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Have you ever had those days or weeks where things just pile up and it seems like “death by one thousand paper cuts?” Well, I had many consecutive that just built up to the point I could no longer function as a human.
Between increasing demands at work, aging parents, and family responsibilities, I needed to get away – far, far away, and fast!
It just so happened that my friend, an ex-pat living in Germany, came up with the idea that we should both get away and meet in Lisbon as a halfway point.
I dug around for cheap flights and found that I could get myself there and back for 20k points through Virgin Air which operated through Delta.
I snagged that ticket and told my friend that I was IN!
I had never been to Portugal before, and knew very little about it…and even less Portuguese. Sounds perfect, right?
This adventure started right after an overnight flight, landing in Lisbon at 8 AM, bleary-eyed but excited. The adventure began in earnest at the airport’s taxi ranks. Assigned to a taxi, I quickly discovered my taxi driver spoke no English and didn’t take credit cards—a hilarious start to what would be a memorable trip. Through a mix of gestures, Google Maps, and broken phrases, we navigated to the Hyatt Regency, an impressive setup almost nestled under the 25 de Abril Bridge along the Tagus River, where I met my friend.
Day 1: Stepping out in Belem
Whenever I travel, my first order of business is to order something to eat from a local shop that’s just a little off the beaten path. I figure that If I can be anywhere in the world and figure out how to feed myself, I’ll be ok.
Even without speaking another language, I’ve never had a problem ordering a coffee and something tasty-looking from the display case.
I finished my breakfast of coffee and my first of many pastel de natas during my stay, and was mindful to slow down and take my time. Part of my promise for this trip was no time constraints or forced itineraries.
As I strolled down the street, and admired the colorful tiles on the buildings and marveled at the cobble sidewalks and streets. It became much more touristy towards Jerónimos Monastery and Belém Tower. I stopped into the iconic Pastéis de Belém for another (or several) pastel de nata, which I sat and ate in the Jardim da Praca do Imperio on that lovely November day.
This day I explored alone and I felt quite safe, although I did make sure to pay attention to my surroundings.
Day 2: A Tuk-Tuk Ride for a Grand Tour
The second day brought more exploration. My friend and I set out to get a lay of the land, so we hopped in a 3-wheeled Tuk-Tuk that wound through and bumped over Lisbon’s cobbled streets for an hour and a half. (seriously, if you have back issues, opt for a 4-wheel version with suspension)
We bumped from São Jorge Castle, the National Pantheon of Santa Engracia, and Miradouro das Portas do Sol, which offered breathtaking views over Lisbon. Later that evening, we hired an Uber from the hotel and hung out at the bustling Time Out Market where we had easy access to sample all kinds of food, including an octopus hotdog!
Mid-Journey Switch: From Swanky to Bohemian
Day three we had to give up our swanky digs and moved from the luxury of the Hyatt to an Airbnb in the heart of Barrio Alto. A lively area that would have been perfect if we were 20 years younger. Perfect if you like the night life and like to boogie, but I would not stay here with family or kids due to the noise and difficulty getting through the crowded streets and people sitting on the stoops to the apartment doors.
Our strategy for sleep was to walk as much of the city as we could hopping from wine bar to wine bar and not return before 1am where we then flopped into our beds too exhausted to be bothered with the noise.
The plus side of staying here is that it was central to everywhere we wanted to go on foot. Warning – it is up a hill – a very big hill and while Lisbon is a very walkable city, you’ll want to be at least a little fit to walk it comfortably.
Love seafood? DO NOT MISS: A Cevicheria in Lisbon
Day 3: Sintra’s Enchantment
We said “No pre-arranged itinerary” for the sake our our sanity, so on a whim we decided to train to Sintra. This is an easy day trip into a fairy tale. Again, on foot, everything is uphill. Both ways. (not really) The Pena Palace, Moorish Castle, and Quinta da Regaleira were as magical as they were historically fascinating. The colors were spectacular, and the dense fog made walking around the edge of the castle feel like it was enchanted. Each site was a step back in time, surrounded by lush gardens and mysterious pathways. By the end of the day, my watch reported that we had walked 10 miles and over 150 of flights of stairs.
Tip: As you’re walking, look for openings in the woods. These trails are a shortcut and get you off the narrow roads, but they’re a bit rooty and muddy at times.
Day 4: Another day in Sintra and the Coastal Charms in Cascais
Our final day took us back to Cascais by train to tour the Initiation Well and the Quinta de Regaleria caves. From here, we wanted to see the coastline, and since there’s no public transport between Sintra and Cascais, we hired an Uber to drive us. (cost about $35 US)
He dropped us at the dramatic Boca do Inferno, where nature’s power is on full display, and from there it was an easy walk into town for dinner and to catch the train back to Lisbon.
It Was A Journey of Laughs, Discoveries, and Memories…and an escape from life’s “noise”
This trip was a blend of all things travel should be—a chance to focus on just myself, unexpected challenges, cultural immersion, and the beauty of discovery. (Sometimes it’s nice to only have to keep track of one person’s shoes) From the initial taxi ride misadventures to the nights in Barrio Alto, each moment was a story in itself. Lisbon’s lively streets, Sintra’s historical allure, and Cascais’s coastal beauty delivered a well-rounded Portuguese experience. It was a reminder that travel is as much about the journey as it is about the destination.
Essential Must-Haves and Must-Trys for Your Lisbon, Sintra, and Cascais Adventure
After sharing my adventure through Lisbon, Sintra, and Cascais, I’ve compiled a must-have list for anyone planning to explore these beautiful Portuguese destinations. Whether you’re navigating the urban landscape of Lisbon, wandering through the fairy-tale palaces of Sintra, or relaxing in the coastal town of Cascais, these essentials will ensure a smoother and more enjoyable experience.
How I Pulled it Off
The trip from Detroit to Lisbon wasn’t that much longer, nor more expensive than going to California, and totally doable for a 4-day long weekend if your main purpose is to disappear for awhile.
- Leave on a Thursday, return on a Tuesday. Not many people travel outside of the weekend and I had a middle row to myself.
- Ask family and friends for after-school rides and sitting for the kids for 2 days.
- Cash in on credit card points for hotels and flights: look at Google flights for best fares.
- Walk. Walk everywhere.
- Use an e-simm for data and use Whatsapp and Facetime for phone calls instead of paying for international phone plans.
- For the best prices, stay away from the tourist areas. Eat where the locals are and ask for recommendations from area shops.
Must-Have List
- Pacsafe Purse: For peace of mind, a Pacsafe purse is essential to keep your belongings secure while you explore.
- Google Translate or a Willingness to Try Some Portuguese: Not everyone speaks English, as my taxi adventure proved. Having Google Translate ready or knowing a few key Portuguese phrases can go a long way.
- Cash and/or Access to Cash: Many places, including taxis, may not accept credit cards, so having cash on hand is crucial.
- Portable Charger: With all the photos you’ll be taking and use of maps and apps, a portable charger is a lifesaver.
- Universal Travel Plug Adapter: I love this one because it charges multiple devices with USB and USB-C as well.
- Uber App: Uber was a convenient option when public transportation wasn’t practical, or we were simply too tired to walk. It’s widely available in Lisbon.
- Layers: The weather can change quickly, so my favorite packable jackets were invaluable.
- Scarves: They double for fashion and function, keeping you warm and adding a touch of style.
- A Base-Level of Fitness: Lisbon is incredibly walkable but also famously hilly. Being in decent shape will make your explorations much more enjoyable.
- Awareness: Traveling anywhere, you need to be aware of your surroundings. When traveling as a solo, or semi-solo female, it’s good to know how to avoid, deflect, and escape situations if needed. I found this and run through the courses my myself and with my daughters so that we can have piece of mind that we’re at least a little bit more prepared to handle ourselves if we ever need to. Use Coupon Code MI0001
Must Try
- Time Out Market: Don’t leave Lisbon without visiting Time Out Market. The Octopus Hotdog and the doughnuts are absolute must-tries!
- A Cevicheria: This place is an experience not just for your taste buds but also for your eyes, with a gigantic octopus hanging from the ceiling. Their ceviche is outstanding and showcases the freshness and flavor of Portuguese seafood.