Why You’ll Never Regret Blowing $20,000 on a 4-Week Trip to Europe with Your Kids

Walking down the road one evening, deep in the heart of Tuscany, my daughter stopped in her tracks. “What’s that?” She exclaimed, pointing to what looked like tiny little stars dancing in the darkened woods. “Are those fireflies?”


The only fireflies we’d ever seen were the fake ones at Disneyland, so we stopped to marvel. More appeared out of nowhere, flitting all around us, doing their little happy dance. My two teenaged daughters twirled amongst them, thoroughly enchanted.

We’d just finished the most amazing, inexpensive meal at a small, family restaurant in the middle of nowhere. Literally, it had been the tastiest, freshest food we’ve probably eaten anywhere on the planet, a 15-minute walk from our rented cottage.

I smiled and turned amidst the fireflies myself, reveling in this magic moment.

In 2013 we took our kids on an epic trip through Western Europe.

Our eldest had spent a year in Belgium as an exchange student. Our youngest, the hubby and I flew over to pick her up and do a month-long loop around the continent.

There were many ups and downs along the way: from that lovely day we spent with my daughter’s host family in Chimay to the hubby freaking out on the TGV when I couldn’t find the Eurail passes, to the sights, the food, the sunset strolls in Paris, to my daughter blowing up at the hubby for being, well, himself.

Then there was that all night party in the apartment next door, the majestic peaks of Switzerland, that quirky Airbnb host, wandering Old Town Nice, Monaco, Lucca, Lucerne, Geneva, that pile of rock art at the Venice Biennial with the billionaire yachts parked out front… Almost losing the kids on that crowded train platform and playing the crazy mom card to get them on board, no thanks to the snooty Brit… The magic of Salzburg and having our Sound of Music moment after escaping that crazy hostel with the crappy internet and the Abe Lincoln statue that looked like Dad… Finding that amazing tech museum in Munich with the Pleo from a startup that the hubby had co-founded years ago, not to mention the beer… And of course, that wonderful house in Amsterdam with the bikes, the canals, the museums, the haircut, and the, ahem, café… It was a fantastic trip, worth every single cent.

Vacations are fun, but journeys build character.

One week is hardly enough time to adjust to the rhythm of travel, and two weeks are a nice break from your everyday life. But once you get to three weeks, the dynamics start to change, and travel becomes the norm. Everyone has to adapt.

My eldest had been away for a year, living in a gentile, European culture as part of another family. She had to reconcile that experience with us, her snarky, American Simpsons-style family, which took some time. Meanwhile, we had to get used to her walking the streets alone, having a glass of wine and speaking French to strangers.

The hubby as an engineer was used to having absolute control over his environment. Travel, however, is chaotic, especially when you’re changing countries every few days, staying in wildly variable Airbnb accommodations, dealing with different languages and going places you’ve never been. So he had to adapt to that.

My youngest likes to bother, sometimes at the worst possible moment, and my trip planning skills aren’t always spot-on perfect, so we had to deal with a few mishaps. But we did it—we laughed, we cried, we grew together as a family.

That’s nice for you, but I could never do that.

Really? I know the arguments because I had to overcome them all: it costs too much, I’m busy at work, I can’t get the time off, what if the boss says no, my clients won’t wait, there’s always an excuse. But if taking your family on an epic trip resonates with you in any way, then listen to your heart, get creative, and just do it.

We don’t have the money.

Yeah, that’s the first thing we said, too. But you need to put that thought aside and find out what the costs actually are for air, ground transport, accommodations and entertainment. Then look at ways to cut the cost, like staying in cheaper places, cooking your own food and skipping expensive tourist activities.

Once you’ve got a reasonable number, think about how you can come up with the money. We had to save for months to make our trip happen. We scaled back discretionary spending, ate out less and stopped taking weekend trips.

Breaking the number down into a savings plan is helpful. If your trip costs $20,000 and you can set aside $500 a month, then it’s going to take you 3.33 years to save what you need to go. If that’s too long, trim expenses or pick a cheaper destination.

If you’re already on a tight budget, how can you earn more to make your family trip possible? Maybe you can pick up some overtime, do some consulting or find some other side hustle. Open a separate account for your vacation savings, and put all the extra money there. Do not connect it to your checking account.

And don’t go into debt for your journey because it can be difficult to recover.

We don’t have the time.

This is another big one because it’s hard to get away from work and sometimes even the kids’ activities. But it’s all mindset. You just have to make the time.

I put Europe on the calendar and called it our summer activity. I was in real estate at the time, working in a resort market most active in the summer. Did I lose business by being gone all of July? Definitely, and it hurt, but it was totally worth it.

The hubby was always busy at work with a never-ending series of deadlines. But he’d been there a year, proved his mettle, and told his boss six months in advance that he needed to take the time off. Not having accrued enough vacation to cover all of it, he arranged for some weeks to be unpaid.

These conversations can be scary, but where there’s a will, there’s a way.

Work won’t let me go.

Sometimes the boss says no. Sometimes the client throws a fit. Sometimes the deal is so complicated that if you leave, it might all implode in a fireball of misery.

If you really want to do this, get creative, draw on your resources, find people who can help you, even if you have to pay them. It’s just a problem to be solved.

What if you exhaust every avenue and still can’t get permission? The final choice is yours, and no one can tell you what’s best for your situation. But on your deathbed, who’s going to be there? Your boss, client, business partner—or your family?

When the kids grow up, they’re gone.

Think about that. These moments right now are all we have.

Kids wait for no one. They grow and change every minute of every day. As parents, it’s so important to be with them now, while we still can, because time flies, and before you know it, they’re off on their own. Take it from an empty nester, I know.

Time is our most valuable asset.

Time is not money. Money is medium of exchange that can be replaced. It may not be easy, but it is possible. Time can never be replaced. When it’s spent, it’s gone.

$20,000 was a lot for us to spend on a vacation. Practically speaking, that money could have gone toward tuition or retirement savings that we were behind on.

But time was running out. Our kids would soon be gone, and we wanted to do something special with them before they dispersed into their adult lives.

Spending all that time and money on a seemingly frivolous trip? I haven’t regretted it for a second. But if I hadn’t done it, I know I would.

Plan your epic family adventure.

Big trips aren’t for everyone, but if you’re one of those plucky people up for an amazing family experience, here’s how to make it happen:

1) Imagine your trip.

Where would you want to go? What do you want to do? Make a wish list of places your family might like to see. Set any obstacles aside for the time being.

2) Research destinations.

Google places you want to see. Read travel blogs, watch videos and narrow your wish list to a manageable number that can be covered in the time you’ve allotted.

3) Float the idea by your spouse.

Expect objections and look for ways to overcome. Big ideas take time to sink in. Don’t rush it, start early, and keep it casual.

Drip supportive articles to your spouse to help get him on board. Ask him where he’d want to go if obstacles were removed. Incorporate his ideas.

4) Make a spreadsheet.

Form a rough plan. Enter air, ground transport, accommodations, food and activities costs. Don’t be alarmed by initial high numbers, there are always ways to cut.

5) Keep floating the idea.

Share what you’ve discovered with your spouse, including ways to save, how travel benefits kids and address his objections. Tell the kids about your idea and float it by some friends. The more you talk about it with others, the more real it becomes.

6) Hone your itinerary.

Go through your travel plan, editing for time and cost. Pare down cities, switch from hotels to Airbnb, trim your restaurant budget, hunt for transportation deals—whatever it takes to come up with reasonable numbers your spouse can digest.

7) Get commitment.

Share the itinerary and get buy-in from your spouse and kids. Discuss concerns, compromise as needed, beg if necessary and put it on your calendar.

8) Tell everybody.

Tell your extended family, tell your friends, tell everybody you know that you’re going on this trip with your family and the date it’s happening. The more people you tell, the harder it is for you or anyone in the family to chicken out.

Follow your heart for no regrets.

Back in Tuscany two nights later, we returned to the little family restaurant in the middle of nowhere. None of them spoke English, but after a few attempts with our hacked Italian, we managed to understand that they weren’t open yet and that we should come back in 20 minutes.

The hubby, the kids and I wandered further down the rural road. We peeked inside a small church, pet some cats, sat down on a bench and chilled before walking back to the restaurant. A 7-year old girl with an infectious smile showed us to the same table we’d eaten at before, reserved with a piece of paper that said: 4 stranieri.

We sat down for a delightful meal, grateful for this kind Italian family, this amazing fresh food, and these very special moments together.

About Diane Cohn

Diane Cohn runs a mastermind for female breadwinners who want to go from renting to owning with clarity and confidence so that they can build wealth, control their environment, and enjoy the comforts of home. A prior top-producing Realtor, real estate industry marketing executive, and housing market commentator on YouTube, she has profitably bought and sold property in every kind of market over 30+ years.