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WWYD ?
So We?re going to Napa on Saturday night, and Winston can?t come. We?re leaving Saturday afternoon and returning Sunday after we have brunch. We have a couple options.
My mom can watch Winston. The problem is that she 2 hours away . She is actually in town for a Dr. appointment and could pick him up today from day care and take him with her, but I don?t know when I?ll have time to get back and get him (maybe not until next weekend, or I?ll have to drive an hour in traffic after work at some point next week to meet her half way and pick him up) OR wait for my mom to return for another appointment for her broken wrist NEXT Thrusday or Friday. My main issue with this is that he has to be away for extra time. L I will miss the furry puppy face if he?s gone for 4- 5 days he doesn?t really need to be gone for. I mean, especially since we?re not even leaving until Saturday afternoon and will be back Sunday afternoon, seems silly to send him away on Wensday afternoon and not pick him up until possible Monday evening or something, but I just can?t see 1: asking my mom to bring him back Sunday, or 2) driving out to her after coming back from Napa on Sunday.
We can also Board him. We love and completely trust our day care/boarding place and he loves it there, although he?s never spent the night yet (only day care) The main issue with this is it?s $$.... what would you do ? 
Re: WWYD ?
If it were me...
I would have mom pick him up at daycare today, then I would plan to pick him up asap the next week after work, battling the crappy traffic (maybe C could ride with you to make it a less miserable car ride/bonding time??), and if you just didn't have the chance and it was completely impossible to make it to your moms before next week, get him back next week. I KNOW it's hard for you to be away extra time, but think of 1) how fun it'll be for W...time with grandma!, 2) how fun it'll be for mom...time with grandpup!, 3) money you'll save, of course, and 4) how much more peace of mind you'll have knowing he's with your mom.
Personally, I think even when you love your boarding place/daycare (as I love our daycare, and would surely love a boarding place, if I had to choose one...we haven't had to do that yet...), it's still a little stressful wondering how your pup is doing overnight in a new environment. I think you'll enjoy your trip more if he's safe and sound with your mom.
AND, even though you'll miss him, you might kind of enjoy the peace and tranquility of a couple days home with the hubs and kitty just the three of you again, no? Knowing he's safe and happy and content with grandma...?
That's WIWD.
GL with whatever you decide!
I honestly would try out the boarding place. Its always good to have a place you can board your dog (even if its a backup plan). Since its only one night, its a great opportunity to try out this place and you will be back before Winston knows it.
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