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Does he take a pacifier? That sometimes helped my first LO. Unfortunately, it just was bad until we switched him to a convertible seat, and then he was better, but still didn't really like it unless someone was sitting back there with him.

Is it possible to schedule the car rides around naptime?

Ds hated his car seat. Like wailed the entire ride anywhere we went. People told me that he just didn't like being away from me but the cry was a painful cry. I knew it was something more. Especially because he would cry even if someone was in the back with him. I eventually took him to a chiropractor for cranial sacral therapy. Within two visits it was like I had a new baby in the car. Granted he's still a bit fussy here and there but compared to how he was before, night and day!

We just started going through this last week with my 4.5 month old. Like screaming so much he couldn't breathe for our entire 30 minute commute. I was stopping at least twice each way because I could not take it. My coworker suggested dipping his binky in gripe water and it was seriously magic. Falls asleep almost instantly for the whole ride. Every.single.time.

Not to show how dumb I am, but is the infant/newborn insert out of your carseat? I forgot to take mine out well after DS reached 8 pounds and he was much better in it once I removed it. He still didn't LOVE it and he's much happier in his convertible carseat - he's always preferred to be upright - but that insert pissed him off so hard. Also, do you have a sunshade? DS still gets flippin' angry if the sun is in his eye.

It took us awhile -- well past six months -- to switch to our convertible seat, but our son was much happier when we finally did. It might be worth the experiment to try one and see if it helps. We only drive on the weekends so it was not as big of a deal for us.

with LO1, nothing made him like the carseat. it took a long, long time for him to grow out of it. it was painful.

although one thing we didn't try with him was one of those toys that you hang from the handle--we do that for LO2 and i think it helps. it's a little hippo that makes a light chiming noise when it moves. of course there are a ton of hanging toys out there, but i think the sound of this one kinda soothed or interested him enough to make him stop crying.

@DesertDreams88: ugh, I'm so sorry! It's so stressful to hear the baby wail & not be able to help Especially since he'll be in the car every day. I don't know if you remember but C hates driving in the car too. Right at 2 months was the worst!! She's almost 12 weeks now & it's getting a little better. I'm hoping she'll grow out of it soon. Here's what's been helping us:
-timing. I know the sitter's got a set schedule, so maybe she can help with this. If C is tired but not asleep, it's the worst because the stop & go wakes her up/won't let her fall asleep. We shoot for wide awake or rocking her in the seat at home so she's asleep when we put her in the car.
-waiting after a feeding to strap her in. If she hasn't burp/spit up then it gets stuck & she's miserable.
-using as loose of strap as is safe.
-dealing with her food sensitivities. Since eliminating dairy, she's been happier in general & car rides are better.

We also use a soft hanging toy. It'll only be for a few short weeks and then you can limit trips if you need to!