A Conference for Digital Nomads in Madeira
Nomad Island Fest
As the term suggests, digital nomads build their daily lives around digital work and frequent location changes. Their business connections happen mostly online; in-person meetings happen in accordance with their location at any point in time. Yet, they’re humans and as such, even digital nomads need human connections and real-life meetings. Conferences for digital nomads are a great way to achieve both. That’s what brought Charlie to Nomad Island Fest in Madeira.
The Nomad Escape
The Nomad Island Fest is organized by The Nomad Escape, a travel company dedicated to business retreats in different locations around the world. The founder Michelle Maree had a vision to combine business and travelling and facilitate both for digital nomads. She and her team are organizing several business retreats for 10-15 people throughout the year and there is at least one bigger annual event for a larger group of people that brings them together for networking, inspiration and alumni meetings.

Before Nomad Island Fest Charlie had already been to Madeira for a few weeks. She had stayed in a coliving in the mountains and participated in the smaller business retreat by The Nomad Escape, Level Up Club. The inspiration she got out of that week and the friendships that were formed allowed her to experience first-hand why the programme works and why the escapers keep on coming back for the bigger gathering every year.
Networking under the sun
Nomad Island Fest took place in Ponta do Sol in the south of Madeira. It is the sunniest place on the island and the venues are close to the beach. The participants stayed at the Estalagem hotel and most of the sessions and workshops were held there too. The bigger events took place at the John Dos Passos Cultural Centre in the auditorium. It was a 5-minute walk from the hotel to the centre.
The Estalagem is built on a rock overlooking the coastline and the town of Ponta do Sol. There is an elevator to bring guests up and down. There is a lot of open space which makes this hotel a wonderful place to sit under a palm tree, and enjoy views over the coast or the nearby valley and the mountains. There is an outdoor infinity pool and an indoor pool where windows allow for a view over the coast and down to the beach. From the rooms, you can either enjoy a view towards the blue sea or the green valley.
Because of the way the hotel is built on a high rock, you can see the sun rising in the morning and setting in the evening. What more could you possibly want for a relaxed networking atmosphere?
The Estalagem Hotel Ponta do Sol
Business in mind
Nomad Island Fest is about more than networking and meeting alumni. There are also talks and workshops to support personal and professional development.
Masterminds are there to present an idea or problem to a group of people to get their feedback or input in order to get closer to a solution. The talks cover a wide range of topics that are relevant for digital workers from tips for digital nomading to communication strategies, marketing tips and opportunities for passive income. There are interactive workshops for skill sharing, overcoming fears and blockers or developing business ideas.
To form stronger bonds beyond the usual networking and for potential business collaborations and friendships there are connection games. These involve some personal questions and experience sharing in entertaining ways.
Fun and socialising at Nomad Island Fest
The main focus is networking for digital nomads and part of getting to know people is having fun together. After the opening ceremony and speed networking on the first day, there are different activities every night after dinner.
The weekly party for digital nomads takes place at the Estalagem hotel and participants of the fest can equally benefit from it. There is a different DJ every week, the location is always the cliff deck next to the pool.
Morning workouts by the beach in Ponta do Sol & Jeep Safari/image 1: Julie Attallah
The business bingo is a different way of bingo where each participant can ask for help and the audience raises their numbers to offer help. Other nights during Nomad Island Fest are filled with stories about business failures and learnings or getting pampered in the spa. There is a theme party for the last night where the motto is: “dress to impress”. When Charlie attended Nomad Island Fest, the theme was Gatsby, and some beautiful dresses and gentlemen were to be seen.
There is one day without any talks or workshops, usually the Sunday, for an island exploration trip in Jeeps. When Charlie was there, the weather was unfortunately not on their side, and they couldn’t see much. Instead, they turned the music up in the back of the jeep and turned the safari into a party. Once back at the hotel, they warmed up with food by the fireplace and enjoyed the spa facilities. Charlie had spent that day with the same people that had been on the business retreat the week before and they decided for that rainy evening to revive the memories and created their own karaoke night at the hotel bar. More and more participants of the Nomad Island Fest joined, and they turned this night into even more memories of a nomad escape in Madeira.
images: charlieonthemove.com & Julie Attallah