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Lisa | Road to 50 Before 40 | Family Travel

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🌏 Road to 50 before 40
🧑‍🧑‍🧒‍🧒Family adventures with Matt, Winnie & Florrie
✈️44 countries visited
📍London | Stories, guides & memories

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43 countries visited. 7 to go before 40 🌍

For years, travel has been a huge part of my life.
It’s taken me around the world as a backpacker, allowed me to explore new places while working as British Airways cabin crew, led to some of the biggest moments in my life (including getting engaged in Lakshadweep, India ❤️), and now gives us the chance to create memories together as a family.

As I get closer to 40, I’ve set myself a challenge:

To reach 50 countries before my 40th birthday in February 2028.

But this page isn’t really about numbers.

It’s about the stories behind them.

The places that surprised me.

The trips I’ll never forget.

The family adventures that didn’t always go to plan.

The lessons I’ve learned travelling through different stages of life.

Along the way I’ll be sharing family-friendly city guides, travel memories, cabin crew stories, practical itineraries and The Road to 50 by 40.

If you’ve found your way here, thank you for following along ❤️

I’d love to know:

What’s the one place that had the biggest impact on you, and why?

#50by40 #bucketlisttravel #familytravel #traveldiaries #intro by @50_by_40

🌍 The Road to 50 Before 40 🌍

Country No. 31: India 🇮🇳

As I work towards visiting 50 countries before 40, I’ve been thinking about the places that shaped my life in ways I never expected.

Lakshadweep is one of them.

Years ago, we got engaged on a tiny stretch of beach on these remote Indian islands.

Before we left, I picked up a small shell from the sand and brought it home with me. It wasn’t valuable. It wasn’t even particularly unusual.

I just couldn’t bear to leave it behind.

What I didn’t know was that Matt had secretly borrowed it.

Two years later, on the morning of our wedding, my dad handed me a small box in the taxi on the way to the venue. Inside was a necklace created from a cast of that tiny shell, a gift from Matt.

I still have the original shell.

And I still wear the necklace every day.

When people think of travel souvenirs, they usually think about something they bought.

Mine was something I found by accident on a beach on Thinnakara, an island that can no longer be visited in the way we experienced it.

Yet somehow it became one of my most treasured possessions.

Sometimes the places we visit become part of our story forever.

❤️ Do you have a travel souvenir that means more to you than anything you could have bought?

#Lakshadweep #India #TravelMemories #proposalstory #50by40

My beautiful necklace was made by @ssssjewellery
Wedding photography by the amazingly talented Ben Selway by @50_by_40

Not every stop on my Road to 50 is about ticking off a new country. Sometimes it’s about keeping a promise.

This was our final adventure of Summer 2026.

After Scandinavia and Ibiza, Winnie and I took our first solo mother-daughter trip together. Earlier this year, her best friend moved to Barcelona and I’d promised we’d go and visit.

What started as a weekend to see a friend became one of my favourite trips of the year. We stayed with her friend’s lovely family, explored the city, laughed our way around the Paradox Museum, ate dinner by the sea and watched Barcelona come alive after dark.

But the moment that will stay with me most was watching two little girls reconnect as though they’d never been apart.

And then there was the Sagrada Família at night. I’ve visited a lot of places over the years, but standing beneath it completely took my breath away.

Barcelona may not have added another country to my 50 before 40 challenge, but it certainly added another city we’ll always remember.

Most importantly, it reminded me that some trips aren’t about the places you visit. They’re about the people waiting for you when you get there ❤️

Have you ever taken a trip just to keep a promise?

#50By40
#MotherDaughterTravel
#BarcelonaWithKids
#FamilyTravel
#TravelMemories by @50_by_40

This is why I love to travel with kids. Seeing their little faces when experiencing something new for the first time is priceless. You quickly forget all the difficult stressful parts ❤️

Florrie’s little mind was completely blown experiencing the Turkish drums for the first time. Her jaw was literally on the floor 🤯😂

Thank you @anadoluatesi for an incredible show 😍🇹🇷 by @50_by_40

We had a wonderful flight with our 8-year-old passenger, Winnie! Contact us to fly with us too 🎉🪂 by @50_by_40

43 countries. One alphabet. And country #44 is next. 🌍

When I started my Road to 50 Before 40 challenge, reaching this point felt a long way off.

But these are the 43 countries that have shaped the journey so far, from family holidays and life-changing adventures to places filled with memories I’ll never forget.

This week, I take another step towards the goal.

Can you guess which country will become #44?
Leave your guess below, but no spoilers if you already know!

Follow @50_by_40 to see if I can make it to 50 countries before 40. ✈️ by @50_by_40

TW: This post discusses pregnancy loss and baby loss. 💙

Country #40 was supposed to be remembered for a different reason.

Greece was my 40th country.

It was my first trip to Greece and, sitting in the sunshine in Crete, I remember looking at my list of countries and thinking for the first time:

“Maybe I really can do this. Maybe I really can reach 50 before 40.”

A few weeks later, after we got home, I discovered I was pregnant.

We were overjoyed.

At the same time, I was terrified.

After Winnie arrived early at 32 weeks, pregnancy never felt like something I could take for granted. But as the weeks passed, our excitement grew.

Then we found out we were having a little boy.

His name was Peter.

We told our family and friends. We told Winnie she was going to be a big sister. We started dreaming about the future and imagining the adventures we would share as a family of four.

Sadly, on 13 August 2023, during my second trimester, we lost him.

For a long time, I couldn’t look back at photos from Crete.

The trip had become a reminder of what could have been.

Even this page, and the 50 Before 40 dream that started there, sat dormant before it had really begun.

Three years on, with our beautiful rainbow baby Florrie in our lives, I can finally look back differently.

Not without sadness.

Not without wondering what Peter would be like today.

Whether he would love our family adventures as much as his sisters do.

But also with gratitude.

Peter changed me forever in the short time he was with me.

He made me a better mum, gave me a deeper appreciation for life, and taught me a level of empathy I didn’t know was possible.

Losing a baby, whether at 6 weeks or 6 months, leaves a mark that never truly disappears.

Every life matters.
Every life is loved.
Every life is remembered.

Today, on Baby Loss Awareness Day, we’re remembering Peter.

Always loved. Always missed. Always part of our family. 💙

#babylossawareness #waveoflight by @50_by_40

The skydive wasn’t the part I want my daughters to remember.

This was.

This was my favourite moment of the whole day.

Not the freefall.

Not the adrenaline.

Not ticking something off my bucket list.

Seeing Winnie waiting for me afterwards with the biggest smile on her face.

I want my daughters to grow up knowing it’s okay to do things that scare you.

It’s okay to feel nervous.

It’s okay to doubt yourself.

And it’s okay to take a chance on something you’ve always wanted to do.

Because some of the best experiences in life sit just outside our comfort zone.

What I hope they remember isn’t that Mum jumped out of a plane.

I hope they remember that being brave doesn’t mean you’re not scared.

It means doing it anyway. ❤️ by @50_by_40

Today is World Mental Health Day, and it has me reflecting on a trip I took back in June.

Not because it was a new country.

Not because it was a bucket-list adventure.

But because it might have been the trip I needed most.

At the time, I was exhausted, overstimulated, and stressed.

I work full-time in a high-pressure corporate environment while raising two young children. After returning from maternity leave, I realised I wasn’t doing a very good job of looking after myself.

So I did something I hadn’t done for a long time.

I booked a solo trip.

Not to tick off another destination on my Road to 50 Before 40 journey, but to slow down, reset, and recharge.

I spent my days sailing around the beautiful coastline of Andratx and Sa Dragonera, swimming in crystal-clear water, snorkelling, reading a book from cover to cover, and enjoying having absolutely nowhere to be.

Well... apart from the jellyfish that decided to sting me. 🪼

That trip did me the world of good.

What surprised me most was how many women, friends, and colleagues told me afterwards that it inspired them to think about taking time for themselves too.

I’ve learnt that taking time for yourself isn’t selfish.

You can’t keep showing up for everyone else if you never make space to look after yourself.

So, on this World Mental Health Day, let this be your reminder to check in with yourself and listen to the signs.

Sometimes, a solo trip might be exactly what you need 💙

Have you ever taken time away just for yourself?

#worldmentalhealthday #solotrip by @50_by_40

The skydive might have been the reason we visited the Lake District... but these were the moments that made the trip special ❤️

After I’d ticked a lifelong dream off my bucket list, we slowed things down and spent the rest of the weekend exploring some of the Lake District’s most family-friendly spots.

If you’re planning a trip with younger children, here’s exactly what we did:

🚂 Lakeside & Haverthwaite Railway

We boarded the heritage train at Haverthwaite and enjoyed a beautiful journey through the Leven Valley before arriving at Lakeside.

The girls loved the train ride and it added a little bit of magic to our day.

🍴 Lunch at Lakeside Hotel & Spa

After the train journey we stopped for lunch at Lakeside Hotel & Spa before enjoying a walk along the shores of Lake Windermere.

The views were stunning and it was the perfect way to spend a relaxing afternoon.

🐰 Peter Rabbit Café

A huge hit with the girls.

If your children love Beatrix Potter, this is a lovely stop to add to your itinerary.

📚 The World of Beatrix Potter

One of our favourite experiences of the weekend.

It was surprisingly quiet when we visited and the girls had the best time spotting all their favourite characters and exploring the exhibits.

For younger children, it feels genuinely magical.

🏡 Our cottage in Backbarrow

We stayed in a beautiful cottage right beside the River Leven in the village of Backbarrow.

Some of my favourite moments weren’t activities at all, but the slower parts of the trip. Morning coffees outside, watching the river flow past, and simply spending time together as a family.

It turned out to be the perfect base for one of our favourite UK family weekends.

Have you visited the Lake District with children?

👇 I’d love to hear your favourite family-friendly recommendations.

📌 Save this post for your next Lake District family adventure

#lakedistrict #familytravel #ukstaycation by @50_by_40

The main reason we visited the Lake District wasn’t for the walks or the scenery.

It was because Matt bought me a skydive for Christmas.

I’d wanted to do one for as long as I can remember. It was one of those dreams that sat quietly on my bucket list for years. Something I’d always talk about doing, but never quite got around to booking.

Matt knew this.

He knew this wasn’t really about the skydive.

It was about doing something I’d dreamed about for years.

Something that would make me feel truly alive.

So last Christmas, he made sure I couldn’t back out.

As the day got closer, I started questioning whether I’d actually go through with it. Standing at the airfield is very different from talking about a dream you’ve had for years.

Then the plane took off.

A few minutes later, the door opened.

And suddenly I was free-falling over Lake Windermere.

For those few moments, nothing else mattered. Not work. Not the never-ending to-do lists. Not the stress that comes with juggling life, work and family.

Just the feeling of being completely, utterly alive.

Terrifying?

Absolutely.

Worth it?

Every single second.

And the best part wasn’t even the jump itself.

It was landing back on the ground and seeing Winnie waiting for me with a huge smile on her face.

Some dreams stay on the list forever.

Others require you to step out of a plane.

❤️ One unforgettable memory on my Road to 50 Before 40.

Have you ever done something that made you feel completely alive?

#skydive #firstjump #bucketlist by @50_by_40

A boat in Thailand, two grandmothers called Winnie, and a little girl we didn’t even know existed yet... ❤️

Some of the most important moments in life don’t feel important at the time.

In 2018, Matt and I spent our honeymoon travelling across Southeast Asia, island hopping our way up Thailand’s coast after completing our PADI course in Ko Lipe.

Before we left, Matt bought a hand-carved wooden long-tail boat from the father of the lady whose Airbnb we were staying in.

It was a lovely keepsake.

It was also completely impractical for the rest of our journey 😂

That little boat became a running joke as we dragged it between islands, airports and border crossings.

One of our stops was Koh Kradan, a tiny island with the softest white sand and crystal-clear water I’ve ever seen.

One evening, as we sat on the beach talking about our travels and dreaming about the future, we noticed a long-tail boat moored on the shore.

Its name was Winnie.

What made the moment even more special was that both of our paternal grandmothers were called Winnie.

As we sat there, looking at that boat, we both said the same thing:

“If we ever have a daughter, we’ll call her Winnie.”

What we didn’t know was that our future had already begun.

I was already pregnant.

Only a few weeks.

We had absolutely no idea.

When we later discovered we were having a little girl, the name felt like it had chosen itself.

Winnie arrived six months later at 32 weeks. Tiny, determined and our little miracle. ❤️

And that hand-carved boat that Matt carried all around Southeast Asia?

It now sits proudly in Winnie’s room.

A reminder that sometimes the journeys we remember most aren’t the ones we planned.

They’re the ones that quietly change our lives forever. by @50_by_40