Let me just say from the outset which side of this debate I sit on. Spontaneous travel is WAY more fun.
Please don't think that I'm suggesting you don't plan at least some part of your holiday/trip in advance. Let's start with the essentials: dates, airline tickets, first night's accommodation and .... well, that's pretty much it. Whilst not having the security of knowing where you are going to stay is a scary thought, spontaneous travel allows you to shape the type of experience you WANT rather than worryng about sticking to the plan.
Exhibit 1: Plans don't always go according to plan.
Whilst I was travelling through Italy, a country I adore for it's amazing food, wine, landscapes and of course, eye candy, I made a couple of serious logistical mistakes. These mistakes ensured that my final memories are marred by blunders and unflattering experiences. And it was all because I had a plan I was supposed to stick to.
So there I was in Venice. Undoubtedly one of the most beautiful cities in the world. I was saying goodbye to the group of girls I'd been travelling with. We'd been staying on an island near the old town of Venice, which ensured a pleasant escape from the narrow, crowded streets of the central city. I was due to change my accommodation to a smaller hotel closer to the mainland but still within floating Venice. I caught the ferry with my friends and we went our separate ways at the Bridge of Sighs. I had a paper map in my hand but my phone was on international roaming so I wasn't prepared to brave the costs of google maps. Rookie error.
It was around 2pm and I was due to check in at the hotel any time after 3. So, off I went, towing 15 kg of luggage behind me. Having been in Venice for 7 days, I was fairly confident with my navigational abilities and I was interested in exploring some back streets of Venice along the way. Rookie error number two. Duh, Venice is a maze. Two hours later and I was still wandering the back streets of Venice. Every now and then, I called upon my broken Italian to ask for directions to a Hotel that most people had never heard of. Venecians, apparently, do not wander the back streets of Venice. I was mostly asking tourists.
During my walk I passed numerous hotels, many with vacancy signs a top. But, for the life of me, I could not find the alleyway that housed my destination. I continued walking. Eventually, I came close to the major bus stop with direct routes to the Airport. I was exhausted by this point, not to mention I had to be up early for my flight to Rome in the morning. I decided to cut my losses and take a room at the nearest hotel, which turned out to be super close and affordable.
Now, there are so many things that I could have done to avoid that situation. One of them is planning better, yes I'll admit it. But, the simple fact is, if I had no plan and no arranged accommodation, I would have settled for a hotel much sooner without the stress of trying to figure out where mine was. Believe me, save the time wasted on planning and just go with the flow. Venice looks a whole lot more beautiful when you're not desperatley searching for familiar streets, or carrying a stack of belongings mind you.