I remember when I was expecting my second baby and I wondered how in the world I was going to shop with two? I mean, who do I get out of the van first? If the baby carseat is in the front of the cart, do I put the toddler in the back and just hope she doesn't poke holes in the hamburger? Or do I put the carseat in the back and toddler up front, leaving very little room for groceries? What do I do if both break out in tears and the entire shopping trip turns into a nightmare? Well, I learned a few tricks very quickly, and it soon became a breeze.
1) Park right next to a cart return. You've got a cart right there at your immediate disposal and you won't have to leave the cart uncorraled afterward. (Yes, I am one of those that does not always put the cart away. If I can't prak within one vehicle's depth from the cart return when I have my kids with me, I just push it in the four corners of the parking spots. I will not leave my kids in the van while I walk half a parking lot away just to return a cart. My kids' safety is that important to me.)
2) Go with your entire shopping trip planned to the T. This eliminates the need to think, which we all know is impossible in the presence of babies and toddlers and preschoolers.
3) Don't stress the small stuff. So you don't normal give your kids snacks right before dinner, but if that's when you're shopping, let them eat. It will keep them busy and avoid the "I'm hungry" meltdown.
4) DO NOT take them out during naptime or near bedtime. It's not worth it. THE END.
I only shopped with three a few times. My wonderful, spendiferous mother in law began to come once a week to babysit while I ran errands. With the addition of the fourth child and the aquirement of a new job, requiring my husband to travel further, we now have two vehicles. This has given me the opportunity to take the kids out during the week (instead of their only outing being church on Sunday). So sometimes, while out, I swing by a store or two to grab a few things. I found right away that shopping with four is really a stenuous feat. I mean, just the logistics of gettig everyone through the store in a timely manner without returning home minus a kid and plus several items I never knew were in the cart... just overwhelming to think about.
Here are two items I have found that greatly reduce the stress and increase the enjoyability.
1) The giant brand spankin' new (at our store anyway) Walmart shopping carts with a bench for two kids in front and the normal kid seat and a regular sized basket in back. (I tried in vain to find a picture. Might have to take one myself.)
2) A sling from sevenslings.com. (BTW, I hear you can get a free sling from them by entering "babies" at checkout. I haven't checked that out though. You will have to pay shipping, which is overpriced at around $11.75ish)
A combination of these two wonders allows me to have NO kids walking or running away or lagging behind. I put C and D on the cart bench, E in the kid cart seat, and wear F in the sling. Love it! I can then walk my own pace, grab what I need quickly and let the baby sleep on my shoulder, instead of fuss in her car seat and I have the entire full size basket to fill with the required groceries. Now if I could just find a way to tie E's legs to the cart, so he'll stop kicking C and D.