Seeking advice for scheduling back to back

Any strategies you have for scheduling consecutive sits? I see so many sits I’m interested in but locations and timeframes vary so much I don’t know where to start. For those of you with lots of experience I would love for tips!!

Welcome @corinbarnett

Are there particular locations that you want to visit ? Is this a permanent thing ( so you will be booking up sits for the whole year ) or a long trip so you will be booking up consecutive sits over a specific number of months ?

If this is something that you plan to do all year round and location is not important to you I suggest that you look for the long sits first ( 3 week - 3 month sits ) apply for these and after these have been confirmed and later fill in the smaller gaps .

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This is a great suggestion. I am doing this as a way to explore the country for at least the next 6-9 months. I’ve been focused on cities within the EST and CT time zones and warm climates. So I have a few cities in my favorites, etc. I am looking for 2+ weeks at a minimum but one month I agree would be ideal

We sit full time, it took us a few months at the start to figure it out, so to keep it simple we do two things.

  1. Book a pet sit in and find out the owners approx return time (and add another couple of hours just in case they are delayed), and then the one that follows is the one that needs to be flexible, so with the owners of the one that follows, we would say at the point of applying that we wouldn’t be able to get there until 5pm or whatever time, and it either works with the owner or not. If it doesn’t, then it’s not the right sit. Most owners have a back up plan that can pop in for just 1 feed, or 1 toilet-break, and it’s never been a problem for us if it’s cats. We ‘sell’ ourselves first in our message, and put the time thing at the end.
    It helps if you book your sits in date order, so that it’s always the one that follows that has to slot in correctly. But obviously, if there’s a particularly attractive sit that knocks that out-of-kilter slightly, then so be it.

  2. Now, we’re 2 years in, and we have a lot more 3 week to 6 week sits, so typically we will just book into a cheap hotel for 1 night in between, because it’s nice to have a “night-off”.
    As you’ve already figured, longer sits are great if you are doing it full-time (even for 6-9 months), no extra travelling costs, no extra cleaning-days, no extra packing & unpacking of cases.
    Also, if you’re planning on doing the same each year, and want to return to the same locations, then if the owners are happy after you sit, let them know you’ll be returning to the area and when, because what we have found is that a lot of owners that booked us for 2 weeks initially, booked us for even longer when we returned. It’s happened with just 4 owners over the last year alone, and they extended their second vacations to between 3 to 6 weeks, which is brilliant, because we already know their pets and their location, so it’s a brilliantly different type of stay.

Also, keep in mind, you don’t need many owners to fill up your diary when you sit for longer, so if you feel sits with the dates you need aren’t appearing, remember it only takes one sit to sometimes to fill up a whole month, so don’t be too eager to fill your diary with dates that don’t run fluidly, hold out for a sit that starts within a day of the date you want, because there’ll be plenty, that’s how we only typically stay 1 night in a hotel at the most.

Hope that helps

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@HappyDeb fantastic advice.
We echo the ‘it’s nice to have a night off’ between sits. And also: ‘don’t be too eager to book in advance if it doesn’t quite fit’ sentiment. Something will come up, don’t force it, be patient.

One last thing: once you committed to a sit - stop looking at other sits for the same dates!! Why? Because you might see a better fitting sit come along and consider cancelling. Never do this. Once you commit, stick to your plan.

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You can also look for sits with no pets. Ive seen a few that want a sitter for 3 months to keep their garden and flowers taken care of .

My husband and I are full-time sitters from the US and booking back to back sits has been very easy for us and in our last several stints back home, we have rarely had to pay for a hotel in between. But we are open to a range of areas and have our own car. Not sure if your interest in city sits is just because you prefer urban areas–but would be open to other places as well-- or because you can only visit areas that you can reach/get around in by public transport. If the latter, that could narrow options.

We are originally from NJ and the bulk of ours have been on the East Coast ranging from New England to down south–though we have never sat in Florida yet.

The broader your criteria the easier it is to book sits. You mention warm climates and given that it is already April and will be warm pretty much everywhere for at least the next several months, you have lots of places open to you, especially since summer is a peak travel time–there will be way more sits than sitters actively seeking them.

But if you are only interested in very specific cities or regions that could narrow your options somewhat.

If it is important to minimize gaps in your schedule, you want to resist the urge to book sits strictly out of fear you won’t find something, thereby potentially leaving gaps in your schedule you may have difficulty filling later on. Filling larger gaps is often easier than filling smaller ones of only a few days, especially since you will be limited to an area near the sit on either end or somewhere in between depending on the distance.

Another thing to consider is whether you are strictly interested in only staying in areas with high touristic appeal, or you are open to different types of places. When my husband and I are sitting in the US, this isn’t as important to us as if we were traveling internationally. We often gravitate towards more suburban or rural locations rather than urban areas so loads of options.

I know you mentioned cities --not all US cities are created equal as far as popularity goes. How easy it will be to secure back to back sits in cities specifically will depend on whether you are open to different urban areas or only have very particular cities in mind. It will depend if you are interested in staying in areas close to cities as well or just directly in a city itself.

When looking to book sits back to back it is really important to discuss departure and arrival times with hosts prior to confirming. This is especially important with departure times–a sitter should not just assume they can leave any time on the day the sit ends. Depending on the host’s arrival time and the needs of the animal, they may prefer you stay until X time.

If we have already booked a sit that starts the day one we are currently applying to ends and we already know what time we need to leave, we always put that in our application message so they can know right away if that would work for them.

If we are applying to a sit that starts the same day a currently booked one ends, we let them know when is the earliest we would be able to arrive right in the application message so again they can know right away if this would work for them.

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@corinbarnett, we are full-time sitters.
First, our encouragement is to relax and apply for housesits. Application is non-committal and often listed dates are inaccurate or flexible. Initially we spent significant time on due diligence before applying for housesits. But popular housesits are taken quickly. And Pet Parents may request that housesitter arrive one day (or more) before listed start date and/or stay one day (or more) after listed end date. We now apply a quick-and-dirty filter to applications and a more critical eye after video call. Given experience we’re getting better but we’re totally ok with withdrawing application after video call (say if there is an expectation gap or surprising disclosure).
Secondly, like @HappyDeb then we sometimes have to bridge a day or two gap with paid accommodation. It happens. Unavoidable.
Third, backup plan and sit cancellation insurance helps. We now realize that cancellations happen. Two Pet Parents cancelled on us at last minute on international housesits. Each had their reasons. In one instance THS Sit Cancellation Insurance applied (other was ineligible). But that insurance was helpful and reduced financial impact. Perhaps less important if you intent to housesit close to home-base but that’s not our situation.
Finally, periodically take a break. We’ve been housesitting for two years. Bonkers really. But we enjoyed a break over winter. Multi-month housesit without pets, although we did help some friends. We may to do the same in Q4 2025 or Q1 2026. Good to recharge.
Good luck!

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