TOD -
Best: The three and a half week driving trip we took in 1996 when our son was almost 11 years old. We called it our "See the USA" tour, making a big loop up to the Black Hills, across northern Wyoming to Yellowstone, down to Salt Lake City, Zion National Park, and Las Vegas. We spent a 5-day weekend in the LA area, doing Disneyland on Friday and Universal Studios on Monday. Then we drove to Phoenix, picked up my mom, and she came back to Ohio with us. Early in the trip, we'd left a bag of toiletries behind in Greybull, WY, and I said if that was the worst thing that happened we'd be fine - it was and we were.
In 1999, we did "See the USA II," to the east coast and in 2001, "Colorado, Rocky Mountain High."
Worst: Flying back from visiting my mom in Phoenix, we were on TWA landing side-by-side another jet in St. Louis. The plane next to us landed and we didn't. The pilot said, "We're going to try that again." My husband said, "I didn't hear the landing gear open, did you?" I had visions of them foaming the runway for our wheelless landing and seeing fire trucks and ambulances waiting for us, but we landed fine the next time around. No explanations, nothing.