Originally, I was going to say all of the trips that we took to Canada when I was a kid to visit family, but those weren't really interesting....just long.
I'd say my most interesting vacation was the first trip Keegan and I took together when we went to Gatlinburg in August 2010. A co-worker Keegan had met during his internship in Memphis told him about American Patriot Getaways which is a company that has really great deals on the cabins in the mountains. Keegan and I had never been on a vacation together, but Keegan wanted to get away for a few days in between him coming off his internship (and us being apart for 8 months) and the fall semester starting.
We rented a cabin in Gatlinburg for four days. Since we were still living in Missouri at the time, it was about a 12 hour drive. We had decided to leave at midnight so that we could drive through the night with less traffic and we would arrive at our destination in time to sight see a bit. I had to work that afternoon, so I told Keegan to take a nap so that he would be somewhat rested for the drive. I come home from work at 10:30 and he's up playing Donkey Kong with my roommate. So much for the nap. We decide to leave a bit earlier than planned and settled in for the long trip ahead of us.
I fall asleep pretty quickly in cars, especially at night, so I was no help to Keegan throughout the drive. I fell asleep in Missouri and woke up in Nashville just as the sun started to rise. Keegan was exhausted but determined to drive on. We got to Gatlinburg around noon and were beyond ready to get into our cabin to take a nap. However, when Keegan made the reservations, he was told that we weren't allowed in our cabin until 4. I begged him to call and see if they could let us in early, but he refused to. Since we were exhausted, we ended up taking a nap off the side of the road in the middle of the forest. I'm really surprised no one pulled over and made us move along. Come about 3:30, I begged Keegan to call again to see if they would let us in, and lo and behold, they did. The nice person we talked to even said they would have let us in at noon when we first arrived! I gave Keegan so much shit for that, I still do to this very day.
We stayed at the Lumberjack Lodge that had our own balcony in the forest with a hot tub. One of the first things I did was make a s'more over our stove. I ate at least two s'mores every day during that vacation.
Throughout the week, we went sight seeing in Gatlinburg (a total tourist attraction, but fun anyways,) went for a ride on a ski lift that took us over Gatlinburg, did many auto tours, went hiking to see some waterfalls, looked at some old churches of the first settlers of the area and overall just relaxed and caught up with each other after being apart for 8 months.
I'd say this was my most interesting vacation because it was full of firsts. It was our first vacation together, our first road trip, my first time to see mountains, my first time in Tennessee, my first vacation without my family, and so on. We had so much fun and it was the perfect mix of laziness and things to do that we went back for our honeymoon. We upgraded for the honeymoon and got a two story cabin with a heart shaped tub as well as a hot tub *wink.* We also went white water rafting which was one of the most fun things I have ever done. Now that we only live about 6 hours away, I keep trying to convince Keegan that we need to go back for a long weekend.