How to Overcome the Challenges of Planning a Family Vacation

A recent graphic from USA Today that was made from a Holiday Inn study, found that saving enough money, finding the right dates, getting time off work and agreeing on a destination were the top challenges families have while trying to plan a vacation.


Here are a few tips to help with each of these challenges:

Saving enough money: Set aside a “piggy bank” when you first start thinking about taking a vacation so that money gets set aside from each paycheck and goes right into this account where it can’t be touched until it’s time to book everything. Even if you just get an inkling of a desire to go on one in the near future, but haven’t figured out all the details or even location, start setting aside money because once it’s time to plan you will have saved up enough already and you can book it immediately.

A possible tool to use to help you is Smarty pig, an online piggy bank approved by the FDIC, where a part of your paycheck can go directly into this account. You can set goals and it will tell you what percentage you are at until you reach your goal. If for some reason you decide not to go on this vacation or an emergency happens, you can just take this money and transfer it into your regular checking/savings account.

Finding the right dates: It’s hard to take kids out of school, so I think summer vacation is the best time to take a big family vacation. You only have to worry about your time off from work and not theirs too.

If you do want to take a vacation during the typical February or April vacation, try to find a place that’s off the beaten path, but at the same time somewhere you have always wanted to go. Disney World is amazing, but probably not the best place to go because prices sky rocket due to all of the school breaks during this time of year.

If you are traveling with young kids try not to go anywhere warm/tropical in the months of March and April because you will most likely find college spring breakers partying all night long. If you do want to go somewhere like that during these months, do a little researching to see which places will be the hot spots for college spring breakers and avoid it.

Flights during the school break weeks will always rise, unfortunately, we can’t change that, but like I said not every location will always have a flock of vacationers/spring breakers during these times.

Getting time off work: If you plan ahead correctly, you can book a trip months out in advance and ask for time off early before other people do. This way your managers will know not to book business travel or any important meetings for that week.

I tend to ask for the time off when I know exactly the dates I am looking to go and I have it all planned out- I just have to click purchase on everything- so I know for sure that the days are approved and I can book everything with a peace of mind. If you ask for vacation a few months ahead of time it’s tough for them to argue why it can’t be approved. You get vacation time for a reason, take it!!

Agreeing on a destination: When it comes to traveling with kids, it is easier than you think to find good vacation locations. First, think of their age and what you will need to pack such as strollers, sippy cups, diaper bags, etc. Make sure you pick a place where you won’t wish you had to drag that around with you all day at an amusement park or a busy city. Maybe a beach vacation is a better option. Once you get all their stuff to your beach chairs it sits there all day until you have to leave, doesn’t that sound much better than carrying it everywhere you go while bustling past hundreds of people? While you read a book and relax, they can entertain themselves in the sand.

Second, if they are a little older, ask what kind of things they want to do while on vacation, do they want to play in the sand, do water sports, go skiing, go hiking, etc.? Most kids don’t know what each location offers and might fear the unknown so instead of saying “We are going to Florida!” when they have never been and don’t have a mental picture in their head, say “We are going to Florida, while we are there you can go snorkeling, make sandcastles, see fish and turtles, go to an Alligator Farm, go boogie boarding…” tell them what you know will appeal to them.  

Remember kids get tired and cranky easily, especially when they are over stimulated with a new environment, so make sure where you choose to go isn’t so expensive that you wished you waited until they were a little older to take them there.

Make sure to switch it up every year too, allow them to see the world. If you read my recent blog post, you know that traveling allows kids to be more interested in education, learning and other cultures.

Do you have any other tips for helping a family plan a vacation? 

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