Thinking of planning a family vacation?
There are so many great travel blogs that can give you ideas on where to go and what to do. Today, I want to talk a little about the mechanics of planning—the behind-the-scenes steps that help make those dreamy trips actually happen.
Last Christmas break, we decided to plan a week-long vacation to the Florida Keys with another family. Both of our families had been to the Keys before, and we’ve traveled together to Universal several times. We love to travel—and more importantly, we love planning experiences that give the best bang for our buck and allow everyone to truly enjoy the time away.
Before I go any further, I want to say this:
I know not everyone is in a season where travel is possible. Life comes with chapters—some for adventure and some for simply staying afloat. We’ve had those seasons too. We’re incredibly grateful to be in a place right now where we can plan a trip like this, and we don’t take that for granted.
So, let’s pull back the curtain and talk about where to even start when you’re ready to make a trip happen—whether it’s now or sometime in the future.
Step 1: What’s Your Goal?
If you had to describe what you want to walk away with from your trip, what would it be?
Try not to include the location right away—unless that’s truly non-negotiable. Focusing first on the feeling or experience you want makes the next steps easier.
For our trip, here were our key goals:
- A house with a pool where we could cook
- A dock for boating and fishing
- A laid-back vibe with enough fun, flexible activities
- Within driving distance (we live in Florida)
Step 2: What’s Your Budget?
We’ve made a shift as a family to pay for vacations before we go—no post-trip credit card stress here. That means affordability is a top priority. But you don’t need a huge budget to have a fulfilling vacation.
A few ways we stretch our dollars:
- Split costs (we shared the rental house with another family)
- Bring groceries for meals, especially in high-cost areas like the Keys
- Cook in instead of eating out daily
- Use credit card points and perks (like travel insurance)
- Mix one big “splurge” with low- or no-cost activities
I use YNAB (You Need a Budget) to track everything—accommodations, gas, groceries, restaurants, activities, and more. It helps me see the full picture and avoid those sneaky surprise expenses.
A quick note about points: Travel rewards are awesome only if you pay your balance off each month. Otherwise, interest charges will eat up any benefit you gained.
Budgeting with your goal in mind is what makes the difference. There are lots of options—state parks, hotels you can book with points, staying with family—that can make your dream trip more doable when you’re focused and intentional.
Step 3: When Can You Go?
Like money, time is a valuable asset—and it’s often more limited.
Look at your calendar and factor in:
- Work schedules and PTO balances
- School breaks and testing windows
- Holidays and special events
- Peak travel times (which usually mean higher prices)
We wanted a full week with school-aged kids, which meant spring or summer break. You can also align your trip with holidays to maximize your PTO (I have a whole post on using ChatGPT to help you do this—link here).
Let’s Put This in Action
We already talked about our goal. Now let’s talk about that budget.
According to SquareMouth, the average cost of a vacation is projected to hit $7,249 in 2025. That’s up 11% from last year—and more than double the cost from just a couple of years ago.
That’s way more than we like to spend. We try to stretch our Fun Money (another post you can check out!) as far as it can go.
For this trip, we set a target of less than half that average for a full seven-night trip, trying to get closer to a quarter of that cost.. Our key? Looking at the budget holistically, not just per line item.
For example, yes, we spent more on the house rental—but we drastically cut food and entertainment costs because we could cook, swim, fish, and hang out right at the house. We had zero paid activities planned. Our costs were essentially:
- House rental (split with another family)
- Fuel
- Bait for fishing
- Maybe one dinner out
- A state park entry fee
Don’t forget to plan for extra expenses! Although we didn’t have paid activities planned, a few rainy days landed us at some local attractions.
Here’s the real secret:
Pick what matters most to you, and build the trip around that.
For this trip, it was the house. On another, it might be baseball games and more costly activities—balanced by staying with family and using hotel points. The key is being intentional.
Don’t Waste the Time You Hustled For
Intentional time with family and friends—time to relax, explore, and try new things—is a big part of my fulfilled hustle. I hustle so we can do this.
Sometimes it takes creativity. Sometimes it takes planning a year ahead.
For this trip, one of our friends had to pick her vacation week eight months in advance. Her husband worked extra hours (even the morning we left!) to clear the time. But we made it work—because we planned for it.
Final Takeaway
This might feel like a lot of effort for a single trip—but trust me: the best vacations start with planning.
Travel stress usually isn’t about the trip itself — it’s about where the responsibility sits. In my work, I think of this as capacity design — how everything flows and who it ultimately depends on.
Want a trip that doesn’t leave you needing another vacation to recover?
Then plan it for you:
- Plan it for your goals
- Plan it for your budget
- Plan it for your schedule
Because a trip built around what matters to your family? That’s the kind that creates real memories—and you’ll never regret making the time for it.
R