You know where you want to go and why. You’ve got goals, dreams, maybe even a Pinterest board. Now it’s time to tackle the unsexy but oh-so-necessary question: how exactly are you going to get there and (fingers crossed) back again?
In my book, travel planning splits into two camps:
Time-constrained travelers. Those still chained to school calendars, bosses with Outlook fetishes, or PTO balances that vanish faster than gelato in July.
The blissfully unconstrained. Retirees, solo business owners, or anyone who can disappear for three weeks, without anyone but their cat noticing.
I’m talking here about the second group—because that’s me. But the strategies work for both, so lean in.
Economy? Not today, Satan
Let’s rip off the Band-Aid: I am not flying long-haul in economy. Not. Happening. I’ve done my time in the sardine tin, knees jammed, seat reclined into my eyeballs, praying for unconsciousness that never comes. The result? Landing in Europe looking like I’ve been steamrolled.
So, unapologetically, I go for first or business class. These days, they’re basically flying cocoons—lie-flat seats, actual bedding, and enough privacy that you could have a mid-air existential crisis without anyone noticing. Do I emerge in Rome looking like a Dolce & Gabbana model? No. But at least I’m functional instead of feral.
Points are my love language
Can I afford to drop five figures on a ticket? Cue hysterical laughter. Hell no. Enter the points game.
TL;DR: it’s possible, and it’s deliciously satisfying when you “pay” for a $6,000 seat with a pile of digital Monopoly money.
Back in the day, loyalty meant racking up miles one sad pretzel packet at a time. Now? Banks practically fling points at you if you so much as breathe near their travel cards. American Express, Chase, Capital One—pick your sugar daddy. Opening one of their travel cards comes with a pile of points, provided you spend x dollars in y amount of time.
If you want to play the points game successfully, I recommend working with Travel on Points, because the rules make Dungeons & Dragons look straightforward. These experts have webinars, a solid Facebook group, and the patience of saints.
Deal-hunting without losing your mind
Some people treat flight deals like fantasy football. I’m not that hardcore, but I do like an occasional win. My tools of choice:
Thrifty Traveler Premium – sends me “drop everything” emails about points deals.
Google Flights with the Points Path extension – lets me sanity-check and cross-compare.
(Need more details? Check this out.)
The rule here is flexibility. Maybe you don’t fly there from your home airport. Maybe you don’t land exactly where you planned. It’s a little like speed dating: lower your expectations, stay open-minded, and sometimes you’ll land The One.
Case in point: I’m flying first class with Iberia from Boston to Madrid on a great points deal. Do I live in Boston? Nope. Am I staying in Madrid? Also no. But this is the best points deal for the date I want to travel, and I found a points flight from San Francisco that linked up nicely to the Boston flight. Voilà. Add a hop to Rome, and I’m golden.
The get-me-there itinerary
San Francisco → Boston (stop in Phoenix for good measure) – October
Boston → Madrid – October 2, arriving bright and hideously early on October 3
Madrid → Rome – later that day
Bonus! My Boston friend Rachel is fetching me from the airport at midnight, feeding me, and throwing me into bed before my next flight. Everyone needs a Rachel.
When airlines play the hokey-pokey
Book early, they say. Lock it in, they say. And then the airlines do the hokey-pokey and switch everything up anyway. Planes swapped. Departure times shifted. Seat assignments nuked.
My flights both changed. Now I leave San Francisco at noon (instead of 5:30 pm) and Madrid at 4:30 pm (instead of 9:30 pm). Meaning a ten-hour Madrid layover. Ugh. Coffee, tapas, repeat…especially the coffee. I’ll hit Rome around 7 pm and walk to my room at the Rome Airport Hilton to get some shuteye before heading to the train station the next morning.
Don’t let this freak you out. Still book early. Then expect changes and build flexibility into your plan. That way, when the likely event happens, you’ll curse less loudly in public.
Cruise control: my return ticket
Fly out, cruise back (or the other way around)—that’s my favorite combo platter. I booked Virgin Voyages’ fall transatlantic from Barcelona (October 26) as the first leg of getting myself back home.
If you’ve never floated across the Atlantic with bottomless food, entertainment, and hot tubs, it’s worth trying. It’s like rehab for jet lag. (That article I mentioned earlier? It’s got cruise stuff too.)
Not a Virgin fan? No problem. Lots of lines do transatlantic sailings. Check Cruise Plum; they’ve got itineraries and deals galore.
And that’s the story
Fly on points + cruise back = maximum joy, minimum wallet pain. If you’ve got the time, I highly recommend it.
Stay tuned for my next installment: (drumroll, please) the Big Luggage Controversy. Sneak peek: it involves me, a suitcase, and a bit of drama.
I agree! Naps are good for your health! Especially your mental health! 😆