Even before Queen Victoria’s arrival, just across the bay from Osborne House Cowes was becoming the center of British yachting. It still is. The first America’s Cup race took place at Cowes in 1851. Throughout the clement months, regattas and boat racing take place in one form or another virtually every weekend. The biggest single annual Solent race is the Round the Island Race from Cowes held in June. The event can attract 2,000 yachts. There is also the 600-mile Fastnet Classic that starts in the Solent off Cowes. The famous Cowes Week Regatta, held annually the first week of August, dates from 1826.

At the end of The Parade is Cowes Castle, home of the Royal Yacht Squadron, Britain’s most prestigious yacht club. Prince Philip is the admiral. In front, a sign advises “The starting cannon may be fired at any time.” Lining the parade are holiday condos, many dating from the Art Deco era, their broad balconies facing north over the Solent—the better to view the racing. The massive working boatyard bears the sign: “Welcome to Cowes Yacht Haven, the home of international boating since 1800.”

Carisbrooke Castle near Newport is the island’s most important fortress. There has been some sort of defensive structure on its grounds since Roman times. Anglo-Saxons fortified it in the 8th century, and walled it against the Vikings 200 years later. After the Norman Conquest, William the Conqueror gave the castle, and the island, to one of his friends. For succeeding centuries, ownership of Carisbrooke Castle went with lordship of the Isle of Wight. Most famously, Carisbrooke was the prison of King Charles I for the last 14 months of his life – before the unhappy monarch was returned to London for his trial and beheading in 1649. Personal relics of Charles I, documents and Civil War armor and weaponry form the principal exhibit of the castle’s museum, founded by the island Governor and youngest daughter of Queen Victoria, Princess Beatrice, in 1898. As Governor of the Isle of Wight, Princess Beatrice resided at Carisbrooke Castle until her death at 87 in 1944.

Among the castle’s distinctive features is a well-house with a donkey-powered treadmill that dates from the 16th-century. Yes, it is still in operation, and the Carisbrooke donkeys are one of the island’s most famous attractions. Like Osborne House, Carisbrooke Castle is in the keeping of English Heritage, and ought to be on any visitor’s island itinerary.

Though Newport is the county town, the largest community is Ryde, with a population of some 30,000. From Ryde you can catch a Hovercraft over to Southsea in Portsmouth Harbor. That 45-minute ferry ride takes just 10 minutes by Hovercraft. Ryde’s commercial downtown looks similar to that of any English town its size. Down on the Esplanade, though, it becomes obvious the town was built for seaside pleasures. In a freshwater lagoon, you can ride swan-shaped paddle boats, sharing the water with real swans. Across the Solent rises the skyline of Portsmouth and the Spinnaker Tower.

Near the eastern tip of Wight, the Bembridge Windmill is the only surviving windmill on Wight. Built in the early 1700s with local limestone, the tower stands 38 feet with a wooden cap resting on oak beams. The cap with its drive wheel and sweeps turns on original wooden cogs to face into the wind. It remained in continuous use grinding flour and cattle feed until it ceased operation in 1913. It’s now maintained by the National Trust, and well worth seeing.

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