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Vacay Planning 101

 I get a lot of questions on how I plan our vacations and several of you suggested I write a blog post about it. So, since summer is upon us and we are all more than ready to start traveling again (can I get an amen?), I thought what better time than now.

There are few things I love more than planning a trip with my people. Especially a summer trip. It means the boys are out of school, my husband takes off work, and we have a solid week of uninterrupted family time to create memories that will last our entire lives. For me, planning the trip is every bit as much enjoyable as the actual time away. The anticipation, the research, the excitement ... finding just the right places and activities you know your family is going to love - I just eat it up!

I have my own personal planning process that has evolved throughout the years, so let me take you along on how I plan our family summer vacations!

First things first: Get a cute notebook.

It's important, trust me. The notebook holds all the things, and we will elaborate on that later. Now if you're a spreadsheet kind of person, that's perfectly fine too. I'm not real tech-y when it comes to computer programs and I'm old-school in a lot of ways, so pen and paper is my thing. I jot a lot of stuff down and like to have it handy. My compact little travel journal is great since I can toss it in my purse and tote it around on our trips, whipping it out whenever needed. I started documenting our travels in this journal in 2018, and it's sort of become a journal of memories now. I love that I can look back on it and remember exact names of restaurants and hotels, and see what all we did. I've even written special notes inside of things my boys can look back on one day. 

Step Two: Decide where you're going and nail down dates.

You're going to need to whip out the calendar for this one. Take note of downtime in your calendar and choose a week that works best for everyone. We typically vacation the last week of June - it's smack dab in the middle of summer and so far it's been excellent timing for us. As far as deciding where you'll go - I feel like people typically have a running list in their minds of places they'd like to visit, so that part is fairly easy and personal to your own family preferences. 

Step Three: Head to the Bookstore and Grab Some Travel Books.

I live for and swear by travel books. My mom always bought one every year for wherever it was we were going, and they provide such great insight! They have sections for best hotels, best restaurants, things to do, towns nearby, endless tips and things you need to know, etc. I always buy a Frommers and Fodors travel book for our trips - they are the best on the market, in my opinion. Barnes & Noble has an excellent travel section! Grab some highlighters and pens to jot down notes in the margins.

Step Four: The Brainstorm.

Also known as The Big Brain Dump. As you start researching your trip, jot down anything you run across that you definitely want to do and may want to do in your notebook. If it looks even half-way interesting or fun, write it down. You will go through a process of elimination later, but for The Brainstorm, you will write down all the things. Think of it as The Master List of everything there possibly is to do. 

There have been times that The Brainstorm has saved us! If one of our main plans falls through, we go back and refer to The Brainstorm and we simply choose something else. It is important to over plan so that if something happens to an original plan, you're not scrambling to try to come up with something else to do and wasting valuable vacation time!

Step Five: Get Family Input and Make a Rough Itinerary.

After you have a master list of everything there is to do, determine what's most important and go from there. There should be highlights and goals to hit for wherever you're going and then smaller "if we have time" options as well. You will plan mostly around the highlights and if you get to hit some extras, great! 

Get input from everyone going on the trip and try to hit something that each person will especially enjoy. It's important that everyone feels like they have something to contribute and look forward to on the trip. As soon as you narrow down your Must-Do's, figure out which day in the week you want to do it and what makes the most sense for where you'll be and when. This is when you make a rough itinerary - listing the main things you want to accomplish for each day. We will go back and fill it all up later! 

Step Six: Road Trip Advice.

You can skip this step if you're flying. We really enjoy driving across the country on our trips and experiencing new places along the way. Here are some tips that have helped us on road trips: map out your route and plan each step of the day accordingly - locate approximately where you'll be for lunch, dinner and where you plan to land for the night - and then aim to hit those goals. Search for all the fun/interesting/exciting stops along the way that add a little something special to your tip and allot time for those. After all, the journey becomes as much a memory as the destination. (This was especially important on our Route 66 trip!)

Step Seven: Book it! 

Book flights, hotels, and tickets for attractions ASAP. As soon as you nail down your itinerary, book it. Tickets sell out, hotels fill up, and flights just get more expensive. You want priority for what it is you want to do and it provides great peace of mind for having your tickets and accommodations pre-purchased. 

We are driving to this years destination, and we heard last week that rental cars are already completely unavailable this summer in the area where we will be. For reasons like this, it is important to plan ahead and book as quickly as possible. The worst thing in the world would be to get there assuming to buy tickets the day-of or even week-of, and there not being any available. This happens to people all the time. Be prepared and book it!

Step Eight: Focus on the Food!

Once you know where you'll be and when, hit up the internet and start researching restaurants/bakeries/snacks, etc. Dining is as much a part of the vacation experience as anything! I like to find novelty restaurants: ie chuck wagon dinners, dinner shows, etc.; featured food spots (Food Network or other viral spots); and must-haves when in that area. If we are in the same spot all week, I like to plan the most special meal on the last night. It is fun to have something exciting to cap off the trip and a time to share our favorite memories from the week as a family. It's always one of the most special and bittersweet times of the trip for me. 

Step Nine: Detailed Itinerary Time!

This is where things are narrowed down and set in stone! (Or pen.)

Dedicate one whole page to each day, jotting down all the details. Here are some examples of what I have listed for 1.) a travel day, and 2.) a vacation day.

Travel Day

- Destination, hotel accommodations
- Weather/temperature 
- Time it takes to get from point A to point B
- Lunch plans
- Planned stops
- Dinner plans
- Hit if we have time
- Arrival Time

Vacation Day

- Town you're in, hotel accommodations
- Weather/temperature
- Lunch/dinner/treats plans
- List of goals for what you want to see/where you want to go that day, ranked in order of importance
- Addresses and times those things (including restaurants) open/close
- Tips/anything important to note
- Hotel pool closing time

This makes looking at your itinerary a breeze. At a glance, you have everything you could possibly need to know. You can see exactly where you'll be, what you'll be doing, and approximately what time you'll be doing it. After all, every day runs together on vacation - it's like an alternate universe. The visual itinerary is vital!

*Weather is important to note. For example: when we were in AZ, Flagstaff was 20 degrees cooler than Phoenix, so we made sure to plan for a light jacket. We ran into the same type scenario in Colorado, too. You'll need to prepare for rain if you're planning to be outdoors. 

Step Ten: Enjoy the Fruit of Your Labor.

By the time you finally go on your trip, you will have spent hours planning and you're going to be raring to go. Now that all the work is done, it's time to sit back and enjoy your vacation! If things don't go exactly according to plan, don't panic. Don't be Danny Tanner with the Clipboard of Fun. Go with the flow and be flexible! Enjoy your time and be in the moment. Sometimes we completely scrap a plan and end up doing something completely off the cuff. Spontaneity oftentimes brings about some of the very best memories! 

A Personal Vacation Preference Note:

If you're looking at this planning process and you think I have lost my marbles, I get it. A lot of people like to go on relaxing vacations and the last thing they want to think about is an itinerary. But for us - we love to see and cram in as much as we can - we hit the ground running. We always say we need a vacation from our vacation! To ensure we get the most out of each trip, we often split the week up - spending several days in one particular spot and then traveling 2-3 hours to spend the rest of our trip exploring elsewhere. Having done this, we have been able to see and experience so many more places, and it adds so much to the adventure. 

I am a modern day homemaker with a passion for family, cooking, celebrating, decorating, travel, and memory making! The Lord has blessed me with the desires of my heart in my husband and our two sons. We recently built our dream home and cultivating a loving and happy haven for my family is where I find so much joy.


  1. Last year for our vacation we were able to book a week on Cape Cod in July in May. I wanted four new walls to stare at while being safe during a pandemic. It was the most relaxing week of vacation because we stayed in an Airbnb house and not a hotel. I decided this year to do it again. Wanting something to look forward to again, we booked a week on the Cape in January. So glad we planned ahead because everyone else has the same idea this year. Early planning and booking is definitely key!

    1. YES! It is vital! And that sounds so dreamy. What a great idea! And definitely a perfect trip to relax on. Love it!

  2. We all needed a vacation after our family vacations, didn't we? Great times!!❤️❤️

    1. Every single time!!! Thanks for instilling the importance of family vacations in me! 🥰

  3. I love this! I am planning a three-day vacation to Berlin, Ohio (Amish country), Although it's real touristy and not exactly #1 on my husband's list of places to see, I want to include lots of things for him to enjoy as well. I really appreciate all your ideas.

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