The Realities of Holiday Planning: Lessons Learned from a Multi-Destination Trip

You're going on holiday. Wow. Fantastic.

But let's talk about the reality behind the excitement. The person who plans the holiday carries a lot of responsibility. Planning the packing, transport, tickets, insurance, accommodation, and more can be overwhelming.

Recently, I planned a trip to Italy with nine different locations, two car hires, and one internal flight. I researched thoroughly to ensure everything was perfect. But as we set off, I felt the weight of responsibility. If anything went wrong, it would be my fault.

On our first day, I shared my worries with my husband. He surprised me by saying, "Whatever happens, we'll have a great holiday. I'm grateful you took on all the planning because I was super busy at work." That helped, but I still felt anxious each time we changed locations.

Of the nine places we stayed, two didn't work out. One had a wonderful host and a gorgeous view but was filled with unwanted creatures. My husband suggested we find somewhere else. The next place had terrible reviews about dampness and sewage smells, so we skipped it too.

In a moment of frustration, I found a new villa with a pool. It was more expensive, but the owner offered a discount, and it turned out to be the best part of our holiday. Flexibility and a willingness to adapt saved our trip.

We learned that staying in one place with a pool suited us best and decided future holidays would be simpler to plan. So, if you haven't planned your holiday yet, take some time to think about what truly works for you. Reflect on past holidays and what made them special, then start planning.