great cuisine and little gems hidden in the back streets away from the tourist avenues.
Lagos is the perfect base from which to explore the incredible natural landscapes, coves and beaches along the Algarve coast. The other perk of travelling outside the tourist season (other than avoiding the tourists), is finding accommodation smack on the beach, waking up to the sounds of the ocean, salty waves, seagulls and Atlantic ocean. Warm enough to tan, run and spend time on the expansive beaches, getting a good dose of that prana life force I mentioned earlier.
Lagos is a great place to get lost in, wander aimlessly around, discover some cool street art, local Portugese wall art, traditional Algarve design, ceramics and craftsmanship... and explore local museums. The little cinema is also cool. We watched The Gladiator in Portugese, and had the movie theater all to ourselves on a rainy day. Bliss.
Also, the food. The food was amazing.
5. Tavira: Pretty As A Button
As we made our way East in Algarve towards Andalucia, we discovered the incredibly pretty and charming town of Tavira. Set on two sides of the Gilão river about 35 km East of Faro, flanked by waterfront cafés, beautiful building façades, little parks filled with colourful flowers and exotic plants, accordeon players and a Roman bridge, this town is a people-watching lover’s dream, as well as a perfect place to wander aimlessly around and get lost in for a day or three, surrounded by beauty and a rich history dating back to the Bronze Age (1000 years ago).
Tavira was first settled by the Phoenicians (800BC), followed by the Romans, Moors and Spanish, and was destroyed, along with most of the towns in the Algarve by the giant earthquake and subsequent tsunami of 1755. The Roman bridge is still standing.
The town, along with its 37 churches (!) and hilltop castle ruins (with a fabulous view) was rebuilt in the18th-century, along with a sprinkle of Gothic and Renaissance buildings showcase its historical charm. An inviting mix of restaurants and guesthouses makes it a perfect base for exploring the eastern Algarve.
We loved it.
6. Alcoutim: Reunion & Cossido Coma
Alcoutim is a small inland town that we probably would have never seen if it weren’t for Thibeault (remember him?), his boat and an impromptu reunion 5 years after our Canary Islands sailing disaster. You can read about this sailing misadventure here.
Long story short: Thibeault was a French pilot working in Canada, and a friend of Jeremy’s from his pilot days. Thibeault quit aviation, bought a sailboat, and has been living on it ever since. He's done multiple solo Atlantic Ocean crossings, and he's awesome.
Five years ago we all went sailing together in the Canary Islands, got stuck in a storm on the Atlantic Ocean, and our nautical misadventure made me swear off sailing life for life.
Insert Covid and fast forward through 5 life-transforming, sometimes bumpy but beautiful years. We're in Portugal, and it turns out that so is he; moored with his boat and his new Czech girlfriend smack dab on a river dividing southern Portugal from southern Spain, in a little river port town called Alcoutim. We couldn’t NOT go a little out of our way to say hello.
And we're very glad we did. The view approaching the town is a miniature postcard, the star of which is the white hilltop town on the Spanish side, directly across from the Portugese town of Alcoutim.
Speaking of boats, here’s a crunchy history kernel: In 1371, a peace treaty was signed on a boat anchored in the middle of the river, marking the end of the war between Portuguese King Fernando I and Castilian King Henrique II. Ironically, there is still no bridge linking the Spanish side to the Portugese, so if you wanted to cross over and say hello to your Castillian neighbours, you’d have to take the ferry, swim (not recommended), or drive 30 minutes to the nearest crossing.
Alcoutim is a small, quiet riverside town where you won’t hear anything other than Portugese, and will eat incredible local food (the coma-inducing Cossido is a must), made for, and by, locals.
Small streets lined with flowering gardens and surrounded by orange groves and vibrant sunsoaked green fields, trees, and a riverfront beach add to the charm, as do unexpected traditional blue tile artworks adorning the masonry walls around the town. We loved the vibe, authenticity, food… and our reunion with Thibeault.
7. Carrapateria & Praia di Bordeira: Surfer Heaven. And Prana! On Crack.
The drive to Carrapateria through a remote dirt path through the middle of a deserted nowhere gave nothing away of the spectacularly undeveloped wild landscapes, seascapes and prana-fest to come. This place is a mecca for surfers, yogis and nature seekers: 100% straight-up boho and free-spirit heaven.
As we approached the coastline and passed hundreds of simple surfer huts, van life communities and wild fields bathed in wind, we reached vertiginous red cliffs that took our breath (and my hat) away with the force of its beauty, powerful waves and expansive vistas that stretched out as far as the eyes could see.
We ran down to sea level with glee, fighting against the overwhelmingly powerful, salty, wind, sand and sea mist until we found ourselves in what I can only describe as a desert between sea and prairie. Here, you have to work for your surf – but it’s worth it.
After about 30 minutes of walking through desert dunes, we reached the breaking waves and got hit by over-caffinated winds coming at us in 360 degree circles, lifting our hair, clothes, and overwhelming all our senses.
Linear time and rational mind flew away, and we were left with the elemental presence of surf, wind, sea, and mist... the sounds of the wildness and the power of nature vibrating in every cell of your body. The tide was out so far that the packed sand and receding waves gave the illusion of standing on mirrors. Every way we looked was a shifting mirage of inexplicable beauty. This was nature's prana at its very best.
When our ears gave way and the bite of the wind became too intense, we made our way back inwards towards the desert to read and nap in the sand. Or so we hoped. The blowing sand made it impossible, but as I embraced it and let the sound of sand and wind grit through my senses while the sunlight warmed my sandy toes, I slipped into what I can only compare to a deep state of mindful presence and contemplation. If these billions of random sand grains on this particular beach represent not even a small fraction of the number of stars in our galaxy… how many grains of sand would it take to fill the entire universe?
And this was me, sober, after only a couple of hours in this topsy-turvy Alice in Wonderland vortex of prana. I can only imagine how the surfers & yoga people come out of here after a few weeks of eating sand and forging a prolonged, deep connection with their surroundings.
This place should come with a warning: profound restorative power. Enter at your own risk.
8. Sagres: To The End Of The World, Just In Time For The Sunset.
To cap off our Portugal wanderings, we ended up at the end of the world. Literally. Sagres a place loaded with myth and meaning. Its history stretches back to the Stone Age, when it was believed to be a gathering place of the gods by Phoenicians, Greeks, Carthaginians and Romans; it’s name was derived from “Sagrado” (aka “holy”), due to the local rituals practiced here during the nation’s pre-history.
Portugese locals, as we were told, lovingly and proudly refer to it as “the end of the world”, due to its unique location in the extreme southwest of continental Europe – basically its most Western point.
Cape São Vicente, once thought to be the edge of the known world, sits at the southwestern tip of Europe and played a pivotal role in the age of global exploration, led by the Portuguese. The first ever school of sea navigation was founded here, charting routes for Portuguese explorers venturing down Africa’s western coast and beyond. Also, Christopher Columbus was shipwrecked near Cape São Vicente in 1476.
As we made our way to the end of the world, both Jeremy and I were grateful that this was not a couple-bickering-on-vacation kind of day… and (half) jokingly pondered that perhaps on a not-so-good-day, IF one was tempted to lovingly nudge their partner off of a cliff, this would be kind of the epic place to do it . Go big or go home, right?
All jokes aside, an epic experience (other than throwing your partner off of this cliff) is to watch the sun setting at the end of the world. It’s beautiful, hypnotizing, meaningful… and a bit more romantic than we are.
9. Setubal: Unpolished & Authentic
As we made our way back to Lisbon, we stopped in Setubal: an old city laden with history, azulejos, cute city squares, charming narrow streets begging to be explored. Here’s what I loved most about it: it’s got grit, authenticity, REAL people who actually live here (not just a vacation colony), and faded grandure. If you prefer authentic charm over more manicured, tourist-facing facades, this city is the third largest in Portugal, and worth a few days of digging into.
The town was bursting with local life, cafés and a little too much xmas music, but overall there was a faded beauty and charm that I personally really connected with. I loved the fact that it’s a city “dans son jus” and feels authentic rather than simply catering to mass tourism; there’s a palpable grit, local culture and authenticity we loved.
After delving in, talking to locals, and poking around, we discovered that Setubal has a wealth of history, culinary richness and proximity to natural parks, beaches, coastal beauty and outdoor activities worthy of another longer trip all on its own.
The Art Of Getting Lost: Parting Thoughts
I’ll always remember this trip as two tired clams that were revived by getting lost and allowing each unpredictable moment discovering the coastlines of Portugal to bring their life energy (prana) back. I filled a sketchbook with moments, places and new experiences that I’ll keep in my heart forever. Travel changes us, doesn't it?
For me, art is a way of keeping fleeting magical moments alive. It forces me to look (really, really look) at everything that surrounds me and see beauty where others may not.
Through that process of observation, time stops and the moment expands. Only then can I begin to fully appreciate and contemplate the amount of time, skill and artistry that created the very things I’m observing, whether they're made by nature or by human hands. Through drawing, sketching, and creating art, I feel connected to the past, and rooted in the present.
Art is simply my way of freezing that significant moment from the sea of fleeting moments making up the waves of our lives… as if I can keep that time, and who I was in that moment on the pages of my travel sketchbooks.
Perhaps what drives most artists is the fact we have a hard time letting go. Instead of being ok with releasing fleeting beauty, we want to bundle it up, keep these moments close, and bring them out into concrete form out in the physical world, gaining comfort from knowing they’ll live on a little longer this way.
I don’t think all the yoga, meditation and practicing non-attachment in the world will ever teach me to let go of the need to create and re-interpret these precious fleeting experiences into art, or the need to freeze and paint these beautiful moments – to marvel, to look, to seek out new sights, experiences, and to enjoy every second of the journey, to cherish the art of getting lost… and make new art along the way.
This Portugal trip was one where I had to disconnect completely in order to reconnect. In disconnecting from emails, screens, ever growing to do lists, meetings, schedules, and tight deadlines, I reconnected with the present moment, and with who I am when I’m not expected to be anyone at all: the girl who wakes up and draws first thing in the morning, seeks beach prana, finds her mind still while in movement, bursting with new ideas while getting lost with someone she loves, wrapped up in a cocoon of precious moments that suddenly seem eternal because she’s lost the notion of Google calendar time.
This disconnection gave us the space to reconnect with who we are, both individually and as a couple: free, adventurous clams, happiest when we're getting lost together, exploring new places, having spontaneous adventures, and absolutely zero plans. And through the art of getting lost, we found ourselves again.
If you're in the mood for some more Portugal inspiration, here's the Portugal travel art collection I've been working on for the past few months.
This Portugal art collection is a contemporary and eclectic mix of colourful Portugese inspired pattern art, natural landscapes, monochrome seascapes, and urban city drawings I weaved together and remixed with my special signature blend of traditional art and design. The result is wall art that's sometimes bold, sometimes zen, and sometimes both. You can mix it, match it, and above all, have fun with it. I hope it reminds you of your own special travel moments and souvenirs:
The Portugal Travel Art Collection.
You may also like the Europe Travel Art Collection, the Urban Wall Art Collection, and the Colourful Wall Art Collection.