How to Plan a Nostalgic Trip That Feeds the Soul

Disclosure: This post contains affiliate links. If you click through for more information or to make a purchase, it may result in a small commission coming my way. Please note that there is no extra cost to you associated with this. Thank you so much for supporting my site.

There’s something uniquely tender about returning to a place that once held your younger self. It’s not quite the excitement of a brand-new destination, nor is it the practical familiarity of travelling somewhere you’ve been many times as an adult. Instead, nostalgia travel carries its own rhythm - a quiet, steady heartbeat that pulls you backwards and forwards at the same time.

In my last post, Why We Return, I explored the growing trend of nostalgia tourism: why so many of us are feeling the pull to revisit childhood holiday spots, old family homes, and places that shaped who we are. For me, this theme is woven into daily life. I now live in the very coastal town where I spent so many of my childhood holidays, in a little chalet just like the one my grandparents owned. It’s a place where the past and present overlap with surprising grace - familiar, but never frozen. That experience has shaped the way I think about nostalgia travel: gentle, mindful, emotionally nourishing.

But how do we actually plan a trip like this? How do we prepare for the emotional journey of returning to a place that’s held inside us — sometimes for decades?

This post walks you through that process. Not a checklist or a to-do list, but a way of approaching nostalgia travel that feeds the soul.

Choose the Place That’s Calling You Back

A nostalgic trip always begins with a tug - a gentle ache under the ribs, a flicker of memory that appears uninvited when you’re washing dishes or scrolling through old photos. Nostalgia tourism isn’t about going back everywhere; it’s about returning to the one place that still whispers your name.

Ask yourself:

• What place lives most vividly inside me?

• Where does my mind wander when I think of home, comfort, or beginnings?

• Was it a seaside town, a park, a cottage, a street, a field?

Nostalgic destinations aren’t always grand. Sometimes they’re beautifully ordinary. It could be a chip shop where your grandparents bought dinner, a bandstand where you danced as a teenager, or a woodland path you once walked with someone you loved.

Follow that feeling. You’ll know the right place because when you picture it, something inside you softens.

For some people, the destination is obvious. For others, it’s a mosaic of memories. It’s okay if your nostalgic place isn’t clearly defined. Begin with the strongest fragment. The place will take shape as you plan.

Pack with Meaning, Not Just Necessity

Packing for a nostalgic trip is different from packing for a typical holiday. Here, your suitcase isn’t just functional, it’s symbolic. You’re preparing not just for a journey but for a reunion with a younger version of yourself.

Consider taking:

• A photograph from the last time you visited

• A postcard someone once sent you from there

• A small object that reminds you of that time - a keyring, a shell, an old holiday journal

• A playlist of music from that era of your life

• A scent - perfume, suntan lotion, or soap - that reminds you of that time

These small anchors help bridge the space between memory and reality. They connect you to the emotional thread that started all this.

Beyond mementoes, pack tools that help you slow down and reflect:

• A notebook or travel journal

• A pencil case filled with your favourite pens

• A small stitching kit if, like me, you enjoy crafting as part of your travel rituals

• A lightweight camera or simply an intention to photograph with purpose

You don’t need to take much. Nostalgia travel thrives on lightness - not in belongings, but in presence.

Embrace Change with Kindness

Perhaps the most important part of nostalgic travel is accepting that the place you return to won’t look or feel exactly as it once did. That is its own kind of beauty.

Shops close. Beaches erode. Roads change. The chip shop becomes a gallery. The candy-striped deckchairs are replaced by wooden ones. The playground is newer, safer, shinier. And yet, somewhere beneath the surface, the soul of the place remains.

Nostalgia travel asks us to be gentle - with ourselves, and with the place.

When you arrive:

• Notice what is the same

• Notice what is different

• But don’t judge the changes as losses

Try to greet them with curiosity, not disappointment:

“So this is what it has become.”

Places evolve because life evolves. The fact that something has changed doesn’t undo the memories. They remain intact, living inside you. Sometimes, change brings new beauty. Sometimes, it brings sadness. Both feelings have their place.

Let the landscape speak to you as it is now. This moment, too, will someday be a memory.

When Reality Doesn’t Match the Memory

Sometimes nostalgia travel is comforting. Sometimes it feels strange, disorienting, or unexpectedly emotional.

You might find:

• The cottage has been demolished

• The street seems smaller

• The café is louder

• The colours are different

• The magic feels harder to access

If this happens, take a breath. Sit somewhere quiet. Let yourself feel whatever you’re feeling - disappointment, sadness, confusion, even anger.

There’s nothing wrong with you, and nothing wrong with nostalgia. Sometimes revisiting a place simply reminds us how much time has passed and how much we’ve changed.

A few gentle grounding exercises can help:

• Write a few lines in your journal: “I remember this place as…”

• Take a photo of a detail: a pattern on a wall, a sign, a corner of a garden

• Close your eyes and listen: to the wind, the sea, the birds, the distant murmur of life

• Hold the object you brought with you: the photo, the shell, the postcard

And remember this:

You didn’t come back to reclaim the past.
You came back to reconnect with its meaning.

Even if the place is unrecognisable, the journey is still valuable. It tells you something about yourself - about who you were and who you've become.

Reflect Creatively: Let the Trip Become Art

One of the most nourishing parts of nostalgic travel is the creative reflection that follows — the way we turn memory and experience into something tangible.

Here are a few ways to do that:

Keep a Nostalgia Travel Journal

Not a diary of what you did, but of what you felt.
Write down:

• Sensory details (the smell of the air, the colour of the morning light)

• Emotional notes

• Memories that surface unexpectedly

• What surprised you

• What changed

• What stayed the same

Let the notebook become your companion on the journey.

Create a Photo Diary

Photograph small, meaningful details rather than postcard scenes:

• The gate you once ran through

• The pavement texture under your feet

• The horizon you grew up with

• The tiny corners that feel familiar

These images become a visual story - a bridge between then and now.

Hand-Stitch Your Travel Map

This is a beautiful slow-craft project.
You could:

• Stitch the outline of the place

• Add tiny motifs (waves, trees, cabins, pebbles)

• Mark significant spots with French knots or running stitches

• Embroider a quote or date that matters to you

As your needle moves, memory becomes tactile, something you can hold, mend, and honour.

Make a Memory Collage

Combine:

• Old photos

• New photos

• Tickets

• Rubbings

• Sketches

• Bits of fabric

Create a layout that feels like an unfolding of time rather than a before-and-after comparison.

Creative reflection allows you to inhabit the experience more fully. It offers closure, insight, and connection. It turns nostalgia into something new.

Allow the Journey to Change You

A nostalgic trip isn’t about walking through a museum version of your past. It’s about letting your past walk with you in the present.

You may leave with:

• A deeper sense of self

• A renewed appreciation for where you come from

• A bittersweet awareness of time passing

• A surprising sense of peace

• The beginning of healing

• Or even a newfound love for the place as it is today

Nostalgia travel gives us the chance to integrate our story, not by escaping to the past, but by bringing the past forward with grace.

Closing: A Return Is Also a Beginning

Planning a nostalgic trip that feeds the soul is not about perfection. It’s not about recreating old holidays or expecting the world to remain unchanged. Instead, it’s about opening yourself to the layers of memory, emotion, and meaning that arise when you revisit a place that once held your heart.

Every nostalgic journey is part homecoming, part discovery.
Part remembrance, part renewal.
Part past, part future.

When you gently walk through a landscape that shaped you, you connect with the person you once were, and the person you are becoming.

And perhaps the greatest gift of all is knowing that every return is also a beginning.

✍️ Coming Next in This Series

I hope you've enjoyed this post and my previous one on nostalgia tourism.

In my next post in this series, I’ll explore the bittersweet beauty of change - how places evolve, and so do we.

Until then, I’d love to hear from you. Have you ever gone back to a place from your past? Did it feel like coming home, or stepping into a memory, or was it disappointing and something you wish you hadn't done?

If you're travelling soon, please use these links!

Are you travelling soon? Use these links when making your bookings. These are the companies we use. It won't cost you any extra, but we will earn a few pennies to help keep Happy Days Travel Blog going. Thank you!!

• Make sure you take out travel insurance. If you are a digital nomad or long-term traveller, try the specialist provider SafetyWing. (Never leave home without protecting yourself, your trip and your belongings!)

• Book your flight with Skyscanner

• Book your accommodation with Booking.com

• Book a tour with Tour Radar

• Book city tours and activities with Viator or Get Your Guide

• Check out my Resources Page for more companies we recommend.

Disclosure: This post contains affiliate links. If you click through for more information or to make a purchase, it may result in a small commission coming my way. Please note that there is no extra cost to you associated with this. Thank you so much for supporting my site.