Rich because I was brave enough to go alone

My First Solo Trip to Lisbon, Portugal

Like many of us, I’ve spent so much of my life worrying what others would think of me. The thought of sitting alone in public used to feel daunting and humiliating. But when I planned my first international solo trip, everything changed. That solo trip taught me not only how to enjoy my own company but also how empowering it can be to navigate on your own terms. I soon learned most people admired me for going alone. You can continue to wait for permission, or you can choose to take control of your life. I choose to take control. 

One thing I loved about my solo trip was the ability to make decisions without considering anyone’s feelings but my own. I went from being the indecisive girl who usually copies your drink order to actually having an opinion… who knew!  In the past, I’ve wondered if I was too boring for other people. Planning this trip around my own interests taught me to value myself a little more. Solo travel is a life changing experience and if you have the resources I think you should do it. 

If you don’t know where to start, here’s my itinerary for 5 days in Lisbon, Portugal. I’ve already had one friend copy this itinerary. She texted me recently to say it empowered her to add a solo extension to her work trip in Italy!

Day 1

I arrived in Lisbon early in the afternoon. I checked into my hotel, changed, and joined a free walking tour with guruwalk. The tour gave me a great overview of the city and was both fun and informative. Plus I had the chance to meet other solo travelers and try some local bites! The walking tour ended with a shot of local liquor followed by a bunch of strangers huddled up laughing under an archway during a big rainstorm. It was a blast! After the tour I made my way back to the hotel to change out of my wet clothes and find some dinner. My one regret from this trip was not doing more research on restaurants in advance. I ended up eating somewhere random this first night.

Day 2

For my second day, I planned to spend the morning exploring Chiado, a lively and historic neighborhood. I started with a bite to eat at A Brasileira before stopping into the oldest operating bookshop in the world, Bertand – both recommendations that came from my walking tour. In the book store I ended up purchasing a book on a poet my tour guide had mentioned too! After wandering around for a while, I stopped for an Aperol Spritz and enjoyed live music and people-watching.

I went back to my hotel to drop off my new book before heading to a vintage sailboat ride at sunset — a relaxing and scenic way to take in more of Lisbon. After the boat, I had dinner and dessert at a nearby Michelin-starred restaurant called O Frade, where you sit at a round bar and can watch the chefs prepare each dish in front of you.

Day 3

My third day was probably my favorite. I spent the entire day on a tour exploring Sintra, visiting the gardens at Quinta da Regaleira, wandering through Pena Palace, and walking the streets of the medieval town. I loved learning the history of this unique architecture and landscaping. That evening, I went to dinner and a fado show at A Severa. It was a beautiful end to the day. A must if you visit!

Day 4

Although I was still pretty tired from the day before, I had an early morning walking tour to see Belém and Jerónimos Monastery, followed by a Portuguese tile painting class. I especially enjoyed the class because it was relaxing and I got to bring home a souvenir that felt unique to my experience. I ended the day with pizza at Valdo Gatti — just what I needed!

Day 5

I left my last full day in Lisbon open, with the freedom to explore. In the morning, I decided to visit Cascais Beach, where I people-watched and ate a sandwich by the water. Later in the day, I made my way back to catch the sunset at Castelo de São Jorge — a historic castle that overlooks the city. By this last day, I was grateful to have left my schedule flexible.

Looking back, I’m so glad I did this solo trip — not only because I discovered somewhere new, but because it taught me how to enjoy my own company and trust my own opinions. Even though I went alone, I rarely felt lonely, bored, or embarrassed. I hope it inspires you to step outside your comfort zone too.