This gift of wine arrived 2 weeks after the sit ended… purportedly from the two dogs who miss us! What a lovely surprise.
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Always err the side of generosity.
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I have read many comments on this forum and realize there is a wide range of views. I’d like to say that if you can be generous to those around you - then do so. You will make the world a better place and your kindness is appreciated and always noticed.
Sitters often take on considerable expense/time for a sit and showing appreciation with a gift is a nice way to recognize that effort. As a former pet owner, I know how many hundreds of dollars you are saving by having a sitter stay at your home without paying them.
As a sitter, I always bring a handmade gift of pottery with a card to the HO as a thank you for staying in their home. It is a small gesture that is always appreciated when reciprocated.
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I think we are quite generous hosts but it’s easy to overdo things.
We always prepare a welcome basket with various items, voucher for a cafe or a grocery store, wine, sweets and whatever comes my way in the weeks before the sit.
Our last sitters gifted us with a voucher for a cafe and I think they felt obliged to give something back. So maybe I cut back a little, because there really is no need to give anything back.
A voucher for such an expensive restaurant would feel awkward in my opinion and some of our former sitters would not have used it. Of that I am very sure.
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I’m nowhere near as generous as the OP! But I do leave goodies. I also started to leave a little cash when when there was some repair work going on to the outside of my building and nearby ones as it caused slight inconvenience with the exits/entrances and some noise during office hours on weekdays. So the idea was sitters could use the cash to work from a nearby indoor public space or cafe if necessary and have some coffee money or chuck work and enjoy a museum or something. I’ve kept that up but a lesser amount in case there is any “inconvenience” like an elevator not working or something else beyond my control that might make the stay less fun. While I encourage sitters to spend the “fun money” whether or not something happens, some sitters leave it and I respect that choice too. I thought of offering a gift cert to a local gourmet shop/upscale bodega but they don’t do that!
I think this is why the sitters insisting that homeowners “should” pay their booking fees are so irksome to me. I work to make it a fair exchange, and would find an “ask” for perks insulting.
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I have very rarely even been left a bottle of wine (even at Christmas) so you are very generous. I think it’s entirely up to you what you would like to offer and feel comfortable with. I’m sure the sitters will be very appreciative. Thank you for your kindness
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I feel that way too. It’s a bit different when HOs treat me to dinner, either in their home or a restaurant, we share that and enjoy it together. If there’s a chance, I still try to somehow reciprocate.
For me, it’s the gesture that counts not the amount of money spent.
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It’s extreme, it’s amazing, it’s generous and very kind but most of all it’s probably considered very over the top American and out of proportion
Of course it would be appreciated but it would also make me very uncomfortable because it’s just not how THS works for me as a European
I’ve had pet owners leave me a goody basket, a bottle of wine or a delicious home made soup and it’s nice to feel appreciated
But I also did a 16 day sit over Christmas and New Year in Amsterdam and they left me an empty fridge and panty apart from a sip of milk and some spices
You win some you lose some but by setting such (well meant) high standards you might create expectations most people (both sitters & pet owners) can’t or don’t want to live up to 
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Well, other sitters and owners don’t need to know. As a sitter I have often made meals for returning hosts, mainly if we’ve had a good connection and they’re returning home late or very early after a long flight. I will usually ensure there is bread and milk for them also. I do ask them not to mention this in their review so future hosts won’t expect it!
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As a sitter, I never expect anything but am delighted when gifted wine, chocolates or dinner, home cooked or taken out by the host. As a home owner I usually leave a bottle or 2 of wine some chocolates for my sitters and a $50 voucher to the cafe in my building so my sitters can have a nice breakfast on their first morning (as I normally leave early for my flight).
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As a mature house sitter, I think taking them to dinner the night before is a wonderful idea for both of you. I suggest, and personally would find it helpful, if the HO would inquire as to what I might need for the first day or so. I’m talking 3 meals, but rather milk and sugar for coffee in the morning, eggs, coffee, tea or waffles or whatever they might eat. Or something for lunch and a couple of basics. I find sometimes, getting to the store before I go may not be possible or I have to put stuff in a cooler like milk and butter. knowing that this stuff was there would save me a bit. Usually trying to acclimate to the house and pet, I don’t like to run out the door and go to the store the first day. So something that you know they eat or drink for whatever their first meal might be. If you ask and they like chicken, then maybe a prepared chicken and makings for a salad. Or if they like burgers, some fresh ground beef and rolls and cheese. That type of thing. And then let them know what they can help themselves too. I think most people assume that it’s okay to use milk for coffee or sugar or butter or bread. Especially if it’s a long stay and it will go bad. But stating help yourself to xyz is helpful. That’s what I find very helpful as a sitter along with detailed instructions!
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I’ve been watching this topic as a Homeowner of 1 year and 6 sits in (all 5Star al around). As for SO many topics, this one widely varies in opinion as well. Personally, I dont have a budget. Instead, what we offer differs for every sitter. Here are examples of what we’ve done:
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took sitters grocery shopping
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tour them around the town
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took them to dinner
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let them stay in our free standing 1-bedroom casita extra days from the sit on either end
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picked them up at the bus station
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let one sitter borrow our car during sit (this is NOT something we regularly do, asked them not to mention it in review)
We offer nothing extravagant yet show appreciation. So my opinion on the actual question at hand is that a $250 certificate to a fancy restaurant seems REALLY over the top. And there’s the chance they wont use it and your money goes to waste. I’d say a certificate to the local grocery store is a much better option that would be used readily by any sitter. Youre clearly very generous to think of gifting such a pricey item, but seems out of place for THS.
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Thanks everyone! I think we’ve landed on the side of too extravagant. We don’t want to make them uncomfortable either, or give them a feeling that they have to reciprocate.
So we’ll do a home cooked meal the first night they are here (they are coming 3 days early to fill in gaps between sits), then the final evening before we depart we’ll order some simple takeout and invite them to join us. The rest of the time we’ll hand them the car keys and let them explore 
What I am going to do instead is get them one of those those cool Trader Joe’s mini totes (supposed to be restocked soon) as their ‘basket’, and leave sunscreen, moisturizer and foot balm (SoCal weather can be sunny but also sooo dry) and then a gift card to the local cafe we like, and a gas gift card too. Also a couple of metro passes if they want to go downtown. I think that’s all pretty reasonable for 3.5 weeks.
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@felinelover The gas card will surely come in handy with gas prices going through the roof! I’m in the LA area also and on the news this morning a gas station had a gallon of gas at over $8! I think they just wanted to get on the news, as it’s nowhere near that amount anywhere.
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Yep. Most definitely!!! We already have the most expensive gas so I think that will be way more useful to them!
I’m also leaving them my Costco card - they won’t be able to go in the store since they check photo IDs now, but the gas station is automated so they can use our membership for cheap(er) gas. We’ll also leave them with a full tank but tell them not to worry about doing so on return.
And also why the metro passes will come in handy
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I’ve found the wine tricky as sometimes sitters don’t want it, or it isn’t going to work for religioius/cultural reasons. So sometimes it’s something else. Maybe like chooses like, but I’ve been gifted wine on around 20-25% of the sits I do.
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I always ask about a week ahead if they drink, and any dietary restrictions.
If they don’t drink I just add a bit more on the gift card, but that’s easy enough to sort out.
Are you sure it’s Trusted Housesitters you are on @GoodHomeOwner? Certainly doesn’t sound like it 
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