I think I've discovered the secret to travelling with babies; travel in large groups. The closer you are to being considered a convoy the better. Theo and I set out with my family for a trip from Michigan (where I grew up) to Albany, Newport, through Cape Cod up to Provincetown, past Plymoth Landing and finally into New Hampshire for my cousins stunning wedding. The saying the more the merrier rings true in most situations but counts double when travelling with a toddler. Theo not sleeping? Let Uncle John wear him out with some extreme hotel bed jumping. Theo's shoe breaks? My father (perhaps a cobbler in a far past life) gets thread and needle from my aunt and sews it together. Dreaming of a relaxing tan on the beach? My mom and Theo collect rocks and seashells until her purse reaches load barring capacity. Prior to the trip we were all a bit weary of toddler road tripping but I would do it again in a heartbeat. There is definitely some logic to the whole living near your family theory and after a year and a half in Bali and Paris with oceans between us, it was so great to have a family vacation.