Step back in time and follow The Churchill Trail! Walk in the famous wartime Prime Minister's childhood holiday footsteps, from building sandcastles on Compton Bay, to dressing up as a Victorian at Dimbola Museum & Galleries!

  1. Cowes

Winston’s parents first meet and become engaged.

In 1873 Lord Randolph Churchill is rowed to the Cowes Week guardship HMS Ariadne, sees dancing a beautiful American Jennie Jerome. At once he falls in love: they meet on Cowes Esplanade the next day, without her mother knowing. On day three, Jennie plays piano at the Jerome rented Rosetta Cottage, in Cowes, with Randolph a guest. They walk in the garden. He proposes: she accepts. They marry. Winston is born the next year.

  1. Osborne House

Winston swims with Queen Victoria’s grandsons.

In this room Winston’s grandfather and father deliver their Seals of Office to Queen Victoria in 1873 and 1888. Winston’s mother’s friend, Anne, Duchess of Edinburgh, married to a son of Queen Victoria, asks that 13 year old Winston swims with her sons at Osborne Beach. She wrote she’d “bring the boys to play with your very amusing oldest son (Winston)”. A dozen descendants of Winston visit Osborne in 2013.

  1. Priory Bay

Statue of Winston and Roosevelt ‘The Allies’.

The famous statue of Winston, seated with American President Roosevelt, is in the garden of Priory Bay Hotel. The named masterpiece “The Allies” is by famous international sculptor Lawrence Holofcener. Lawrence frequently stays on the Island. Three other famous statues of his are of Laurence Olivier, John (Winston) Lennon, and Shakespeare.

  1. Sandown/Shanklin

Winston sees HMS Eurydice sink, sees 18 ton guns, praises PLUTO.

Walking the South East Coast in 1888, four year old Winston sees HMS Eurydice sink, with 360 lives lost. Young Winston writes “Some of the divers fainted with terror when they went to recover the bodies, as the fish were eating them”. He’d journeyed past Shanklin Chine when young. There was built PLUTO (Pipeline under the ocean) snaking to France underwater in 1944 pumping fuel to the Normandy landings.

  1. Ventnor

Winston’s four holidays with his brother and nanny.

In the war Winston was asked to write of his first recollections. “I loved Ventnor” he said. He, his brother Jack, and nanny Mrs Everest spent at least four holidays here in the 1870s and 1880s, frequently on the beach (above). He wrote his first ever surviving letter from Ventnor in 1882. And later he noted “went in the sea this afternoon... very comfortable... well, I think this has been a successful day…we had a good ‘go’ at some raspberries and gooseberries we picked ourselves to eat”.

  1. Churchill Chine/Mottistone

Home of Winston’s friends the Seelys.

“Winston regularly visited Brook (near Mottistone) in the early 1900s” wrote the then Rector of Brook. Winston stayed at his friend ‘Jack’ Seely’s homes at Brook and Mottistone Manor, an Elizabethan House with famous garden today (above). When here Winston helped dig out a blocked lake allowing it to flow easily into the sea at a Chine, from then on called Churchill Chine. His friend bred a horse here, now famous as ‘War Horse’.

  1. Compton Bay

Winston builds sandcastles on a dinosaur beach.

In the 1900s Winston helped the Seely children build sandcastles on Compton Beach – and there today is an annual event of building sandcastles. The cliffs above the beach are one major site on the island rich in dinosaur bones. At Dinosaur Farm Museum, nearby, a painting shown here, is of the major dinosaur fish eater, plant eater, flesh eater and scavenger bird once common to the Isle of Wight, by local artist John Sibbick.

  1. The Needles

A dozen of Winston’s descendants visit.

In 2013 a dozen of Winston’s descendants, insisted on seeing the Needles. There they saw giant Palmerston guns, sited on many Island fortifications in the 19th Century, first noted by eight year old Winston in 1882 “went to see the forts & guns at Sandown there were some enormous 18 ton guns”. Every two years the world’s most gruelling ocean yacht race, the Fastnet, from the Island to a lighthouse off Ireland and back, takes place and the Churchills saw the race pass by the Needles.

  1. Yarmouth/Newtown

Winston’s famous ancestor, John Churchill, first Duke of Marlborough, made MP.

Family fortunes started with John Churchill, famous war leader, later made Duke of Marlborough. One first step towards stardom came when Sir Robert Holmes, based in Yarmouth and Governor of the Isle of Wight, invited John to be an MP on the Island – in 1678 – at nearby Newtown, once the Island’s capital, burnt by the French. It did not recover. It is now a famed ecological area, a National Nature Reserve, Site of Special Scientific Interest, and Area of Outstanding Natural Beauty. Sir Robert’s House is now the George Hotel in Yarmouth.

  1. Calbourne/Dimbola

Statue of Winston/Churchill visit.

One Winston statue to note is at Calbourne Water Mill. Defiant, Winston is seated outside a small museum to 41 (Royal Marine) Commando who trained here in the War. At nearby Dimbola Museum is a statue of Jimmy Hendrix, gifted by the Isle of Wight Festival promoter John Giddings. The museum honours and was home to famed Victorian photographer Julia Margaret Cameron, friend of poet Tennyson who lived nearby at Farringford. At Dimbola as tourists, four young Churchills dressed up in Victorian clothes, in 2013.

  1. Newport

Winston sees prisons: electioneers.

As Home Secretary, in 1910 Winston visited Parkhurst Prison, near Newport It used to hold young offenders. He later wrote “The mood and temper of the public in regard to the treatment of crime and criminals is one of the most unfailing tests of the civilisation of any country”. In 1910 Winston also electioneered in Yarmouth, Wootton Bridge, Ryde, and Newport, where his meeting was closed to women, as suffragettes were spied in the town, thought to be planning to disrupt his meeting.

  1. Carisbrooke

The Island’s Castle noted by Earl Spencer.

Winston’s relation Earl Spencer, brother to Princess Diana, came to the Island in 2014, after writing on King Charles 1, held prisoner in Carisbrooke Castle. Charles had tried to escape saying: where my head will go “the body would follow.” It didn’t, and he stuck between bars in a window. Still a prisoner, he was taken to London to be executed. Winston must have thought that eleven years before his visit to nearby Newport, he too had been captured (in the Boer War). He too had tried to escape, and had succeeded. If he hadn’t, what then? No Winston?