Outsite Madeira Review: My First Co-living Experience in Ponta do Sol

Madeira already had a special place in my heart before this trip. I'd been before as a holidaymaker and loved it, so when the chance came up to go back and stay at Outsite Madeira, I was in. But this time was different. This time I was going as a working nomad, staying at their Ponta Do Sol location, and I genuinely had no idea how much that would change the whole experience.

If you're the kind of person who wants to take your work on the road but you're not quite sure how to make it feel like more than just working from a hotel room, this one's for you.

What is Outsite and why did I go?

If you haven't come across Outsite before, the short version is this: they create co-living spaces in beautiful locations around the world, designed specifically for people who work remotely. Not hostels, not hotels, something in between that somehow manages to feel better than both.

Madeira has been on the radar as a digital nomad destination for a while now, and coliving Ponta do Sol has become its own thing entirely — the village has quietly positioned itself as the nomad hub of the island. When I heard Outsite had a location right there, it felt like the right time to go back to an island I already loved and see it through a completely different lens.

If you want to look into Outsite for yourself, you can explore locations and availability [here].

The space

Worth mentioning upfront: this particular Outsite Madeira location used to be a hotel, so it has more of a hotel feel than the house-style setup you'll find at some other locations. I actually really liked it, but it's worth knowing going in if you're expecting that cosy shared-house atmosphere.

The rooms are a dream. Spacious, full of natural light, with a bathroom that didn't feel like an afterthought. But the thing that got me, the thing that several of us kept coming back to, was the ocean view. Every single room has it. I'm talking lying in bed watching the sun go down over the water. A few people mentioned falling asleep with their balcony doors open just to hear the waves, what a dream.

Each room also has a proper desk and a large wardrobe, which matters more than you'd think if you're staying for longer than a few days. Having a quiet space for calls away from the communal area makes a real difference when you're actually trying to work.

Speaking of which, the co-working space is bright, relaxed, and genuinely easy to work in. It flows naturally into the communal kitchen and living area, so you can go from focused work to a chat with whoever's around without it feeling like a big shift. The wifi was solid, the seating was comfortable, and I never once found myself scrambling for a spot.

The community

This is honestly the bit I wasn't fully prepared for and it ended up being the highlight of the whole trip.

Every Outsite has a WhatsApp group for current residents, and it sounds like a small thing but it completely changes how easy it is to actually connect with people. No awkward hovering in communal areas trying to work out if someone wants to chat. You just send a message saying you fancy dinner or a hike, and people show up. It removes all the friction.

The community at this particular location was something a few of the longer-stay guests mentioned unprompted. Several people who had stayed at multiple Outsites said this one was one of the best they'd experienced. A lot of that credit goes to Elisa, the community manager, who is genuinely lovely and clearly puts real effort into making things happen.

During my stay there were hikes, dinners out, a workshop, beach workouts, dog walking at the local shelter, and Purple Friday, which is exactly what it sounds like and very much worth experiencing. The mix of people was great too. Everyone was there for similar reasons, which meant conversation came easily and plans came together quickly.

It is worth knowing that community quality can vary between locations. A smaller Outsite with six rooms is naturally going to have a different energy to a bigger one. This one had a really good mix of people while I was there, but it's not guaranteed everywhere, so it's worth reading recent reviews before you book.

Ponta Do Sol and getting around

Ponta Do Sol is a beautiful, sleepy little village carved into the mountains with ocean views around every corner. As digital nomad Madeira destinations go, it's one of the most well set up. There's a free coworking space courtesy of the Digital Nomad Village initiative, small cafes, a beautiful local hike, the famous waterfall on the road, and a relaxed pace that makes it genuinely easy to settle into a working rhythm. What it doesn't have is a whole lot going on beyond that, and that came up regularly in conversation among the guests.

If you're staying for a few nights like I did, it's perfect. But if you're planning a longer stay, almost everyone I spoke to who had been there a while wished they had a car. Public transport is limited and taxis add up quickly, so without wheels you can start to feel a bit isolated, especially if you want to explore the rest of the island. Funchal is close enough to visit but not close enough to nip to on a whim without transport.

My honest advice: budget for a hire car, or put a message in the WhatsApp group when you arrive and see if anyone wants to split one. It genuinely opens the whole island up.

The experiences that stuck with me

Three nights isn't long, but I left with more than I expected.

Meeting so many good people in such a short time. The WhatsApp group made it easy from day one and I ended up spending most evenings with people I'd only just met, which doesn't usually happen to me.

The sunset at Pico do Facho. Worth every step.

A Mexican dinner cooked by other guests in the communal kitchen, which turned into one of those long evenings that you don't plan but end up being the ones you talk about.

Walking the dogs at the local shelter. Someone mentioned it in the group and a bunch of us went. Do it.

And ending Purple Friday sharing samosas in the kitchen at some ridiculous hour with people who had been strangers forty eight hours earlier.

Would I go back?

Yes, yes, yes. I’m already thinking of a month over winter. And I'd recommend it to anyone who works for themselves and wants to experience what it actually feels like to be somewhere, not just visit it. There's a difference between travelling and building a temporary life somewhere, even for just a few days, and Outsite makes that second thing genuinely accessible.

If you're a solo founder, a freelancer, or a remote worker who's been curious about coliving Ponta do Sol or co-living more broadly, this is a solid place to start.

Take a look at Outsite locations and find one that works for you [here]

[Note: The links provided are affiliate links. We only ever recommend with companies we use or plan to use]