Time to Travel Part 1 – Planning the Timeframe & Destination

Time to Travel Part 1 Feature Photo

I really enjoy planning things.  Whether it’s something as small as a quick weeknight dinner or something larger like a long-term plan to pay off all of my debt, mapping out the path to reach a future goal just really makes my heart happy.  Having the main details already figured out before you get into whatever the task may be makes everything go smoother and faster, and who doesn’t value saving themselves some time and frustration?  The past few weeks, my boyfriend and I have been slowly narrowing down the specifics of our next vacation, which will be in October.  The planning gears in my brain are hard at work, so I thought I would share the process in this two part series.  This first post will cover picking a destination and timeframe, while the second will cover choosing a place to stay (with a fun spreadsheet!  Those exist, right?).


How to pick a timeframe & destination for your trip:

1. Determine your budget. Don’t go broke trying to have a good time.  The trip will not be worth the remorse you will feel when you get back and can only afford Taco Bell for three months to financially recover. Start saving as far in advance as you can to make it easier on your wallet when you go to booking your transportation and lodging.  Keep a $20 bill a week.  Keep a coin jar.  Make small sacrifices while reminding yourself of the reward that is to come later.

2. Decide What You Want To Do.  Do you want to be lazy on the beach or enjoy the nightlife in a big city?  Deciding what you want to actually do on your vacation will help you decide later where you want to go, but it will also help you pick a timeframe.  A winter getaway to someplace warm and sunny would be a nice break.  As would NYC if you live somewhere more rural and want to be surrounded by skyscrapers.  Remember your budget while you consider your options.

3. Pick A Season. Most of us have one common daily activity that determines our schedules–work. Summer trips are generally associated with the most desirable weather conditions, but also remember that for most places they are also peak travel months.  If your workload cycle mimics mine, then you also have to consider how hard you want to make it on yourself when you do return to work afterwards.  To avoid the excess stress at my desk (say that three times fast) and higher price tag, it makes sense to opt to book a trip for the spring or the fall.  Of course, if you are looking to enjoy certain activities, like skiing, this may determine the season for you.  Whether you found your season by analyzing your work schedule or researching the best time for your preferred vacation activities, move to step 2.

4. Pick The Length. Several factors come in to play here–budget, activities, and how much time you can take off from work.  Obviously one of these might totally overrule the others, such as only having five days available in paid time off.  If one of these factors does take precedence over the others, figure out the rest around it.  On the flip side, if you have a generous budget, two weeks of paid leave available, and are planning 10 days to relax on a beach in Mexico….can you please contact me and let me know how you pulled this off?  Thanks!

5. Choose The Dates. Again, your job may dictate this for you.  Maybe you’re an accountant and closing the books at month end isn’t something you can skip.  In my case, I am busiest at the beginning of the month AND at the end, so my dates end up being somewhere mid-month.  Keep in mind that airfare and hotels are typically less expensive on weekdays and more expensive around holidays, so if you are budget-conscious do not plan to start your trip on Labor Day.

6. It’s Time To Pick A Destination! You’ve got your goal activities, your season, and your dates.  Browse around different cities and areas to see what fits your budget and has availability.  In the second post, I’ll pick up on the next super-organized but super-helpful step after this.  Be prepared to do some research!

Click here to read part two and download a pretty, helpful travel planning sheet!

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  1. This is really helpful. Planning a trip can be overwhelming when you do no know where to start. I will be using this tip the next time I plan a trip.

    Thank you for sharing!

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