It depends on your frame of mind
There are lots of websites out there trying to sell you the “perfect getaway.” While trips like these may satisfy the majority of those out there looking to get away from it all, that doesn’t mean that you need to conform to what others are doing. The key to successful trip planning is to do exactly what you feel will result in your enjoyment and peace of mind.
Unplanned vacations are very popular amongst young folk, and have been for some time. They make up the majority of the stories that you’ll hear at dinner tables and on bar stools. My mother entertained us with stories of backpacking across Europe, living under bridges and in people’s backyards, hopping trains, and bumming lifts from strangers. Trips like my mother’s are characterized by the growing of long facial hair or dreadlocks, a general avoidance of any personal hygiene products outside of baby wipes and travelling toothbrushes, and a pressing need to inform anyone even remotely associated with you immediately, in the event that something sketchy happens. Recommended accessories for a trip like this are seflie sticks, GoPros, a backpack big enough to carry the population of a small Polynesian island, and enough cash to bribe your way through a Kazakh border crossing.
In all seriousness, these types of adventures are lauded as being life-changing journeys of personal improvement, and a culture has grown around subtly shaming those who haven’t travelled in this format. If you’re thinking you really should, bear in mind that, to accomplish this kind of travel, you really need to be of a certain constitution, and in a certain frame of mind. I have a friend who did just this, travelling around Europe, southeast Asia, and New Zealand for six months. She’s a hyper-smart, hyper-competitive law student and debater – the last person I’d see travelling like this. But then, one night, she and her fiancée split, and her mindset changed. Within a month, she was off, and, six months later, she was back, with a new outlook on life, four new tattoos, and an entire hard drive of pictures to help her remember her experiences. She couldn’t have done it before the breakup, but, after, she almost couldn’t avoid it.
Similarly, the meticulously-planned trip is favoured by control freaks and families with young children. Every minute of every day is accounted to maximize fun and minimize relaxation. Activities are booked months in advance to get the best deals and beat the lineup, hotels are only booked on special rates, and any transportation should either be affordable rental car or air conditioned tour bus, complete with that distinctive, barely-tolerable scent of BO and flop sweat. Typically, vacations of this nature are not immediately shared with friends and family through social media, because, frankly, you look pretty miserable in most of the photos.
As with the unplanned trip above, these types of trips do have their place, and can be a lot of fun when pulled off right. Again, relating it back to my family, when I was younger, my mother planned all our trips down to the finest detail – in strange and stark contrast to her free-wheeling trips as a rebellious youth. All of it meant to ensure that the rest of us had a great time, while she worried non-stop about all that could possibly go sideways. The benefit was, with that meticulous planning, rarely did anything ever go awry. To the point that we were able to travel to places that would otherwise have been quite difficult or dangerous to get to, but we were spared the drama thanks to my mother’s on-point planning and execution. We travelled to the Middle East during the winter of 2001, and we made our way into Peru and Chile months after a violent coup and some cross-border territory disputes. All these experiences were made possible (and cheap!) by my mom’s phenomenal attention to detail.
Both these types of trips have worked for my family and friends, because they’ve both been applied to appropriate situations. When life demands that you embrace your wild side and admit that you do indeed live only once, an unplanned trip to an unknown destination will return you revitalized, rejuvenated, and with a whole new pocketbook full of friends and travel companions. If your life demands a carefully scripted experience designed to achieve a specific adventure-related goal, planning is the way to go. When execution is paramount to your enjoyment of an experience, there is no substitute.
Whatever you choose, travel is never a bad choice. And things can always change. So do what you’re comfortable doing, and try to absorb the advice of others with their past and present mindsets as context. And them’s the facts.