An Isle of Wight Staycation: a surprisingly relaxing break for parents of teens

The hallway at Leeway Cottage, Isle of Wight
The small details really add to this house's boutique hotel feel

The Isle of Wight isn’t a normal staycation. There’s something about the ferry journey and that trip across the Solent that makes you feel like you’ve left your worries behind and are starting afresh for your holiday. Usually, we pick remote and rural destinations for our staycation family breaks, but this year, with teens in tow, we made a decision to stay in West Cowes. Our week in a bustling town on the sea with three teens between 14 and 18, was so restful we’ll definitely be doing it again!

Where to stay in West Cowes

We stayed in accommodation called Leeway House, and while it was absolutely fantastic for a family full of teenagers, it would have been equally perfect for a group of friends getting away for a celebration – and judging by the quite mindblowing drinks fridge and the impressive collection of empty champagne bottles, this house has seen some really fun parties!

Leeway Cottage in West Cowes, Isle of Wight
Leeway House is based in West Cowes about ten minutes from the sea

We were staying in the house courtesy of Classic Cottages, who have some incredible homes on their books, across the Isle of Wight, the West Country and the rest of the British Isles. The suggestion of a Cowes rental came from them and the benefit of being in a town with teens was undeniable. They were entirely self sufficient and West Cowes is a really gorgeous spot – with high end shops and boutiques, coffee shops, bars and restaurants galore.

Leeway House is a quick 10 minute stroll to the beach (you can see the coast from the house as it’s on a gentle hill) where we swam on days we didn’t go further afield. It’s easy to wander into town for a drink or a bite to eat, and it’s such a dream location I have to admit to having poked my nose into a few estate agents windows – it really is the most perfect second home destination!

The kitchen at Leeway Cottage, Isle of Wight
The kitchen at Leeway House is suitable for entertaining

The house itself is generously proportioned with four double bedrooms with king sized beds. The décor is stunning – it’s been recently done up and you can tell whoever did it has a real eye for design. The little maritime-inspired touches – such as the longitude and latitude digits painted on the stairs, and the proliferation of painted oars – are inspired, giving boutique hotel vibes and an air of luxury.

There’s a huge table in the kitchen (and another outside) which makes you just want to throw open the doors and entertain. The living room is cosy and the bath, with a window out to sea, complete with a wine glass holder, made it necessary to spend at least one afternoon luxuriating in a bubble bath, sipping bubbles of a different kind!

The bathroom at Leeway Cottage has a book rest and a hole for a glass of wine
The bathroom at Leeway House has a book rest and a spot for a glass of wine

Sailing at Cowes

Cowes is a sailing town, and while I love being on a boat, I can’t sail myself so I did wonder if we’d feel a little left out. I couldn’t have been more wrong! We were on holiday over the Cowes Classic Sailing Week and the experience really made our holiday. Cowes Week is a sailing event that even non-sailors such as myself had heard of, but Cowes Classic Week is different – it’s a series of races for those with classic yachts and from what I could see, it was almost as much about having a lot of fun off the water, as putting your crews and boats to the test on the Solent.

A blustery morning out on the Solent
A blustery morning out on the Solent

HQ was at the Royal London Yacht Club (Princess Anne is patron) and the welcome we got there as interested but definite novices, was remarkable. Everyone we met was passionate about the Isle of Wight, Cowes and sailing and we were quickly converted. We were in good company too! The day we arrived, Orlando Bloom and Katy Perry popped over to Cowes to hang out in the neighbouring Royal Yacht Squadron. We were truly bitten by the bug and even managed to stow away on a motor boat to watch the start of a yacht race up close – it was thrilling.

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What to do on the Isle of Wight

There’s a lot to do on this pretty, laid-back island, and much of it we’ve done before. From the multi-coloured cliffs at Alum Bay to a visit if Queen Victoria’s holiday home at Osbourne House, there are plenty of traditional tourist spots you should take in if you're new to the island. We discovered a few less obvious tourist treats this holiday though which I think are worth sharing!

The view from the bathroom window to the sea
The view from the bathroom window to the sea
  • Visit the Milkshake Machine at Cowes Milk

Discover flavours of milkshake you’ve never dreamed of at Cowes Milk – just a few minutes drive from town. You buy a glass bottle and then fill up with your flavour of choice from their milkshake vending machine! There’s chocolate, vanilla or strawberry, plus the more unusual flavour of the month like coconut and salted caramel. We each got litre bottles each and pretty much downed them. Bit of a mistake! My recommendation is to get one bottle to share and let each kid choose the flavour when you return to refill the bottle. The bottles are a fun keepsake too.

A blissful walk of the Hamstead Heritage Trail
A blissful walk of the Hamstead Heritage Trail
  • Walk the Hamstead Heritage Trail

We stumbled upon this area of outstanding natural beauty, after pouring over a map and feeling the need for a walk on an overcast day. We’re so happy we did – we barely met a soul and the countryside and coast was just sensational. Wooden boardwalks taking you out across flat plains, it felt like a cross between Norfolk and Florida. Absolutely stunning and a place we’ll be returning to with a picnic.

The Hamstead Heritage Trail on the Isle of Wight is simply gorgeous
The Hamstead Heritage Trail on the Isle of Wight is simply gorgeous
  • Treat yourself to dinner at The Hut

Colwell Bay beach is lovely and the traditional beachside café opposite the carpark is perfect for a jacket potato, ice cream or a cuppa on a windy day. We stopped here for lunch and had no complaints – but walk down the beach and turn left and … wow! The (modestly titled) Hut looks like it would be more at place on the French Riviera than the Isle of Wight, with its floor to sky glass windows, retractable roof and free-flowing champagne. Chelsea on sea it might be but it looks like a lot of fun. We’ll be booking in for dinner (and Aperol Spritzes) next time we’re in town!

If you fancy a visit, Leeway House can be booked via Classic Cottages, with 7 nights from £1375. Shorter breaks and late deals are also available.