Windsor Castle and Windsor: Highlights

Deborah Gilbert | June 4, 2018
Windsor Castle, royal residence in Windsor.

Windsor Castle, royal residence in Windsor. Photo: Diane Masciale

“We made it!” That’s what I exclaimed to the British Airlines crew after we landed at Heathrow. I am terrified of flying and the crew took extra care to reassure me we would get to London, especially a steward named Alan who came over and knelt down beside me for a chat obviously meant to help calm my nerves. He was very kind and when he spoke of the sights I’d be seeing from the plane, I asked if we would see the squiggle of the Thames (like on the opening credits of EastEnders) as we flew into London. He said no, that we would be approaching from the west (passing over Windsor) to annoy the Queen. And here was I thinking I’d have to wait until the first day of our tour to annoy the Queen! Thankfully, the flight to London was easier than the New York City cab ride to the airport!

I got in a day early to spend time in London before traveling by train to Windsor, where the WLIW tour begins. The trip between London and Windsor averages 42 minutes, so it can be an easy day trip. The tour’s first lodging, The Castle Hotel in Windsor, is just a short walk from the train station, and easy to spot: it’s stone facade is painted a lovely shade of Martha Stewart green. Andrew Lennard from Transcendent Travel greeted us in the lobby. He clearly takes great care and attention to every detail. There will be many group meals on this trip, and I had told Andrew I have Celiac and need to eat gluten free. When I arrived, he had already confirmed with the chef’s restaurant which menu items at that night’s meal would be gluten free (and he even put some gluten free goodies in my welcome the bag). Much appreciated! After settling into my room, I was off with my pre-arranged ticket to tour Windsor Castle, which is right across the street from the Castle Hotel.

Windsor Castle and St. George’s Chapel

Windsor Castle

Windsor Castle. Photo: Kate Legg/WLIW.

Windsor Castle was built by William the Conqueror, in the 11th century and is the oldest and largest occupied castle in the world. Other monarchs since have all put their stamp on it. The castle itself is 13 acres, and does not get its name from the royal Windsor family; the Windsors get their name from the castle! (They changed their name from the too-German Saxe-Coburg and Gotha to Windsor in 1917). Windsor Castle was a favorite weekend retreat of Queen Victoria, and Queen Elizabeth is said to consider it her home.

Windsor Castle is everything you’d want it to be, and even more than you’d expect after seeing it on TV. The castle itself is a fortress, as immense as it is beautiful.

Stonework at Windsor Castle

Small flint stones in the mortar of Windsor Castle. Photo: Deborah Gilbert

Even its stonework construction is beautiful and fascinating. You’ll notice tiny rocks stuck into the mortar between the castle’s building blocks. They look almost like shells but are actually flint and are there to help with the spacing and leveling of the larger stones.

Inside the Castle

Photography is not permitted inside Windsor Castle, but trust me, the interiors are a must-see! The State Apartments house an amazing art collection: paintings by Rembrandt, Rubens, Holbein, Lawrence, and more, all kinds of assorted royals, both immediate family and European cousins. It’s got to be the most valuable family picture album in the world! And not for nothing, when you see them all together, room after room, you notice they are all doing pretty much striking the same poses. Yes, they look like they are posing for Ye Olde Sears catalogue. I’m sure you’ll notice and agree when you see them.

Also on view is Queen Mary’s doll house. It wasn’t a doll house she played with as a child, but rather it was made for her in the 1920’s when she was an adult, because she loved miniatures. I’m guessing that living in a such huge castle could make a person obsessed with miniatures – in the same way someone living in a Manhattan studio apartment wonders about living in a castle.

St. George’s Chapel

This clip from Royal Wedding Watch provides some history and inside viewing of the chapel for those at home.

St George’s Chapel, site of the recent Royal wedding between Prince Harry and Meghan Markle on May 19, was probably the most surprising sight inside the castle grounds. On TV it looks huge, but it is, in fact, a very intimate space, built in the 15th century. The stained glass windows, from medieval to Victorian eras, are gorgeous, as are the ornate carved chairs where the Royal tushies are planted. Though at the back in the Nave are folding chairs.


Queen Elizabeth figurines in window at Windsor Castle, one of her royal residences.

Queen Elizabeth figurines in window at Windsor Castle, one of her royal residences. Photo: Deborah Gilbert

By keeping a careful lookout, I saw this inside the castle grounds: someone had a little figurine of the boss on his window sill. Long may she wave.

I asked one of the castle staff if she’d ever met Queen Elizabeth. She said she had a couple of times, and that she’s lovely. I then asked if she just bumped into her around the castle, and she replied, “One doesn’t just bump into the Queen!” (Well, I guess she told me.)

A girl working at the Royal Ice Cream stand said she’d only met her once, but had dreamed about her the night before, about how tiny she is. It made me wonder if the Queen pops up in the dreams of other castle staffers but when I asked a couple of them, they just laughed.

The only thing I wanted to do at Windsor Castle that I could not (aside from casually encountering Her Madge), was to find the headstone of Queen Victoria’s dog, Dash. It turns out he is buried with other animals in a private family plot, in a part of the grounds not open to the public.

Souvenirs and Strolls

Necklace at Windsor Castle gift shop. Photo: Deborah Gilbert

Necklace at Windsor Castle gift shop. Photo: Deborah Gilbert

At the gift shop I bought a replica of the engagement ring Prince Harry gave Meghan, for the bargain price of £30. I’m guessing Meghan’s ring cost a bit more, but then, I doubt hers is adjustable like mine. Then again, hers comes with a prince. Also in the gift shop are replicas of Queen Elizabeth’s jewels, including the big diamond necklace her great, great grandmother Queen Victoria had made for her Jubilee (to help her get over losing her family jewels to dastardly Uncle Cumberland of Hanover). I thought about getting a replica tiara to wear to Highclere Castle later on our tour; only the £150 price tag stopped me.

I strolled what they call The Long Walk, the road leading to the castle through Windsor Great Park. Imagine living in the neighborhood and being able to do your power walk here? Now, if I was more enterprising I’d have scooped up dry remnants of horse droppings and marketed it as Official Royal Wedding Horse Poop. There’s a reason why I’m not a millionaire.

Of course, what would a royal residence be without the iconic red coated, fuzzy hatted guards? These guards are not here just for show; they are all active duty military soldiers guarding the Queen with real guns – but that doesn’t stop tourists from treating them like they are characters, posing with them like they’re Mickey Mouse at Disney World – as they keep their famously straight faces all day long. Here I am flashing my replica Meghan and Harry ring, but hunky guard and I are not engaged; we’re just good friends.

Writer Deborah Gilbert and Windsor Castle guard.

Town of Windsor

Windsor shops

A former inn where Ann Boleyn stayed before marrying Henry VIII. Photo: Deborah Gilbert.

The town of Windsor is rather charming as well. While it is full of modern shops, the buildings that house them have a history. For example, the timber frame building along the pedestrian mall Penscod Street. It was built in the 16th century and was originally an inn where Anne Boleyn stayed when she was preparing to marry Henry VIII. Today it is home to a florist and an Oxfam thrift shop.

The leaning house in Windsor. Photo: Deborah Gilbert.

The leaning house in Windsor. Photo: Deborah Gilbert.

Then I found this little leaning tower. I was told that shortly after it was built, over 330 years ago, it was painted, and the theory is the drying paint made the building tilt. No one has ever come up with another theory so they are sticking with it. Inside the little shop that sells and strings Jersey Pearls (and when they say ‘Jersey’ they don’t mean ‘New’) is a replica of Princess Diana’s Elvis dress.

Replica of a pearled dress worn by Diana, Princess of Wales, at Jersey Pearl in Windsor.

Replica of a pearled dress worn by Diana, Princess of Wales, at Jersey Pearl in Windsor. Photo: Deborah Gilbert

Travel Tip

Get to where you’re going early and talk to locals. Today I got to Windsor Castle early. The gates open at 9:30 a.m. and I struck up a conversation with staff, who told me that even though the attractions inside don’t open until 10 a.m., St. George’s chapel often opens early, so I might get in. So while others were shopping and walking around, I was able to go into that gorgeous chapel and have it pretty much to myself for about ten minutes. A real treat!

As I am writing this, our whole group is about to meet for dinner where WLIW Vice President Diane Masciale will welcome us and we’ll get the show on the road! Everyone I’ve met so far is excited to be here and tomorrow we are off to Highclere Castle!

As your home for the best British dramas and comedies, WLIW’s travel program takes you to the seaside villages, historic castles, and baking challenges you know so well on the To the Manor Born Tour. Follow along with our hashtag #WLIWTravel, check out our travel blog on and look for Facebook lives, daily photos and observations on WLIW’s Facebook page and via @WLIW21 on Twitter and Instagram. You can follow Deborah Gilbert on her Instagram at @GothamTomato and Twitter at @E20Launderette and WLIW Vice President Diane Masciale at @dianemasciale.

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