Home > Blog > How to Plan a Year-Long House Sitting Adventure
A year-long house sitting adventure does not require a detailed plan — it requires two anchor sits, a direction, and enough financial buffer to fill the gaps comfortably. Our year started with a Halloween party that ran too long, a moving-out deadline at 8am the next morning, and a single house sit booked in Italy. Everything since has been built around those two anchor sits and the freedom to move between them at our own pace. The van solves the gap problem. The long sits solve the burnout problem. The rest is surprisingly manageable.
I want to tell you how our year-long house sitting adventure actually started, because it does not match any planning guide I have ever read.
The night before Caro and I were due to move out of the Bochum apartment and into the VW T4 permanently, three things happened simultaneously. Caro had her farewell ceremony for the practical students whose exams had just concluded. We stayed too long at a Halloween party. I consumed a quantity of alcohol that did not simplify the events of the following morning. At 8am, the apartment owner was arriving to check the property and finalise the handover. We had not entirely finished moving out.
It was the most chaotic 24 hours of the entire adventure. Since then, everything has fallen into place.
This article is about how a year of house sitting actually gets planned. Not the colour-coded spreadsheet version, but the real version, based on 7 months of doing it across twenty sits and twelve countries via TrustedHouseSitters.
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The Anchor Sit Model
The research describes booking a long "anchor sit" first and building the year around it. This is the correct approach, and it is exactly how our year has worked. We just had two anchors rather than one.
The first anchor was Cortona, Italy. The house sit we drove toward directly after leaving Bochum. Italy in winter made geographic sense: heading south while northern Europe was cold. From Italy we had time. We kept exploring, applied for more sits, and in December applied for the six-month Portugal sit that became the second anchor. From that point, the five months between Italy and Portugal became a route we could design at our own pace, with a destination and a deadline.
Having an anchor sit does two things that change the quality of everything around it. It gives you a direction. A place you are working toward rather than simply moving through. And it gives you a time frame that is specific enough to plan against but generous enough to allow genuine spontaneity between now and then.
We arrived in Portugal with almost exactly one day to spare. The five months between Cortona and the Portugal sit covered Greece, the Balkans, the Dolomites, and the south of France. None of that was meticulously planned. It was possible because the anchor gave the whole period a shape.
The Gap Problem: What It Actually Costs
The longest gap we have had on this trip was approximately two months between Athens and Manosque. We used it to drive through Serbia, North Macedonia, the Balkans, the Dolomites, and down through southern France. We stayed in two Airbnbs. Roughly €240 for a week, which in the context of a European summer is truly affordable. The total for the three-month period including fuel, accommodation, food, and tours was approximately €4,000 for both of us.
That is still significantly cheaper than conventional tourism for the same distance and duration. But it is also the most expensive period of the trip. The sits cost almost nothing. The gaps cost real money.
The campervan changes this equation fundamentally. A van means no accommodation cost in the gaps, no advance booking required, and no arrival-time pressure. When a gap appears. Whether planned or unexpected. The van absorbs it. You continue moving, continue exploring, continue adjusting the route, and arrive at the next sit when the dates align.
For sitters without a van, the gap strategy needs to be explicit. Budget hostels, family visits, short-notice Airbnbs in cheaper cities, or simply scheduling a week somewhere affordable that you wanted to visit anyway. The gaps will come. The sitters who manage them well are the ones who planned for them in advance rather than improvising when they arrived. Our campervan travel between house sits guide covers the mechanics of the van-as-gap-solution in detail.
Visas: An EU Perspective and the Wider Reality
For Caro and me. German and Polish passports, EU freedom of movement. The visa question within Europe is essentially invisible. We move between Schengen countries without any of the 90/180-day calculation that occupies so much attention in digital nomad planning guides. This is a significant privilege and it is worth naming in truth.
For non-EU sitters, the Schengen 90-day rule is the most important planning constraint in Europe. Building an itinerary backwards from the visa limit. Not forwards from a wishlist. Is the correct approach. Leave every Schengen country with days to spare. Do not cut the limit close.
The broader insight that applies to everyone is this: house sitting within your own country or continent removes the visa question entirely, and the opportunities within a single continent are more than enough for a year. I regularly ask Caro how many of our friends and family have explored Europe or Australia to the depth we have. Most people spend their entire lives within a much smaller radius of their home than a year of continental house sitting covers. The privilege of exploring your own region thoroughly, without visa calculations, without long-haul flights, without the logistical weight of intercontinental travel, is underrated.
Our digital nomad visas and house sitting guide covers the specifics for non-EU sitters and the countries currently offering digital nomad visa programmes.
Burnout: What It Actually Looks Like
The research describes a burnout wall at around eight months of continuous travel. The experience I recognise from our trip is slightly different. It is not a wall so much as a gradual accumulation of readiness to stop.
By the time we reached Portugal, I was truly looking forward to not driving. After five months of changing environments regularly, meeting new animals in new homes, learning new routines, and constantly moving toward the next destination. I was ready for one place with its own rhythm. The campervan stacks the fatigue faster than house sitting alone because you are processing new environments constantly, not just occasionally.
The remedy is exactly what the research suggests: longer sits. Not longer in the sense of enduring more, but longer in the sense of actually settling. The first two weeks of any sit are still adjustment. By week three, something shifts. The routine becomes natural, the place starts to feel familiar, and the mental overhead of constant transition dissolves. Our slow travel article covers this transition in detail.
A six-month sit is the extreme version of this, and it is working exactly as I hoped it would. Knowing what the week looks like. Knowing when the chickens want lettuce. Knowing which coffee shop opens at eight. The predictability is not boring. It is the relief that makes everything else possible.
Planning a Year Without a Van
Not everyone who reads this has a campervan or wants one. The year-long adventure is entirely achievable without one. The adjustments to make:
Choose sits within closer geographic range of each other to minimise the cost and complexity of transit. A year spent in one country or one region is more manageable logistically and often more satisfying in terms of depth.
String shorter sits closer together at the beginning to build reviews quickly, then apply for the longer and more desirable sits that open up with a strong profile. Early in your house sitting journey, proximity and volume of sits matters more than location prestige. Our house sitting profile guide covers how to build the profile that makes the best sits accessible.
Build a financial gap buffer explicitly. Before the year starts, set aside €3,000-€5,000 specifically for gap periods, unexpected cancellations, and travel between sits. Treat this as a non-negotiable line item rather than emergency savings to avoid using.
Have a backup accommodation list for your key regions. A budget hostel, a reliable Airbnb, a family contact. The most stressful gap is one you did not see coming. Having the list prepared means the response to a cancellation is looking up the hostel, not panicking about where to sleep.
The Hardest Thing in Practice
If you are planning to work consistently while house sitting throughout the year. Remote work, a website, a project. The hardest single thing is protecting working time from the constant invitation to keep moving.
Travel interrupts work. Not dramatically, but consistently. A day of driving, a day of settling in, a day of exploring the new location, a day recovering from the previous three. These accumulate. On a short sit it does not matter. On a year-long adventure it matters a great deal.
The six-month Portugal sit has been the first period of the whole trip where I have truly worked for six to eight hours a day, most days. The sit provides the structure. The structure protects the time. The time produces the results. This is not something you can manufacture on a two-week sit or in a week-long gap between sits. It requires exactly the length of settled time that most house sitting planning guides treat as optional rather than essential.
If work matters to you, plan accordingly. Build in at least one sit of three months or longer. Everything shorter is travel. Three months is where work becomes truly possible alongside it. Our remote workers and house sitting guide and save $10,000 guide cover the financial and practical side of working while sitting.
The Year in Summary: What the Planning Actually Looks Like
| Phase | What we actually did |
|---|---|
| Before leaving | Booked one house sit in Italy. Had very loose plans beyond that. |
| Months 1 | Drove south to Italy via the most chaotic departure imaginable |
| Month 2-3 | Cortona Italy sit (Teddy and Lucca, Labradors, 10 days). Applied for Portugal in December. |
| Months 3-5 | Greece, Balkans, Dolomites, south of France. Filled with additional sits, Airbnbs, van camping. |
| Month 6 onward | Six-month Portugal sit. Settled. Working. Building. |
The planning philosophy: one anchor at a time, a direction to move toward, a van to absorb the gaps, and enough financial buffer to make the unexpected manageable rather than catastrophic.
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Frequently Asked Questions
How far in advance should I plan a year-long house sitting adventure?
Book your first anchor sit as far in advance as possible. Two to three months minimum for a desirable long sit. Everything else can be planned around it. A year of house sitting does not require a complete itinerary; it requires a direction, a first destination, and enough financial buffer to fill the gaps. Build the year forward from the anchor, not backward from an ideal.
How do you manage the gaps between house sits when you do not have a campervan?
Budget hostels, pre-identified cheap accommodation in desirable locations, and family or friend visits. The key is to plan for gaps explicitly before the year starts rather than improvising when they arrive. Set aside a dedicated gap fund of €3,000-€5,000 before leaving. Treat every gap as a trip within the trip, with a light budget and a low-pressure agenda.
How do you avoid burnout during a year-long house sitting adventure?
Prioritise longer sits over more sits. The burnout comes from constant adjustment. New house, new animals, new routine, new location, repeat. Three weeks in one place starts to resolve this. Three months largely eliminates it. The most experienced long-term sitters consistently report that one well-chosen three-month sit is more restorative than six two-week ones. Book at least one long sit per year and treat it as the anchor around which everything else rotates.
Can I work remotely while doing a year-long house sitting adventure?
Yes, but it requires deliberate planning. Short sits and frequent gaps interrupt work consistency in ways that add up quickly. To work effectively, you need a minimum of three months in one place, reliable WiFi confirmed before arrival, and a daily routine that protects working hours. The six-month Portugal sit is the first period where we have worked consistently at full capacity. Shorter sits are travel with work alongside. Three months or more is where the balance truly works.
