After a month in Madeira, I couldn’t resist exploring Lisbon 🇵🇹. Known for its thriving digital nomad and entrepreneurial scene, the city drew me in with its vibrant energy, beautiful architecture, and laid-back lifestyle.
I booked a stay at Outsite’s Lisbon location in the Intendente neighborhood, which was quiet yet close to everything I needed. Initially, I planned to stay for a short time, but I ended up extending my stay to three months, exploring Lisbon’s best spots, day-tripping to nearby beaches, and connecting with some amazing people.
The Outsite house in Intendente was perfect. This spot, nestled in a peaceful neighborhood yet close to the action, was a quiet retreat and base for exploring Lisbon. With Outsite’s relaxed, communal vibe, I had a fantastic group of digital nomads to explore the city with, which made the experience even better.
One of the things I loved most about Lisbon was how walkable it is. The city’s hills, tiled streets, and colorful architecture make every walk an adventure. I spent countless days exploring neighborhoods, admiring Lisbon’s classic azulejos (ceramic tiles), and just soaking up the atmosphere. Lisbon’s charm is unlike anywhere else.
Only a short trip from Lisbon, Costa da Caparica became a regular hangout. The beaches 🏖️ are stunning, with golden sands and great waves for surfing. We took several trips with our Outsite crew, enjoying long beach days, sunsets, and Portuguese beach culture. I also explored nearby spots like Cascais and Nazaré, the famous surf town known for the world’s biggest waves.
While in Lisbon, I had the chance to learn how to make pastel de nata (Portuguese custard tarts) with my digital nomad group. These sweet, flaky pastries are a Lisbon staple, and learning to bake them from scratch was such a fun, hands-on experience—and they were delicious!
Lisbon’s food scene did not disappoint. I explored countless restaurants, wine bars, and tried the famous Ramiro for their unbeatable seafood. The city has so many options, from casual spots to refined dining, making every meal an experience in itself.
Lisbon is packed with architectural wonders, from its historic neighborhoods to contemporary landmarks. I loved checking out the unique blend of old and new buildings, colorful façades, and classic Portuguese design that gives the city its charm.
A highlight was Hotel Ivens in Chiado, with some of the most incredible interior design I’ve ever seen. I stopped by Rocco, their Italian restaurant, and it was fantastic—a beautiful space, great food, and the perfect spot to relax with friends.
We rented a car and took a road trip down the coast to the Algarve, Portugal’s southernmost region. Known for its rugged cliffs, turquoise waters, and hidden beaches, Algarve’s beach hikes were incredible. I hiked through beautiful coastal trails, discovering secluded spots along the way, making it one of my favorite parts of my Portugal experience.
During my time in Lisbon, I didn’t have much client work, so I focused on a big personal project: building my HubSpot website theme: Generator. One day, inspired by the mega menu on Stripe’s website, I had the idea for the Mega Menu module.
I spent 24 hours straight developing it, and this feature became a major reason why HubSpot users love the generator. Creating this module in Lisbon was a breakthrough, and it’s still one of my most popular features.
After my stay with Outsite, I rented a beautiful penthouse in Chiado, one of Lisbon’s best neighborhoods. The apartment was on one of the city’s most scenic streets, offering amazing views and a perfect spot to end my Lisbon journey. I spent about two months here, getting to know the city even better and feeling like a true local.
Toward the end of my stay, my friends Peter and Kyle from Miami came to visit. We did all the classic tourist activities, including a trip to Sintra to see the castles. Exploring Sintra’s fairytale-like Pena Palace was incredible—the place is filled with vibrant colors, unique architecture, and views that look like something out of a dream.
Funny enough, during their visit, I introduced Peter to a girl I met at Outsite, and they clicked instantly. They’re still together today, which is a pretty awesome bonus from our Lisbon adventure.
The three of us then road-tripped up to Porto. This city is smaller and more laid-back than Lisbon, with a charming riverside area, historic architecture, and incredible food. We enjoyed exploring Porto’s cobbled streets, tasting the famous Port wine, and taking in the city’s unique character.
Lisbon left a lasting impression on me. Between the vibrant Outsite community, the city’s incredible architecture, nearby beaches, and all the adventures we packed into three months, I felt like I got a true taste of what it would be like to live there. Lisbon has all the elements of a fantastic digital nomad city—beautiful scenery, a buzzing social scene, and endless things to do. It’s no surprise I ended up exploring options for a digital nomad visa and even considered calling it home.