The Planning: How to Make Family Travel Happen

Updated: Aug 19, 2023

How do you begin the planning process? Family travel is a lot to organize, and I am here to make this easier and affordable for you! The biggest difference for children from lower socioeconomic families and higher socioeconomic families boils down to one thing: NOT money - Experience. This plan works for any budget. Enjoy them while you can, they grow fast. If you have 18 summers with your children, let's make the most of them! Affordably of course.

Virgin Islands

#1 Pick a Destination

This can be anything from the park up the street to a plane trip across the Country! Got one? Good.

#2 Budget

No one likes this part but really ask yourself: How much will this cost? Include food (even if you are bringing it with you) and any other necessities. Then compare what this trip needs to happen to what you have, and come up with an amount.

I like to plan/ budget in this order:

Accommodations. I pick the locations of where we will sleep. This can be a big factor when traveling with 4 kids. Many of the times I am staying with friends or family. When I'm finding Hotels, I may pick based on proximity (being as close as possible to my other goals) or there may be things like Free Breakfast or parking I prioritize.
Once I have an idea of where I want to stay and secure the availability for my times, I secure transportation (this may be flights/ rental car)
Then I account for the spending on those necessary unavoidable costs. Now I look at my bank account. Then I figure out how much I am comfortable spending. If that number is low - I am mainly looking at free things to do and grocery shopping. If I feel comfortable my itinerary may include some items that have one costly activity daily and all others are free. For example: Horseback riding on the beach at $50/ per person. Family of 5 = $250 to walk in the door. All the other things we do that day will be free or very low cost. Like walking some nature trails, exploring local history, and maybe a state park.
Itinerary planning - this is my favorite part. I look at how long this trip is and consult my family to help them build excitement. What do they want to do? Is there something they are excited about? A food request or certain location they'd love to hit? Then I build an itinerary with something fun planned for each day! Which leads us to the next section.

#3 Time

How long will this take - to ENJOY! Always plan your trips to be enjoyed. If you are not able to make the best of it, you are missing the point of going places. I also tell my family once you lock your door and walk away, the vacation is officially started! Getting to your destiny should be part of the fun. It's all an adventure.

If you are hiking, give yourself a little extra time. When you are going to a place like the movie's times are advertised and easier to be predicted. But create a timeline that flows. Research Trip Advisor for places in that area and see what you would like to explore in the area. You don't want to find out after you return that you were right by a landmark you would have loved to see. Also look at free options in the area. Make a wishful itinerary. Then break down the itinerary and compare with your budget. But also, don't be married to your itinerary, stay flexible. I just find having a plan can calm any angst.

Put it on the calendar. Visually!!! How much time it will take to enjoy + how much time you have is the formula needed for success. When can you do this? Once it is written on the calendar, we are out of the dreaming stage and officially in the planning process!

#4 Pay $$$$$$$

Once you have a schedule, then see what you can start paying for prior to the trip. This will free up funds when you are actually there. If there is a flight or road trip (gas funds) these costs you know well in advance and can either pay in full or put to the side. Keep this money separate, you will know what spending money you have available. Excursions often need to be reserved ahead of time. Be sure if you are looking to book a place it is available during your intended time frame. Some people utilize credit cards that give points, and this is a whole art that I will talk about more later!

** While you are waiting for your trip continue to research ideas and tips. Read blogs. Read Trip Advisor. People sharing itineraries can help you save time or energy getting lost or off course once you arrive. Prepare for the weather or climate. Need bathing suits or hiking shoes? These be given as gifts in this in-between time or budgeted for. Plan for items you may like to have like a travel pillow or even a new camera. I've been known to upgrade my phone prior to travelling.

#5 Be Flexible

This may be the hardest. Sometimes plans just don't play out as planned. Still focus on being a problem solver and making the most of the day. It started raining on your picnic... maybe puddle jumping sounds fun, or maybe you need to move to another location, maybe you have to eat in the car. But try to make it look to your kids like you have the solution even if you have to fake it.

#6 Designate

Once those kids can walk they are helpers! Kids love to help, it gives them pride and self confidence. Let them help carry. Put them in charge of somethings - part of this may be knowing your kids and their strengths and weaknesses. Keep it fun but always have a designation, even if it's something like "you count how many trees there are" which you may have no real need of, then praise them for doing the job well. This creates the expectation and engages more. Teaches some accountability which will come in handy later down the road as they grow. I prefer jobs like you wipe the table with a baby wipe before we eat or you collect the trash and put it in the bag, but really any job is better than no job!

#7 Forgive

Yourself and Kids

For all of the imperfections of the day

There will be good days and bad days. If it all fell apart, that's ok. Parenting is brave and courageous. It is NOT easy. But pick yourself up and try again. Sometimes you may need to bring in reinforcements. Can a friend or grandparent come? Can you adjust a part of the outing to make it easier on yourself? Figure out where it's falling apart and lets trouble shoot. Whatever you do: Do NOT GIVE UP.

Boston, on a hot summer day!

ANYTHING you can plan you can do!

Make those bucket lists and dream big.

Don't feel intimidated by reality, it's time to organize and make it happen.

Ready for more? Let's take a trip.... 🚎✈🚂

You will see as you browse through my adventures that I share the itinerary and costs of each place we go. This is to make your planning process and itinerary building as seamless as possible. I typically pair an expensive activity, or bucket list item with a bunch of smaller free things in the area to make a whole day of fun. This always makes me feel more satisfied with how I spend my money and budget my time - I want the most bang for the buck so to speak.

I specialize in helping families spend more time enjoying their quality time together and less time having to figure it all out. My four children have been my test subjects of how to plan a great family adventure for many years and now that my youngest is 18, many of my travels are work related, or grandma related! As time has changed, I've evolved but I still LOVE TO TRAVEL, explore, wander, visit, discover, learn and love. If nature is there, I can find my happy place. I use the term single not to emphasize my status but to signify that if I can manage some family fun on a limited teacher's salary with four children, anyone can do it. I am just very intentional in how I spend my time and earnings. I typically seek out budget friendly ways to enjoy my time, but will occasionally splurge for the right reasons :-)

Happy Travels!!

God Bless every road you travel on. xo