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Europe's Best Warm Autumn Escapes
There’s something rather appealing about the idea of not just going away this autumn, but actually living somewhere else for a while.
You don’t necessarily need to quit your job, become a full-time digital nomad or pack up your entire life.
Maybe you work remotely and fancy a change of scenery. Maybe you’re between homes. Maybe you’re house sitting your way around Europe. Or perhaps you simply want to find out what it feels like to wake up somewhere completely different for a few weeks.
And autumn (or 'fall' for some) is a particularly good time to do it.
The summer crowds have gone, temperatures are generally more comfortable, and there are still plenty of places where you can find sunshine without travelling halfway around the world.
So this week, we’ve picked five warm European escapes we’d consider for a longer autumn stay - not just somewhere to tick off during a long weekend.
1) Madeira, Portugal 💛
If your idea of an autumn escape involves dramatic coastlines, mountain walks, swimming spots and plenty of outdoor life, Madeira is hard to beat.
It’s particularly appealing if you want somewhere that gives you lots to do without needing a packed itinerary. You can have a slower morning, get some work done, then head out for a levada walk or explore another corner of the island.
Why stay longer? Because Madeira rewards slow travel. A few weeks gives you time to experience more than the obvious highlights - and to work out which part of the island you’d actually choose to live in.
2) The Algarve, Portugal 💛
The Algarve is an easy one to overlook if you’ve only experienced it as a summer holiday destination.
But autumn changes the proposition.
The beaches are quieter, the pace is slower and there’s plenty more to explore beyond the big resort towns, from small villages and coastal walks to local restaurants and inland countryside.
Why stay longer? It’s a good option if you want the combination of European lifestyle + sunshine + relatively easy access to everyday amenities, rather than feeling like you’re permanently on holiday.
And for anyone working remotely or house sitting, that distinction matters.
3) Sicily, Italy 💛
Sicily is one for anyone who thinks a good trip should involve excellent food, beautiful places and a little bit of chaos.
Autumn is a lovely time to experience the island without the intensity of peak summer. You can explore historic towns, eat extremely well, swim when the weather allows and spend considerably more time simply wandering.
Why stay longer? Because Sicily isn’t somewhere I’d want to rush.
A longer stay lets you choose a base and really get to know the area which is exactly the kind of travel we love!
4) The Canary Islands, Spain 💛
If the main objective is simply:
“I want some SUN.”
…the Canary Islands deserve a look.
Tenerife, Gran Canaria, Lanzarote and Fuerteventura all offer something slightly different, so it’s worth thinking about the type of lifestyle you want rather than treating the islands as interchangeable.
Why stay longer? They’re particularly interesting for remote workers and digital nomads because you can combine a relatively normal working week with beaches, hiking, outdoor activities and that very welcome feeling of not needing a coat.
And yes, they’re also a great place to look for a house sit if you’d rather experience island life with four paws involved.
5. Malta 💛
Small, sunny and packed with history, Malta is an interesting choice if you want Mediterranean living without feeling completely cut off from city life.
You can spend a morning exploring Valletta, find a swimming spot in the afternoon and still have dinner somewhere completely different that evening.
Why stay longer? Its compact size makes it easier to explore while maintaining a routine, useful if you’re working remotely or have other commitments alongside your travels.
It’s also the kind of place where a few weeks can tell you much more than a traditional holiday ever could.
The Freedom List way to travel
The common thread between all five isn’t simply that they’re warm.
It’s that you don’t have to experience them as a tourist.
You could house sit.
You could work remotely.
You could rent somewhere for a month.
You could combine a few weeks of travel with a longer-term plan to see whether somewhere actually feels like your kind of place.
Because sometimes the best way to discover where you want to go next isn’t to visit for four days.
It’s to live there for a little while.
🎥YouTube Pick
House Sitting in France
And talking of experiencing somewhere rather than simply passing through...
This week on the vlog, head to France with us for a beautiful house-sitting adventure.
If you're dreaming about an autumn escape, this one should put you in the mood: beautiful scenery, slower days, four-legged company and the chance to experience France at a very different pace from a conventional holiday.
It's a reminder of one of our favourite things about house sitting: sometimes the opportunity to stay somewhere beautiful comes with a rather wonderful added bonus - you get to live like a local for a while.
This Week's Remote Jobs
Here are 7 newly advertised part-time or contract remote creative, comms and education roles you can do from anywhere:
– Marketing & Events Manager – Singapore
Plan and deliver marketing campaigns and events, helping to build brand awareness and engage customers or audiences.
– Content Writer – UK
Create clear, engaging written content for websites, campaigns, blogs or other digital marketing channels.
– Senior Marketing Technology Project Manager – USA
Lead marketing technology projects, coordinating teams, systems and timelines to deliver digital marketing initiatives.
– Video Editor – Mexico (and more)
Edit and produce engaging video content for digital platforms, turning raw footage into polished, audience-ready videos.
– Whitepaper Writer – Singapore
Research and write in-depth whitepapers that turn complex ideas or industry knowledge into clear, authoritative content.
– Senior English Teacher – Australia
Deliver engaging English lessons online, supporting students to develop their language skills through virtual teaching.
– Virtual Teacher – USA
Teach and support students remotely, creating engaging online learning experiences from wherever you are.
That's it for this week. Happy travels, Sarah & Cooper :)
