Stock up on plenty of water and snacks at a grocery store or big box store at the beginning of your trip. It saves on money and extra stops when someone is hungry or thirsty.
Route 66 entails a lot of driving. The road time is just as much a part of Route 66 as the old hotels and pit stops. Make it fun, joke around, play music, talk. We actually spent a lot of the road time looking up the history of the places we were going to visit so we would know something about them when we arrived. If everyone has headphones in or is playing games on their phones the trip won’t be the same.
On our trip I created a Google spreadsheet with a possible trip itinerary. On the spreadsheet, each town we went through was listed and then under the town was a list of anything interesting to see or do.
I then shared this spreadsheet with the rest of the trip goers and anyone could add to it. Then when it was time for the trip I had a rough outline of things to see and do. Some we did and some we didn’t but at least we never had the issue of getting home and then discovering we’d missed some great attraction.
It also helps to have one person sort of leading the group, like a tour guide. This person is not in charge but steers the voyage. Otherwise you’ll waste a lot of time arguing over what to do and for how long etc.
When you travel with a group you have to be flexible and patient. Sometimes you have to spend more time at a spot than you would normally do and sometimes you have to rush. But you have to go with the flow and enjoy the journey.
We booked our hotels in the car, the day of arrival. We never knew how long we would be at a place or even where we would end up for the night until later in the day so there was no way to book any hotel in advance.