With three days left in the school holidays, we packed the car and explored Oamaru and Dunedin, New Zealand using a planning system that removes the stress and keeps the focus on fun, family, and discovery.

⏱ 5-7 min read

How I Plan a Weekend Family Road Trip (in a Few Hours, Not a Few Days)

A few days before the end of the school holidays, we realised something.

We’d just spent weeks hosting Christmas, I’d disappeared into the mountains for a week-long hike, and suddenly the holidays were almost over.

We had three days left.

We could stay home… or we could go somewhere new.

So we threw together a last-minute road trip from Christchurch to Oamaru and Dunedin with our two kids (8 and 10) and it ended up being one of the highlights of the summer.

Not because it was perfectly planned.

But because we’ve built a system that lets us move fast.

The goal: exploration, not optimisation

We’ve lived in Christchurch for two years and explored a lot of the South Island — Queenstown, Wānaka, the West Coast, Kaikōura, Arthur’s Pass, Lewis Pass.

But the southern cities were still sitting on the “someday” list.

This trip wasn’t about doing everything.

It was about:

• seeing somewhere new
• having fun as a family
• making the most of the last few holiday days together

Three days. Two nights. First time in both towns.

That constraint made the decisions simple.

We started with a destination backlog

I always have a running list of trips I want to do: hikes, bike tours, family weekends, all at different stages of planning.

So when a free window appears, I’m not starting from zero.

Dunedin was already on that list.

Once we looked at the map and the driving time, the rough shape of the trip was obvious:

• Christchurch → Oamaru (night one)
• Oamaru → Dunedin (night two)
• Dunedin → Christchurch

No overthinking. Just something that fit the time we had.

Last-minute by design

We only started planning a couple of nights before leaving.

And that was intentional.

We locked in:

• accommodation
• a few key points of interest

Everything else stayed flexible.

That flexibility paid off.

We didn’t expect Oamaru to be such a highlight, but the Victorian Precinct was incredible, so we slowed down, wandered, and gave it more time.

If we’d over-planned, we would have rushed through it.

Accommodation: frugal, safe, well-located

For family road trips, our rule is simple:

We don’t pay for luxury, we pay for location and convenience.

That usually means:

• holiday park cabins
• budget motels
• the occasional well-priced hotel

On this trip we scored a great deal on a hotel right in the Dunedin city centre.

Being able to walk out the door and explore with the kids mattered far more than having a bigger room.

The system that makes this possible

The real reason we can plan a trip like this in a few hours is that we’re not actually planning from scratch.

We have a reusable template that already contains:

A default packing list

So we don’t forget:

• chargers
• water bottles
• spare socks
• the small things that derail a trip if you miss them

A pre-trip task list

Things like:

• charge devices
• download offline maps
• print bookings
• lock the house
• download entertainment for the kids

That mental load is already done.

So the only thinking required is trip-specific.

Food: self-sufficient where it matters, flexible where it counts

We run a hybrid food system.

On the road:

• snacks and drinks packed
• lunch sorted

So we’re not constantly stopping.

But we intentionally leave space to:

• eat out at places that are part of the destination
• spend money on experiences, not convenience

Being frugal on accommodation and road food gives us permission to splurge on:

“that famous spot”

or

“that activity the kids will never forget”.

Planning just enough

For this trip we had a few anchor points:

• Moeraki Boulders
• exploring central Dunedin

Everything else we figured out as we went.

Because it was a road trip, we could:

• adjust in real time
• plan in the evenings
• change the schedule based on weather and energy levels

That’s a completely different mindset from a backcountry trip.

Built for kids (and real life)

With an 8- and 10-year-old, the priorities are different from my solo hikes.

We optimise for:

• fun
• variety
• short adventures instead of big missions

We’ll start driving early and let them sleep in the car so we arrive with a full day ahead of us.

That one small tactic massively increases what’s possible in a short trip.

Why this matters so much to us

These trips create our core family memories.

Not the big, perfectly planned holidays.

The spontaneous ones.

The ones where:

• we nearly didn’t go
• we booked at the last minute
• we figured it out as we went

There were definitely times in the past where we stayed home because we didn’t feel prepared.

Having a repeatable system has changed that.

Now when a window opens, we go.

The quiet role my planning template plays

For this kind of trip, the biggest benefit isn’t deep planning.

It’s speed and confidence.

The template means:

• the essentials are never missed
• the plan comes together in hours, not days
• we can keep refining it on the road

And that’s the real goal.

Not to build the perfect itinerary.

But to make it easy to say yes to adventure — even at the last minute.

The result

Three days.

Two new towns.

A flexible plan.

One of the most memorable family trips of the summer.

Planned in a couple of evenings.