Arriving by sea, you pass a harbour packed with yachts and motor cruisers, a wooden pier, and a castellated building on the point that turns out to be a clubhouse. That is Cowes Castle, built by Henry VIII in 1539 as a defence against France and the Holy Roman Empire, decommissioned in 1854, and now the headquarters of the Royal Yacht Squadron. Its cannons are a gift: twenty-one brass pieces handed over by the Prince of Wales after William IV's miniature frigate was destroyed in 1877.
The High Street runs back from the water as a working shopping street of chandlers, sailing outfitters and clothing shops that serve the yachting trade. Partway along it stands an 18th-century sail-makers' loft, once part of Ratsey & Lapthorn, who made the sails for the King's racing yacht Britannia. The loft is now the Sir Max Aitken Museum, full of maritime and nautical artefacts and open in summer.
The Anchor Inn at 1-3 High Street has been named CAMRA's Isle of Wight Pub of the Year, serves home-cooked meals and real ale, and puts on live music Wednesday to Saturday. The Fountain Inn, a waterside hotel dating to 1793 with long ties to Cowes Week, keeps twenty dog-friendly rooms. The Union Inn, off the Parade, has a three-sided bar wrapped around a lounge, snug, dining area and conservatory, with a fire lit in season. The Globe puts a rooftop terrace over the seafront for watching the yachts, and the Duke of York, family-owned since 1969, looks out across the Solent from the edge of town.
The seafront walk west is flat, paved and suitable for wheelchairs and prams. It runs about 2.3 miles to Gurnard, passing Egypt Point and its lighthouse, with the Solent opening out toward Lymington and Yarmouth one way and Portsmouth the other. This is also where the Isle of Wight Coastal Path begins its full circuit of the island. Behind the town, Northwood Park gives you green space in the centre — the former grounds of Northwood House, home of the Ward family, whose mausoleum is the Greek Revival tower John Nash designed for St Mary's Church in 1815. When the rest of the church was rebuilt in 1867, the tower was left standing.
Cowes has no railway; the line closed in 1966 and the trackbed is now a cycle path. You arrive instead on Red Funnel's Red Jet catamaran from Southampton, a foot-passenger crossing, with a car ferry running to East Cowes across the estuary. Between the two towns runs the Cowes Floating Bridge, a chain ferry that carries up to twenty cars across the Medina roughly every ten or fifteen minutes; the alternative is a ten-mile drive. Southern Vectis Route 1 handles the buses.
East Cowes, minutes away over the bridge, holds Osborne House, where Queen Victoria died in 1901, and the Classic Boat Museum with its ninety-odd vessels. In early August the population swells for Cowes Week, the oldest and largest sailing regatta in the world, and the harbour fills with what feels like everyone who owns a boat and several who wish they did.