👨‍👩‍👧‍👦 Family travel as a points Padawan

Estimated read time: 4 minutes and 16 seconds

Ciao again! It’s Austin 👋 I’m still drifting into Italian despite writing from cold and wet Tennessee, but welcome to Daily Drop Family Edition #2 (#1 here ICYMI). I’m the family travel-hacking Padawan to Mike and Tiffany’s full Jedi-mastery of the topic.

If you have aspirations to be a family-focused travel hacker, I hope you’ll get inspired after today’s Drop.

• 💳 Earning: How my family accumulated points

• 🔥 And burning: How we spent our points

• 🐌 Slow Travel PSA

💳 Earning: How my family accumulated points

I’m always impressed with Mike’s crazy itineraries, but I have to say, I feel like I’m holding my own with flights I’ve booked in 2023 (for myself, my superhero wife, and my three kids all under age seven)👇

Let’s start with how my family earned enough points to pull this off.

I had dabbled in miles and points after watching some Kara and Nate videos a few years back, but I had since downgraded all of my cards to no annual fee options because traveling with three infants was just a little overwhelming for us at the time…

Since it is Throwback Thursday… Anyone else remember this napkin? 👇

Between my wife and I, we’ve earned signup bonuses from six different credit cards since the launch of Daily Drop. No hypocrisy to be found here!

Here’s what we got:

• 100,000 [[ the-platinum-card-from-american-express.points-program-override.points-currency ]] with the [[ the-platinum-card-from-american-express.name ]]

• 80,000 [[ chase-sapphire-preferred-card.points-program-override.points-currency ]] with the [[ chase-sapphire-preferred-card.name ]]

• Two Companion Passes + 60,000 Southwest points from both of us getting the [[ southwest-rapid-rewards-priority-credit-card.name ]]

• 175,000 hotel points with the [[ ihg-rewards-premier-credit-card.name ]]

• 75,000 miles on the Capital One Venture X Rewards Credit Card

It feels a bit like an addiction, but when I see what some other folks have pulled off in the Daily Drop Lounge, I try not to worry… 👀

On top of these big welcome offers, I also accumulated plenty of points with everyday spending. As I mentioned, I spend for a family of five—so it’s a meaningful amount of points.

But the real fun comes next… 😏

🔥 Burning: How we spent our points

Now for some epic family travel hackery…

After we made it to the land of la dolce vita (that’s Italy, in case you were wondering), I had a very specific goal for how I wanted to redeem the bulk of our points…

BUSINESS CLASS. WITH KIDS. 😎

Like big, swanky, lie-flat business-class seats that could swallow my children whole.

But finding business class reward space at a decent redemption rate FOR FIVE PEOPLE on a single flight isn’t something that comes around every day. In fact, it almost never comes around.

Thankfully, I had the wisdom of Daily Drop to guide me, thanks to our amazing and super-cool writer, Mike (who definitely didn’t add this sentence in while editing this).

It all started with a positioning flight. I transferred 40k points to Avianca LifeMiles to get a direct flight from Bologna, Italy to Vienna, Austria for all five of us.

Since there are so many Star Alliance carriers in Europe (Lufthansa, Austrian, Swiss, LOT, Brussels Airlines, Aegean, etc.), LifeMiles is an easy way to get pretty much anywhere on the continent… for cheap.

So after a few evenings of the best Christmas markets in the world, I made the largest single-point expenditure of my life… 😮

For 50,250 miles each, I got FIVE Air France lie-flat business class seats from Paris to Chicago (including the connecting flight from Vienna!).

None of us had flown business class before, and the experience exceeded every expectation.

From the Air France and Delta lounges at all of our connecting airports, the chuck roast and gnocchi that were probably the best I’ve ever had in my life, to the simple comfort and space of the seat, it’s going to be difficult to return to the back of the plane 🥴

The first thing out of the kids’ mouths whenever we talk about their three-month trip to Italy, is their “big, fancy flight.”

Let’s hope it doesn’t affect their egos too much now that they’re bougie business class travelers…

So yeah… the biggest point redemption of my life has pretty much ruined my kids for all future air travel.

The good news is that we’re roadtripping in December, so hopefully I can get their heads out of the clouds before their return to reality… for our next economy flight. 😅

Keeping with the theme of family travel…

🐌 Slow Travel Public Service Announcement

If you’re a parent who has dreams of traveling (and optionally working) around the world with your family in tow… you’ll want to listen up because I have two words for you 👇

Boundless Life

This company was founded by parents during the pandemic and focuses on providing safe and culturally immersive travel experiences specifically for cohorts of families throughout the year.

In fact, my family just got back from three months in Tuscany, Italy.

But, maybe Italy isn’t for you. 🤷🏻‍♂️

Not to worry—they have three other stellar options: Portugal, Greece, and Bali. And rumor has it some additional locations will be announced in the near future… 🤫

Once you’re there, Boundless takes care of pretty much everything:

• Education for kids one year old and above

• Co-working spaces for all the digital nomad parents

• Curated cultural experiences. 

• Opt-in community nights

Speaking of community… To be honest, my expectations weren’t very high.

But the friendships each of us made with the 15 other families from 12 different countries whom we spent three months with were our favorite part of the whole experience.

The way Boundless is set up between daily school drop-off and pick-up, community dinners, and a vibrant What’s App group (for impromptu park, coffee, and piazza visits) is such that you won’t find yourself lonely.

The Italians have the saying “la dolce far niente” which means to slow down and enjoy the sweetness of doing absolutely nothing.

Boundless Life has provided just that for my family. Beyond just making memories, the experience will be a part of them for the long haul. 

Interested in learning more or possibly signing your family up for a similar adventure? Fast track your way into slow travel with Boundless Life.

Thanks for tuning in with me today, folks!

I hope this newsletter series showed that despite what you might think, you CAN travel hack as a family.

Regardless of your travel style, there are ways to hack your way around the world... Even in business class with kids. 😎

See you next time ✌️

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