7 Random But Super Helpful Tips For Vacationing Well

Photo credit: Simon Matzinger

Photo credit: Simon Matzinger

Vacation season is almost over, but I wanted to share a few things I’ve been thinking about on our family getaways this summer.

I hope they help you as you squeeze in a final weekend away before school and the fall kick-off is upon us.

If not, let’s plant some good seeds in your heart and mind before your next getaway.

Tip #1 Leave work behind but not every other discipline that works for you.  

Despite popular belief, the universe will survive if you take a break from work.

Your life, business or career will not be sucked into a black-hole if you completely disconnect from email and social media for a few days.

Science has all kinds of data now to show how much of our energy is exchanged (to our deficit) through regular technology interaction.

You may feel naked leaving your phone and not taking it with you, but trust me, it’s worth it.

Your brain with thank you.

Your family will thank you.

Leaving vocational “work” behind doesn’t mean you have to throw out all work or discipline. Some of the greatest vacations I’ve ever had are when I still gave myself time in the morning to read, reflect and exercise.

Taking a break from working out or casually getting out of rhythm with God is a quick recipe for a downward spiral in my energy and perspective.

I’ve found that if I neglect those daily disciplines, my energy is sapped and my attitude is negatively affected. Both of these drop offs impact everyone around me.

Let the routines that serve you in your everyday life, continue to serve you on vacation! We need a break from work, not from the things that serve us well in our everyday lives.

#2 Experiences > things. 

I used to think we needed to save and spend large amounts of money on things. I didn’t realize how much I thought “toys” would make our family happier.

Then my wife helped me discover a huge life-lesson:

“Toys are temporary but memories are with us forever.”

Memories can often cost as much as toys, but that’s not really the point. I wasn’t out to save money; I was after lasting memories.

Instead of buying the nicest cars or largest TVs, we’ve regularly chosen to take some incredible family trips.

The pictures, memories, blunders, laughs and overall experience is FAR more valuable to me than something that will eventually break, go out of style or need to be sold on Craig’s List.

I’m certainly not against having nice things.  

I’m just convinced that people, places and experiences carry far greater value and bang for your buck!

#3 Be realistic with the ideal vs. the real. 

When we plan to go away we sometimes have this idyllic view of what it will be like.

I think we should have high expectations. However, we need to be prepared for “real life” to happen on vacation so that we don’t think the whole trip is ruined when it does.

Talking to my friend, brilliant marriage coach (Susie Miller), opened my eyes to a very interesting and relatable pattern.

She was helping to coach a mastermind group I was leading and shared this rhythm with us:

·      Phase One: The family is tired and still in a fog from the busyness of life to fully be present or engage.

·      Phase Two: People are rested enough to fight about the backlog of things in their heart that they now have time to let come to the surface!

·      Phase Three: People are ready to bond and have a good time together before going back home.

In so many ways this is the God’s honest truth!

So when you make your kids take a break from their screen time, expect a mild meltdown.
If you and your spouse have been passing ships in the night due to hectic schedules, expect some frustrating conversations to surface that have nothing to do with your current vacation surroundings.

“Protect your vacation ideal by preparing for and expecting the real.”  

#4 Make sure to visit before you visit.

Businesses live and die by online reviews. Customer reviews have become the new currency of business.

With so many resources available, it’s wise to check out the place you are going to stay, visit, eat at and explore before you get there.

I’m a planner and my wife (Anna) is more creative and spontaneous. If things are too planned she can often feel trapped.

The box of my strategic planning can stifle her joy of spontaneity.

So, if I have a plan in my head after researching a place, I do my best to hold it loosely. This way we are prepared but can also call an audible and experience something brand new together.

It’s easier said than done. 

But a little research can go a long way. 

Who doesn’t hate coming home and hearing from someone, “Oh, you were in such and such place, you should’ve hit up this place while you were there it’s the best restaurant, experience, spot to visit in that whole area! Next time you are there (to a place you may never get to visit again) make sure you stop by there. You’d LOVE it.”  

Trust me, visit before your visit.

#5 Don’t break the bank when you can just leverage a system. 

Years ago a mentor and friend of mine tried to open my eyes to a whole world of travel benefit that I did not know existed.

Purchase great seats on planes with points?

Reserve awesome hotel rooms without money?

Lounge in nice sky clubs at the airport on layovers?


When he told me about it, I immediately thought, “That sounds amazing, but I don’t think I have the time or bandwidth to learn this whole points system.”

For the next few years I didn’t cash in on regular purchases I was making and trips I was already taking.

I was wrong and hope you learn from my mistake.

Slowly, I began leveraging my purchases with a rewards credit card to earn air miles. We’d pay off the balance each month and store up the points.

Before you knew it, we were having free nights in hotels and flying our whole family on amazing vacations all on airline points.

My boys were lounging in the Delta Sky Club at the airport like kings. Who doesn’t like free wifi, A/C and unlimited food instead of being stuck in a terminal without a phone charger available for miles?

To create amazing memories with your family, you don’t have to break the bank, you can simply leverage a system.  

#6 Remember, the best part of going away should be coming home. 

There is a very real pressure for vacation to be a “savior” when you can’t stand your vocation.

Going away on a vacation can never solve the problem of not enjoying what you are coming home to.

The truth is, God wants you to enjoy all of your life.

I’m passionate about helping people live a brilliant life.

“The glory of God is man fully alive.” -St. Irenaeus

I’m not saying you won’t dread coming back to some stressful part of your life after vacation.

What I am saying is that you should begin to shape your life after the one you actually want to live.

“Be a shaper of your life not a victim of your circumstances.”

Don’t view vacation as a complete jail-break escape.

That mentality will put way too much pressure on your getaway and likely will sabotage it.

Far too many people come home from vacation depressed and don’t know why.

On vacation you have margin to think about things at a deeper level:

  • What do I want to change when I get home?

  • What parts of my life are going better than anticipated? Which aspects are behind?

  • What relationships do I want to give a greater priority to?

Here’s probably the greatest tip I could give you about vacation.

“In moments of margin, practice gratitude.”

Instead of thinking about what you don’t have, what you want to have, or what others have, practice gratitude for what you DO have.

This is actually a really powerful exercise.

It’s grounding.

It’s energizing.

Neuroscientists are now saying that gratitude actually lubricates our brains! The “oil” of gratitude softens our brain tissue to be able to be flexible, creative and establish new pathways.

 Recently while walking a New England beach with my family, I was grabbed by this idea of gratitude.


As I watched seagulls trying to search for food they could scavenge, people searching for the perfect sea shell to bring home, guys with metal detectors on the sand and in the ocean searching for someone else’s treasure, and people trying to look their very best to hopefully attract the perfect person into their life...this thought occurred to me:

“Rather than searching for the treasure that eludes you, celebrate the treasure that’s in front of you.”  

Photo credit: @nicobhlr

Photo credit: @nicobhlr


#7 If all else fails, treat yourself to a Romano’s Tour to Italy.

Here’s a SNL clip to help brighten your day :)

Photo credit: Travel Weekly

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  • What’s the best place you’ve ever visited on vacation?

  • What’s a helpful vacation tip you can share?

  • What’s something you’ve learned this vacation season?


Joshua Finley4 Comments