Vacation Planning Done Right: The Membership Stack

Monthly Money Man on June 12, 2026

Part 2 of a 4-Part Summer Series

Most people do their vacation planning and then figure out what it’s going to cost them. I do it the other way around.

Before I book anything, I ask one question: what memberships do I already have — or could I get cheaply — that make this trip dramatically less expensive?

It sounds like a small shift. It isn’t. Over the years this habit has saved our family hundreds of dollars every single summer, often turning a trip we thought was out of reach into something completely affordable.

Today I’m walking you through the memberships worth considering and a planning approach that will change how you think about family vacations entirely.

The Membership Stack

Think of these as tools in your pack before you hit the trail. Each one costs something upfront. Each one pays you back — often many times over.

The National Park Pass

If your Layer 1 or Layer 2 plans involve any national park, this is a no-brainer. The America the Beautiful Annual Pass runs about $80 and gets you unlimited access to every national park in the country for a full year. One visit to a national park typically runs $20–$35 in entrance fees. Two visits and this pass has already paid for itself.

If you spend more time in your state’s park system, look into your state park annual pass. Same concept — one flat fee, unlimited access, done.

Scenic view of Yosemite National Park valley with granite cliffs and pine trees

The Zoo Pass

Here’s one most families don’t know about. Many zoos across the country are members of the Association of Zoos and Aquariums — and if your local zoo is a member, your annual membership pass gets you free or discounted admission at hundreds of other zoos nationwide.

I actually built a zoo bucket list for my boys during their childhood — specific zoos I wanted to hit across the country. We checked them off one by one. Our entrance fees were free nearly every time because so many of the best zoos in America are part of this network. Check whether your local zoo participates before your next renewal.

The Museum Pass

Same idea, different world. Many local museums belong to reciprocal membership networks that give passholders free or reduced access to hundreds of participating museums across the country. If you have a curious family — or if you’re doing any kind of thematic trip planning (more on that in a moment) — this pass can be extraordinary value. Check what your local museum is affiliated with and what that membership unlocks before you write it off as just a local perk.

The AARP Surprise

Here’s one that catches people off guard: AARP doesn’t require you to be a certain age to join. Membership is open, and it comes with a long list of travel discounts — hotels, rental cars, and more. If you travel even occasionally, it’s worth a look regardless of where you are in life.

The Thematic Vacation

Now here’s the part I really want you to think about — because this approach turned our family trips from good to genuinely unforgettable.

Instead of planning a vacation around a destination, try planning one around a theme.

When we were homeschooling and studying the history of flight, we didn’t just read about the Wright Brothers. We went to Kitty Hawk and Kill Devil Hills in North Carolina — where they actually did it. We flew kites on the same stretch of coast where they studied wind and lift. We walked through the Wright Brothers National Memorial. We camped on the beach for a week and spent evenings doing flashlight hunts for ghost crabs in the surf.

Every single activity connected back to the theme. The kids weren’t just on vacation — they were inside the story.

This works for any interest, any age, any budget. Is your family into wildlife? Build a trip around a national park known for animal sightings and pair it with a member zoo stop on the way. Into history? Pick an era and find the place where it happened. Into space? There are NASA visitor centers in multiple states, most of them free or nearly free.

The thematic approach also solves one of the biggest vacation problems families face: what do we do today? When everything connects to a central idea, the itinerary writes itself.

Putting It All Together

Here’s how this connects back to last week’s layer system.

Take your Layer 1 — your Summit experience for the summer. Now ask:

Is there a membership that reduces the cost of getting in?

Is there a theme I can build around this destination that would make the whole trip more intentional and memorable?

And for your Layer 2 experiences — your mid-range adventures — run the same questions. A zoo trip with a membership pass. A museum visit that’s free because of your reciprocal card. A state park afternoon that costs nothing because you bought the annual pass in January.

The memberships do the heavy lifting. The theme does the rest.

Your Assignment Before Next Friday

Pull up your Layer 1 and Layer 2 lists from last week.

For each one, ask: is there a membership that could reduce or eliminate the entrance cost? Do a quick search on your local zoo, museum, and state park system. See what networks they belong to and what a membership actually unlocks.

Then spend ten minutes thinking about theme. Is there a subject your family is curious about right now — history, nature, science, art, adventure — that could become the thread running through your biggest trip this summer?

You might be surprised how quickly an expensive-feeling trip starts to look a lot more affordable.

Next week we’re going deep on points travel — how I flew my family to Costa Rica for about $30 a person, and how you can start building toward the same kind of trips.

You’ve got the system. Now let’s sharpen the tools.

See you at the top.

Summer Spending Done Right

Monthly Money Man on June 5, 2026

Part 1 of a 4-Part Summer Series

Last summer I rappelled down a waterfall in the Costa Rican jungle with my boys. The flight there cost us about $30 a person.

I’ll explain that in a future article — because points travel is a whole conversation worth having. But I mention it because people around here ask me some version of the same question every spring: “So, what do you have planned this summer?”

I’ve built a bit of a reputation as the dad who always has a plan. What most people don’t know is that I built this system about fifteen years ago, when the Summit was a camping trip two hours from home and the budget was tight. The system didn’t change as our finances improved — it just had more to work with.

That same summer we hit Costa Rica, we also grabbed some kayaks with a few friends and spent an afternoon floating a local river. At one point, a beaver swam right up alongside our kayaks. The kids still talk about it. That trip cost almost nothing.

And one evening, we took my mom to the free airshow at the local airport and watched jets light up the sky.

Three very different experiences. One summer. One budget. One system.

Today I want to walk you through it — because whether your summer spending budget is $500 or $5,000, the same approach works.

What Most Finance Experts Get Wrong About Summer

Spending money on experiences doesn’t get a lot of love in the personal finance world. Some experts treat it like a guilty pleasure — something you do after you’ve checked all the responsible boxes.

I disagree. Respectfully, but firmly.

We’ve spent the last six months building your foundation together — safety nets, debt strategy, investing basics. That work matters. But so does this question: what is the point of climbing if you never stop to enjoy the view?

Your kids are growing up. Life is short. You’ve worked hard, and summer is one of the few stretches of the year where the whole family has space to breathe together.

Planned, intentional summer spending on experiences isn’t a detour from the climb. It’s part of it.

The Three Layers of an Epic Summer

I take whatever summer budget we have and sort it into three layers. Every year, same system.

Layer 1: The Summit

This is your one big bucket list experience for the summer. The thing you’ll talk about for years.

It doesn’t have to be international — it just has to feel epic to your family. A national park road trip. A week at a lake cabin. A camping adventure somewhere you’ve never been. One per summer. Give it the budget it deserves, and if you can, book it early. Prices are almost always cheaper in January than in June.

Layer 2: The Day Hikes

These are your medium-range experiences — memorable without being extravagant.

A kayak trip down a local river. A weekend at a waterpark. A baseball game. A day trip somewhere new. These fill the calendar between the Summit and everyday life. Aim for two or three depending on your budget, and don’t underestimate them. Some of our best memories have come from a $40 afternoon on the water.

Layer 3: The Boredom Busters

This is where the magic actually happens — and it’s the layer most families skip.

Boredom Busters are the low-cost, high-creativity activities that fill in all the gaps. A free airshow. A neighborhood game of flashlight tag after dark. A new set of pickleball paddles. A backyard movie night. Fireworks at the park with grandma.

These aren’t filler. They’re the connective tissue of a great summer. When there’s nothing big on the calendar and the kids are starting to melt into the couch, you pull from the list — and suddenly the day has a plan.

The families who have an epic summer aren’t always the ones with the biggest budget. They’re the ones who never run out of ideas.

Your Assignment Before Next Friday

Here’s what I want you to do this week.

Set your summer budget. Sit down and figure out what you realistically have available for summer fun. Not what you wish you had — what’s actually there. If the number is $1,000, that’s a solid Layer 2 experience and a full Boredom Buster list. That can be a genuinely great summer.

If money is tight this year, lean hard into Layer 3. Free festivals, library programs, state park trails, an airshow, a river walk. Summer doesn’t have a minimum spend requirement — but it does reward a plan.

Then make your three lists. Dream a little. What would your Summit look like this year? What are a couple of Day Hike ideas your family would love? And start a running Boredom Buster list you can pull from all summer long.

Don’t overthink it. This is supposed to be fun.

Next week we’re getting into vacation planning — how memberships, timing, and a little strategy can make a real trip more affordable than you think. It’s one of my favorite topics, and I think it’ll change how you look at summer expenses going forward.

You’ve done the hard work this spring. Now let’s make sure you actually enjoy the climb.

See you at the top.