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Be brave, my friends, it is doable, with a little preparation and a lot of snacks. I recently tried the following tips out while traveling with a nearly seventeen-month old (and my highly-spirited ten-year old).
In the car
Try to time your road trip with a nap time. and if not, make sure someone who can play with him (nicely) is next to him
Bring his favorite books and toys in the car, for those moments he is resisting sleep and his car-mate has lost interest in entertaining him.
Play kid-friendly or bouncy music to distract him when he starts crying. It might not put him to sleep but at least he will start dancing and get in a better mood.
In the hotel
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Bring his favorite bedtime book to keep his nighttime ritual going in the hotel. But be prepared for some choppy nights as little ones don't always adapt well to new surroundings.
Bring a portable booster chair in case high chairs are not available in the hotel or restaurant. There are some small, portable, fabric models available on the market.
Out and about
When you see a playground, give her free time. The more they play and run, the happier they will be and the more tired out too!
Schedule some kid-friendly activities like petting zoos and parks where kids can walk and interact. Under 5s could care less about architecture and cathedrals in general so don't pack only these types of events into your trip.
Know your limits. The world is not always stroller-friendly. If you or dad have to let the rest of the family climb the steps to the castle while you hang out with baby, so be it. There will be other opportunities. But as I mentioned in the last tip, do find some kid-friendly fun to break up the more boring (from a kid's POV) sightseeing.
Eating out
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BYOC. If only every restaurant had the wisdom to provide crayons and coloring pages for its youngest patrons! But alas, many don't think about them so Bring Your Own Crayons. And a notepad while you're at it, to make the wait for the others' meals seem less tedious.
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