If you’re planning a trip, then this week’s guest author is for you. Stacking paper is thrilled to partner with Henah Velez, author of Departure. Her travel articles range from fighting jet lag, the magic of traveling slow, and how she’s making it all happen financially.
We’ve all been there. You work tirelessly to get to a good financial place, and then the moment you have some semblance of savings, bam: You’re added to the “Greece 2027” group chat. Time to pour one out for your bank account.
Don’t get me wrong, as someone who lives to travel, even suggesting a trip will get my wheels turning with ideas. But the reality is more complicated than a simple “I’m in—and I’ll start the trip spreadsheet!”
Over the years, I’ve been to more bachelorette parties than I can count, alongside group trips with friends, family, my partner, colleagues, and even strangers as roommates on boutique tours. As I’ve honed my own approach to travel (depth over breadth, less party vibes and more local living, investing in thoughtful experiences), I’ve also come to terms with understanding who my best travel partners are and what’s worth considering before agreeing to a trip. Because was the trip worth it if you come home miserable, ready to be alone, and with hundreds of dollars in unexpected expenses?
So first, we’ll cover what to ask yourself before committing, and then how to set yourself up for success—let’s go. 💪
Part 1: What to Ask Yourself Before Saying Yes
Travel offers you the chance to widen your perspectives, whether you’re going on a weekend road trip an hour away or a three-week jaunt across Southeast Asia.
But… your time away isn’t just influenced by the destination or the culture; who you choose to spend it with can also make or break your trip (and I’m speaking from experience)! For that reason, I usually only travel with my husband, best friend, or trusted small friend groups nowadays.
Here’s what I ask myself now before I say yes:
Do I want to go with another person or group, or is this a good opportunity for a solo endeavor? I sometimes prefer time alone to recharge or to push myself out of my comfort zone, but most of the time, I’ve learned I like to be with one other person. As an introvert, larger groups often overwhelm me, but I’m open to it if it’s for someone I love (read: every bachelorette).
What is their travel style versus mine? What are everyone’s expectations around how the trip will go down?
Do they prefer early mornings, super late nights, somewhere in between? I myself lean towards sleeping in a bit, being up and at ‘em by 9:30-10AM, not staying out too late…and you definitely will never catch me on a sunrise hike at 6AM. But do you!
Are they easy to share a bedroom or bathroom with? Am I? Everyone has different expectations around cleanliness, personal space, and comfort. Will your travel partner tolerate blackout curtains or white noise machines? Can they only sleep in pure silence, or will your snoring be a dealbreaker? Is 70 degrees going to feel too cold for them?
Are they open to trying new cuisines, or do they prefer to stick to the creature comforts from home? Are they willing to find spaces that can accommodate my vegetarian needs, and/or am I okay with their own dietary restrictions? Based on past experiences, I know I prefer to be with travelers who like to sample new flavors or even take local cooking classes.
How do they like to let loose on vacation? I love a ‘00s pop music night and a delicious cocktail, but I’m not a big drinker or rager. Conversely, if my plantar fasciitis is acting up, I try to take the time to find a soothing treatment—will that be terribly inconvenient for my travel partner’s plans? Will any chronic illness flare-ups I deal with derail their plans or sow resentment?
What’s their budgeting philosophy around travel? I spent years in the world of personal finance, so I’ve heard many a story of friends who’ve fallen out over money after a trip. (Ask me one day about two friends who came home from a group trip with a $17,000 credit card bill!) The beliefs we hold about money are deeply personal, and it’s vital to make sure you’re on the same page with your travel partner prior to accidentally booking the penthouse suite.
Do you require a set budget for a trip, or will expenses be more fluid? At the very least, I like to go into a trip knowing a general scope like “I’m setting aside $1,200 for this four-day visit to New Orleans, because I will be eating my weight in beignets and at the jazz clubs.”
What’s the vibe for our transportation and accommodations? Are you hoping to: ball out in first class and level up your hotel stay, be more low-key at a boutique hotel, or book a shared hostel situation?
Do you want your own bed, or are you willing to split a room (or sleep on a sofa-bed) to lower costs? My friends who aren’t in relationships often find themselves paying the “singles tax” here, so I suggest splitting the overall accommodation cost per person, rather than by bedroom.
What’s the deal around food? I’ve traveled with friends who like spending every meal at casual fast food restaurants, and those who dig a Michelin-level dining experience with expensive tasting menus for a special occasion. I’ve also been stuck splitting the bill on group trips where I only had an appetizer and water, while others ordered two to three rounds of drinks and multiple courses. In those scenarios, I’m usually okay to split as long as I know and prepare financially—so it’s a question worth asking ahead of time!
Additional considerations might be around tickets and passes (like multi-day passes to a music festival, or at a theme park), unique experiences like custom tours or club reservations, or if you’re celebrating a special someone and want to cover part of their expenses.
TL;DR: Who’s the YOLO-style traveler, and who’s more of a strict budgeter? Do you want slower travel like me, and your friends want to visit three cities in one week? And ultimately, are we okay with mixing these financial scripts?
Look, I’m not saying to show up with a checklist the moment “Greece 2027” starts popping off, but pausing to ask these questions will save you a massive headache later.
Part 2: How to Set Yourself Up for Success (Financially, Emotionally, Etc.)
As a #PersonalFinanceNerd, I know I’m one of the few people who loves a spreadsheet (I am who I am), so I’m happy to take this on for most of my trips.
Prior to travel, I usually log what the expense is, the projected cost to know what to expect, the actual cost when booked, who booked it, the payment date, and if it’s been paid back. This lets me know how my budget is shaping up and where I might have more wiggle room once we’re there for last-minute expenses or splurges.
I also love racking up credit card points, so I’m typically the first person to offer booking any and every expense (and if I’m on my way to a solid sign-up bonus, even better!), but in general, I think it’s safest to have each person in the group be responsible for one major expense like accommodations or dinner reservations.
Once anyone from the trip starts racking up costs, I recommend dropping them both into the spreadsheet and into an app to track and simplify expenses amongst friends. That makes settling up at the end way easier than manually doing the work—which you can do with a service like Zelle or keep it simple with cash.
Here are a few other tips I recommend to make the economics of a group trip a little bit easier:
The second you have an inkling this trip might actually make its way out of the group chat: Start figuring out your savings plan. You never know how early people will start booking, and you want to be prepared when those notifications pile up like a landslide.
Between you and me, I find most people have no clue about special credit card offers on their premium cards—and you can find some really worthwhile savings there. For example, when I casually checked my card offers on the Chase Mobile® app, I noticed there was a hotel chain that gave me a substantial amount back on an upcoming stay. You could theoretically book with three friends, and have your portion fully covered by your credit card perks. Or, if you’re more generous, you could apply those savings to the original balance and split the remaining bill four ways. Always check!
Several years ago, a friend of mine booked me on a trip using her family’s points because she needed a travel buddy (#dreamcometrue), but when my flight was cancelled over two days, my travel insurance didn’t kick in because the booking wasn’t under my own name. So make sure you understand what travel insurance or coverage you have available, and how it applies to you if you have shared reservations with folks.
Communicate expectations around paying each other back ahead of your trip. No one wants to be the downer on the last night of vacation saying, “Don’t forget to settle up with Zelle tomorrow!” Instead, as you inch closer to your departure date, you can simply send a message like, “I’m firming up all of our shared expenses and my credit card bill will be due on the 21st. Can we all agree to settle up by the 15th, so I can pay off my statement in time?”
Finally, remind yourself that it’s okay to say no. You might opt in to most activities but decide to hold back for budgetary reasons or simply personal preference (remember the sunrise hike I refuse to do?). Setting the boundary to say “I’ll fly in for the trip and will join every dinner, but I’m skipping the four-hour walking tour” is A-okay in my book.
Being able to travel with friends and family is a gift—but the next time your group chat lights up with, “Santorini or Mykonos in August? Peak season, but YOLO lol”, take a second before responding “Hell yeah!” I promise it’s worth pausing.
Ask yourself the questions; be honest with your answers. Decide what you’re actually opting into, and if the math will be mathing at the end of it.
Because, if you plan it right, you could be lying on a beach in Greece next year—and come back with incredible memories, a healthier bank account, and stronger relationships with the people you love most.