Cowes

Royal yachts bob alongside modest dinghies in the harbour here - it's that sort of place. Cowes manages to feel both grandly nautical and refreshingly unpretentious, split neatly by the River Medina into East and West Cowes, connected by a small chain ferry that's been puttering back and forth since 1859.

The sailing calendar revolves around Cowes Week in August, when the town fills with everyone from Olympic champions to weekend sailors. But visit outside the regatta madness and you'll find a proper working harbour town with genuine character. West Cowes clusters around the Royal Yacht Squadron's imposing castle, while the eastern side feels more industrial but offers better views back across the water.

Philip Island Shipyard still builds boats here, and watching craftsmen at work gives you a sense of the maritime heritage that runs deeper than the designer sailing gear in the shops. The high street mixes chandleries selling serious kit with cafes serving proper bacon rolls to early-morning fishermen.

Getting here means taking the Red Funnel ferry from Southampton or the hovercraft from Portsmouth - both land you right in the thick of things. The Solent's northern shore stretches away to either side, with the New Forest's ancient woodlands beginning just across the water on the mainland.

Staying at one of the nearby parks like Thorness Bay or Waverley Park gives you easy access not just to Cowes but to the entire northern coast of the Island. You're well-placed for exploring Osborne House, Queen Victoria's beloved retreat, or simply messing about on the water yourself.