Traveling with small children gives lots of parents anxiety and although all children are different I firmly believe that if traveling is your cup of tea, having children should not limit this. It's important to incorporate and adjust them to your lifestyle (not vise versa). We take Elle almost everywhere with the exception of our couples trips we like to take as often as possible.
The key to making car and plane rides as painless as possible is keeping them entertained, easier said than done. I make Elle carry a back back full of small toys and activities, I like "Craylola mess-free" markers and coloring books (no stress about stains), "Silly Putty" (doesn't stick to anything and easy to pick up), and small figurines. I also pack low-sugar snacks such as nuts, gold fish crackers, and dried fruit because the last thing you want to be cooped up with is a hyper sugared-up toddler (especially on a plane). If you do a tablet I recommend downloading never before seen movies and shows along with the favorites and don't forget the headphones.
In my purse or bag I pack extra backup toys such as blind bags and extra snacks and candy, just in case I need to go rogue LOL! I also pack in my suitcase different coloring books and toys for the ride home.
The day before we leave for any trip I like to uptake Elle's vitamin C consumption, I usually give "Honest Co immunity booster" or "Emgencee for kids" and also give it to her the day of travel. The last thing you want is a sick kid away from home. I also carry bandaids, wipes, and aspirin.
Don't forget that kids are kids, they get bored and restless. They might not be into the same activities that you dream about doing but that doesn't mean you shouldn't try to expose them to it. Find a balance of kid-friendly stuff and things you want to do and don't forget to schedule things around nap times if your child still naps. I find that nap and bedtimes are usually later but I try never to skip them.
Have fun and relax, don't expect perfect behavior and perfecting eating habits. At the end of the day it's a vacation and you're in the business of making memories and forming bonds. Do that!