Savvy Talks: How are People Affording These Summer Trips?
(Spoiler: It’s not all Aperol and private jets.)
You may have noticed that your social feed is suddenly filled with sun-drenched European rooftops, sparkling beaches, Aperol spritzes, and people casually living their best lives abroad. So naturally you ask:
“How is everyone affording this?”
Trust me, you’re not the only one wondering.
Behind those filtered, perfect-looking vacations is a lot more strategy—and reality—than you might think. Some folks really do have deep pockets (or generous travel perks). But for the rest? There’s a wide mix of tricks, tradeoffs, and occasionally… a little debt.
So let’s break it down.
1. They’re Prioritizing Travel Over Everything Else
Travel isn’t about being rich—it’s about choosing it. Many people are cutting back in other areas—eating out less, skipping new clothes, driving old cars—so they can afford one amazing trip.
2. They’re Obsessive with Credit Card Points
From airline miles to bonus sign-ups, a lot of travelers are experts at playing the points game. Tools like PointsYeah or cards like Chase Sapphire help them fly, stay, and upgrade—for free. It’s a whole subculture, and yes, we’re asking our friend Rob way too many questions.
3. They Work While Traveling
Remote work has changed everything. People are extending business trips or working abroad—like our son, who’s currently working full-time from Italy. His workday starts at 5pm, which leaves the whole day for pasta and piazzas.
4. They Plan Way in Advance—and Save Like Crazy
Some treat vacation planning like a second job. Booking flights 8–10 months ahead, setting travel alerts, watching deals like hawks, and saving every spare dollar. It’s methodical—and it works.
5. They’re Strategic About Hotels
One trick? Book the cheapest room at the fanciest hotel. You still get the spa, the pool, and the concierge—but at a much better price. Others use (often free!) travel agents to score perks like free breakfast or room upgrades.
6. Someone Else Is Paying
Some are tagging along on their partner’s business trip. Others are staying with family abroad or—let’s be honest—traveling with someone more financially flexible who wants them along for the ride.
7. They’re Doing House Swaps or Skipping Rent
Platforms like HomeExchange let you swap homes with someone across the world. Some sublet their place while they travel. Others time trips between leases and live rent-free for a month.
8. Side Hustles + Freelance Freedom
Freelancers and content creators are designing their lives around mobility. For them, work is travel—and vice versa. Sponsored content, remote clients, or flexible gigs make those dreamy destinations part of the job.
9. Social Media ≠ Reality
That dreamy cappuccino-in-Rome shot? It might be coming from a tiny Airbnb with one towel and no AC. What you see online is curated. Most vacations look way more luxe than they actually are.
10. They Might Be in Debt
Yup. Some people are just putting it all on the credit card. They’ll pay it off later—or not. It’s not ideal, but for many, the memories feel worth the interest.
11. They’re Just Wealthy
Let’s be real—some people just have money. They travel all the time, they post all the time, and they’re very visible. But they’re not the norm.
Bottom Line:
It might look like everyone’s on a yacht in Greece, but that’s just the internet. Some are saving like mad. Others are strategic, scrappy, or simply lucky. And some just have good ol’ fashioned cash.
Listen to the talk:
Originally aired on 08/01/25 for WGN Radio 720.