How to plan a vacation
An exercise to pay for the trip you want and become a better financial team.
Every summer, millions of Americans hop off their hamster wheel for a vacation.
These core family memories don’t come cheap. According to NerdWallet’s 2026 Summer Travel Report, 45% of Americans expect to spend an average of $3,940 to take a trip that requires a flight and/or paid lodging this summer. But before you spiral down an “everyone’s in Spain but me” rabbit hole, let me share some cold hard financial truth that might make you feel better—or not, depending on whether this is you.
Out of the 2025 travelers who put their travel expenses on a credit card, only 26% paid off their balance on the first statement. Six months after summer, when this year’s travel report was published, more than one-third of vacation credit card users had still not paid their balance off. What this means is that many families are holding onto the financial consequences of their decisions long after their tans fade away, allowing high-interest debt to bleed into this year’s vacation planning. You may feel like scratching the vacation itch is worth it, but the perpetual cycle of “book now, worry about it later” is the type of hamster wheel behavior you can’t pause with an OOO message. The stress and insecurity move in like a rain cloud over your all-inclusive resort—if not this time, then next time. If not for you, then your partner.
Doug and I get asked all the time how couples can get better at managing money together. Not just the theoretical stuff I love to wax poetic about, but what you can do this very month to become a stronger financial team, especially when one of you would rather do literally anything else than talk about money.
Don’t start with something you dread.
Start with something you both want.
Like a vacation!
When you have a shared goal that you’re excited about, you naturally begin practicing the behaviors that make every other financial goal possible. You communicate. Prioritize. Make tradeoffs. Save consistently. Adjust when life gets in the way. The muscles you’ll use to plan a vacation are the same you’ll use to buy a house, pay for college, or invest for retirement. The vacation is just a practice run with a very tangible, near-term reward.
The key, of course, is making sure the vacation fits in your financial life instead of derailing it. We want it to feel like proof that the two of you can work toward something together and enjoy it without sacrificing your stability and sanity in the process.
If you’ve been thinking about planning a vacation, run through this exercise at your next money date. And if you’ve never had a money date, well…maybe planning for something positive, like this, is the place to start.
1. What is our goal for this vacation?
Before you dive into any research or logistics, sit down together and talk about what you’re trying to get out of this trip. It’s kind of like a vacation thesis.
Does your family need rest, or are you looking for your next adventure? Are you hoping to spend time with the grandparents or reconnect as a couple just the two of you? Is this a milestone celebration or just some respite from cold weather?
Choosing your destination comes second to making sure you’re on the same page about the purpose of traveling, because once you are, you will back into more mindful decisions that align with that purpose. It’s also a great time to understand how everyone’s feeling at home and level-set your lifestyle expectations.
For example, we take the girls to South Florida during winter break every year to see Doug’s family. Over this peak week, hotels and flights are astronomical, and the weather is a crapshoot, but our purpose is really to drive around and see loved ones and friends. So, we don’t book an expensive beach resort, because we probably won’t get to use it. We stay in a corporate hotel in the middle of the action that’s convenient to the places we need to go. It just makes more sense.
A more expensive vacation isn’t automatically a better vacation if you’re paying for things you won’t use.
2. How much will it cost?
Okay, now it’s time to DYOR (that is, do your own research). You want to make a reasonable effort to understand the full cost of your desired vacation.
This warrants more than a quick scan of your airline app. If you’ve got flexibility, check multiple arrival and departure dates. If you’ve got optionality on hotel or room type or even the destination itself, understand the price differentials. The goal of this isn’t to race to the bottom for the cheapest trip possible but just to understand how much you’d be paying for what you’d be receiving.
Don’t stop with travel and accommodations. Think broadly about other costs and less visible expenses that will arise, depending on where you’re headed. Will you need to dine out for every meal, or are you looking for accommodations with a kitchen? Will you be walking, renting a car, ride sharing, or never leaving the resort? How about activities—are they included, or do they deserve a separate line item? Will you be shopping? I mean…shopping shopping?
For a host of reasons, you may wish to purchase travel insurance, and that comes at a cost, too.
If putting this much effort into researching a vacation is overwhelming, you’ve got options. Cruises, all-inclusive resorts, and pre-fab vacation tours will be more straightforward from a cost perspective, so at least you know what you’re biting off. You can also review your existing membership programs for travel packages (i.e., American Express, Costco, AAA). Lastly, you can consider using a travel agent who probably has insight on these cost-to-value decisions and might even have access to exclusive rates and deals.
Again, the point isn’t to value-maxx yourselves into the cheapest option but to understand how much the trip you want to take will actually cost.
3. When do we want to go?
Timing is everything, and when you travel is as much a financial decision as where you travel.
If you are beholden to the school calendar or a particular work schedule, there might be less you can do to avoid peak travel windows, which means higher costs overall. This is why timing matters not just in the context of how expensive flights and how busy the airports will be, but how long you have to financially prepare for the trip.
Let’s say you’re planning for spring break next year, so you’ve got about seven months. Assuming you’re within the realm of reason around what kind of trip you can afford (more on that next), you’ve got runway to implement any changes you’d need to make to have the funds available when you need them. In other words, putting the vacation on the calendar creates a time horizon for your financial goal. Then, you can begin to figure out what you’ll need to do get there.
4. How will we pay for it?
This is where the teamwork really happens.
Start by asking whether this vacation already has a place in your financial life:
Do we have cash set aside specifically for travel?
If not, would using some of our available cash reserve leave us comfortably prepared for emergencies? (Remember, we aspire for you to hold at least six months of living expenses in cash!)
Where does this vacation fit alongside our other financial goals?
These aren’t questions with one right answer. We’re not here to tell you that you should never reduce your 529-plan contributions for a year so your family can take its first meaningful vacation together. That’s a values decision everyone needs to make for themselves, which is why talking about it from an educated standpoint, with the numbers right in front of you, is so critically important. As a couple, you want to make conscious decisions together. One of you can’t just trip and land on a lounge chair with a $7,000 price tag.
When you don’t have enough cash available for the vacation you’re looking to take, turn to your budget.
If you’re consistently running a surplus every month, awesome. How much of that do you want to direct towards this goal? If you’re just breaking even on your living expenses or running a deficit, that’s a different conversation. You can’t build a vacation fund with money that doesn’t exist.
This is when you discuss what’s within your control. Are there areas of spending you can temporarily cut back on? Is there a way for you to earn additional income specifically for this purpose? Maybe you just need a longer runway and should aim for 2028. Whatever you choose to do, make the plan together so that you can always remember you’re working toward something you both agreed on and want to happen.
In terms of mechanics, we don’t believe you necessarily need a separate high-yield savings account to earmark your vacation funds, but if it creates more visibility and helps you stay motivated, go for it. This might even be a really good idea if one of you has historically been disengaged from money conversations in your relationship. Consider it a baby step toward more meaningful work in other areas of your financial life.
Planning a vacation might be discretionary but it isn’t trivial. You’re learning how to work toward a shared goal. This is a chance to practice handling money together by: identifying what you want; estimating the true cost; agreeing on a timeline; and making intentional tradeoffs about where your money should go.
Next time, the goal might be bigger, and the stakes might be higher. Hopefully, you’ll rely on these same practices no matter the destination, because the teamwork comes home with you every time.
How do you save for your next big vacation? Share your best tips with us!
This was a big one for me. For the past seven years, I had been paying between $1,600-$2,400 annually to see a concierge primary doctor with MDVIP in our town. Though we neither had a strong nor trusting connection, the convenience of having a doctor return my calls, run bloodwork, and fit me in for same-day visits was very important to me, as someone with a history of chronic and sometimes scary autoimmune issues.
But over time, his annual membership costs rose, as did our health insurance premiums when I left Corporate America and joined Bone Fide Wealth. I began to feel like my chapter of extreme health anxiety was coming to an end, and I am in a much better place to navigate traditional healthcare systems with confidence. I also want to build a team of healthcare professionals that can help me navigate midlife as a woman. So, I’m taking my chances with a new female primary doctor who is in-network. Physicals are free. Sick visit co-pays are $20. Her office staff seems lovely and responsive, and that’s half the battle. We’ll see how it goes, but I am feeling very confident for now. -Heather
Want to go deeper? Money Together is everything we’ve learned about love and money, told through real stories with lessons for people who want to build a financial life together without losing themselves in the process. Order your copy on: Amazon, Barnes & Noble, Bookshop, or Audible (narrated by Heather!).
Love it already? A review on Goodreads and wherever you purchased helps other couples find us and means more than you know.
Bring us to your organization! We speak on money, relationships, and what it really takes to build a financial partnership that lasts. Available for corporate events, conferences, and private engagements — virtually and IRL. Reach us here.
Connect with us on social: @averagejoelle + Douglas A. Boneparth
The content shared in The Joint Account does not constitute financial, legal, or any other professional advice. Readers should consult with their respective professionals for specific advice tailored to their situation. The information contained in this post is general in nature and for informational purposes only. It should not be considered as investment advice or as a recommendation of any particular strategy or investment product. This post is not a solicitation or an offer to buy or sell any specific security. Bone Fide Wealth cannot guarantee the accuracy of information from third parties.