
After 20 years of living in London, my husband and I moved back to the Isle of Wight in October. And this summer we’ve stayed local – because why not when the country is in the middle of a heatwave and the local tourist board’s tagline is ‘so much to see and do!’?
They’re not wrong. Just off the south coast of the UK, the Isle of Wight – or ‘the Island’ as we locals call it – has a hugely diverse range of stuff on offer, from its lively sailing community and endless paddle boarding opportunities, to myriad festivals (walking and cycling as well as music) and a unique biodiversity of nature, including shy, rare red squirrels and ancient woodland.
So when I was planning this guide, rather than taking in the whole 380km2 I decided to focus on two specific areas; the parts of the Island that I would go on holiday to if I didn’t live here. In fact, inspired by writing this, I’m planning a weekend away that doesn’t involve crossing the water as we speak!

HOW TO GET THERE
The Isle of Wight is easy to get to from London and beyond, with ferry services from Portsmouth, Southampton and Lymington. There is no bridge or tunnel, and you won’t need your passport as a UK resident (I get asked this a lot!). While the passenger ferries are much cheaper, and link up easily with trains from London, the public transport options once you get to the Island are limited, so I would advise bringing a car if you can unless you are staying in one of the towns that the ferries arrive in (Ryde, Cowes and Yarmouth) or don’t plan on going further afield than your host town. The car ferry is pretty pricey, but hotels and campsites often do packages when you book that make it much more affordable, so I’d advise arranging your accommodation before you book a ferry.

WHEN TO VISIT
The Island is lovely year-round, but my favourite months are September and May. It’s less busy outside the school holidays and we often have glorious weather (especially in September). In fact, according to the Met office, the Isle of Wight is the sunniest place in Britain, second only to the Channel Islands. If you like the hustle and bustle of high summer, the August bank holiday is always fun as thousands of mods descend to Ryde and Sandown for Europe’s biggest scooter rally. Always a winner for vintage fashion pop-ups and lusting after a Lambretta (every year I think I’m going to get one!). I would avoid coming the same weekend as the Isle of Wight Festival, unless of course you are going to the Isle of Wight Festival.
WHERE TO STAY
You’ll find the north east side of the Island the most populated, but venture to the south and west of the Island and it gets a bit more remote. We love Yarmouth and nearby Freshwater – on the north west tip – and Ventnor, which is so far south your phone might send you a ‘welcome to France’ text when you get there. Glamping The Wight Way offers safari tent-styling camping near Yarmouth, and Ventnor is well serviced by AirBNB, but if you have a car we’ve also been dying to stay at the airstreams at Vintage Vacations and to try scandi-cool of Tiny Homes Holidays.

YARMOUTH AND FRESHWATER
WHAT TO DO
Yarmouth is a beautifully quaint town, with a strong sailing community (great for jaunty sailing boat pictures even if, like me, you’d rather not get in a boat) and plenty of property porn to ogle at while you wander the pretty streets.


There are some lovely art galleries and shops, and a brilliant deli if you fancy some local food on the hoof. We love the walk along the old railway track that runs alongside the River Yar – you’ll find The Red Lion pub at the far end for a well-earned refreshment before you head back. In Freshwater, which was a favourite of Alfred Tennyson, visit Dimbola Lodge and its Julia Margaret Cameron exhibition, the groundbreaking photographer who lived there in the late 19th Century. Here you’ll also find a line of retail loveliness on the high street: Whistle and Hound, a gorgeous gift shop with a focus on local artists and sustainability, The Rabbit Hole tea and chocolate shop, and Mrs Middleton’s vintage book shop.


WHERE TO EAT AND DRINK
Coffee lovers will love PO41 – a converted post office that serves its drinks in beautiful paper cups illustrated by local artist The Constant Doodler. The Terrace is a new bistro perched on top of the ferry terminal that takes in stunning views of the harbour, or for something a bit different try Off The Rails, a cafe/restaurant located in the old train station, complete with themed pullman seating and a terrace on the old platform (we especially like breakfast here). If you fancy a non-frugal treat, head to The George Hotel’s plush restaurant and bar. We’re also big fans of The Piano Cafe in Freshwater with its amazing Victorian window frontage – you’ll often find live music here in the evenings.

VENTNOR AND SOUTH WIGHT
WHAT TO DO
Ventnor is weird! And it embraces its quirky personality around every corner (it has many), from the graffiti from Bristol artist Phlegm to the winding road that snakes from the top to the bottom of the town and back called Zig Zag Road (for anyone old enough to get the reference, one of the road signs once made it onto The Big Breakfast).



It has enough bric-a-brac shops to keep any vintage enthusiast busy for hours, and vinyl lovers will get lost in The Ventnor Exchange, which is an arts venue as well as being well-stocked with records, beer and coffee. Ventnor even has its own Fringe Festival, which usually runs in July, and during which you might find improvised hip hop in a launderette or a 1930s Parisian ‘book bus’ on the streets of the town.

Either side of Ventnor along the seafront are Bonchurch and Steephill Cove – the latter is a must-visit regardless of where you are staying in my opinion. Only accessible by foot, it’s a cluster of tiny seafood restaurants (don’t miss out on the Crab Shed’s crab pasties) and there are a couple of places you can stay, too. The scenery is more rugged on this side of the Island, but well worth the hills for the views. If you fancy a trip from Ventnor to Freshwater, drive along the Military Road for some stunning scenery.

WHERE TO EAT AND DRINK
In town, try Cantina (great for cocktails as well as dinner and fresh baked bread during the day), or The Spyglass Inn (gets super-busy but often has live music from local bands, including my dad’s). The Bonchurch Inn is an absolute gem (you’ll feel like you’re in Italy, and not just because of the authentic food), but our favourite recent find is The True Food Kitchen at nearby Castlehaven. The kitchen is in a static caravan serving delicious poke bowls and bao buns to customers on simple picnic tables with an absolutely stunning view. If you go at lunch time, head down to the cove for a secluded swim. You can also stay in one of the six static caravans, which I reckon would be just as fun in a storm as in the heatwave that was happening when we visited.

I could write the same amount over again to cover other popular spots on the Island – Seaview, Bembridge and Cowes are always a good bet – but that’s for another time! Meanwhile, please check before visiting that establishments are open as some are operating on limited hours because of covid, or are book-in-advance only. And pandemic or no pandemic, many places on the Island don’t open on Mondays, so double check to avoid disappointment!


Thanks for very useful article and lovely photos !!! Next time in Yarmouth walk a little further along the high st and see “westerly” for me the most beautiful modern house and also lovely bookshop in alleyway opposite. One groan !! Yarmouth pubs don’t sell real ale brewed on the iOw hich I think disgraceful !!! Apart from that. Many thanks. Warren
This is a fantastic article. I have never been despite living in Portsmouth for many years! I am already planning a trip.x