I don't have much experience in this area. From the few trips we've taken, the greatest piece of advice I have for traveling with a baby is this:
DON'T. Just… don't.
Ok, so that's not always practical. Life presents several situations that require us to travel. We've taken a few day trips here and there - once to Salinas for Christmas, again for my Grandma's funeral, a couple times to my parents' place in Pine Grove, and once to San Francisco to a Giants Game (Reese's first!). We took one overnight trip to Tahoe for my sister's wedding and a 5 day trip to Las Vegas when Justin's father passed away this last summer. That's about it in Reese's 10 months of life so far.
All these trips have been STRESSFUL. Some of that's probably just a product of my personality and my baby's personality.
I always overpack and then I can't find what I'm looking for at the moment. Babies need so much. Clothes, food, diapers, wipes, bibs, medicine, toys, stroller, etc. Every inch of the car is jam packed with Reese's personal effects.
But it just seems like no matter how much I pack, write out lists, schedules, etc, I always forget something. And it's always something important. Because everything is important with babies.
Staying overnight somewhere new with a baby is challenging at best. Babies thrive on routine and familiarity. New places mean many new sights and sounds. Baby's routine is completely thrown off. Mama's routine is completely thrown off. It's a recipe for disaster.
I seriously almost snapped in Vegas trying to meet all of Reese's needs, monitor him constantly, keep him quiet enough not to disturb other hotel occupants, and be strong for Justin as he watched his father slip away. I didn't have a break from the baby for 5 days and I was incredibly sleep deprived. No one offered to help out even once. And by no one I mean Justin and Justin's mom. I don't fault them for this. They were dealing with a huge loss that I can't even imagine. But 5 days straight with baby and no break… that's how moms snap.
Now that I've written this out, I realize that the reason my experiences of traveling with baby haven't been positive is probably that most of our trips have been compulsory in that they were trips we were (at least morally) obligated to take. The only trip we've really chosen to go on for no other reason other than to just spend time together is our day trip to the Giants game. And OH MY GOODNESS, did we have fun. It was a little stressful here and there but for the most part, everything worked out very well.
So maybe my takeaway from this is that Justin and I, now that our lives have calmed down a little, should plan a trip with Reese that we WANT to take. Maybe after that I'd have some good tips or at least positive experiences to share.