It started, like so many good things do, with a library book.
My daughter came home a while back completely captivated by Henry VIII, by Anne Boleyn, by the whole tangled, tragic, glittering world of the Tudors. At first it was just dinner-table trivia — did you know he had six wives, did you know she was beheaded, did you know, did you know. But somewhere along the way, her fascination turned into something else. She started asking if we could actually go there. Stand where they stood. See it for real.
That’s how this trip was born. And that’s the one sitting near the top of my DreamMap right now: a mother-daughter journey through England and Scotland in early June 2027, built entirely around the history she loves.
I’ll be honest — there’s something about planning a trip like this that feels different from planning any other trip. It’s not about checking boxes or seeing “everything.” It’s about handing my daughter a piece of the world she’s already fallen in love with in books, and watching her fall in love with it again in person. If you’ve ever traveled with your own child chasing something they care about — dinosaurs, space, a favorite author, a period of history — you know exactly the feeling I mean. It’s a particular kind of joy, watching someone else’s curiosity light up in real time.
So we’re not trying to see all of England and Scotland. We’re following one story: kings and queens, castles and courtrooms, love and betrayal and the women who lived through all of it. And we’re doing it together.
One small joy of this itinerary — we won’t need a car for most of it. England and Scotland have wonderful rail systems, and there’s something almost meditative about sitting across from your daughter on a train, watching the countryside blur past, instead of white-knuckling a rental car on the wrong side of the road. Some of my favorite travel memories with her have happened in those in-between moments — not at the landmark itself, but on the way there, when there’s nothing to do but talk.
I’m also slowly working through hotels and historic inns using my travel membership, comparing options as I go. It’s one of my favorite parts of planning — not just finding a place to sleep, but finding somewhere that feels like it belongs in the story we’re telling.
Days 1–5: Tudor London
We’ll start in London, letting the city’s Tudor history wash over us for several days.
First stop: the Tower of London. We’ll walk through Traitors’ Gate together, stand at the site where Anne Boleyn was executed, and talk — really talk — about the fear and ambition and power that defined that era. I imagine my daughter going quiet in that spot. I think I might too.
From there, Westminster Abbey, where centuries of monarchs were crowned, and where Elizabeth I and Mary I — two sisters, two queens, two very different paths — are buried within feet of each other. I want my daughter to see that. To sit with what it means.
And then, the moment I think she’s most looking forward to: Hampton Court Palace. Henry VIII’s favorite home, still standing, still breathing sixteenth-century life through its Great Hall, its kitchens, its gardens. It’s an easy train ride from central London, which means we get a full day of wandering without the stress of navigating anything complicated. Just the two of us, and five hundred years of history.
Day 6: Anne Boleyn's Childhood Home
This is the stop I refuse to cut, no matter how the itinerary shifts: Hever Castle.
London tells the story of who Anne Boleyn became. Hever tells the story of who she was before any of it — a girl, in a home, long before the crown and the scandal and the executioner’s sword. We’ll take the train into Kent and spend the day there, maybe stay the night nearby.
I have a feeling this is where the trip stops being “history” and starts being real for my daughter. There’s something about standing in someone’s childhood bedroom, centuries later, that closes the distance between a name in a textbook and an actual human life. I can’t wait to watch her face when that happens.
Days 7–8: Castles and Countryside
From Kent, we’ll head into Warwickshire by train, trading city streets for rolling countryside and some of England’s most breathtaking castles.
Warwick Castle is everything a castle is supposed to be — towers, battlements, grand halls, the whole fairy-tale silhouette. And nearby, Kenilworth Castle carries its own quiet weight, tied closely to Elizabeth I and her lifelong companion Robert Dudley. It’s a chance to keep following Elizabeth’s story past the palace walls of London, into the places where her private life unfolded.
We’ll likely stay in a countryside inn through this stretch — the kind of place that becomes part of the memory itself, not just a bed at the end of the day. I love hunting for those spots. The right inn can make a whole day feel like a storybook.
Days 9–12: Scotland's Royal Legacy
For the final leg, we head north — by train, not plane. It takes longer, but that’s sort of the point. I want my daughter to feel the landscape change beneath us, to watch England slowly become Scotland out the window, rather than blink and suddenly be somewhere new.
Edinburgh will be home base. Edinburgh Castle first, high above the city, thick with centuries of Scottish kings, queens and battles. Then the Palace of Holyroodhouse, still the monarch’s official residence in Scotland. And a day trip — an easy one, by train — to Stirling Castle.
Stirling holds a special kind of magic for this trip, because of its ties to Mary, Queen of Scots. She wasn’t a Tudor, but her life was hopelessly, heartbreakingly bound up with Elizabeth I’s — two queens, two cousins, two rivals who never once met face to face. I think that story might be the one that stays with my daughter longest.
I’ll spend this stretch of planning hunting down Edinburgh hotels through the membership, trying to stretch loyalty points as far as they’ll go, because every dollar saved on a room is another dollar we get to spend on something that matters more.
Why This Trip Means So Much to Me
Here’s what I keep coming back to: this itinerary isn’t really about castles.
It’s about my daughter and me, walking through the pages of every book she’s read, standing where the people she’s spent months thinking about actually stood. It’s about the conversations we’ll have on trains, in courtyards, in the quiet after a long day of walking — the kind of conversations that don’t happen back home, in the rush of ordinary life.
We begin with the Tudors in London. We follow Anne Boleyn home to Hever. We trace Elizabeth’s story through castle after castle. And then we cross into Scotland to meet the queen whose fate was tangled with hers from the very beginning.
Traveling slowly, by train, means we get to live inside that story instead of rushing past it. It means more time together, more time to talk, more time for her to ask the questions that are really about so much more than history.
This is the kind of trip I hope I remember when she’s grown. Not just the castles — though I’m sure those will be stunning — but the version of her sitting across from me on a train somewhere between London and Edinburgh, completely lit up, completely herself.
For now, this June 2027 adventure is still just a dream on the map. But every castle I research, every train route I trace, every quiet little inn I find — it all brings it a little closer to real.
So here’s what I’d ask you: what does your daughter love? What story is she living inside of right now — in books, in movies, in her own imagination — that you could actually walk her into? Because I promise you, there’s a version of this trip out there for the two of you too. You just have to start dreaming it.
And if a trip like this — one built around her passions, whatever they may be — is something you’ve been dreaming about too, I’d love to help you plan it. Reach out and let’s start building your own version of this story together.
