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Isle of Wight travel guide: Where to eat, drink, walk and stay

Simon Calder’s Travel

If you set sail from England’s southern shore to the quietly cool Isle of Wight for a staycation, you’ll find a destination that values the simple pleasures: food, fresh air and good old-fashioned fun. The Hampshire isle, once the home of dinosaurs and now a haven for the illusive red squirrel, marches to a gentler beat than the mainland, with over half of its countryside now recognised as an Area of Outstanding Natural Beauty.

Beyond pocket-sized villages like Godshill that epitomise “chocolate-box”, a population of almost 142,000 call The Needles’ famed land of military forts and royal residences home. Classic beach days full of salt and sand meet the reinvented style of seafront restaurants and luxe hotels on the island that’s going from musty to modern.

Here’s what you need to know if you’re planning an Isle of Wight holiday.

Best time to travel for price, weather and crowds

While weather-dependent ferry crossings may not make it the easiest locale to access on a drab winter day, the Isle of Wight is rich with seasonal delights from March to November.

Notable as the southern shore that basks in some of the UK’s sunniest days, springs are green and autumns orange before big-name headline acts descend to serenade the island and kickstart the al fresco activities at the Isle of Wight festival in June.

With August comes Cowes Week, the sailing regatta that draws a nautical-loving crowd of over 8,000 in the height of the summer holidays. Accommodation prices, slow traffic and a dearth of car parking spots tend to peak – it’s always best to book ferries in advance for the lowest price.

The Cowes Week sailing regatta draws a nautical-loving crowd of over 8,000

(Getty Images)

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Where to stay

With parapets and battlements from Henry VIII’s lifetime, Ryde Castle’s grand four-poster beds and ambient dark wood accents are an affordable option situated among a hotchpotch of traditional shop fronts, decorative stucco and Georgian townhouses.

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