I've had three before and all was fine as they were all trained to walk properly! However, I'm looking after a friends dog for the weekend and have just tried walking them and managed halfway up the street before giving up and chucking them all in the car!
My big dog walks like a dream, friends dog is a very big lad and pulls like a tank; I've looked after him before and managed as I only had one dog myself then and put one in each hand. I now have a small puppy as well who I'm still training, and who tends to freeze when large cars go past, plus is quite excitable (I agreed to dog sit months ago, before it got the pup, and had actually forgotten I'd said I'd have him this weekend!).
So... Do I put my dog plus excitable pup in one hand and large pully tank like dog in the other? Or excitable pup and large pully dog in the same hand alternating so as I don't end up with one arm longer than the other and my girl in the other? Or just take the cheats route and drive to the park for a couple of days preferring this option I think! ?
If they were all yours then I'd say you needed to work on training at least one of the puppy and the tank to walk to heel so you could have two heel-ing dogs on one side and work on training the one on the other side.
As it's only a weekend's dog sitting then get thee into the car and just get back to training your pup once your guest has gone home.
He's an odd one, this borrowed dog! His owners have had him for about a year now, and have tried everything to deal with the pulling; he's so much better than he was, but he seems to panic when his lead goes on. He's a rescue and there's a possibility he was used as a bait dog in the past and associates the lead with being attacked. Off lead, he's an absolute dream, has perfect recall and is fab with dogs. On lead, he's up on his back legs snarling if a dog comes within 50 yards, and pulls your arm out of the socket.
That's what I'm worried about tbh. Pup is doing so well, but give him an inch and he'll take a mile, and I don't want to let him get away with pratting about on the lead for a couple of days, as I'm just teaching him that's acceptable when it's not. He's only 15 weeks and is go good and so easy to train. He walks fab on the lead, providing I'm paying attention to him, apart from when large noisy vehicles go past, when he freezes then tries to run away. We're working on this and he's getting better, but I don't want all my hard work to be undone because I'm being towed along by another dog!
I'm going to just drive everywhere for a couple of days; my big dog and my friend's dog can just be let out to run, and I can spend a bit of time walking round the field with pup on a lead whilst they burn off some energy!