Is everyone but me taking $10,000 vacations?

I think Instagram has broken my brain.

Hi! It’s less than a week out from the election, and I’m honestly having a hard time focusing on anything! I’ve been trying to write this essay about travel since August, and I had a hole in my calendar this month, so I’m sharing it today, even if the timing feels a little weird.

This is supposed to be silly, not serious. It’s embarrassing to admit how Instagram has broken my brain! Also, I do recognize how privileged I am, and these are truly champagne problems. But I’d also be surprised if I’m the only one feeling weird about the cost of travel. 

Anyway, thanks as always for following along with my adventures at The Purse. The future might feel uncertain, but my appreciation for you dear readers never waivers! 

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In March, I took a girls trip to celebrate my friend’s 40th birthday. Unfortunately for you, this newsletter is not about that trip—what happens in Punta Cana stays in Punta Cana, right, Lil’ Danger?

Suffice to say it was an amazing vacation—I hung out by the pool and read a book, drank fruity cocktails in the afternoon, laughed ’til I cried, stayed up late dancing, and came away with a bunch of inside jokes and a few fun stories (just nothing I’m willing to share with an audience of 11,000 Purse readers).

The only photo from Punta Cana that made my Instagram grid.

The best part: It was affordable for me. Was it the most luxurious resort in the world? No. Was it perfect for a group of 10 tired women who needed a break from their kids and spouses and careers? Absolutely yes. I would say the trip was worth every penny I spent on it.

When I was weighing whether I could attend the birthday weekend, I had to have a hard conversation with myself about what I might have to forgo to pay for the trip. If I took this vacation, could we afford a family trip over the summer? And what about the anniversary getaway Ken and I had talked about? Thankfully, there were several months in between each trip, so there was time to save and plan. 

We didn’t end up taking a big family vacation this summer (for many reasons), but Ken and I are going to Northern California in December to celebrate our 15th wedding anniversary. And in planning that, I’ve found myself once again wrestling with how much to spend. The flights and rental car are one thing—there isn’t a ton of wiggle room there. But when you start looking into hotels, restaurants, and activities, the prices range from budget to billionaire. As I research the trip, I loosely know how much I want to spend, but I can’t help feeling sort of bummed about what I can’t afford. 

It’s hard to articulate exactly what I want, but I guess there’s a little piece of me that feels disappointed that I’m in my 40s and I can’t afford to stay at luxury resorts, a la some outdated Sex and the City fantasy. I’d file this feeling in the same category as how I feel about not living in an exquisitely decorated Brooklyn brownstone. The daydreamer in me wonders why my adulthood isn’t fancier. Is this the result of growing up on Travel & Leisure and Martha Stewart Living and then spending too much of my adulthood following influencers on Instagram? 

In the real world (not online), my core group of friends do not regularly weekend upstate at four-star hotels or summer in the Hamptons. They don’t spend spring break traipsing around Europe or Asia with—or without—their children. They are busy with careers and kids, and when they do travel, it’s often to visit family out of state, or to stay at their weekend homes¹, or every once in a while to take advantage of a grandparent-subsidized resort vacation (hi, it’s me). (Some do go to Disney World, but that’s another story for another day.)

Yet, my Instagram feed serves up a whole other way of life. We’re talking 20-somethings staying at gorgeous $800-a-night hotels in the Catskills, and 40th birthday weekends at the Rosewood Mayakoba, where rooms start at $1,000. (And no, it’s not all-inclusive. I googled it.) Also, who are all these people in their 30s living it up in Italy like they’re extras on The White Lotus?

Source: HBO via Giphy.

Do I sound jealous? Well, I am! And I’m also confused. I might be an adult, but there’s something about Instagram that makes me forget that it’s not real life. In my head, I truly believe everyone is staying at Rosewood Hotels, when in reality, I don’t personally know anyone who has. 

But still, how do people afford these fancy vacations? Are these trips comped or deeply discounted by PR firms? Do they have a trust fund or a rich spouse? Are they up to their eyeballs in credit card debt? (FWIW, a Bankrate survey from March 2024 found that 36% of Americans were planning to go into debt to pay for travel this year.) 

More importantly, why do the exorbitant vacations of strangers make me feel so bad about potentially booking two nights at a Marriott in Napa. My plan is not to spend that much time in the room! And these budget-friendly hotels typically offer free breakfast, parking, and Wi-Fi—meanwhile, if you peek at the prices at the Fairmont Sonoma Mission, you’ll see the luxury hotel chain wants to gouge you for all three. It just seems insane to charge for internet access when you’re already paying $500 a night for the room!

Realistically, all I need is a safe, clean, and comfortable place to sleep. Eight-hundred-thread-count sheets not required. And yet, I feel overwhelmed by the travel industry telling me I should shell out for something more expensive. I related when Rebecca Jennings wrote for Vox about her visit to Positano, Italy, in October 2022:

“Everything about the way the [travel] industry works now—booking websites, credit cards, Chase points, Instagram—makes us believe that actually, we can afford to visit a place like Positano, and that it will look just as glorious as the photos taken from the most expensive resorts,” she wrote. “Being adjacent to luxury, though, is not the same thing as experiencing it. In fact, it can make us feel bereft of something we never had in the first place, but somehow felt like we deserved.”

I’m not going to open the can of worms that is the problem with believing that we “deserve” anything (except basic human rights). But falling into a travel recommendations rabbit hole can be similar to reading too many fashion newsletters on Substack. You begin to believe that the only way to be stylish is by wearing The Row, and that the only way to travel is to stay at the hottest Instagram-approved properties. And even when you’re smart, you somehow forget that these influencers sharing their recommendations are often rewarded with free or discounted clothes and hotel rooms and dinners—benefits us mere mortals simply don’t have access to.

I don’t begrudge the influencers these benefits. They work hard. The summer I took a sabbatical from Refinery29 (a short-lived but lovely perk!), a younger colleague with a huge Instagram following was also planning hers. Our time off looked very different. While I deleted all social media from my phone and spent the four weeks with my family, she posted regular well-styled updates from her travels in Italy. It looked gorgeous but exhausting. When did she rest? I might feel a twinge of jealousy that she stays in nicer hotels, but I don’t think I want to work that hard on vacation.

Erica Ho, founder of the travel site Map Happy, pulled me out of my Instagram-fueled travel pity party when I talked with her over the summer. Erica has traveled all over the world, and she’s quick to remind me that the most Instagrammable locales are usually somewhat overrated and what you see on social channels is just a snapshot of a single moment, not the entire trip. 

Erica Ho in Castelo de Vide, Portugal. It looks so gorgeous! I want to go!

Leslie Stephens

, who writes

morning person

, agrees with Erica. I’ve enjoyed following Leslie’s recent travel adventures as she spent six weeks on an incredible trip around Asia. I asked her via email if Instagram influenced her itinerary.

“If anything, Instagram-popular locations are a major red flag for me,” she wrote. “I'm sympathetic to the pull the social media has on our attention, but one of my absolute pet peeves is when I see people visiting a once-in-a-lifetime destination, pausing to take a selfie, then continuing without taking the time to look around and actually marvel, a large reason I barely post on Instagram. I also noticed an epidemic of tripods this trip—there are people everywhere! Ask someone to take your photo and invite the possibility of connection with another traveler!”

Morning Person Travel Guides (and Exclusive Maps!) to 12 Must-Visit Destinations

Leslie also doesn’t accept trades or sponsors on her newsletter, so none of her travel is comped. She saves $500 a month in a travel fund, and she paid for her big trip (which she says costs around $10,000) out of the advance she received for her book, You’re Safe Here. It feels good to me that Leslie pays for her trips herself. As a result, it’s more likely the recommendations in her travel guides are going to be a better fit for my budget.

As Erica and I chatted more about travel, she pointed out that most people will have one travel expense they want to splurge on, and they’ll cut corners on other areas—and one of easiest ways to save is choosing cheaper accommodations. Erica prefers hotels to Airbnbs, because she feels like it’s easier to know what you’re getting (and as a single woman traveling alone, it’s easier to ensure it’s a safe place to stay). Leslie told me she spends less on accommodations so she can spend more on food.

Earlier this summer, Rufina wrote a piece in her newsletter,

Total Rec

, that stuck with me. She talked about the extended trip she took last summer, walking 600 miles around Spain, without booking hotels in advance. 

“At first, it was fucking nerve-wracking and my brain HATED the uncertainty,” she wrote. “I’d walk all day wondering if I'd end up in a place with loud snorers or bedbugs. But I got into a groove and balanced it out by treating myself to a nice hotel every now and then based on good reviews. Turns out, I was barely in my room, mostly out walking or hanging out with people I met. The uncertainty of my days stirred up a ton of irritation and amusement, turning the friction of my life into a really great story.”

We shouldn’t underestimate the pleasure we can derive from pushing ourselves outside our comfort zones—and then giving ourselves a little reward for the trouble. The end result might not be picture perfect, but it will give you something to talk about later. 

I didn’t travel much in my 20s, and I sometimes feel a bit of regret. But at the time, I didn’t know a lot of people who were jetting off to exotic locales. And I somehow missed the destination bachelorette/wedding phenomenon that seems to have a vice grip on our culture these days. When Ken and I did travel in our 20s and 30s, it was pretty modest but still a lot of fun.

There’s no photographic evidence of our NYC-to-Milwaukee road trip, so a photo of us in Tokyo a year before our kid was born will have to suffice. We didn’t stay at the Park Hyatt a la Lost in Translation, but we did go to the karaoke bar featured in the movie and sang “More Than This."

Our first big trip together was the summer we were 27 and newly engaged, road-tripping from New York City to Milwaukee for a wedding. We stopped in Cincinnati to see my high school friends, and in a cost-saving measure, we slept on the floor of my childhood friend’s apartment. One night, we woke up to see her drunk, naked boyfriend stumbling across the living room in search of the bathroom. It’s a sight I cannot unsee, and we still laugh about it. 

On the trip, our big splurge was for a nice-ish hotel room in downtown Chicago one night. We spent another night in the suburbs with family friends, who treated us to a fancy sushi dinner and tickets to Cirque du Soleil. When we finally arrived in Milwaukee, we stayed at the same bland Holiday Inn-esque hotel as all the other 20-something wedding guests. As I remember it, the rooms were fine, and it didn’t matter anyway, because we didn’t spend any time in them. We were too busy at the wedding and then at the bar down the street for the after-party. 

Of course, I’m no longer a 20-something, and the idea of sleeping on the floor of a friend’s apartment sounds like murder on my back. Still, I hope I’m not too old for a good high-low travel adventure. I’ll just have to get over the fact that my high still taps out around $300 a night. Oh well. 

When it comes down to it, I really want to take the trip, and ultimately the accommodations are not that important to me. Yes, it looks luxurious to stay at a five-star hotel, but getting a room at the clean and efficient two-star bed-and-breakfast is better than staying home and way better than going into debt. And I’ll probably get a few good stories out of it.

I want to know: How do you budget for your trips? And what do you prioritize?

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