A playful and wonder-filled journey into the history of the Isle of Wight. Feel the past through your footsteps, imagine and play with the stories left behind by Romans, royals, warriors, and watchful stones.

1. The Castle on the Hill that Watches Time | Carisbrooke Castle

📍 Castle Hill, Newport | PO30 1XY

High on a green hill stands Carisbrooke Castle, where donkeys walk in circles to pull up water, and a brave princess once outwitted her captors. King Charles I was held prisoner here. He tried to escape through a window, but it was too small! Walk the ramparts, explore the old prison rooms, and look out over the same hills where ancient warriors once marched.

Time Traveller's Challenge: Can you sneak through the castle like a spy and find the room with the secret staircase?

2. The Stone That Stands and Listens | The Longstone at Mottistone

📍 Near Mottistone Manor, Mottistone Down | PO30 4EA (closest nearby – walk to site from road)

Long before castles, someone stood two great stones upright in a quiet green field. The Longstone is older than written history. Some say it's part of a burial place, others think it marked a sacred path. Stand between them. Close your eyes. The wind might tell you something.

Ancient Echoes: What do you think the stones are guarding?

3. Footsteps of the Romans | Brading Roman Villa

📍 Morton Old Road, Brading | PO36 0EN

Here, hidden under a meadow, are the tiled floors of a Roman villa. The mosaics are still there: wavy patterns, gods with wine cups, strange creatures. The Romans brought underfloor heating, sandals, and strange new words to the island. Walk where they walked. Sit where they feasted.

Secret Symbol Hunt: Can you find the mosaic with the mysterious "cockerel-headed man"?

4. Sea Fort of the Watchers | Yarmouth Castle

📍 Quay Street, Yarmouth | PO41 0PB

This little castle sits on the sea, and it was built by King Henry VIII to keep invaders away. It has thick walls, cannon rooms, and secret corners. You can see where soldiers once stood guard, scanning the waves for sails on the horizon.

Defender's Game: Pretend you're the lookout. What do you see coming? A ship? A sea serpent?

5. Queen Victoria's Seaside Palace | Osborne House

📍 York Avenue, East Cowes | PO32 6JX

This was Queen Victoria's holiday home. She came with her many children to swim, paint, and play on the beach. The rooms are grand, but full of warmth. There's a little museum of royal toys, and a tiny Swiss Cottage where the children learned to cook and garden.

Royal Mission: Imagine you're a prince or princess here. What games would you invent?

6. Clifftop Secrets and Sky Watchers | The Needles Old Battery

📍 West High Down, Alum Bay | PO39 0JH

Perched high above the sea, the Old Battery looks out toward France. There are winding tunnels, wartime stories, and views that stretch forever. Later, rockets were tested nearby, giant engines that reached toward space.

Hidden Time Portal: What historical moment do you think left the strongest mark here?

7. Undercliff and the Lost Lands | Landslides, Myths, and the Edges of Maps

📍 Blackgang Road, Chale | PO38 2HN

The southern coast is shifting—cliffs fall, roads crack, and whole gardens disappear into the sea. Blackgang Chine, once a coastal village, now lies under the ocean. What remains is a magical mix of amusement park and memory. Children laugh where land was lost.

Mapmaker's Task: Draw what you think the coast looked like 100 years ago. What will it look like in 100 more years?

Castles, Kings, and Hidden Things