travel-tips

What Our Greece Catamaran Trip Taught Us About Group Travel, Splurging Intentionally, and Doing It at the Right Time

/ michellejimerson / Leave a comment

We don’t usually think in terms of “bucket list” travel. We’re much more interested in experiences that fit naturally into our lives and values.

But every once in a while, something really does live up to the hype.

Our week sailing in Greece with two other families was more expensive than most of our trips — and very intentionally so. It was a splurge, no question about it. And it was also one of those rare experiences that felt completely worth what we paid for it.

Why We Chose This Trip (Even Though It Was a Splurge)

This wasn’t the cheapest way to travel, and we knew that going in.

What made it appealing was the combination of:

  • A truly special place
  • Time slowed down by the rhythm of sailing
  • Traveling with close friends
  • A format that let us be present rather than constantly managing logistics

We weren’t trying to check something off a list. We were choosing a week that felt meaningful — one that centered connection, shared experience, and being fully in the moment.

In that sense, this trip fit our definition of frugal travel: not cheap, but intentional and values-driven.

The Timing Made a Huge Difference

One of the biggest factors in making this trip feel reasonable was when we went.

We traveled slightly off peak, just before prices jumped for the high season. Traveling even a week or two later would have nearly doubled the total cost.

The tradeoff was cooler water — but that didn’t bother us at all. We’re used to swimming in colder conditions, and the quieter experience more than made up for it.

This is something we’ve seen over and over again: when you’re flexible with timing, you can often access experiences that would otherwise feel out of reach.

What the Trip Looked Like in Practice

We spent the week sailing between islands on a catamaran, traveling with two other families and living aboard together.

The pace was naturally slow. Days revolved around weather, swimming, meals, and time together rather than schedules or checklists.

There was space for both shared time and quiet moments — reading, floating in the water, watching the coastline drift by.

That rhythm was a big part of what made the trip feel special.

A Thoughtful Splurge: Having a Cook Onboard

One of the biggest reasons this trip felt so restorative was having a cook onboard.

Was it costly? Yes.
Was it worth it? Absolutely.

Not having to plan, shop for, or prepare meals freed up an enormous amount of mental and physical energy. Instead of defaulting into logistics mode — which often happens on trips — we were able to actually experience where we were.

This is a good example of how we think about splurges. We don’t spend more just to spend more, but we’re willing to pay for things that meaningfully change how a trip feels.

In this case, outsourcing meals gave us back time, presence, and ease — and that felt like money well spent.

Why Traveling With Other Families Still Mattered

Even with the onboard support, traveling with other families was a huge part of what made the trip work.

Sharing costs across families made a high-end experience more accessible, and sharing the experience itself made it richer. Kids had built-in community. Adults had conversation and connection without effort.

It didn’t feel like a group tour or a logistical exercise — it felt like a shared adventure.

What Our Kids Took Away From the Experience

Learning happened naturally, without us needing to manufacture it.

Sailing made geography real. Weather influenced decisions. Cooperation mattered. Living in close quarters required awareness of others.

More than anything, our kids experienced what it looks like to move through the world slowly, attentively, and together.

Would We Do This Again?

Yes — but not all the time.

This isn’t how we want to travel every trip. It was special because it was different from our usual approach. The splurge made sense in this context, at this moment, with these people.

It’s the kind of experience we’d happily repeat occasionally — when the timing, the people, and the intention all line up.

How This Trip Fits Into How We Travel Overall

This trip reinforced something important for us: frugal travel doesn’t mean avoiding expensive experiences altogether.

It means being selective.
It means choosing when to spend more.
And it means doing so in ways that genuinely enhance time together.

This week in Greece was a reminder that sometimes, a thoughtfully chosen splurge can be just as aligned with our values as the most budget-friendly trip.

How We Find Flights That Are Worth the Cost (and Skip the Ones That Aren’t)

/ michellejimerson / Leave a comment

Flights are often the biggest single expense in our travel budget — and one of the easiest places to either save money or make travel miserable.

For us, finding flights isn’t about chasing the absolute cheapest option. It’s about finding flights that strike the right balance between cost, time, energy, and flexibility, especially when traveling as a family.

Flexibility Is the Biggest Money Saver We Have

One of the biggest advantages we have is time flexibility.

Because we aren’t bound to a traditional school calendar, we don’t need to travel during the same narrow windows as most families. That opens up enormous savings.

We’ve repeatedly seen the exact same flights drop dramatically in price simply by shifting our departure or return dates by three or four days. Sometimes the difference is hundreds — or even thousands — of dollars.

When you’re not limited to a one-week or two-week break, flight prices start to look very different.

Why We Use Google Flights

We use Google Flights almost exclusively because it’s incredibly powerful for flexible travelers.

Instead of starting with:

“We’re going to X on these exact dates”

We often start with:

“Where could we go around this time that’s reasonably priced?”

We’ll search broad destinations, flexible date ranges, and multiple departure airports. Sometimes the flight prices themselves shape the trip — not the other way around.

More than once, we’ve chosen a destination because the flights were unusually affordable for a specific window.

Cheap Isn’t Always Worth It

We rarely book the very cheapest flight.

In our experience, those flights often come with tradeoffs that aren’t worth it for us:

  • Extra connections
  • Very long layovers
  • Red-eye flights that leave everyone exhausted

Saving a bit of money doesn’t feel frugal if it makes the first few days of a trip miserable.

Instead, we look for good value — flights that are reasonably priced and reasonable to take.

How We Think About Budget Airlines

We don’t automatically avoid budget airlines, but we also don’t pretend they’re cheap in the way the headline price suggests.

When flying budget carriers, we assume:

  • Everything costs extra
  • We’ll pay for carry-on bags
  • Seat selection may cost more

We factor those costs in from the beginning so there are no surprises.

Some add-ons are worth paying for right away. Others we skip.

For example, we almost always add carry-on bags upfront. But we rarely pay for seat assignments — many airlines have policies that allow kids under a certain age to sit with a parent, and that’s usually sufficient for us.

The key is knowing what you’re getting into before clicking “buy.”

Why We Don’t Over-Optimize Flights

It’s easy to turn flight booking into an optimization problem: cheapest fare, perfect timing, best airline, ideal seat.

We’ve found that over-optimizing usually leads to stress.

Instead, we aim for:

  • Fewer connections
  • Reasonable departure and arrival times
  • Flights that don’t wipe everyone out

Flights are just the beginning of a trip. We’d rather arrive feeling functional than save a small amount of money at the cost of exhaustion.

Letting Flights Shape the Trip (Not the Other Way Around)

Some of our favorite trips started with a flight search.

By staying open to different destinations and timelines, we’ve been able to plan trips that might not have made sense otherwise — financially or logistically.

This approach only works because we prioritize flexibility, but it’s been one of the most effective ways we’ve found to make long-term family travel sustainable.

A Frugal Choice That Protects Our Energy

Finding the “right” flight isn’t just about saving money. It’s about protecting our energy, our time, and our ability to enjoy the trip once we get there.

For us, frugal travel means choosing flights that support the experience — not undermine it.

Why We Buy Travel Insurance (Even When It Feels Optional)

/ michellejimerson / Leave a comment

Travel insurance isn’t something we buy automatically for every trip — and it’s not something we think about as a way to “get our money back.”

For us, travel insurance is about risk management and peace of mind, especially as parents. It’s one of those places where frugality shows up not as spending as little as possible, but as spending intentionally to protect against the things that would matter most if something truly went wrong.

The Coverage We Care About Most: Medical and Evacuation

The primary reason we buy travel insurance is medical coverage, especially medical evacuation.

When we travel internationally — particularly in places where access to high-quality medical care may be limited — we want to know that if a serious emergency happened, we wouldn’t be making decisions based on cost or logistics alone.

Evacuation coverage matters to us because:

  • It can cover transport to appropriate medical care
  • It can help get us home if needed
  • It removes uncertainty during already stressful situations

This becomes especially important on trips to places like Central America or South America, where medical infrastructure can vary widely depending on location. On trips within Europe, we sometimes feel less urgency about this coverage — but we still think carefully about it.

As parents, that peace of mind is worth a lot. Knowing we have a plan in place lets us travel with less background anxiety and more presence.

Would We Think About This Differently Without Kids?

Probably.

Or maybe not entirely — it’s hard to say.

But having kids absolutely raises the stakes. When more people are involved, and when those people depend on you, the cost of uncertainty is higher. Travel insurance helps reduce that uncertainty.

It’s not about assuming something bad will happen. It’s about acknowledging that if something did, we’d want support immediately — not a financial problem to solve first.

Cancellation Coverage: A Hedge, Not a Guarantee

We do like having some cancellation coverage, but we’re realistic about what it’s for.

We don’t try to insure every dollar of a trip. Instead, we think about cancellation coverage as a hedge — especially for:

  • Large, non-refundable expenses
  • Trips booked far in advance
  • Experiences that would be difficult to rebook or reschedule

We don’t expect travel insurance to make us whole in every scenario. That’s not how we use it, and that expectation would push us toward buying more coverage than we actually need.

For us, the goal is to soften the impact of major disruptions, not eliminate all risk.

Why This Fits Our Definition of Frugal Travel

Buying travel insurance is a good example of how we think about frugality.

Frugal doesn’t mean:

  • Gambling on best-case scenarios
  • Ignoring low-probability, high-impact risks
  • Optimizing every dollar at the expense of peace of mind

For us, frugal means:

  • Thinking through consequences
  • Spending a little to avoid catastrophic costs
  • Making choices that support sustainable travel over time

Travel insurance helps us travel more confidently and more calmly — and that has real value.

When We Might Skip Travel Insurance

We don’t buy travel insurance automatically.

For example, we might skip it for:

  • Short domestic trips
  • Trips with fully refundable bookings
  • Low-cost travel where the financial risk is minimal

Like most travel decisions, this isn’t all-or-nothing. It’s contextual.

A Quiet Form of Preparation

Travel insurance isn’t the most exciting part of trip planning, and it’s not something we think about once we’re actually traveling.

But that’s kind of the point.

Having it in place allows us to focus on the experience itself — exploring, learning, and being together — rather than worrying about what-ifs.

And for our family, that peace of mind is well worth the cost.

Why We Put So Much Thought Into Our Family’s Luggage

/ michellejimerson / Leave a comment

Luggage doesn’t usually feel like an important decision — until you’re traveling as a family and everything you own has to move with you.

For us, choosing luggage wasn’t about finding the “best” bag or the trendiest brand. It was about reducing friction. We wanted travel days to be manageable, predictable, and calm enough that the trip itself didn’t start with stress.

That made luggage a surprisingly important part of how we travel.

Frugal Doesn’t Mean Cheap — It Means Intentional

We think about frugality as a way to protect what matters most to us: time together, flexibility, and energy.

That means we’re willing to spend money on things that:

  • Make travel more sustainable over time
  • Reduce stress and decision fatigue
  • Help us avoid ongoing costs later

Luggage fits squarely into that category. A bag that makes travel harder ends up costing more in other ways — baggage fees, delays, physical strain, or just exhaustion.

The Problems We Were Trying to Solve

Before buying new bags, we were clear about what wasn’t working.

Traveling as a family means:

  • Everyone needs to manage their own bag, at least some of the time
  • Airports involve long walks, stairs, and uneven surfaces
  • Not every kid wants to carry a backpack all day
  • Checking bags adds cost and complexity we’d rather avoid

We wanted luggage that supported independence without making travel days harder than they needed to be.

Why Carry-On Size Matters for Us

We’ve found that keeping everything carry-on sized changes the entire feel of a trip.

It:

  • Avoids checked baggage fees
  • Reduces time spent waiting in airports
  • Makes transfers and connections easier
  • Forces us to pack intentionally

Packing less isn’t about deprivation — it’s about simplicity. When everything fits with us, travel feels lighter and more flexible.

Why Rolling Backpacks Made Sense for Our Family

We chose carry-on–size bags that can both roll and be worn as backpacks.

That flexibility matters more than we expected.

Rolling works well in airports and smooth spaces. Backpack mode matters for stairs, cobblestones, and uneven terrain. Having both options means no one is stuck struggling when conditions change.

For kids especially, this has made a big difference. They can roll their bags when it’s easy and switch when it’s not — without needing constant help.

What We Didn’t Optimize For

We didn’t try to:

  • Find the lightest bag on the market
  • Chase the cheapest possible option
  • Choose something that would only work for one type of trip

We were more interested in durability, versatility, and long-term use than in saving a little money upfront.

That tradeoff feels very aligned with how we approach travel in general.

Who This Setup Works Well For (and Who It Might Not)

This luggage setup works well for:

  • Families trying to avoid checked bags
  • Trips with lots of transitions
  • Slow or long-term travel
  • Kids who can manage their own bags part of the time

It may not be ideal if:

  • You pack heavy or bulky gear
  • You prefer checked luggage
  • You’re doing very short, single-location trips

Like most things in travel, it’s about fit — not finding a universal “best.”

A Small Choice That Makes a Big Difference

Choosing luggage won’t make or break a trip. But for us, making this decision thoughtfully has removed a surprising amount of friction from travel days.

When logistics are smoother, we have more energy for what we actually care about — being together, exploring, and learning as we go.

And that’s a tradeoff we’re happy to make.

How We Travel Slowly as a Family

/ michellejimerson / 2 Comments

For a long time, travel felt like something we were doing to our kids instead of with them.

We planned trips packed with highlights, landmarks, and “must-see” moments — and then wondered why everyone was exhausted, cranky, and overwhelmed by day three. The trips looked great on paper, but they didn’t always feel great while we were living them.

That’s when we started traveling more slowly.

What Slow Travel Means to Us

Slow travel isn’t about moving as little as possible or staying in one place forever. For our family, it means less rushing, fewer transitions, and more room for real life.

We stay longer in one place.
We plan fewer activities.
We leave space for rest, boredom, and spontaneity.

Instead of asking, “What can we fit into this trip?” we ask, “What would make this place feel livable for a while?”

Traveling With Kids Changed Everything

Traveling with kids makes it very clear when a plan isn’t working.

Kids don’t care how famous a sight is if they’re tired, hungry, or overstimulated. They care about pools, animals, snacks, playgrounds, and having time to just be kids.

Slow travel lets us honor that.

When we’re not bouncing between hotels every night or racing to the next activity, everyone is calmer. Mornings are easier. Afternoons don’t feel like a battle. And we actually enjoy being together — which, honestly, feels like the whole point.

What Our Trips Look Like Now

A typical slow travel trip for us might include:

  • One base for several days (or weeks)
  • A mix of planned activities and totally free days
  • Familiar routines alongside new experiences
  • Time to return to favorite spots instead of always moving on

Some days we explore.
Some days we do almost nothing.
Both are valuable.

And some of our favorite memories come from the “in-between” moments — chatting with locals, revisiting the same beach, or letting the kids lead the plan for the day.

We’ve also found that this slower pace makes learning feel more natural — history, geography, and culture tend to stick when kids experience them over time rather than in short, rushed bursts.

Why We Keep Choosing Slow Travel

Slow travel helps us:

  • Connect more deeply with a place
  • Reduce stress and burnout
  • Travel in a way that actually works for our family
  • Come home feeling restored instead of needing a vacation from our vacation

It’s not about doing travel “right.”
It’s about doing travel in a way that feels good for us.

Why I’m Sharing This Here

I’m starting this blog to document how we travel as a family — what works, what doesn’t, and what we’ve learned along the way. I want to share honest experiences, not perfect itineraries.

If you’re craving travel that feels more spacious, more human, and more doable with kids, you’re in the right place.