I think the best and most logical way to start a trip is to decide where and when you want to get away. My boyfriend and I just recently decided to take a trip, and this is how we planned it from scratch! The first thing we did was to figure out the best time to take the trip. I’m finishing my last semester of school, and he’s working full time, so it needed to be at a time that could work for both of our schedules. We decided that at the end of May would be most ideal because by then, I’ll be out of school and he’ll be done with busy season, so there will even be reason to celebrate! We also had to consider him taking off work and when he would have built up enough vacation days. Related to this, weather should be a big consideration. Depending on the time of year, some places may be more ideal than others, especially if your trip involves a lot of time outdoors. Research what the weather might be like in your destination before making any arrangements.
Next, we started to brainstorm about where we might want to go. This really comes down to how you want your trip to be spent. Do you want relaxing time on the beach, hiking through a national park, visiting with family/friends you might not have seen in a while, checking out museums and monuments, etc. Figuring out what you want out of your trip will help ensure you pick the perfect spot. Finally, we realized that we want a trip that will give us ample time to ourselves, somewhere that is drivable and something affordable. After we had these specifications, we tried to narrow it down further by deciding we wanted somewhere with things to do outdoors. Neither of us had ever been to the Smokey Mountains, and we both wanted to check it out. The drive is also only about 8 hours from Chicago, so we settled on that general area as our destination. We knew the weather would be perfect for hiking and hanging out outside.