For fabulous family fun
Morning Start the day with waffles, bacon and maple syrup at popular new Wootton high street all-day eatery Cibo — or a bottomless Prosecco brunch for the grown-ups. This should set the kids up nicely for a trot around the nearby Island Riding Centre. Tucked away among the rolling hills and winding lanes just five minutes down the road, the centre consists of smart accommodation, stabling, an indoor and outdoor riding arena and, soon, a restaurant.
Lunch Head to nearby Briddlesford Farm Dairy and its Bluebells Café for great burgers, steak sandwiches and cracking Scotch eggs produced from its own meat, then stock up for supper in its farm shop, which is packed with Island-made and grown produce. Don’t miss Briddlesford’s award-winning cheeses (it won a gold for its delicious Cheddar just two years after it first started making it) and there’s also a butcher on site.
Afternoon Get up close and personal with birds of prey at Haven Falconry in Havenstreet. It has 50 different bird species — 21 from around the world, including eagles and vultures, as well as more familiar owls, hawks and falcons. There are also talks and bird handling sessions. Afterwards, nip next door to the Isle of Wight Steam Railway and step back in time with a ride on one of this award-winning attraction’s beautifully renovated vintage steam locomotives. Just up the road is another trophy-winning destination, Monkey Haven, a primate rescue centre where you can meet lemurs and gibbons, marmosets and capuchins, among other mammals.
Evening/overnight Go for a late afternoon stroll through Parkhurst Forest to catch a glimpse of a red squirrel, the only native squirrel to the British Isles. It’s disappearing fast due to the prolific North American greys — but thanks to the Solent, the Island is a grey-squirrel-free zone. Stay overnight in a Tiny Home, a unique development of four bespoke off-grid eco homes in a meadow on the edge of the Forest, with activities available including writers’ talks and yoga.
For loved-up couples
Morning Make tracks to Two Elements in Cowes, a short walk from the Red Jet terminal, and pick up mountain bikes to hit the Red Squirrel Trail for as far as you dare along the meadow-edged Medina River (the trail finishes in Sandown), before returning to explore Cowes, home to the biggest sailing regatta — Cowes Week (8-15 August). Explore the yachtie hub on foot, grabbing a coffee at Art Nouveau gem Joliffe’s Eatery and browsing the shops, which include everything from stylish homewares at Staples & Green, to covetable clothing, jewellery and gifts at Live Like This.
Lunch Hit the road to stunning Appley Beach and the much celebrated, New England-styled Three Buoys restaurant for superior crab risotto and 32-day dry-aged sirloin, washing it down with a glass of bubbles. For something more casual, try a beef brisket Reuben and dirty fries accompanied by an Island-made Mermaid G&T at the panoramic view-boasting Dell Café on Puckpool Sands at the southern end of the beach. Then enjoy the stretch of glorious golden beach after, one of the best on the Island.
Afternoon Follow the coast path into Ryde and have a browse around the historic town. You’ll find all your mid-century needs (1970s coffee pot, anyone?) at Dig for Vintage and plenty of smart smellies at Liz Earle’s flagship store, stopping for tea and cake at No.64. If shopping is not your thing, try a spot of forest-bathing at Firestone Copse, notable for its wide range of tree species, from oak to soaring Douglas Firs.
Evening/overnight Upmarket Seaview is picture-postcard pretty, with its art galleries — for local art, try the Seaview Art Gallery — cafés (find excellent coffee at Lily’s Cafe) and yacht club. Sailing rules here, along with other watersports. Before settling into your comfortable bed for the night at the classy Seaview Hotel with its Michelin-rated restaurant, make time for an early evening stroll on popular Seagrove Beach.
For seniors who just want to have fun
Morning Start your immersion into Queen Victoria’s life on the Island at St Mildred’s Church in Whippingham, rebuilt by Prince Albert so the royal family could worship here. Then continue on to Osborne House, the Island’s most famous attraction. The royal pair bought Osborne in 1845, transforming it into their Island retreat and it opens a fascinating window on to their private family life.
Lunch You need time to do justice to Osborne House, from the opulent State Rooms to the Swiss Cottage, where the royal children used to hang out — and be sure to explore the well-kept grounds. Keep with the royal theme and enjoy lunch in Osborne’s Terrace Restaurant, housed in Queen Victoria’s magnificent private chapel. Feast on classic British staples with a twist, such as locally made pork and leek sausages with truffled mash, followed by cherry bakewell sponge pudding.
Afternoon Nip down to the Classic Boat Museum, also in East Cowes, and check out The Boat Shed with its impressive collection of more than 70 boats, from classic yachts to motorboats. Jump on the chain ferry to West Cowes, where more learned institutions await, including the Sir Max Aitken Museum on Cowes High Street, which is housed in an 18th-century former sail loft stuffed with Sir Max’s personal collection of historic and nautical artefacts. If you’re a fan of armoured tanks, then take a 10-minute drive to The Wight Military & Heritage Museum, where tours are conducted by ex-service volunteers — you can also test your shooting skills on its air rifle range. Craving solitude? Then head to Quarr Abbey, a working Benedictine monastery housed in an imposing 1912-built brick building. It also boasts an oasis of a tea and farm shop that serves superior cakes.
Evening/overnight Hunker down in Wootton at the Lakeside Park Hotel & Spa, a four-star hotel with a smart brasserie overlooking a 20-acre tidal lake (helicopter landing available), a short walk from the coast and surrounded by woodland. The real draw is the spa, which offers dozens of different treatments and pamper packages, from massages to hydrotherapy.
For mad-for-it millennials
Rent an inflatable paddleboard from Two Elements in Cowes, either picking it up from the shop, or it will deliver it straight to your accommodation. It will recommend the best spots for beginners, but for experienced hands head to Gurnard for a paddle on the Solent — starting first with a healthy breakfast of barista-made coffee and avocado and poached eggs on toast at Gurnard Press. Two Elements also rents out mountain bikes, in which case you could follow the Round the Island cycle route until your energy runs out.
Lunch Return from a bracing morning and head to The Little Gloster Restaurant with Rooms, voted the 2020 Good Food Guide’s Best Local Restaurant in the UK, and feast on co-owner and head chef Ben Cooke’s well-executed dishes (with local fish a feature) scoffing them on one of the outside tables overlooking the Solent. Snooze it off on the “secret” beach after — they’ll point the way.
Afternoon Energy restored, get the adrenaline going again at Wight Karting, an all-weather, 520-metre outdoor track where you can channel your inner Lewis Hamilton. Then start the party at the Isle of Wight Gin Distillery’s Mermaid Bar, situated on the outskirts of Ryde in stunning countryside. Learn about the distillation process and sip Mermaid G&T while overlooking the verdant valley, before snapping up one of its design award-winning bottles to take home.
Evening/overnight Continue the party back in Cowes with more cocktails at Coast Bar & Dining Room — the Elderflower Gin Fix is a highlight — before retreating to your super stylish bed for the night a few minutes’ walk away at chic boutique hotel North House, which is owned by the same design-minded folk. Dinner is a treat in its buzzy restaurant, where you could start with scallops, cauliflower purée and pancetta, followed by steak cooked in a charcoal oven, finishing with a killer lemon posset.