Anne Boleyn Tour – In the Footsteps of a Queen with Simply Tudor Tours

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For Tudor Fanatics – Anne Boleyn Tours

If you’re a Tudor fan (like me!) and mesmerized by the rise and fall of Anne Boleyn, a week-long tour into her life with Simply Tudor Tours is a good way to explore some of England’s most juicy history.

As a travel writer, I go on a lot of hosted tours, so it’s rare I sign up for one on my own. But there I was one night, randomly searching for Anne Boleyn tours, found The Rise and Fall of Anne Boleyn Tour by Simply Tudor Tours, and the next thing I knew, I’d signed up.

Bye, husband! You’ll find me at Hever Castle.

On our first day, we met up in London and – after some delay due to a transit strike (not their fault, obviously) – we were off in our comfy bus to Windsor.

Then, within a couple of hours, we were standing outside the Windsor Castle and Prince Harry passed by in a car (I’m not making that up.)

I was very curious about what kind of history-nerdy people would sign up for a trip like this.

The group was almost all women, except for one man from Australia. Some were absolute experts, while others were only there because their moms wanted to go.

I thought I knew a lot – I mean a lot – about Anne Boleyn, but during our pub night Tudor trivia contest, I only ranked in the middle.

I can’t tell you how happy that made me, (apart from losing) because it meant I could rant on about endless Boleyn minutiae and the others had all sorts of interesting rants of their own. Plus, shopping figured highly in the mix.

There were lectures. In a castle. And a number of private tours.

For lovers of history—especially of the intrigue and drama of the Tudor court—Anne Boleyn tours offer a chance to walk through one of England’s most compelling royal stories with other like-minded courtiers travellers.

Rather than rushing through famous landmarks, this carefully curated Anne Boleyn tour allowed us to experience Tudor England with expert context, exclusive access, and a depth of storytelling that made us feel like we had a backstage pass to the 1500s.

Specialist Anne Boleyn and Tudor History Tours

Simply Tudor Tours was created by Tudor historians and writers, including Sarah Morris (The Tudor Travel Guide) and Adam Pennington (The Tudor Chest).

The Rise and Fall of Anne Boleyn Tour — What You Can Expect

Scheduled for 8–14 September 2026, this seven-day Anne Boleyn tour traces the key locations of Anne’s life, blending guided visits, historic settings, and immersive evening experiences.

Day 1 — Windsor Castle & Setting the Scene

As I said, the tour begins with a London pickup and transfer to Windsor Castle.

Highlights include a visit to St George’s Chapel, the burial place of Henry VIII, Jane Seymour, and Queen Elizabeth II.

A welcome talk introduces Anne’s story and the political world she navigated. This is the good part … the welcome talk took place over high tea in our hotel!

Day 2 — Hampton Court Palace

At Hampton Court Palace, one of the great centres of Tudor power, we explored Anne’s life at court.

This was no standard visit.

When Adam told us it was closed that day, we were devastated. When he then told us we were still allowed in and would have the palace to ourselves, we were beside ourselves. I called my husband that night, and told him I was living the dream.

One of Hampton Court’s curators led our group through spaces tied directly to Anne’s rise, offering insight into court politics, marriage negotiations, and the shifting favour of Henry VIII.

Most heartbreaking: The room where Jane Seymour died in childbirth and where Anne Boleyn most likely miscarried, changing the course of history and sealing her fate.

Note to Hampton Court Palace: Fix that room up! It looks like a meeting room.

Day 3 — The Tower of London

One of the most moving sites on the Anne Boleyn tour takes place at the Tower of London. (Except it was raining, and there was a bit too much standing around.)

Sarah took us to the spot of Anne’s execution – the real spot, not the one that is marked as the spot – and read the moving speech Anne gave from the Scaffold. A powerful moment.

Coolest sighting: Graffiti carved by George Boleyn, Anne’s brother, while he was imprisoned in Beauchamp Tower. Another heartbreaking bit from the past.

Day 4 — Westminster Abbey

From our London hotel by the Thames, we went to Westminster Abbey. Anne had her coronation here, the Lady Chapel has the most magnificent fan vaulted ceiling you will ever see, and at the Jubilee Galleries many stories up, I managed to find a fragment of Tudor glass I’d been trying to track down.

Tip: During your free time at the Abbey, nip over to St Margaret’s Church to see the Crucifixion, a Tudor era stained glass window.

Days 5–7 — Hever Castle and Tudor Life

Yes! This is what we were all waiting for. Two nights sleeping in a castle. Or, at least, castle adjacent, in rooms connected to the castle by a passageway.

Hever Castle in Kent was Anne Boleyn’s childhood home and the pinnacle of the Anne Boleyn Tour.

Here we had lectures, lots of free time, a private out-of-hours tour and dinner in the atmospheric dining room, where Henry VIII would have courted Anne.

It’s my second stay at Hever, and hard to believe a place like this still exists.

It was a whirlwind tour, but our two days there also offered space for reflection, a bit of group tour bonding, and a deeper immersion into Anne’s world.

Experts and Hosts

One of the strengths of this Anne Boleyn tour is the calibre of its hosts and historians, including:

Sarah Morris, co-author of In the Footsteps of Anne Boleyn

Adam Pennington, Tudor historian and writer

Estelle Paranque, specialist in early modern queenship

Their insights brought nuance to Anne’s story, weaving together political intrigue, personal relationships, and historical context at every location.

Why an Anne Boleyn Tour?

Exclusive Access

We had in-depth experiences at Windsor Castle, Hampton Court, the Tower of London, Hever Castle and Penshurst Place, with behind-the-scenes elements unavailable to standard visitors.

For example, at Penshurst Place, a palace once owned by Henry VIII, we had a private tour and a grisly lecture by a travelling barber. Trust me, you wouldn’t have wanted to have a tooth ache back in the day.

A Community of Tudor History Lovers

Small group sizes encourage conversation and shared discovery, making the experience both educational and social.

Practical Details

Despite its scholarly depth, the tour is designed for comfort and ease:

Accommodation at historic locations including Windsor and Hever Castle

Luxury coach travel between sites

All breakfasts, dinners, expert talks, and entry fees included

Lunches and personal travel to and from the tour’s starting point are not included; travellers should check booking details for full terms.

Final Thoughts

For travellers seeking more than a checklist of historic sites, the Anne Boleyn tour by Simply Tudor Tours offers an exceptional blend of scholarship, atmosphere, and storytelling. It allows you to follow Anne’s footsteps with clarity, context, and emotional resonance—bringing one of England’s most dramatic lives into sharp focus.

If you enjoy exploring Anne Boleyn’s story independently, you may also like my self-guided Anne Boleyn footsteps trail, which focuses on visiting key locations at your own pace. Together, these experiences offer two complementary ways to engage with Tudor England.