I Need to Pick My Next Outsite Coliving. Help Me Decide.
If you've been following along, you'll know I recently stayed at Outsite in Ponta Do Sol, Madeira, and it genuinely changed how I think about travelling while running a business. The community, the space, the feeling of being somewhere properly rather than just passing through. I came home already thinking about where next.
The problem is I now have four Outsite coliving locations on my list and I genuinely cannot decide. So instead of going back and forth in my head about it, I'm doing what I always do when I'm stuck — ask you guys as I know you’ll give me some sweet reccs and opinions. Here's where I'm at, what I know about each one, and where my head is landing. I'd love to know what you think.
If any of this has you thinking about your own trip, you can explore all Outsite coliving locations [here].
First, what is Outsite?
If you haven't come across Outsite before, here's the quick version. They create co-living spaces for digital nomads and remote workers in some great locations around the world. Think private rooms, fast wifi, communal workspaces, and a built-in community of people who are all there for similar reasons. Not a hostel, not a hotel, but something that somehow manages to feel better than both.
Every Outsite coliving has a community manager and a WhatsApp group for current residents, which sounds like a small thing but completely changes how easy it is to actually connect with people. No awkward hovering in communal spaces. You just send a message and people show up.
I stayed at their Madeira location earlier this year and it was one of the best trips I've had in a long time. If you want the full breakdown you can read that [here]. But the short version is: I'm hooked, and now I'm planning the next one.
The four at the top of my list
Let’s be honest, I want to check them all out. But I’ve pulled a short list of…Marrakesh, Morocco. Ericeira, Portugal. Sagres, Portugal. Santa Teresa, Costa Rica.
Four very different vibes, four different trips. Here's a breakdown of each (incase you also want some travel inspo).
Outsite Coliving Marrakesh, Morocco
The Outsite coliving in Marrakesh is a traditional riad right in the heart of the Medina. Twenty rooms, a rooftop terrace with views over the Koutoubia mosque, a hammam, a pool, and a communal workspace. On paper it sounds incredible. In reality, the Medina could be loud, slightly chaotic, and full-on in a way that most coliving destinations aren't.
Although it’s not the sleepy surf town I’m craving, it does excite me.
The thing that gives me pause is the mid-workday culture shock factor. Marrakesh is not somewhere you can nip out for a quiet coffee and a think. It's immersive in a way that needs the right headspace and probably the right amount of time. A few days feels like it might not be enough, too long feels like a big commitment.
It's still very much on the list, but it probably needs its own trip (& then visiting some coastal spots) rather than being squeezed into a spare week.
Outsite Coliving Ericeira, Portugal
Ericeira keeps pulling me back and I think it's because it feels like the easiest yes on the list.
Portugal's first World Surfing Reserve (I can’t surf, but love to watch the surf all day), a growing remote work scene, great food, beautiful coastline, and close enough to Lisbon that getting there is genuinely straightforward. Outsite actually has two options here which is worth knowing about.
Outsite Ericeira Centro is the classic coliving setup, right in the heart of town, close to the surf spots and the cafes and everything that makes Ericeira what it is. Then there's Outsite Ericeira Praia do Sul, which is a collection of four modern villas above the Atlantic, each with sea views and a private infinity pool. Same community feel, noticeably different setting.
The villa option is the one I keep coming back to if I'm honest. There's something about the idea of working with an Atlantic view and jumping in a pool at the end of the day that feels like exactly the kind of reset I need. Familiar enough to be low-stress, beautiful enough to feel like you've actually gone somewhere.
For a few days or a week, this feels like the sweet spot.
(All images are taken from Outsite)
Outsite Coliving Sagres, Algarve
Sagres is the one that surprises people when I mention it, because most people associate the Algarve with busy beaches and holiday crowds. Sagres is the complete opposite of that.
It sits at the southwestern tip of Europe, which already tells you something about the vibe. It's quiet, dramatic, the kind of place where you can actually hear yourself think. The Outsite coliving there has a rooftop, an outdoor pool, and is walking distance to three beaches and everything you need day to day. Several people who stayed mentioned they kept extending their trips, which is always a good sign.
The surf culture is strong here too, which suits the kind of people drawn to a more off-grid coliving experience. It's not a party destination, it's not a city break. It's somewhere you go when you want to genuinely slow down, do good work, and spend your evenings watching the sun drop into the Atlantic.
The honest caveat is that it's small and quiet, and depending on what you need from a trip, that's either exactly the point or a reason to think twice.
For me right now it feels like a strong contender for that first shorter trip.
(All images are taken from Outsite)
Outsite Coliving Santa Teresa, Costa Rica
And then there's this one. The one that lives in a completely different category to the others (kind of).
Santa Teresa is jungle, ocean, outdoor pools, open-air co-working spaces, natural wood finishes, and a pace of life that I suspect ruins you for normal existence. Outsite has two properties there, both with that lush, relaxed, tucked-into-nature feel that you simply cannot replicate in Europe.
This is the trip that needs proper time. A week feels like you'd barely scratch the surface. This is the one you go to for a month (or more), properly settle in, find your rhythm, and come back fully reset. Or at least that's what I'm telling myself.
The distance is obviously a factor. It's not a spare week decision, it's a commitment. But for that reason it also feels like the most exciting thing on the list, the one that would genuinely shift something.
I'm not ready to book it yet. But it's sitting at the top of the longer trip list without much competition.
Check it out here 🔗
(All images are taken from Outsite)
Where my head is at
Here's how I'm actually thinking about it.
Sagres and Ericeira are the ones I'm looking at first. Both feel doable for a few days or a week, both are easy to get to, and both would give me a proper sense of how different Outsite coliving locations compare. If Madeira taught me anything it's that community can vary a lot depending on where you are, and I want to explore a bit more before committing to a longer stint somewhere.
Then Costa Rica is the bigger trip. The one I'm building towards. The one that needs a proper window of time and the right moment to just go for it.
Marrakesh I'm holding onto separately. It feels like it deserves its own adventure rather than being compared to a quick trip to Portugal, and I want to go with the right headspace rather than squeezing it in.
So that's where I am. Genuinely undecided between Sagres and Ericeira for the first trip, and very decided that Costa Rica is happening at some point this year.
I’d love to hear your thoughts/reccs/experiences…
If you've stayed at any of these Outsite coliving locations, or if you've spent time working remotely in any of these places, I really want to know what you think. Have a strong opinion on Sagres vs Ericeira? Think I'm sleeping on Marrakesh? Been to Santa Teresa and want to convince me to just book it already?
Come and tell me over in The New Kind community. This is exactly the kind of decision that's better made with people who actually get this lifestyle, and I'd love to hear from anyone who's been.
And if any of this has got you thinking about your own trip, explore Outsite coliving locations [here] and see what pulls you.