Optimizing the Fun: The Art of Vacation Planning



Have you ever come home from vacation and realized you forgot to do something you had thought about doing while on your vacation? That feeling of regret is the absolute worst, especially for once-in-a-lifetime vacations like traveling overseas. Or, if you’re like me, you don’t like to repeat vacations ever because there are so many places in the world to see! A helpful way to prevent this post-vacay regret is to build vacation itineraries in advance of your travels.

It is best to section out the parts of the itinerary for the planning stage. The biggest categories for vacationing in the terms of planning are: attractions, food and lodging. If you’re staying in one place during your vacation, the lodging is pretty easy – when you have decided where you are staying, add the details into your itinerary format. If you are doing multi stop and day road tripping, you will want to add your lodging information for each stop. Different people have different preferences when it comes to formatting, but many people lean towards Word. After a few tries, you’ll figure out exactly what you like, and the formatting within that system that you prefer.

Once you know where you’re staying, you can figure out what you’re going to do while you’re there. If your vacation is focused around one particular attraction, such as Disney World or the beach – then this can make it a lot easier. Discuss with yourself or your partner if you want to take any days off of that one particular attraction; if so, do some research on what is nearby (and think about how long you are willing to travel from your location). Make a list of a few options, and here’s where your customization can come in. Some people chose to have each day fully planned out, while others prefer to have a shopping list of choices that they can pull from depending on their mood and the weather that day. For this discussion, we will assume that we are going with the shopping list, as it’s the most flexible for beginners. For each option that you choose to list on your itinerary, make sure to include the following information: name of the attraction, address, business hours and cost. It’s also really important to check if there are any days that they are closed – for example, most art museums are traditionally closed on Mondays.

When you have figured out all of the places you will be visiting, it’s time to decide where to eat! Food is a great way to get to know new regions and to open your horizons. It’s also just honestly really, really tasty. However, it can also be really, really bad if you go to the wrong restaurant. While the story of that time you took your kids to the restaurant that served mac and cheese that tasted just slightly worse than burnt plastic can be funny to recite at family gatherings, it’s a much more pleasant experience to simply find some fantastic eateries to enjoy while on your vacation. One of the best places to find high quality food is to check out TV food maps online to find restaurants that have been featured on food television shows.

Planning your vacations in an itinerary format like this can be a little more upfront work, but it will pay off. Knowing where you are going in advance, you can plan better financially – as well as know that you won’t come home with regrets again. Better yet, if you print out your itinerary, you can make notes on each attraction and restaurant. If you are one to repeat vacations, then you can build on this itinerary each time depending on how you rate each place – or you can share the itinerary with others!


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