Traveling Italy
To me, the magic of Italy is the layers - and I don’t just mean the lasagna.
At the base you’ve got Caesar, Sulla, and the glory of Rome. Drizzle on the middle ages with Pope, the Vatican, and the whole “center of Medieval Europe” thing. Toss on Michelangelo and Renaissance Florence and for the final topping, add the expressive people and sun-kissed arches that make up modern Italia.
What Makes Italy Unique
Italy wasn’t just the center of the world. Italy was the center of the world multiple times for multiple reasons. What takes your breath in Italy is the stratified symphony of interconnected layers. It’s empire, worship, and art, all telling the story of us.
My Italy Trip
Much ink has been spilt on this iconic destination, so let’s bring this post back down to earth. Here’s a personal take on my first big trip to Italy.
5 Places | 4 Foods | 3 Thoughts | 2 Keys | 1 Celebration
5 Places
Florence: Beautiful and world-changing. But in 2023 the most over-touristed place I’ve ever been. Let the Duomo and the Uffizi stun you - and then get out as fast as you can!
Tuscany and Umbria: Ancient hilltop cities sprinkled over lush, vineyard-filled valleys. The quiet beauty in the upper hills of Cortona is a spiritual experience - that you will need after bustling Florence :)
The Amalfi Coast: What’s makes a beautiful landscape? Mountains? Or sea? How about both. Might as well make it an endlessly tall cliff jutting out over the Mediterranean. Stack charming, ancient fishing villages one on top of another until they disappear into the clouds and BAM! You’ve got the Amalfi Coast.
Must-do: Path of the Gods and a sunset boat ride.
Rome: Fight the crowds to see the iconic sites- or if you’re like me, just watch Fall quietly creep in from the banks of the Tiber. St. Peter’s and the Pantheon are the must-sees. Everything else makes for a great “bike-by”.
Bologna: Go for the food and the arched sidewalks! … And did I mention the FOOD?
About that…
4 Foods
I ate all the carbs in Italy. Sue me. Here’s a few food highlights:
Olive Oil: Between mafia exports and no US regulation, the olio d'oliva we get in the states is very hit-or-miss (deep dive here). Olive oil in Italy is a wonder for the tastebuds and a miracle for your health!
Gelato: Most gelato is a 2x improvement on ice cream. But the shop by the two towers in Bologna? Nirvana.
Aperol Spritz: Aperol, prosecco, club soda, slice of fresh orange. One innkeepers secret: tonic water instead of club soda.
Pasta! Handcrafted, with 10x more variety than I knew existed. Must do: Ragu and Carbonara
In Italy, it’s the beauty in the little things. But the little things may just give you space to think about some bigger things…
3 Thoughts on Travel
Travel in 2023 is the best bang for your buck on the planet.
Let’s face it, America: housing, college, medical bills- most big things are wildly more expensive for millenials than they were for our parents.
The one thing that’s cheaper and smoother than ever before: seeing the world. Between miles, apps, and the advent of a little thing called “AirBnB”, travel is one thing we can do today with an ease that would blow the minds of our predecessors.
Anyone can travel- which brought me to my next realization.
Travel has been Democratized (for better and worse)
Upside: In 2023, everyone can go to Italy!
Downside: In 2023, everyone can go to Italy :/.
With travel becoming easier and cheaper, seeing popular sites, especially during peak season, is becoming a recipe for misery. The new key going forward? Finding the hidden gems.
And even when you nail it, travel only goes so far in life.
The Diminishing Returns of Travel
There is a diminishing return to getting away.
To be clear, I believe in travel. Travel and books are powerful ways to get outside of our “normal” routine… and more importantly, our “normal” assumptions about life.
But going is not an end in and of itself. As an idol, travel will leave you unfulfilled.
Time away serves its purpose to the degree that it re-awakens you to the meat and potatoes of a good life: spirituality, relationships, and meaningful work.
2 Keys to Avoid Misery
I’ll shoot straight with you. The iconic Italian spots were the most touristy places I’ve been to in my whole life. Once you’ve identified what you want to see in this sought-after country, the key in trip-planning is to solve for crowd-avoidance.
To do that:
NEVER GO TO ITALY IN PEAK-SEASON: A trip to Italy in the summer is a sure-fire way to spend two weeks on a hot, crowded bus being shuffled off to hot, crowded lines. We went in early October… I might go even later.
Biking is a Superpower: No exaggeration- biking saved our trips to Florence and Rome. Bypass the the packed subways and overflowing sidewalks, stay in a quiet spot, and see more in a day by bike than you can see in a week on foot.
And finally, it was a ten-year anniversary that brought us to the boot of Europe in the first place.
1 Decade of Marriage
They said marriage would be tough. Three kids, ten years, and a whole lot of life later, I see what they meant. But even if it ain’t always easy, it’s always good. In a world that increasingly pushes us towards atomization and dissolution, marriage is one of our last remaining tethers to connection, to family, and to unconditional love. And that’s worth strengthening - and celebrating.
It’s been an awesome 10 years- here’s to the next 10. Andiamo!
Booking Italy
Some of our friends think we’re super rich.
And of course, by any global or historical metric, we are (we all are). In reality things are often tight for our one-income, three-kid family.
What these friends (who, for the record, actually make >2x our income with less kids!) are thinking is:
How do you guys take such bougie trips?
Let me give you a peek behind the curtain. As a case study, we recently took a luxury-hotel-filled ten-year anniversary trip to Italy.
Turn Big Spend into Points
In 2022, the silver-lining to the death of our air conditioner was the chance to purchase a replacement mini-split with a brand new credit card. So we applied for a new Amex Platinum card, and four days later bought our $6000 mini-split with it, netting us an instant 131,000 Amex points.
Later that fall when it came time to put some down payments on two roof replacements, we applied for the IHG Business Premier card, which gave us a quick 143,000 IHG points.
Those points sat idly in our rewards accounts until we had the spark of an idea: 2 weeks. No kids. Italy.
To do it, we just needed to turn those points into tickets.
Turn Points into Tickets
Italy costs more points than other European destinations, but the nudge that pushed us over the edge was a 25% transfer bonus to Air France that popped up in Fall of ‘22 - making the Italy flights more reasonable.
Once we found some flights and dates that worked w/ our backup-child-rearers, we transferred the points from Amex to Flying Blue (Air France’s mileage program) and for 92,000 points (RT) my wife and I were on our way to Italy. But we were still homeless.
Turn Points into Hotel Rooms
With a flight into Bologna and a flight out of Rome booked, we plotted a rough north-south itinerary. Where would we stay? We let the IHG travel portal guide the way. After some exploration we landed on a few “Mr. and Mrs. Smith” estates:
Three nights in Florence (Riva Lofts)
Two Nights in Tuscany (Fontelunga)
One Night in Umbria (Aethos Saragano)
Paying for roofs never looked so good. The IHG points landed us six free nights in some swanky villas.
We had to snag two AirBnBs for the last week, but at <$150/night (and with AirBnB gift cards regularly on sale for 10-15% off), we felt like we got some pretty good value.
Beautiful Loft on the Tiber
Morning Coffee from the Amalfi cliffs
Not Totally Free
In full transparency, money was still spent. Between car rental, gas, a sunset boat ride, credit card/ticket fees, and all the gelato and pasta in Italy, the whole thing was still over $2000. For us, that ain’t chump change.
But be honest. If this girl was willing to stay married for ten years, wouldn’t you take her to Italy, too?!
My next post explores what all that hassle and cost got us:
For more explicit instructions on how to break into the game of points and travel, read my old post:
Of Pyrenees and People
I’m 35,000 feet over the Pyrenees. Out front, clouds rise above the Bay of Biscay. Is that Bilbao in the distance?
Back home, I know Late Winter Despair must be settling in. So, it must be time for a travel post from my 500-mph chair in the sky.
These last two weeks have swept me from a windy work conference in seaside Malaga, Spain to the steep hills of Lisbon, Portugal with a few stops along the way.
Here’s what I saw.
Malaga, Spain:
Quaint beach city with beautiful Spanish center. I quickly realized, however, that living on the Cote D’Azure last year has spoiled me for life as far as beach towns go.
Granada, Spain:
Quiet mountain city with snow-capped Sierra Nevada backdrop. People go here for the Al Hambra craftsmanship and are not disappointed. The stonework will boggle your mind.
Algarve (Southern coast of Portugal): Picturesque and cliff-lined beach resort region on the edge of the old world. Its people are noticeably kind and this was the perfect place (with free hotel nights!) to relax after an intense conference.
Lisbon, Portugal: Is this hilly, tiled city the hottest spot in Europe right now? Maybe. For whatever reason… I found it underwhelming.
It struck me as dirty and only “generically” European feeling. For me, the tiled exteriors couldn’t compete with the iconic vibes of a France, Italy or Germany. Finally, any remaining traces of affordability or “undiscoveredness” seemed to have drifted to sea by the time I showed up. I was glad I came, but was ready to leave by the end.
Sevilla, Spain:
I finish with this city because it blew me away. The crown jewel of Southern Spain is endless winding streets of riverside beauty on a surprisingly large scale. Add the quiet, the parks, and the pedestrian-friendliness and you’ve got an eminently livable city that may warrant a return.
History Below My Feet
One thing that set this trip apart from others was the unshakeable weight of history that seemed to emanate from the bumpy Spanish cobblestone. I sensed it on sunset walks through the breathtaking Plaza de Espana. I felt it as I made my way deep into the heart of Alhambra.
Was it the ghost of Columbus, who once made his world-shaking pitch for a few ships on this very spot? Was it memories of Peru, and the gravity of standing where Pizarro once embarked from on his way to bringing Atahualpa and the entire Incan empire to its knees?
In slower moments, I meditated on the reality that these streets once unleashed the most prolific explorers and brutal conquerors of all time.
Belem Tower
From Cortez and Columbus in Spain, to every Portuguese sailor ever waved off by the king from Belem Tower, how could this tiny corner of the Iberian peninsula have rewritten the tongues of every man, woman, and child, from northern Mexico to the southern tip of Chile? (short answer: Guns, Germs, and Steel).
Maybe it was the reflection-inducing solo nature of my travel, my growing appreciation for history, or perhaps some secret ingredient in the acorn-fed jamon iberico, but my “N” mind couldn’t help wandering beyond the tapas in front of me and into the distant past. This place deeply shaped the world we know today - and the significance of it was in the air.
Finally, the best aspect of my trip wasn’t pasteis or cathedrals, or any thing in Andalucia itself.
Jobs and Friends
It had been three years since I had seen my coworkers. Three years. Finally, from the desert of isolation, I emerged to drink from the firehose of human connection.
Of course, there was the expected death-by-powerpoint which you’ll get at any work conference. But between sessions, there was ample time to dig deep with old friends, yak it up with Frenchmen and Aussies alike, and discuss life in Tokyo with Japanese companions.
So far, the Great Resignation hasn’t shaken me loose from the “company of my youth”. Twelve years in with my current place of employment, and I know that there’s probably more money out there and certainly novelty and excitement in the world of other tech careers.
But I wonder. Where else can I reminisce with people who knew me as a 23-year-old kid? At what company can we laugh about the old startup days, working from a cheap container behind a little church in southern California?
I haven’t ruled out a career change. But staring out at the darkened Mediterranean sky, dusting off memories piled up over the years with old friends from far reaches of the planet - wasn’t it clear that there are some things that money can’t buy?
Maybe what I’ve got at my job is special - or maybe I’ve just been drinking the kool-aid for too long. For now, the plane is touching down in dreary Amsterdam. With sun-kissed sea in the rear-view, and the place they call me “dad” approaching, all I know is that I’m grateful. And maybe, for now, that’s enough.
Favorite Things: 2022
New (to me) Books
Breath (James Nestor)
My summary:
Most of us breathe poorly.
Breathing poorly creates a myriad of health issues.
Anyone can improve their breathing and feel better, reverse ailments, and live longer.
I enjoyed Breath on two levels. First, as an occasional dabbler into health and self-improvement literature, the book left me wondering why it hadn’t occurred to me to improve the most fundamental activity involved in staying alive.
And secondly, as a wannabe writer, I was floored by Nestor's ability to create a scientific book on breathing (yes, BREATHING) that is utterly riveting.
With eccentric characters playing out the story across time and space (yes, he really illegally journeyed miles into the catacombs under Paris to observe ancient skulls), Breath feels more like The Da Vinci Code than breathing manual.
Here's a teaser passage from his conversation with a group of semi-insane "free divers" (people who dive to ~300 feet below the surface of the ocean- with no gear).
Another diver told me that some methods of breathing will nourish our brains, while others will kill neurons; some will make us healthy, while others will hasten our death.
They told crazy stories, about how they'd breathed in ways that expanded the size of their lungs by 30 percent or more. They told me about an Indian doctor who lost several pounds by simply changing the way he inhaled, and about another man who was injected with the bacterial endotoxin E. coli, then breathed in a rhythmic pattern to stimulate his immune system and destroy the toxins within minutes. They told me about women who put their cancers into remission and monks who could melt circles in the snow around their bare bodies over a period of several hours. It all sounded nuts.
They discovered that our capacity to breathe has changed through the long processes of human evolution, and that the way we breathe has gotten markedly worse since the dawn of the Industrial Age. They discovered that 90 percent of us-very likely me, you, and almost everyone you know is breathing incorrectly and that this failure is either causing or aggravating a laundry list of chronic diseases.
On a more inspiring note, some of these researchers were also showing that many modern maladies-asthma, anxiety, attention deficit hyperactivity disorder, psoriasis, and more-could either be reduced or reversed simply by changing the way we inhale and exhale.
The Count of Monte Cristo
Many classics are good to read in the same way that spinach is good to eat - helpful, but not particularly enjoyable. This is not true of Dumas' classic.
Beginning in Southern France with a hook to end all hooks, the story eventually moves from the legendary Chateu D'If to Rome and Paris at a pace that will satisfy the most attention-deficient modern readers. Dumas' classic tale of revenge and redemption is still a winner for plot-lovers in 2022. Once read, the film will look like a silly, B-list child's play by comparison.
Re-reads
Ruthless Elimination of Hurry (John Mark Comer) and Get Your Life Back (John Eldredge)
Good books give us the truth we need at the right time. Fifteen years since Steve Jobs' placed supercomputing compulsion machines into our pocket, these books are the kind we need right now if our inner life is to survive the exhausting, lonely age of constant connection.
While Comer masterfully puts words to the challenges of the soul in the age of the internet, Eldredge's writing is the balm and direction we need to survive the digital age with spiritual life intact.
4-Hour Workweek
This all-time favorite found me again at just the right time. As my peers graduate to large suburban houses and new cars (along with the associated mortgages, car payments, and oftentimes high stress jobs to support them), Tim's 2007 classic was a timely reminder why we're taking the road less traveled. So far, our family has tried to prioritize freedom over convenience and experiences over stuff. So far, that has made all the difference.
Apps
Obsidian (w/ Readwise)
For all the content you read, the videos you watch, the podcasts you listen to - what percentage do you actually retain? What if the key points of every piece of consumed media along with every noteworthy thought you had were stored in an easily searchable database for instant recall for the rest of your life?
This is the promise of the "Second Brain" - a personal journal / content library on steroids made possible by modern technology. I've chosen Obsidian as the "hub" of my second brain and have been very pleased.
For more on the topic of the second brain, Tiago Forte is your man.
Duolingo
For all the flack it got in the reviews I read, Duolingo was an incredible resource for me. With just 15 minutes / day, I had enough francaise to outfrench 95% of tourists and even hang a bit conversationally. With a big travel year ahead, I will be leaning on the premium version to keep my French sharp and get up to speed quickly in Spanish, Portugese, Japanese, and Italian!
Podcast
Huberman Labs
Picture a muscly, decorated, middle-aged Stanford professor with an encyclopedic knowledge of current health science and incredible ability to communicate it to non-scientists. What if, instead of pushing out esoteric academic papers, this jacked academic put his energies toward distilling the most relevant, cutting-edge health science and making it practical for normies like you and me?
In that case, you’d have Andrew Huberman. Every video he publishes essentially becomes the most helpful resource ever made on that subject.
Whether it's losing weight, unlocking motivation, mastering sleep or using cold exposure to your advantage, the end result of watching him is an "everyman's PhD" in your own mind and body.
Purchase
DIY 4-zone mini split system
If you have an old house like our 1920s gem (complete with microscopic ductwork), I would highly recommend a mini-split system. With our old AC condenser dead on return from France, we eschewed replacing it with a standard condenser and instead, put in a 4-headed mini split. Now, we have hyper-efficient climate control in rooms that previously got nary a trickle of conditioned air from the vent. Newer systems can also heat down to -10 degrees outdoor temperature or colder. We use ours year round!
If you are handy, I highly recommend a Mr. Cool DIY system as it costs ~1/4 the price of what a traditional installation would cost.
Habits
Sauna and Ice Bath
Whether your motivation has to do with heat-shock proteins and longevity (like reducing all-cause mortality by 40%), or just embracing winter while your stress melts away, I highly recommend finding a way to access a sauna. This year, I scored a free freezer and added a cold plunge to my "northern spa" backyard setup.
Guided Lectio Divina
Slow, guided scripture meditations in the age of fast information. The ancient practice, fresh to your Spotify account every day.
Wim Hof Breathing
If you haven't yet discovered him, Wim Hof is, at his core, a crazy Dutch man obsessed with cold water and intense breathing. For years, he was viewed as a bit of a kook- until he started achieving crazy results that continue to baffle scientists to this day (he is the man who directed his immune system to kill the injected E. Coli in the "Breath" passage above). I've done the cold for years, but recently started his breathing regimen, to good effect.
Applying for Credit Cards
With mini splits and new roof bills flying at us, we've been hitting the credit card applications hard. For just a few hundred bucks, we've booked round-trip tickets for the whole family to Montreal, a ten-year anniversary getaway to Italy, and even banked up enough Air France points for a family trip back across the pond in 2024.
Going without alcohol for long stretches
Between all the emerging literature on "Alcohol and the Brain" and a few "bad reaction" type experiences with alcohol this year, I've really put the substance (and its place in my life) under the microscope. Still figuring out what I'm going to do moving forward, but the days of "drinking without thinking" are over.
Moment
La France
Have you ever recognized one of the great seasons of your life while you were in it?
For me, that was our two months in France. Pastries and swims in the old city aside, the experience of visiting my wife’s home for two years, having our moms come with for the ride, and even being "adopted" by an extremely kind French family in Arles was nothing short of magique.
If I get hit by a bus tomorrow, at least we had France. This trip was all the things we wanted it to be and more.
Thought
"What has been will not always be"
I'm convinced that navigating your thirties is a worldview-altering experience. Maybe it was two babies completely rearranging my life in an instant. Or perhaps watching those babies grow to school age and all of a sudden running off and playing with their friends. Or maybe it's just watching the slow march of time slowly chip away at everything from dishwashers to my upper back.
The steady invincibility I felt in my twenties has been replaced by a sense of frailty and temporality in my thirties. These last few years have instilled the realization that things don't last, at least not on this side of the grave. If you're my age, you might even be in the tail end in some areas of your life.
As I walked through the MIA yesterday, this painting grabbed me by the lapels:
“Springtime of Life” - Jean-Baptiste-Camille Corot, 1871
I was overwhelmed by the feeling that I can only describe as fleetingness. As I meditated on this young girl, soon to become an old woman... and now long-buried somewhere in Europe, here was the thought I journaled:
"Oh to be young again" is a sentiment I'm starting to understand, even starting to feel. For the faithless, it must be a sad thought. But for those who hope for more than this “earthly tent", this feeling is another pointer to what should… and will be.
Hope this list finds you well. Cheers to 2023.
Travel with Young Kids - How?
We’ve learned a lot on our current expedition. In honor of the five years of our oldest kids, here are five “commandments” to chisel onto the itinerary of your vacation (with some fake King James English just for fun).
1. Know Thy Family
For some parents, a 12-hour flight to Japan is a serene voyage with their little angels. The rest of us are picturing an emergency landing in the Pacific to quell the inflight cage match amongst our progeny.
Trips should stretch us as a family - but they shouldn't break us. When it comes to distance and intensity, you know where that breaking point is.
No kids in this Japan picture
The same goes for when you take your trip and for how long. With school and work, use whatever unique levers you have to make as much space as you can. Have young kids? Great - pulling them for a few weeks of kindergarten shouldn’t ruin their chance at Harvard. For work, can you do it remotely? Can you aggressively hoard PTO or take unpaid time off?
What languages do you know? What friendly uncles with far off cabins do you have? Do you like urban or rural? What kind of house setup do you need?
Once you take stock of your family’s unique limitations and advantages, preferences and desires, you should have a trip that’s all your own. Maybe that’s six months in Tokyo - or maybe it’s an AirBnB two towns over. Whatever the case may be, make sure to design your trip with your family in mind.
2. Thou Shalt Travel Slowly
If you desire to travel with young kids, you need to learn to travel slowly.
Your trips are no longer jetting around as fast as you can to see the maximum number of possible things. Slow Travel means living your life in a new place and soaking that place in deeply as a family. In addition to being more rewarding (and often times significantly cheaper with weekly/monthly rates), slow travel is much easier on little people.
Slow travel can be illustrated in the difference between the two trips to Europe that I’ve taken.
Fast Trip 1 (Pre-Kids)
11 different stays across 6 countries. Many flights, much driving.
Sllloooowww Trip 2 (Mucho Kiddo)
2 Stays in 1 Country. Spread over twice as long as trip 1.
The need for bedtimes, play, and massive amounts crap don't disappear when your kids cross an ocean. Instead, these things become more important in a new place. And just think about it for a second - do you really want to be figuring out the pack-and-play, monitor, blackout shades, and nap plans in a different spot every single day?
The biggest gift you can give your kids (and yourselves) is to stay in the same place for at least a week.
For fast-traveling sightseers this is tough (for me too - right now I’m an hour away from Italy- Italy!). But for those who are disciplined enough to limit themselves, a richer experience awaits. For our France trip, that meant that we got to know the ins-and-outs of our city - from the best boulangerie in town to the guys at the local bike shop. By the end, our kids were leading us to all our favorite spots and calling it “Our French Home”. We even made some French friends and hung out with their family on the weekends! (That’s not going to happen when you’re flying around with other tourists to all the “must-see” monuments.)
To be specific, slow travel is:
Day Trips - Check out all the cool spots around your home base
Playgrounds - Prioritize kid happiness and fit the rest (cafes, pubs, museums, etc.) after
Recovery - You can have a crazy day! But then you better take it easy the next day.
3. Pay Not for Thy Flights
You thought that trip was expensive before kids? Try multiplying everything by 5. If flights are involved, I highly recommend you travel for free.
4. Thou Shalt Prep Like a Champion (Today)
If you're currently sitting on the plane wondering if you should have brought snacks and activities for your two-year-old, then let me just say… I'm glad I'm not you.
As soon as we booked the tickets (10 months in advance), my wife immediately got real intense about travel planning.
You ain’t the free-spirit solo-travelers you once were - and you need to up your planning game. So book your Airbnb and start packing.
Personal Soapbox: Hit Pause on Idealism
In "normal times" we try to be as screen-conscious, health-conscious, and every-other-kind-of-conscious as the next family. If there’s a place to bend some of those ideals (so that you can live up to others), it is on a plane, a train, or an automobile.
So for eight hours on the flight, my wife and I gave up our ideals for a “light parental Machiavellianism” - we did anything to get us to that next airport. We brought kiddie tablets. We brought their favorite snacks and treats. We did everything shy of slipping our kids the in-flight whiskey as a sleep-aid. And we made it.
5. Bring Thou Reinforcements
We brought two Grandmas to France and it's made everything from grocery shopping to bedtimes to date nights easier and more fun. Extra hands are the difference between a crazy trip and a crazy trip that approaches (though still rarely reaches) restfulness. Because in reality, there are two options for trips with young kids:
Your Family + Big Trip = Fun, enriching, and exhausting
Your Family + Big Trip + Grandma = Fun, enriching, and less exhausting
Now, if it came right down to it, I’d still travel even if we didn’t have help, but the potential gain is worth trying for. If you don’t have grandparents who are willing and able, all is not lost.
Who in your life might be a good travel buddy? A babysitter? A kid-loving friend? A preschool teacher? (seriously - we have friends who do this) Who would be fun and helpful with little ones? Could you buy (or travel-hack) someone’s tickets and lodging in exchange for a few days of childcare per week? With a little creativity, you might be surprised how doable this is.
Summary
There you have it. Henceforth, thou, thine kin, and thy quest shalt not be vanquished!
Know Your Family. Travel Slowly. Travel for Free. Prep Like a Champion. Bring Reinforcements.
In other words, Gird Thy Loins - and then have fun, you adventurous family.
You can do this!
Travel With Young Kids - Why?
So I guess we’re living in the south of France right now.
A few weeks ago, we bid adieu to the US and chartered a plane to the land of baguettes. After a blur of trains, exhaustion-induced naps, and a fitful night of jet lag, we woke up to soft glow of Provencal sun thawing our frozen Minnesotan bones.
For my wife and I, it’s been a breath of fresh air for our "parent-tired" souls.
Resurrecting Adventure
Personally, it’s been the synthesis of two seemingly-opposing sides of me: Adventurous Brett and Parent Brett.
For Adventurous Brett, the need for big, unique experiences lies somewhere between oxygen and food. But just as I was hitting my stride with world travel in my twenties, I kicked off my thirties by having three kids in two years (Three kids. Two years. … yep).
In the blink of an eye, I transformed from world-traveling-wannabe-real-estate-mogul to housebound-changer-of-diapers. There’s been joy these last five years but let’s just say Adventurous Brett has been on life support.
So despite the real challenges that traveling with little people presents, we decided that now was the time to emerge from the “baby years cave”, peek out through our dark-circled eyes, and see if the world was still there - even though we’ve still got three kids under age six.
For some, a big trip with young kids is obvious (“OF COURSE that's a great idea. We're on our way to Patagonia with two toddlers in tow right now!") For others, particularly parents in the throes of potty training, pre-school, and all the rest, the value may be less obvious.
Isn’t a trip with kids 10x the hassle (and cost) and 1/10th the fun?
I won’t sugarcoat it - this trip is not sipping Rosé on the beach all day while my kids fan me with cool air and appreciation. But as a man who types this sentence with hot espresso in hand and a cool Mediterranean breeze on my face, I can tell you that it's been worth it. Here’s how we thought about it.
Why We Traveled with Kids (Four Reasons)
1. This is the Time!
Two super-Grandmas overlooking the Luberon Valley
In my last post, I made the point that windows of opportunity don’t last forever.
Would it be easier to travel with older kids? Maybe. Sure, flights without tantrums and minute-by-minute-needs would be nice.
On the other hand:
How long until summer basketball and can’t-miss friend birthday parties takes over? (“I don’t WANT to go to Paris! I want to go rollerskating at Jonny’s party!”)
How long will your remote work situation last? How long will credit card companies dole out insane bonuses? How long until the next pandemic/invasion/etc/etc makes your trip impossible?
How many more years will grandparents have the ability and desire to tag along?
The trip you’ve been dreaming of for your family might be easier tomorrow - or it might not.
2. Parent Space
Life is tough. For me, my thirties have been a transition from "innocence to experience".
Hint on our town: It’s where a certain famous painter famously cut off a certain hearing organ…
Whether your life includes a year with reflux-laden twins or just surviving the isolation of a global pandemic, life puts all of us through the grinder at some point.
How do you stay positive and intentional in difficult times? How do you keep your marriage afloat when date nights have been replaced by passing screaming babies back and forth? How do you avoid the learned helplessness that threatens whenever we feel a loss of control in our lives?
A book could be written on the topic of walking well through life’s difficulties (here’s a good one).
For me, a good place to start is simply with space. When we travel we get a chance not to escape our lot in life, but to step back and evaluate what our lives have become- the good, the bad and the ugly.
As I watched the sun rise over the Rhone last week, I remembered back to those difficult early days of being a parent. I reflected on how far we'd come. I asked God what might be next - and I was open to an answer.
How do you get that kind of space to work on and not just in your life?
3. Opportunity to Grow
After 20 hours of trains, planes, and automobiles, my family was exhausted. We had arrived minutes earlier in our destination city’s train station. The last leg should have been a peaceful 20 minute walk along the river to our new home. Only it wasn't peaceful. It was raining. And it wasn't twenty minutes. Turns out with kids (especially tired, wet kids) you need to triple the Google Maps estimate.
To make it with all of our luggage, we needed our boys to not only make the 1-mile walk in the rain but also carry their suitcases while doing it. If this had been a few years ago, my boys would have simply sat down on the sidewalk and cried - and we would have been screwed.
Instead, our hardy little men recognized what we needed them to do, dug deep, and they made the walk. Through soaking rain, through up-all-night-weariness, they did it. I was amazed and I was proud.
On this trip, we’ve all been forced to be flexible, try new things, and even rely on one another. This has been a major life experience for all of us.
And with shared experiences being the glue that bonds people together, what greater gift can you give your family?
4. Beware the Coast
I'm not talking about the Cote D’Azure here.
The first chunk of life is usually where all the action happens. The nature of the school years is one of constant dynamism - a constant barrage of new friends, locations and lessons learned.
Beyond the classroom, things tend to slow down. Whether it’s marriage and kids or just the slow inevitability of age, the vigorous spontaneity of youth often gives way to an unplanned, unspoken "coast" as we float down whatever stream our twenties have brought us to.
But what if it didn’t have to be that way? What if there was a way to stay flexible in the face of monotony? To stay intentional even while more and more of our days give way to obligation? What if we could reverse the shrinking of our idea of “possible” - not just for us, but for our whole family?
Traveling with kids is more than just a few fun pictures next to the Eiffel Tower. Travel jars us loose from the idea that our lives are some passive tram ride (which, let’s be honest- parenting can totally lull you into). A new place is often all that we need to remember that we are active participants on the open road of existence, partnering with God to make a difference in our families and a make dent in this world with the years that we have.
Conclusion
Have I convinced you to consider the crazy idea of traveling, even and especially with those high-maintenance love sponges we call our kids?
I hope so. But even if you are brave enough, I should tell you - there are some essentials you’ll need if you want to avoid mid-flight meltdown or regret in Rejkjavik.
That’s what we'll tackle in our next post.
Free Travel FAQ
In my last post, I introduced the concept of using credit card signup bonuses to travel the world for almost nothing. If you're like me in the beginning, you've probably got some questions and concerns. Let's take a look at some common ones.
This sounds scary. Won't this ruin my credit score?
This strategy, used over time, will help your credit score. Mine has been in the 800s for years. The fear around signing up for credit cards comes from not understanding how your credit (or FICO) score is calculated. The factors that go into your score are:
On-time payment history (35%)
% of total credit used (30%)
Length of credit history (15%)
Credit mix (10%)
New credit (10%).
After getting a new card, here’s what happens:
Small dings
Credit pull. (any time you pull your credit there’s a tiny ding). Tiny impact that lasts < 1yr.
New Credit. (because you opened new credit) Minor impact as it’s only 10%. This impact goes away if you cancel card eventually.
Length of Credit History. Minimal impact that becomes negligible if you have an older card that’s been around for a few years. This impact goes away if you cancel card eventually.
Why it goes up
On-time payment history. This is the biggest contributor to your credit score so when you pay on time with a new account you are significantly helping your credit.
% of total credit used. This is the second-biggest contributor to your credit score so when you add new credit, your score goes up (as your utilization % has just gone down).
In the end, your credit should go up. This strategy isn’t much different than what “credit repair” companies do to help their clients increase their credit score.
Who should do this?
People who:
Will for sure pay off their credit cards in full and on time.
All benefits are negated if you end up paying the insane 18% interest or spending more than you otherwise would.
Have a decent credit score
The huge bonuses require an excellent score, but if that’s not you, applying to some smaller cards/bonuses will help you get there.
Can handle some details, are flexible and willing to learn
You’re adding some complexity to your big purchase and your travel. Over time, though, you’ll be able to do it without thinking.
What do I do with the card after I've got the bonus?
You may want to keep using it. For instance, I've kept my IHG card over the years despite the $49 annual fee because they shoot me a free night every year that we use as an excuse for a fancy getaway.
For other cards, you may decide that the long-term benefits aren't worth the recurring annual fee. A good time to close these accounts is 10-12 months after applying for the card.
What if I'm not that into travel?
As much as I love to travel, I get this. After having kids, our appetite for travel all but vanished. The cool thing is that the same habits that get you free travel can also simply net you cash rewards.
Those 100,000 Chase rewards points from last year are also worth $1000 cash. Of course, they could be $2500+ in travel, but if that's where life has you, feel free to take the thousand bucks!
How crazy can I go here? (How many cards can I do at the same time?)
More than you think, but not infinite. The main rule that's come out in the last few years is the Chase 5/24 Rule. Here's the rule:
To be accepted for a Chase card, you can't have opened more than five cards (from any cc company) in the last twenty-four months.
Chase cards are usually the best, so it's good to plan around this (either 2 cards/year or a big splurge and then a long break)
Can I do a card multiple times?
For Amex cards, no (1 bonus per card per lifetime). For Chase cards, yes, after about 4 years. More details here.
Can my spouse sign up for 2x the goodness?
Yes. One great benefit of being married is that all this free travel can be doubled. When you see a good bonus, you can sign your spouse up too for 2x the points.
Do you have any more examples of how you've used this strategy?
I suppose this is where I confess to my exploits to get you fired up enough to try it.
Internationally, I’ve notched free trips to Peru, India, and Europe.
My intense 2015 spreadsheet from our free-flight, mostly-free-hotel, free-rental-car trip to Switzerland, Germany, Italy, France, Denmark, and Hungary
Domestically, I’ve logged free trips to Alaska, New York, Los Angeles (countless times), Milwaukee (countless times - kids under 2 fly free and boy did we know it), San Francisco, Denver, Florida, Charleston, and Minot.
We've used our hotel points and free nights for everything from local getaways to $600 suites in the heart of Paris.
Speaking of free lodging…
I’ve still got to pay for hotels/Airbnbs, though. Is there any way to do those for free?
After booking free flights, many will be content to pay cash for their lodging. For tightwads with remaining gusto, you may wonder: how can I get free lodging too?
There are two ways that I know:
Free Lodging Option 1: Repeat the Process with Hotel Cards
At the time of writing there's an IHG hotels card (think Holiday Inn, Crowne Plaza, and more) that gives you 125,000 points for signup - along with a free night every year. Or there’s a Hilton card that lands you 130,000 Hilton points.
If you are able to meet the spends, this creates a powerful combo of free flights and free hotels.
Free Lodging Option 2: AirBnB Your House while you're gone
By now, most of us have stayed in an AirBnB. Have you ever considered hosting while you're gone? While you're travelling, the reality is that your house is now unused. If you have time to clean it before you go (and move out any sensitive documents, etc), you could have someone pay to stay in your house, offsetting the cost of your own stay.
This option gets interesting as you may be able to net positive income from your trip (i.e. getting paid to travel).
What is the best card for frequent traveling?
For frequent domestic travelers, the holy grail is the Southwest Companion Pass.
At the time of writing: If you get the SW personal card (40k points) and SW business card (80k points) at the same time you will have 120,000 Southwest points. In the process of meeting those spends, you will add another 6,000 points. This gets your total to over 125,000 points in a year which automatically gets you the Southwest Companion Pass for the rest of the year and the following year.
The Southwest companion pass is a reusable BOGO pass for flights. When you have the pass, every flight you book with cash or with your giant point stash nets you another free ticket.
tl;dr: For those who can meet the spends early in the year (January being the best), they essentially have free travel for two years (for two people).
And you can repeat it in two years with your spouse. And then you can do it in four years again…
Isn't travel hacking harder to do nowadays?
Anyone who's been doing this for five years or more could regale you with tales from the "glory days" (ask me about my free month in Europe some time).
This is a game that's always changing and it has gotten marginally more difficult. But if I can still get a family of five to the south of France and back for nearly free in 2022, I'd say it's still a game worth playing.
Where can I learn more
This is just an intro post to an entire world of free travel. For more, check out:
(why are they always guys? What about points girls?!)
How do I parlay my big expense into free travel and help support this blog?
Just use the links on my credit card page. One card signup funds this blog for three months.
You Can Travel for Free
Learn how to play a new game…
This is a brief intermission from the “Faith in the 21st Century” series we’ve been working through. We’ll be back in the deep end soon, but for now, it’s time to travel!
Back in 2012 some friends invited me on an epic trip to Peru. I wanted to go so badly, BUT the $1300 plane ticket (plus everything else) was just too much for my starting salary. With a stack of loans taller than the Andes, I was so sad that I wouldn’t be able to make the trip. Except…
I went anyways.
The key was not “YOLOing” my way into debt, but rather in stumbling upon a strategy that enabled me to be “young, wild, and free” without going broke.
Mystery booth
Before a work flight, I noticed a credit card booth at the airport with a sign that read: "Earn 50,000 bonus miles upon signup". At the time, I ignored it (sounded too scammy).
It was only when faced with my Peru FOMO that I remembered that booth. After a simple search on the airline's website, I learned that 50,000 miles was enough for a round-trip to Cusco, Peru on those exact dates. So… I signed up for the card.
The crazy idea worked. I scaled the Andes, volunteered with a non-profit, and even rode a scooter through the Amazon. I deepened friendships and gained perspective on big decisions (I was married a year after the trip, for one).
Best of all, I did the three week trip to Peru for very little money, with no negative consequences on my finances.
Rinse and Repeat
Emboldened by my South American experience, I repeated the process. Over the last ten years, I've gone everywhere from India to Alaska. In a few months, we’ll be in France.
The thing is… I still haven't bought a plane ticket (with money).
What does this mean for you?
I’m not sure if your hobby is golf, poker, or underwater basket-weaving - but let me share another game with you. This game has rules, details, and strategy too - but it rewards you with free travel for life.
Here’s how you play.
How to Travel For Free
o. Cue: Big Upcoming Purchase
In the free travel game, you get huge miles when you spend a certain amount on a new card (e.g. $2000 in 3 months). Therefore, the process kicks off when you know you’re about to spend a big chunk of money. Rather than putting that new Peloton (or medical bill or whatever) on your standard old 1% back card, you instead get a new card(s) with a juicy signup bonus and put the big purchase on that.
For example, my big purchase last year was finishing my basement. By putting Home Depot purchases (and even my drywaller) on new cards, I realized that I could probably do a pretty big trip.
1.Pick a Destination
When you know you’ve got a purchase coming, you should pick a destination, preferably one that makes your heart beat a little faster :)
For my example, I recognized that with the size of my big purchase I could get ambitious. I asked myself: could I get my whole family to the French Riviera?
2. Create a Card Plan
Now that you’ve identified a purchase and picked a destination, we need to map a “credit card route” to get there.
Figure out your Airline Options
First, we’ll figure out how many “miles” it will take to get to your destination. Just go to a few airline sites, check “book with points”, and write down what you find. For example, here’s a 17,500 mile trip to Los Angeles.
This is Delta. Feel free to check out American, United, or any other airline that goes to your destination.
Card Options
Second, let’s brainstorm some card possibilities to earn those miles (if you’re confused, the next picture should make it clear.) To find the best card bonuses, search Google, check out my credit card page or play with the Mad Fientist’s tool.
You should now have airline options and corresponding credit card options. Now let’s play the matching game.
Here is a real-number example for an LA trip (with a box around the combo I would choose):
Lots of options, but I’d go United - and bring two friends! (50k covers 3 United tix!)
Black-Belt Example: Five to the South of France
For our upcoming France trip, the best airline option was Air France at a steep 300,000 Air France miles.
Thankfully, Chase and American Express were foaming at the mouth for new customers in early 2021 - and their points transfer to Air France. We obtained the needed miles with just three cards.
Me: Chase Sapphire (100k), My wife: Chase Sapphire (100k) and Amex Platinum (125k)
3. Apply, Spend, and Book
Ok, by now you’ve got a purchase, a destination, an airline to get you there, and a credit card (or five) to get you the needed airline points. Congrats! You’ve done the hard work. Now, it’s simply time to execute the plan.
Go ahead and apply for the cards. Don’t be nervous - we'll talk about credit scores and all that in the FAQ. You’ll be accepted on the spot or you can call them if you need to.
When the card arrives, activate it and make your big purchase! (Sign up for autopay too so you don’t forget.)
Once you’ve spent the $, your bonus should show up in your account in a few weeks.
Now go ahead and book your trip with the miles!
Oh yeah, and last step: Go!!!
Conclusion
Travel can be fun, restful, or even life-changing.
In the past, world travel required significant costs, and therefore trade-offs, with other financial goals. Today, that’s different.
Eager credit card companies have made a way for organized middle-class Americans to see the world.
If you are new to free travel, I know you've got questions. Click on the left for some answers. Click on the right to try it out (and support the blog at the same time)!
Where are you headed next?!
or to grab a card…