Best Things To Do on an Isle of Wight Weekend Break… Our 3-Day Road Trip Itinerary…

Are you looking for a 3-day itinerary for an Isle of Wight weekend break? Are you wondering what are the best things to do on the Isle of Wight? And do you want to know the best local experiences, and food & drink to try on the Isle of Wight? Then read on and join us on our Isle of Wight weekend break…

We spent 2.5 days road tripping around the Isle of Wight and managed to see the top sights, hidden gems, and experience some of the best food and drink including blue sparking wine and garlic vodka! Here’s our road trip itinerary packed with the best things to do on an Isle of Wight weekend break…

Which Isle of Wight Ferry… How to Get to the Isle of Wight

We took the Wightlink ferry from Portsmouth to Fishbourne... just a 45-minute crossing with plenty of sailings throughout the day. We stood out on the deck to watch the view of Portsmouth harbour disappear, before relaxing inside with a coffee from one of the 2 cafes onboard. There was also a panoramic lounge to sit and look out the front of the boat through huge windows!

Wightlink runs both car and foot passenger services... with three main routes: Portsmouth to Fishbourne, Lymington to Yarmouth, and Portsmouth Harbour to Ryde Pier for foot passengers only. You can book online in advance, and they even offer flexible ticket options in case your plans change.

TrovenTrippers Tip… It’s recommended to book early during weekends and holidays... contact us troventrippers@gmail.com and we can help you plan and book your ferry travel!

Day 1 Isle of Wight Weekend Break

A day of royal houses… unique local produce… and the UK’s best hidden gem attraction!

Best Things To Do in East Cowes... Step Inside Royal Life at Osborne House

Our first stop is Queen Victoria’s holiday home, Osborne House. Walking through the beautiful rooms really feels like stepping into a time capsule... the décor, the furniture and art, and even the children’s playhouse in the large gardens are almost exactly as they were during her time at the house. It’s unusual to see a house like this with so many original features still in place!

The Durbar Room is the real highlight and our favourite part of the estate... it’s based on an Indian temple, and it’s so beautiful!

Entry: From £20, or free for English Heritage members

Location: East Cowes

Adgestone Vineyard... Taste Blue Sparkling Wine & Fiery Sauces

Next we’re going to sample a true Isle of Wight unique experience… BLUE sparkling wine at Adgestone Vineyard. It’s the world’s only traditional-method blue sparkling wine, and tastes like a sweeter champagne… very nice! 

There’s also a shop full of home made treats like chilli sauces, liqueurs, and local snacks. We can’t resist a chilli beef nacho bowl, smothered in cheese and their homemade Arson Fire hot sauce... delicious!

There’s a mini farmyard too, with baby chicks, goats, and even a white peacock!

Location: Sandown

Appley Tower & Bembridge Windmill

To walk off the nachos and blue wine we head to the North coast and take a walk along Appley Beach and stop at the pretty Appley Tower... a quirky little tower right on the shoreline. It’s a great photo spot, super peaceful in the late afternoon, and on a clear day you can see all the way to Portsmouth.

Location: Ryde

We then head to Bembridge windmill… the island's last surviving windmill. Although it’s closed by the time we arrive, you can still walk around the outside via a public footpath and get a good look.

 Location: Bembridge

Evening in Shanklin Village... Thatched Pubs & Chine Walks

We spend the night in Shanklin, a lovely old village full of thatched cottages and cosy pubs. After trying an Isle of Wight cheeseboard, we explore Shanklin Chine... a lush, lantern-lit gorge that’s been voted one of the best hidden gems in the UK.

At the end of the Chine is The Fisherman’s Cottage, a famous fish and chip restaurant and pub, dating back to the 1800’s. Unfortunately they’ve stopped serving food by the time we reach, so we grab some fish and chips from a takeaway back in town and eat them back at our hotel.

Location: Shanklin

TrovenTrippers Tip… we stayed at The Channel View Hotel in Shanklin. The hotel was fine… but be careful if you book, as there’s another hotel just 5 minutes away with the same name… and that one did not look fine! We went to the wrong one at first and were super relieved to realise our mistake! 

Day 2 Isle of Wight Weekend Break

More local experiences, castles and views!

Shanklin Beach & Isle of Wight Sailing

We start day2 of our Isle of Wight Weekend Break with a walk on Shanklin Beach and watch the local sailing boats practice out to sea. It’s not the best weather so we don’t stay too long, but the beach would be a great place to relax on a warmer and sunnier day.

Location: Shanklin Beach

Best Things To Do in Arreton... Arty Finds & Beach Rock Jewellery

So as the rain starts we get back in the car and start day 2 of our road trip proper… going to Arreton Barns, the island’s largest art & craft village.

There’s something for everyone here... handmade jewellery, iron artwork, leather bags, pretty much anything and everything you can imagine to pick up a locally made gift!

Sneha finds a full matching jewellery set made from beach rocks for just £15... we see someone making art with wax and an iron... and Paul discovers a few vintage cars tucked away out back… a Mini, a Land Rover, a Lotus and a very clean BMW 6 Series. As you can imagine... we love this place!

 Location: Newport

Lunch at The Garlic Farm... Yes, Everything Tastes of Garlic!

We couldn’t visit the Isle of Wight without stopping at the iconic Garlic Farm. It’s an award winning local business famous for growing black garlic, with a restaurant, shop, farm walks, and you can even stay there.

We have lunch and order the garlic sharing platter which comes loaded with roasted garlic bulbs, garlic bread & pitta, garlic mushrooms, garlic stuffed olives, and even Isle of Wight peri peri pork... everything garlic… and everything delicious.

We even have garlic beer and garlic vodka to drink… the beer is quite subtle, but the vodka is pretty strong, but strangely nice!

There’s black garlic ice cream to try too, but we’re feeling a bit full after the platter! So we take a walk around the farm and see the fields where the garlic is grown (although they’ve just harvested a lot so we don’t see much actual garlic).. Working up just enough appetite to try the ice cream after we stock up on garlic supplies from the shop. Our verdict on garlic ice cream… surprisingly good! 

 Location: Sandown

Explore Carisbrooke Castle... Donkeys, History & Hilltop Views

Our next stop on our Isle of Wight Weekend Break is Carisbrooke Castle, the main fortress on the island and once the prison of King Charles I.

We walk the high castle walls, explore the museum, and meet the famous resident donkeys who once powered the old well... super cute! The recreated royal bedroom and chapel inside are beautifully preserved.

Entry: From £12, or free for English Heritage members

Location: Newport

Freshwater Bay & The Needles Viewpoint at Sunset

We drive out to Freshwater Bay and chill at a peaceful viewpoint on the cliffs for a while, before heading down to the bay and getting our feet wet on the beach. It’s a great spot to relax after a busy day!

Location: Viewpoint Car Park | Bay

Our last stop on day 2 of our Isle of Wight Weekend Break is another viewpoint at the Western edge of the island and where we’ll be starting our day tomorrow… the Needles. Although the attraction is closed tonight, we can still access the car park and walk to the fenced cliff edge and get a brilliant view of the rocks from afar… and we have the view all to ourselves!

Where to stay on the Isle of Wight… The Snug at East Afton Farmhouse

We stay in a cosy glamping shipping container called The Snug, part of Tapnell Farm. It has everything we need... with gorgeous countryside views and a peaceful setting.

Location: East Afton Farmhouse

TrovenTrippers Tip… for booking advice & help contact us on troventrippers@gmail.com

Day 3 Isle of Wight Weekend Break

The Isle of Wight’s most famous landmark!

The Needles & Alum Bay... Cliff Views from the Chairlift

We’ve saved the best until last… for the last day of our Isle of Wight weekend break, we’re going to spend it at The Needles and Alum Bay. 

The Needles are dramatic white chalk stacks rising out of the sea with brightly coloured Lighthouse standing against them. And Alum Bay is a hidden beach with brightly multicoloured sandstone cliffs, accessible by a chairlift (or a lot of stairs!)

Even though Paul isn’t a fan of heights, we take the chairlift down… and despite the slightly wobbly-looking chairs, the stunning views totally distract him from the drop!

 Location: The Needles Attraction

Take a Speedboat Around the Needles

At the bottom we take a boat trip out to see the Needles rocks and lighthouse up close. 

There are 2 boats to choose from… a 20-minute slow cruise (£9 adult, £6 child) which goes to the lighthouse, or a 15-minute jet boat (£20 per person) which goes all the way around the lighthouse to Scratchell’s Bay on the other side. We opt for the jet boat, and it’s totally worth it! 

The rocks and lighthouse are amazing to see up close, and the view of the multicoloured cliffs in Alum Bay are stunning as we zip back towards them!

Relax at Alum Bay

Back on dry land we admire the multicoloured sand cliffs up close... they're so bright and vibrant, and so cool to see!

We sit and relax on the beach for a while... not sure whether to look back at the cliffs or out the Needles in the distance!

DIY Sand Souvenirs at Alum Bay

At the visitor centre we have a go at making our own sand souvenir... we choose a glass shape (we pick one like the lighthouse) and fill it with the island’s famous coloured sands. A great way to end our Isle of Wight weekend break!

Isle of Wight Doughnuts

We make a quick pitstop in Yarmouth on our way to the ferry home, hoping to find the famous crab pasties (no luck!), but we do get to try a local Isle of Wight doughnut… our last experience on the Isle of Wight before taking the WightLink ferry home!

TrovenTrippers Moments from our Isle of Wight Weekend Break…

What a weekend! The Isle of Wight is a great mix of everything we like…

World famous sights to see? The Needles & Alum Bay were simply stunning!

History & Culture? Carisbrooke Castle & Osbourne House were great to explore!

Hidden Gems? The illuminated Shanklin Chine was fun to see!

Local Experiences? Arreton Barns was the perfect place to pick up souvenirs and gifts!

Unique Food & Drink? Blue sparkling wine & black garlic EVERYTHING… delicious!

And getting there from England couldn’t be easier with so many daily ferry options from WightLink ferries. If you’ve not been to the Isle of Wight before, we highly recommend it for a weekend road trip break!