Planning an Unforgettable Family Vacation

by Deirdre Jackson
Planning an Unforgettable Family Vacation

One of the reasons we work is to provide for and take care of our families; but, as we all know, sometimes you just need a break— a break from the emails and the office hours, a break from tasks and to-dos.  So, what do you do?  Taking a family vacation is a great way to not only use some of that building PTO, but it also allows you to introduce the kids and family to a new landmark, attraction, or just blow off some steam!  To ensure that the time spent on vacation actually involves vacationing, you want to plan ahead of time and make sure all of your ducks are in a row.

Who is coming on the trip?

It seems like a simple enough question, but the answer will help determine the what, where, and how!  Is this trip going to be family only? Are we bringing the kids or is this just for the parents?  Will grandparents come along and might they potentially watch the kids for portions of the trip?  Knowing who is going will help you understand if you have to plan around a school vacation, any work conflicts, or if you need to find a babysitter.

What is our budget?

Before putting on your idea hat, make sure that you know your budget.  Deciding between an exciting new destination or trying out a stay-cation comes down to dollars and cents.  Are we flying? Are we driving?  We all want to get to our vacation destination as fast as possible, but sometimes you can save quite a bit by adding a short layover or driving (as long as the family party can handle a moderate length car ride).  Sitting down with the other family members who are financing the trip to come up with a budget beforehand will keep you from overspending when a shiny brochure gets you wide-eyed for Disneyland glory.

What is our destination?

This can change depending on who you have chosen for your travel companions and your budget.  There are other factors that can be taken into consideration such as the time of year, weather reports, and length of your time off of work.  Consider if you want to go somewhere new and branch off or stick to the familiar family spots.

Different Tourist Destinations


What will our accommodations be?

Whether you are staying at a 5-star hotel, an RV park, or a resort, coordinating lodging for any sized group can sometimes be a hassle.  So, deciding early where you want to stay is key to a successful family vacation.  If you are staying in multiple cities you will want to plan and reserve your lodging ahead of time, in case your ideal locations fill up.

How will we get around?

Sometimes renting a car is not always the most cost-efficient way to get around on your family vacation.  You will want to start by looking at the distance between your hotel or lodging and the main activities you have planned.  When it comes to traveling from the airport to your lodging, you often have an option for a free shuttle if you are staying at a larger commercial hotel.  If you find yourself staying near your destination, two very popular options to consider are Uber or taxis.  For our family, we have found that Uber tends to be not only the quickest but most convenient and affordable.  Being able to use the Android or iOS app and track where the car is and how far away is awesome, and the fares are really great.  We have a special promo code for Work Parent Sleep you can use,uberworkparentsleep, that will get you $20 off your first ride when signing up.  You can also use our Uber sign-up link as well to receive the free $20 off your first ride.  If you are new to Uber this would be a perfect way to try it out.

Should you take an uber or taxi


How much stuff do we want to bring?

Carry-ons only for the long flight to avoid checked baggage fees or big suitcases in the trunk for a drive to the neighboring state?  No matter the destination or duration of your family trip, you will most likely have to bring supplies for the family.  These can include clothing and shoes, as well as add on items like electronics and/or camping equipment.  Make sure your travel accessories don’t incur you additional costs and confirm that you can fit them in whatever means of transportation you have.


There is a growing trend of travelers like my mom who refuse to check in baggage and it’s completely understandable.  As we all have experienced, airlines are now using baggage fees to increase revenue.  For our family, this is one of the main reasons we like to fly Southwest.  They have an easy check-in policy and allow 2 free check-in bags.  Check out our article on Airline Carry-On and Baggage Fees that breaks down each airline’s individual baggage fees.

For those interested in making the most of the space in your baggage, consider using packing cubes.  Packing cubes are zippered fabric pouches that can be used to separate clothing and other travel items easily.  If traveling to several cities on a stay, one packing cube can be used for each destination; or, packing cubes can separate out clean items from items that need to be laundered during vacation.  They also help to make the most of the space available; we recommend rolling clothing up while using your package cubes.  For a  great set of packing cubes from Amazon, try the AmazonBasics 4-Piece Packing Cube Set which are sturdy, reliable, and reasonably priced.   They also make great gifts for travel-minded family and friends.

Planning our activities

Now that we have our destination, what are we going to do? Are we looking to visit historical sites? Do we want to go to a commercial attraction location such as Six Flags or Disneyland?   When planning a family vacation one of the most important things you will decide are the things you will do once you are there.  Get inspiration and ideas from the family members that are traveling with you, as picking activities that everyone is interested in will create a better environment.  No one wants to have 1 member of the family sulking because they hate rollercoasters and the vacation plan is for 3 days at the theme park!

Book your trip in advance

Whether the flights, lodging, or activity passes, you need to make sure to reserve your spots well ahead of time if possible.  This saves you money, secures your travel arrangements, and puts your mind at ease as you get closer to the big date.


When it comes to booking flights, the key rule to remember is the longer you wait, the more expensive it will be. There have been countless times I have told myself “I will just wait and book tomorrow,” and was then shocked to see the price of each flight ticket go up by a couple hundred dollars the next day.


Nowadays there are multiple options for lodging on a family vacation.  We have stayed everywhere from small, locally owned bed and breakfasts to large resorts.  Generally, we try to keep our lodging prices to a minimum so we can spend more money and time enjoying the trip, not cooped up in our rooms.

There are many times where Airbnb may be the best fit for your family vacation.  Airbnb is the Uber of lodging.  It is an online marketplace allowing people to list or rent short-term lodging including vacation rentals, apartment rentals, homestays, hostel beds, and hotel rooms.  All listings are provided by the owners, so you are not actually renting from Airbnb.  We have used this multiple times including our 2-week stay in Miami.  We not only saved a ton of money as the price per day can be quite affordable, but had the luxury of a full kitchen, dining room, and general house amenities at our disposal.  Something to keep in mind is that you may also find Airbnb properties closer to your destinations than hotels, which can cut down on transportation costs.


There are times when purchasing tickets ahead of time, or reserving your spot is required for smaller activities or places with limited capacity.  The BIGGEST reason to book your activities in advance is for the discounts!  We have found a couple of easy ways to save on your trip activities.

  • Costco – “Gift Cards & Tickets” Section – If you have a Costco membership this section might be worth checking out.  Whether you are looking for discounted movie tickets, admission to the San Diego Fair, or Spa packages there is a change to find it here.  You can get stays at resorts, Six Flags admission, and even restaurant gift cards here.  Last night the wife and I purchased their “Lucille’s Smokehouse Two $50 Gift Cards” for $79.99.  Although we are using them locally for date night, this practice can be applied while the family travels as well!
  • Last Minute Travel – Activities Section – Last Minute Travel is a site that helps you book hotels, flights, and cars just like Travelocity or Expedia.  Where they excel for us is their section for “Activities” which lets you enter in your destination, choose your dates, and let it find some tickets for local activities that might interest you.  This can also be a way to find fun ideas that you didn’t know existed at your destination!
  • RetailMeNot – Retailmenot provides coupon codes for everything from Macy’s, to Best Buy, to Starbucks, but it also has a dedicated section for “Theme Parks” which can come in handy.  It provides the coupon code, discount amount, and expiration of the deal so you know how long you have to book or use.


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