Although this advice is completely out of character for me, I highly recommend taking a camping trip (7+days) with no reservations. Last June, Amy and I took an 11 day trip to Michigan without making any reservations ahead of time. Yes, it can be a bit risky. What if we would have gone to a campground and there were not sites available? However, the first two weeks of June are not high season for Michigan. Students are still in school until June 10th or so and the weather does not warm up until the end of June. So, it was a perfect time to go without reservations. For someone who needs a plan for everything, this trip was quite liberating for me. We camped somewhere for a while and when we were ready to leave, we packed up and hit the road. We never encountered a “no vacancy” situation. It was so nice to know that we were not tied down to any plan other than to find rest and relaxation in our camping experience.
Now, I would NOT recommend this during certain seasons. For example, I would not suggest heading to Florida during the Spring Break season without reservations. Nor would I suggest going anywhere during the 4th of July weekend without making reservations ahead of time. The chances of coming up empty-handed are too high.
But in the end, I still encourage you to try this, especially if you are the type-A personality (like me). You wouldn’t believe how freeing it is until you try it….