My (Mostly) Solo Portugal Trip

Updated: Jul 23

Let's not start with the fact that the airline lost my luggage for 36 hours, a carry-on size which I had just purchased the WEEK BEFORE so that my luggage would be with me for the entirety of the trip, BUT then United ran out of overhead bin storage, and forced me to check my carry on proceeding to 'misplace' it somewhere in between Boston and Portugal... so did I have a change of clothes for the luggage that was supposed to be with me for the entirety of my travels? Of course not. Did I land, cry at the airport in Porto and then remember I was in the Port Wine Capital of the World and proceed to drink and forget entirely what I was wearing? Yes.


See below. Drug store makeup, a borrowed dress, and yes I drank all of that port in one sitting. (But we'll get back to this, the first 6 hours when I'm in the Free People onesie for 48 hours is where we're at - just providing a visual break).


Post-flight debacle, just as I'm debating whether to drink my weight in Port or take a nap, as the universe would have it, the most magical Portuguese man rode up to the Le Monumental Palace (where the staff offered to shop for my lost essentials FOR ME) on a Vintage Ural Ranger Side Car Tour (because he is the owner and tour guide extraordinaire of Porto Side Car Tours). AKA an earth angel named John. *His name is actually something Portuguese that as I proceeded to get drunk, I mean do the tour, I couldn't pronounce so he said John was fine.


FIRST green is my favorite color and secondly, after wiping my makeup free face of my lost luggage tears and explaining my unfortunate first 4 hours in Portugal, John detoured our tour and took me directly to a local hang...and after exactly one bottle of Portuguese rose (to myself, he's driving, he reminded me) and 3 pastel de natas (Portugal's most ubiquitous pastry and sold anywhere you can buy an espresso)... I am one United luggage down but up on my Portuguese luck.


Back to the Nata. The flaky crust is filled with a creamy egg custard that is brûléed and dusted with cinnamon. It’s the kind of pastry you’ll spend your days dreaming about, long after you’ve left Portugal. This famous pastry was invented by monks at Jerónimos Monastery with too many leftover egg yolks. They were first sold down the street from the monastery at Pastéis de Belém, which opened in 1837. For almost two centuries, this pastry shop has been churning out thousands of tarts a day—all according to the original recipe which is kept under lock and key.




EDITOR'S INTERJECTION: TO BE HONEST, I'M SURPRISED AT HOW MANY PEOPLE ARE

SURPRISED I'M TRAVELING SOLO. I MOVED TO ARGENTINA WHEN I WAS 20, BY MYSELF. I HAVE TO BE "ON" ALL THE TIME, EVERY DAMN DAY FOR MY JOB. THIS IS THERAPY FOR ME. NO IM NOT SCARED. NO, IM NOT BOTHERED. YES, I'M TOTALLY FINE. LIKE BEYOND PLEASANT. AND NO, I'M NOT IN "STEALTH" MODE HIDING A MAN. SOMEONE ASKED THAT. SOME OF Y'ALL SHOULD PRACTICE MORE SOLITUDE TBH, BUUUUT I DIGRESS.


BACK TO PORTO AND MY SIDECAR TOUR.

Let me start, or continue... after a few rants, by saying not getting a tour guide anywhere in Europe would be a mistake. I would have missed so much of this history (okay all of it) and it's so rich compared to what we're used to as Americans. In case you forgot, I'm a bottle of rose and natas-deep and this tour hasn't even started because HUMANITY. SO. Porto is located along the Douro River estuary in northern Portugal and is one of the oldest European centres. Its core was proclaimed a World Heritage Site by UNESCO in 1996, as "Historic Centre of Porto, Luiz I Bridge and Monastery of Serra do Pilar".

There are medieval entry points marked by these amazing old bridges which once imported goods in the 1400s. THE. FOURTEEN. HUNDREDS. HUH?!


Locals hang out on the patio and eat sardines, which are the most popular catch. Bacalhau, the Portuguese term for salted codfish, is the most iconic ingredient in all of Portugal’s cuisine with thousands of ways to prepare it, but don’t go around asking where you can try it fresh. The cod is not actually from Portugal, but instead caught in northern European waters and then preserved in salt. Rivaling bacalhau, sardines may be the most beloved fish in all of Portugal. They’re sold all over the city in decorative collectible tins.



NO DIRTY LAUNDRY HERE. Because its clean. Our tour guide says "if you are a nosy person and want to know the life of your neighbor, no need to listen at the door, just look at the laundry drying"


John also took me to see ESTAÇÃO FERROVIÁRIA DE PORTO. This train station has been declared a UNESCO World Heritage Site and as a National Monument of Portugal. Until the late nineteenth century there was the convent of the Benedictine nuns of Ave Maria, precisely where São Bento train station is now.




PLEASE GO SEE JOHN if you're in Porto, and tell him Megan, the blonde with lost luggage who loves rose and nata sent you.


PRO-TIP: Don't try to speak Spanish

Because Portugal is right next to Spain, many travelers assume that using broken Spanish will be helpful when communicating with locals. In reality, most locals have a much better grasp of English than Spanish, especially the under-30 crowd. You should absolutely try learning a few words of Portuguese if you want to ease the communication barrier — but when in doubt, stick to English!


NOW ON TO THE PORT. Follow me on a premium lectured wine tasting at @cockburns_port in the historic area of Vila Nova de Gaia. Located on the Douro River, it's the largest wooden Port cellar in the Port Wine neighborhood, with the largest collection of oak barrels and

wooden vats of any Port cellar in Porto.


This is where they age all the ports and in particular, this is the home of Cockburn's Special Reserve Port. Founded in the earliest 19th century, the Cockburn's & Co Family built a remarkable reputation (this publicist loves a good personal brand), Records at the London Auction houses show that in the early twentieth century, Cockburn's Vintage Ports commanded the highest prices of any port houses.



SPECIAL RESERVE. Rich and vibrant with fine peppery tannins, Cockburn's Special Reserve continues to be the world's most successful Reserve Port, ever since its launch in 1969. Cockburn's has more Port Wine ageing in seasoned oak vats and casks than any other producer in the historic quarter of Vila Nova de Gaia. Additional wood-maturing gives Cockburn's Special Reserve its distinctive elegance and balance, the characteristic of all great

Port Wine.



CHEF'S KISS: Yakuza by Olivier Porto - EASILY one of the best sushi meals I've ever had. Let the chef do the Omakase. You will not be disappointed. The couples nearby asked this solo diner what I ordered from the menu - hint: omakase is where you let the chef pick :)


NEXT STOP. THE ALGARVE COAST. We stayed at the magical Vilalara Thalassa Resort, a 5-star LUSH, upscale resort, set on the cliffs of Praia das Gaivotas along the North Atlantic Ocean. Follow a path to the beach and you'll be met with umbrellas, sun chairs and this view - with waitstaff to bring your cocktails.


While in Algarve, and because I was traveling solo (spoiler alert: my girlfriend Erika flew in from Vegas and surprised me in Algarve) I booked a photographer couple I found on Instagram (mattandlenaphotography). So while Erika was catnapping her jet lag off, they snapped these (more on my Instagram). Highly recommend booking them to capture you while you're visiting this stunning place. Golden hour never looked better.


We then jaunted off by car for our last leg in Lisbon, but not before stopping at Comporta Cafe Beach Club. We had only scheduled 6 hours, but could have easily spent days in Comporta, which turned out being the highlight of the trip, in my opinion. Apparently we missed Elon Musk by a day - this place shits all over Tulum but was also what Tulum was like pre-tourism boom.




After arriving in Lisbon, the seaside city that’s the second-oldest capital in Europe, we checked into the Portobay Liberdade Hotel. Lisbon (Lisboa in Portuguese) is home to world-class restaurants, fantastic nightlife, and colorful historic buildings.


One of Europe’s oldest and most colorful cities, Lisbon’s layout is as winding and varied as its storied past—which dates all the way back to 1200 BCE. Rocked by one of the most destructive earthquakes the world has ever seen, today Portugal’s capital shines with beauty in every tiled building and romantic palace. It’s a city of sprawling vistas, steep hills, and climbing cable cars, where the night air is filled with the beautiful music of heartbreak and the salt of the Tagus River and Atlantic Ocean.


Sample the best of Lisbon at the Time Out Market, a food hall featuring some of the most popular restaurants and bars in the city (and where you can meet other travelers if you’re going solo). There you’ll find locally sourced seafood, addictive cheese-filled Pasteis de Nata pastries, burgers, sushi, pad thai, and traditional Portuguese plates.



In about an hour by train, you can visit two nearby cities where the Portuguese royalty and Lisbon’s upper classes built their mountaintop palaces and seaside mansions. During the age of romanticism, it was here where the upper classes found fresh air and an escape to nature—and today they are the best spots to work some exercise into your sightseeing.


Wander ancient castles in Sintra

Just a 30-minute drive from Lisbon in the foothills of the Sintra Mountains, the town of Sintra is like an ornate medieval village swallowed by a fairytale forest. Across some wooded hills in the Quinta da Regaleira castle, giant towers peak over the tops of trees and are sunk into the ground, connected to each other through a labyrinth of caves. There’s even an Initiation Well of moss-covered stone that spirals down seven levels into the earth where pagan monks once held ceremonies. Bridges and paths take you over ponds and past waterfalls or fountains spread across forested grounds.

Sintra's Pena National Palace is basically what every Disney princess really wanted but either couldn't afford or couldn't relocate to due to some weird spell. It was the brainchild of King Ferdinand II, who had it built expressly to be visible from any vantage point in the entire surrounding hills. Not far from the palace grounds, there’s a medieval castle that was built during the Moorish Era (8th through 12th century) that once served as a lookout point for Lisbon.

And down south in Braga, the tradition of breathtaking European churches really comes to a head. The Baroque-style sanctuary that is Bom Jesus Church—arguably the most bomb name for a religious building ever—actually holds the title of "most photographed church" in Portugal. Fair warning: it also has, like, 600 stairs.



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