From the Norman invasion in 1066 to the perils of WWII, Sussex has been at the forefront of Britain’s most decisive moments. Add to the mix tales of smugglers and pirates, of shipwrecks and ghostly sightings, and you’ve got yourself the ultimate holiday destination for history buffs. Come, let the journey through the ages begin…
Day one: The site that’s seen it all
You’re probably itching to see the site of the Battle of Hastings. But let’s not be too hasty. First on the itinerary is a trip to Pevensey Castle, on the outskirts of Eastbourne. Founded by the Romans in the 4th century, this ancient stronghold has a long, dramatic past, finding itself at the centre of history time and time again.

It was the staging area for William the Conqueror, who camped here before marching inland to clash with Harold and his Saxon army. It imprisoned a monarch, with King James I of Scotland confined to its walls. It’s seen a peasant revolt and multiple sieges. And in World War II, it housed British, Canadian and American troops following the fall of France, when it looked like the fort would once again be called into action. After a morning at Pevensey Castle, make the 20-30 minute walk to the coast, where you’ll find an intriguing piece of military history: the Martello Towers. These are a series of unassuming, 19th century towers, built to stave off the threat of a Napoleonic invasion. Today, some have been converted into homes, more likely to house a family than a cannon. If the stories are to be believed, some of them are also haunted by the spectres of ghostly soldiers.
Still hungry for history? Top off the day with a trip to Herstmonceux Castle, dating back 600 years. (It’s about a 10 minute drive away). Access to the castle is by guided tour and the expansive grounds are very much open. You can explore its stunning gardens, wildflower meadows and ancient woodland – perfect on a spring or summer day.
Day two: The Battle of Hastings
Where was the Battle of Hastings? Well, not Hastings. It was actually seven miles away in a town called – wait for it – Battle. The site of this infamous conflict is now home to Battle Abbey, which William the Conqueror built as an act of piety for the bloodshed. Fun fact: the town was only named Battle following the Battle of Hastings!
On that fatal day on 14 October 1066, the Normans – led by William – met the Saxons at a ridge blocking the road to London. The two sides fought from dawn to dusk, with thousands of men slain. You can even see the spot where King Harold was killed, famously depicted in the Bayeux Tapestry with an arrow in his eye.

Today, you can wander across the battlefield and explore the abbey’s ancient ruins (it was destroyed in the 16th century by order of Henry VIII). There’s also a stunning gatehouse, a walled garden, a visitor centre and even a restored dairy, as well as a picnic area.
Once you’ve delved into the history of the Battle of Hastings, why not acquaint yourself with another famous Sussex attraction? The vineyards. Battle is a short distance from both Mountfield Winery and Oastbrook Estate, which offers tours and tastings in the heart of the countryside, right next to Bodiam Castle, in fact! Both of these vineyards also offer accommodation, perfect as a base to explore.
Day three: Smugglers ahoy!
In the 18th and 19th century, Sussex was at the forefront of the smuggling trade, with smugglers ferrying tea, tobacco, alcohol and more between England and mainland Europe. Their motivation? Simply to avoid taxes. On day three, we start with a trip to a cave network that was well-known to the bootleggers and buccaneers of Hastings. Descend into the darkness at Smugglers Adventure – an interactive, family-friendly experience, where you’ll learn about murderous gangs and discover secrets of this murky trade. (History fact: these caves were later used as bomb shelters during WWII).
Once you emerge bleary-eyed from these underground caverns, we’d recommend making the short walk to the ruins of Hastings Castle. This is Britain’s first Norman castle, built by William the Conqueror to protect from potential invaders. After some time here, you should be ready for lunch – and you can’t go wrong with fish n’ chips from a local institution, Maggie’s.

Next up, we’d suggest quenching your thirst at one of Sussex’s watering holes. With many pubs dating back hundreds of years, you won’t struggle finding one that was frequented by smugglers. Or how about dinner at the Mermaid Inn? It may be a 2 AA rosette restaurant now, but it was once the HQ of the bloody Hawkhurst gang - you can stay there too!
Day four: Into the hills
Today, we’re heading about 40 minutes from Hastings to Seven Sisters Country Park. This is much more than an Area of Natural Beauty, filled with rolling hills and unbeatable vistas. It’s also home to the historic Beachy Head, which became synonymous with the smuggling trade, with many nearby villages complicit in hiding goods or hampering the ‘customs men’.
While here, you’d be remiss to not visit the Beachy Head Story – an exhibition space and visitor centre telling the tale of this iconic landscape, from its geology to its human history. They even have a writer in residence, who works on a variety of projects exploring everything from historic shipwrecks to the natural landscape. Ready for a walk? The centre is just over three miles from The Tiger Inn – a pub which has been pouring pints since the 15th century. You can easily picture the smugglers gathered around the hearth and discussing their plans.

Before the sun goes down, push on towards Seaford to discover the story of Exceat. This was a once-thriving medieval village in the heart of the South Downs, which was thought to be a naval base for the first King of England. It even appeared in the Domesday Book and was later visited by King Edward I. But over time, the village eventually … vanished. It wasn’t rediscovered until 1913, when a boy noticed the outline of a building, which turned out to be the foundations of the Exceat Church. Now, all that remains is a memorial stone – and a lot of unanswered questions!
Day five: Hastings’ lesser-known history
Say Hastings, think battle. But the town is brimming with unexpected stories. And tales don’t get more unexpected than that of the America Ground, which surrounded the site where Holy Trinity Church sits today. In the early 19th century, the shifting of shingle created a new stretch of land near the shoreline. Lying outside of anyone’s jurisdiction, the area became an independent enclave, attracting squatters and libertarians, who lived tax-free and rent-free. This led to the area being known as ‘America’, and even today it’s not uncommon to see the stars and stripes raised on the 4th of July.
A two-minute walk will take you to the True Crime Museum, a macabre attraction delving into the dark side of humanity. If you head along the beach, you’ll then reach the Hastings Fishermen’s Museum and the Shipwreck Museum. Two small, free museums that are packed with facts about maritime history, with passionate staff who are happy to share their knowledge.

Before your five-day getaway is over, there’s still time for a guided walk. You’ll of course find many local experts happy to give you a tour of Hastings. But our tip? Go for something a bit more … ghoulish. Take a ghost tour and hear stories of headless drummers and ancient soldiers. Spoooooooky!
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