In 2021, I moved my home base to Miami, but after 18 months of living a fairly stationary life, the digital nomad itch came back strong. I packed everything into storage, gave up my apartment, and headed to Madeira, Portugal, to stay at Outsite for a month.
Why Madeira? The pictures looked amazing, it was a brand new Outsite location I hadn’t tried yet, and I’d heard a lot about the growing digital nomad community there. Plus, living on an island in the middle of the ocean sounded like a pretty epic way to spend a month.
Travel Dates: March 1 - April 1, 2023
Working on: Building an MVP for an email validation HubSpot app
I spent a month in Madeira, Portugal, staying at Outsite’s Ponta do Sol location, where I worked on a personal project while exploring the island’s stunning landscapes and vibrant digital nomad scene.
Where I stayed:
I stayed in Ponta do Sol, a quiet coastal town that’s becoming a hotspot for digital nomads. My base was at Outsite’s Madeira location, my favorite spot for remote work accommodations. Their space is right on the water, offering amazing views and quick access to the best of what the island has to offer.
The house was filled with a great group of fellow nomads, and we did a lot together—from hiking to deep conversations about the future of AI (especially with the launch of ChatGPT happening around that time). Staying at Outsite was a great experience, and if you’re looking for a place to work remotely, I highly recommend checking them out for accommodation.
What I did:
Ponta do Sol is a small, peaceful town—perfect for anyone looking to unplug and be immersed in nature. While there’s not much to do in town itself, that’s part of its charm. I spent a lot of time hanging out with other digital nomads, and we went on some of the most breathtaking hikes I’ve ever experienced. I also made it to the famous Purple Party, a techno party known across the island. And, of course, I worked on my HubSpot app project in between adventures.
Hiking:
Madeira is known for its world-class hiking. The island’s Levada trails, ancient irrigation paths, offer incredible routes through mountains, forests, and valleys. The views were unbeatable, from stunning waterfalls to panoramic ocean vistas. Each hike felt like a new adventure, and if you’re into hiking, Madeira should definitely be on your list.
Purple Party:
The Purple Party is a monthly techno party held in Ponta do Sol, and it’s a must-attend if you’re on the island. The energy, music, and ocean backdrop made for an unforgettable night. It’s a great way to experience local culture while connecting with both locals and other nomads.
What I was working on:
During this month, I didn’t have any client work on my plate, so I focused on a personal project—a HubSpot app I was developing. The app is a custom workflow extension that validates email addresses using a third-party service to reduce bounced emails, which can hurt your sender reputation.
Originally, I built this app for my own use, but I had plans to partner with NeverBounce (the email validation service) through their affiliate program. Unfortunately, they were acquired, and their affiliate program was canceled, which forced me to rethink the app’s future. I’m still deciding whether to keep it as a personal tool or release it for free to HubSpot users. While I’m not keen on turning it into a paid product, the process of building it has been incredibly rewarding, and I learned a ton about creating custom extensions for HubSpot.
Madeira exceeded all my expectations. It’s a small, remote island, but the digital nomad community is thriving. If you want to be surrounded by nature while still having a strong remote work community, Outsite in Ponta do Sol is a great option. For those who want more city life, Funchal—Madeira’s capital—is a larger hub with more activity and a growing nomad scene.
But if you’re like me and prefer peace, quiet, epic hikes, and ocean views, Ponta do Sol is where you want to be. Whether you're looking to get work done, meet other nomads, or just enjoy island life, it’s a great spot for remote workers.
