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7 Rules for Family Vacation Planning

What do I want to do?

I want to travel.

I want to have a home, a stable place to come back to. I love my house. There are days, months even, when I love my town. But I also long to escape it.

I have traveled. I have been to other countries; Canada, Mexico, Guatemala, Belize, Belgium, The Netherlands, France, England, Sweden, Scotland. I've lived for periods of time in Texas and Kentucky. But it's never enough.

So I'm always planning our next trip.

On VRBO (Vacation Rental by Owner), I have six different houses on reserve over the next year. Now, some of those are for other people. Meaning, I found the places, but the trip is for more than just my immediate family. But three of them are just for us.

My kids are finally at a point in their developments when we can go far away on a long car ride and they are okay. I mean to say, it's bearable. I've decided to dream big. And try to figure out how to find a way to pay for it all. (That's the tough part)

Here's Katherine's steps to trip-planning:

  • Dream big: Where do you see yourself? What are you looking for in a vacation? What vacations have worked well in the past? What vacations have been total bombs? How old are your children and what are their interests? How would you like to expand their horizons?

We took a trip one year to Florida in July. NEVER AGAIN. Now, we were under some constraint. We were there with family and were limited to when we could all go together. But a hot, crowded Orlando in 100 degree weather when the A/C goes out in your rental house on your birthday? Not a fun end to a trip. There were certainly moments of that trip that were wonderful (and other reasons why it was hard), but the HEAT and the CROWDS became big no-nos in our future vacation planning. The next time we went to Orlando---it was in January.

  • Research, Research, Research: This is my favorite part. Get online. Read blog posts about "Best cool vacation spots in the summer" or "Place in the USA most like Scotland" (That's an actual recent search of mine). I will literally spend HOURS researching areas that spark my interest.

The anticipation that builds as I am planning our vacations is part of the vacation for me. My husband will have to say to me "I want to enjoy this [upcoming vacation] but I'm going to be tired of it before it even gets here." I really have to keep some of my enthusiasm in check.

  • Plan way out: To really get the best houses or experiences for the best price in the best locations, plan in advance. The houses with the best views get snatched up. Campsites at Fort Wilderness in Disney World are booked sometimes over a year in advance. Even if you decide to cancel later for some reason, book early. But know the cancellation policy.

My most recent obsession, brought on by the significantly hotter than average summer that we had here in South Georgia this year, has been Maine. First we were going out West to the Grand Canyon and to the Rockies. But tickets for a family of six are not cheap, so flying was out. And the Grand Canyon in July is (according to the reviewers) crazy crowded. A car ride that would encompass more than 70 hours also did not look fun with our kids. That led me to consider cooler places nearer home. As homeschoolers, I would ideally go on vacation when the rest of the world was tied to their school calendars and owners are practically begging people to stay in their houses. Ironically, my husband is the one tied to the school year, since he works at a high school. (My dream is that he leaves his desk job and is able to get an online gig that allows us to travel whenever we want).

  • Save where you can: make a list of your must haves in an area. Do your kids get bored in the country? Do you have teens who can be trusted to be on their own some? Then a house/hotel within walking distance of attractions may be ideal. Do you have toddlers? A lake house might not be the best plan. Do you prefer excitement or solitude? Knowing those things will help you spend where you will get the most benefit.

I have a general knowledge of how much vacation house our budget can bear. I prefer houses, because meal planning is then cheaper which is a HUGE deal with lots of kids. When I was looking at VRBO houses in Maine, I found the perfect house. It was a little big, but the views were STUNNING. Then I looked at the price. Oops. No. Had to keep searching. I ended up finding a place outside of the main tourist area that I was originally looking at. I found that I was willing to sacrifice proximity to town and national park, because of the cheaper rate, while still getting the country setting that I wanted on the water.

  • Splurge where you can: Pick one or two things to splurge on. Oftentimes, it is these one or two things that really add to the enjoyment of the experience, even if in all other areas you kept tight on the pocketbook.

I'll give you two examples of what I mean.

When Ben and Sam were little, one and four years old, we took them to Chattanooga to see a life-size Thomas the Tank engine. We actually made this trip three times because we and they had so much fun. The hotel that we stayed at had room service as an option. Our last morning there, we ordered room service for breakfast. We were sensible. We ordered the complete breakfast and everyone shared, but that little thing ended up being one of Ben's favorite and most memorable moments. Room service breakfast is still something that I love to get.

Mac and I had the extreme privilege to go on a trip to Scotland for our 15th anniversary. When booking the rental car that we would need, I saw that the agency had Mini-Cooper convertibles as an option. At home, we drive eight and nine year old cars. Here was a chance to drive around Scotland in a convertible. A new convertible. So we did. And that car and the chance to put back the top on a gorgeous June day, winding down a single lane road overlooking the bay of something or other as the Old Man of Storr guided us along was worth EVERY PENNY. The trip would not have been the same without that car. Plus, it was awesome when the Scottish people would ask if we wanted a know, because of the rain.

So whether it's the $40 dollar room service breakfast that makes your kids jump up and down or the upgraded room that overlooks the pool, pick that one thing that will turn an okay vacation into an awesome vacation.

  • Enjoy the trip: When it's time to go, enjoy it. I've been guilty of having a wonderful time planning a trip then becoming a Mommy Rage Monster (that's a real beast) when it's time to go or when something doesn't go my way. All the plans in the world can't stop a hurricane or your car unexpectedly breaking down in Epcot parking lot (this happened!). Plan for the unplannable by letting go of your expectations and having fun with the people you are with.

We were late to catch our train that would take us to Gatwick. We were standing in the middle of the train station, when I realized that I had left my wedding rings in the bathroom at the hotel. I lost it, right there in the middle of London. Luckily, when it comes to Mac and I and travel, when I lose it, he seems to hold it together. We were able to make the call and my rings were found, but I was a frazzled mess for those few minutes.

  • Know your weaknesses and talk about them together ahead of time. You can't control life around you, but you can control you. I've gotten better over the years, and Mac and I have developed systems of dealing with each other. Lists are great. Lists say, "This is what needs to happen before we leave." They help to make a stressful situation less so.

Where do you dream of going? What are your travel must haves? What lessons have you learned to make the journey better?

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