Last Family vacation: juggling teens and preschooler Let me start with the basics, I’m Tracy, I’m in my early 40’s and I am the obsessive planner in the family. In fact, my family refused to even discuss our September Vacation until September. Fortunately I had the dis family to help me plan and feed my planning addiction. My family consists of Monty DH 46, Carly DD18, Erica DD16 and Kaitlin DD4. We are from Vancouver, Canada so our original plans were to take just the DH, DD4 and I to Disneyland. But, we have a very persuasive travel agent who found a fantastic deal for us to take DH’s older 2 with us on one last family vacation. (At least one that WE pay for.) We had to adjust our plans from the first week of December to the third week of September but we were able to do that will little difficulty. I will get ahead of myself here (as you find I tend to do as you read on) and say that I will NEVER visit DW in September again. Our last trip was in 2008 in January and I will stick with the winter months. The heat and humidity pretty much did us in. But never did it affect the enjoyment of our once in a life time trip. I say once in a life time because it was DD4 (Kaitlin’s) first introduction to everything Disney and even though I knew she would love it, watching her STILL exceeded my expectations. If you’re still with me, let’s get started and re-visit the happiest place on earth. Our trip began several thousand miles away. We had quite the debate about getting there. Airfare from Seattle was half the price from Vancouver so we decided to drive to Seattle. Option A: Leave at a respectable time and get to the resort at midnight (don’t forget about the 4 year old.) or Option B: leave at the ridiculous time of 5:30am and get to the resort at dinner time, leaving everyone time to eat and relax. But that meant leaving Vancouver at midnight. (Don’t forget about the 4year old). We chose Option B and waivered on spending the night at a hotel in Seattle, however, since we were getting BACK to Seattle at midnight we thought staying in the hotel on the other end of the trip made more sense. (Don’t forget about the 4 year old.) So what would be better to work around a very active (not hyper just very busy) preschooler who is anything but a couch potato. We were banking on her sleeping most of the way. A gamble I know. We hadn’t travelled like this with her before so we had no idea how she would react. So, Day 1 looked like this: Midnight: Leave Vancouver, Kaitlin woke up (I had counted on her sleeping the whole way) and did not sleep for another 2 hours. We drove the 3.5 hour trip to Seattle, parked the car and Kaitlin woke up again. We boarded plane number one at 5:30am and flew 2 hours to San Fran. Kaitlin stayed awake the entire time. (I had counted on her sleeping the whole way.) She did really well for her first plane ride though. We changed planes (thank god I listened to the diser’s here and decided to buy a stroller instead of renting one so that I had airport use) and boarded the next flight to Orlando. A 5 hour flight. Kaitlin was still awake. But I had planned for this, I pulled out the shinny new Leap Pad 2 which I spent a fortune loading with all things awesome for just such an emergency. However, she was handing it back to me within 30 seconds and getting cranky. I realized she was tired (Of course, she hasn’t slept near what I was hoping she would) so I pulled out her blanket and pillow (thank god I listened to the diser’s here) and she cuddled up and slept the entire 5 hours. So, now do I wake her up and risk cranky child on a small cramped plane or let her sleep and risk having her up all night. With consideration to the other passengers, we let her sleep. We were all checked in a ready to go to our room at the Caribbean Beach Resort by 6:00pm. (3:00pm Vancouver time.) The resort was beautiful. It exceeded our expectations straight off. We were located in Jamaica 45 as requested. It was only a 5 minute walk to the pool and concessions so we were thrilled. Although this was our last family trip and most of the trip itinerary would center around Kaitlin, we did have big surprise for Carly (18) and Erica (16). We got to the very small room with only 2 double beds for 5 people and asked them where they would like to sleep. Both of them were troopers but I don’t’ think either had given much thought about the cramped quarters. They masked their facial expressions very well and said wherever would be fine. So I hand each of them a key and said “how about each of you take one bed?” I so should have had the video camera on as the look of shocked realization that they would actually have their own privacy came. As requested we had connecting rooms so total freedom wasn’t going to be had, but at least they could live in their own mess and heat. (They like a very warm room. So warm that there is almost no difference going from their room to outside. In fact, so warm that they attracted not one but TWO hissing cockroaches in their room. I have to state that this resort is beautiful and we found it very clean so it was absolutely no fault of the resort that these girls attracted the bugs. We were right next door in a refrigerator and had no issues.) View from our room. We all settled in and headed out for a bite to eat and to explore the resort. We did not have high expectations on food quality and found it to be neither good nor bad. We checked the pool times as Kaitlin had slept for the last 5 hours and DH did not, I thought I would take her to the pool while Monty got an early bedtime. (with work and all he only had maybe 5 hours of sleep out of 36 hours.) We read the time wrong though and thought it closed at 8pm instead of the actual 11pm. What was I going to do with this kid? We went back to the hotel room to find that Mickey had left a whole bunch of presents. (I had shopped the 50% off sale at the Disney store before we left) Everyone got PJ’s and shirts. Kaitlin didn’t really know what to think as she had no idea about the adventures she was about to have. By 9:30 we were all in bed looking for a good night sleep. (6:30 our time with a kid that had a 5 hour nap.) Somehow though and with a lot less fight than I anticipated, even Kaitlin fell asleep.