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Fabulous Isle of Wight Itinerary For First Time Visitors

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If you’re planning your first trip to the Isle of Wight and want to see all the most beautiful places to visit and some of the very best attractions, then this Isle of Wight itinerary is for you.

From mornings spent in nature to afternoons on the beach and everything in between, here’s how to see the best of the Isle of Wight in just four days. We hope you’ll feel inspired!

Fabulous Isle of Wight Itinerary For First Time Visitors

While this Isle of Wight itinerary is jam-packed, it also reserves plenty of time for relaxing beach days and time spent in nature. Please note that your own transport will be helpful for this particular itinerary, which is based on our time spent exploring the Isle of Wight.

Day 1 – Settling In & Relaxing Beach Days

You’ll likely spend your first day getting to the Isle of Wight and settling in, so take your time to do that. 

Come the afternoon, you might like to spend your time on one of the island’s many gorgeous beaches. Our picks would be Ryde Beach or Compton Beach for your first day.

Compton Beach, Isle of Wight
Sea views and golden sands await you on Compton Beach

Day 2 – Time Spent in Nature

Ventnor Botanic Garden

Ventnor Botanic Garden, Isle of Wight
Ventnor Botanic Garden is home to hundreds of exotic and rare plants

Today will be a long but relaxing day. Let’s start at Ventnor Botanic Garden

This stunning garden is home to hundreds of exotic, rare and sub-tropical plants. You can even see some of the largest Giant Amazonian Waterlilies in the world within the garden’s ‘Tropical House’. 

If you love plants and gardens, then you’ll love exploring this place. It’s a great way to start your day!

You could have lunch here or head straight to the town of Ventnor for lunch instead. 

Ventnor Beach, Pier & Esplanade

Ventnor, Isle of Wight
Ventnor beach and pier as seen from the Isle of Wight Coastal Path

Either way, you should definitely spend the afternoon at Ventnor Beach. This sandy shingle beach is small but charming and the pier and esplanade areas are well looked after. 

So whether you want to while away a few hours on the beach or have a wander along the Esplanade, this will be a relaxing afternoon.

Ventnor Town

While you’re here, you should definitely check out The Ventnorian also known as Crave. 

The Ventnorian Crave ice cream in Ventnor, Isle of Wight
Delicious locally-made ice cream awaits you in Ventnor

This independent ice cream parlour makes inventive ice cream on its premises. They’re also frequently changing their flavours, so there’s something new to try with each visit.

There’s often a queue, but their ice cream is well worth it!

Ventnor ice cream, Isle of Wight
Vegan Bounty “ice cream” and Malted Teaser ice cream from Crave in Ventnor

Scott and I each had a two-scoop cone. My scoops were Vegan Bounty and Malted Teaser. Scott’s were Milky Bar and Kinder Bueno. We loved this ice cream so much!

Crave usually closes at 6 pm, so this will need to be an afternoon treat before dinner. You’re on holiday, though, right?!

Once you’ve had your fill of delicious ice cream, it’s time to head to the town of Shanklin, which is about five miles away.


Just like Ventnor, Shanklin is a charming seaside resort town. 

If you have time to spare, then Shanklin has lots of shops worthy of a mooch. You might also want to grab dinner in Shanklin. You’ve got plenty of choices here.

Shanklin, Isle of Wight
Beautiful Shanklin on the Isle of Wight

Shanklin Chine

After dinner, head to Shanklin Chine – a natural coastal ravine complete with waterfalls. 

On summer evenings, your path is lit up along the way with coloured lights. It looks so magical!

Day 3 – Picturesque Views & Famous Landmarks

Isle of Wight Coastal Path

Isle of Wight Coastal Path
Walking the Isle of Wight Coastal Path

Why not start today with an exhilarating coastal walk? 

If you follow the Tennyson Trail from the Tennyson Down car park (owned by the National Trust), then you’ll be able to walk for just a couple of miles or so and find yourself at a free (and superb) viewpoint for The Needles.

The Needles, Isle of Wight
The Needles as seen from the free viewpoint

Once you’ve finished taking in the view from here, you can continue your walk towards The Needles Landmark Attraction “theme park”, where you’ll see stunning views across The Solent and Alum Bay en route.

Alum Bay, Isle of Wight
Beautiful Alum Bay as seen from the Isle of Wight Coastal Path

You’ll also glimpse a fabulous view of Alum Bay’s infamous multi-coloured sand cliffs. They look so bright and colourful and contrast perfectly with the calming blues and greens of the bay and surrounding landscape.

Alum Bay Multi-Coloured Sand Cliffs, Isle of Wight
You simply can’t miss the bright colours of Alum Bay’s sand cliffs!

Once you’ve seen Alum Bay and the sandstone cliffs, you can continue your walk until it circles back around to the Tennyson Trail.

Here’s the walking trail we followed during our trip to the Isle of Wight. We saw points 1, 2, 3 and 4, but you have the option to make your walk longer if you want to see more.

You might also want to take a picnic with you for today. We paused for lunch in one of the fields we walked across and we had fabulous views of The Solent from there. It was so romantic.

Views of Alum Bay from our picnic spot on the Isle of Wight
Picturesque seaviews as seen from our picnic spot

Carisbrooke Castle

Carisbrooke Castle, Isle of Wight
Carisbrooke Castle is well worth a visit – and free to visit for English Heritage members

Once you’ve finished your walk and had a spot of lunch, you might like to visit Carisbrooke Castle, which is managed by the English Heritage.

Carisbrooke Castle is a historic motte-and-bailey castle, which once housed Charles I as a prisoner. 

You’ll find it in the approximate centre of the island, so it’s probably on your way back to wherever you’re staying during your trip.

While the castle itself is interesting to visit – it even has an Isle of Wight museum on-site – you can also enjoy stunning panoramic views from the top of the castle’s walls.

Views from Carisbrooke Castle on the Isle of Wight
Stunning views from the top of Carisbrooke Castle

The tranquil Princess Beatrice Garden is also lovely to wander through, so a short stopover at Carisbrooke Castle is well worth it.

Psst! You can visit Carisbrooke Castle for free as an English Heritage member. Click this link and use our exclusive discount code: WOWEHM20 to enjoy 20% off gift and annual memberships. Enjoy!

Day 4 – A Right Royal Day Out


Osborne House, Isle of Wight
Your first glimpse of the Royal residence of Osborne

Osborne, a Royal residence in East Cowes, is one of the Isle of Wight’s most infamous attractions – and it’s every bit as beautiful as you might imagine. 

It was once owned by Queen Victoria who used the estate as her summer palace. If you happen to visit on a sunny day, you’ll feel like you’ve stepped into continental Europe such as Spain or Italy. 

Osborne House on the Isle of Wight
Osborne looks like it should be in continental Europe rather than the UK!

Every inch of this palace is stunning – both inside and out. 

Inside Osborne House, Isle of Wight
Inside Osborne House on the Isle of Wight
Inside Osborne House, Isle of Wight
Inside Osborne House on the Isle of Wight
Inside Osborne House, Isle of Wight
Inside Osborne House on the Isle of Wight

The Osborne estate is also fabulous to explore if you love flora and fauna. There’s even a private beach to see here!

Psst! You can visit Osborne for free as an English Heritage member. Find out more >>

As Osborne is in East Cowes, you can easily catch a ferry back to the mainland after your Royal day out.

The ferry terminal for Southampton is just a five-minute drive away, while the ferry terminal for Portsmouth is roughly 15 minutes away.

RELATED: Incredible Isle of Wight Day Trip – Tips & Itinerary

Where To Stay For Your Isle of Wight Itinerary

While there are lots of fabulous places to stay on the Isle of Wight, we’d recommend staying in Ryde on the northeastern coast.

This charming seaside town is conveniently located for both East Cowes (where the ferry to Southampton goes from) and Ryde itself (where the ferry to Portsmouth goes from).

There are plenty of shops and restaurants in the town and there’s even a golden sandy beach just minutes from the hustle and bustle.

During our trip, we stayed at the Dorset Hotel, which was a comfortable stay for a few nights. The breakfast was included in the price we paid and it was varied and tasty. The shops and beach were just a few minutes’ walk away – very handy.

Alternatively, other bed and breakfasts in Ryde that come highly recommended by other travellers include:

Look for more hotels in Ryde via Booking.com >>

I hope you found our Isle of Wight itinerary helpful and full of inspiration for your trip to this pretty little island. What are you most excited to see and do first? Let us know in the comments below…

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Fabulous Isle of Wight Itinerary For First Time Visitors
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Justine Jenkins

Justine is one half of the married couple behind the Wanderers of the World travel blog. She lives in Bristol, UK and has travelled extensively within Europe and beyond since 2013. After her trips, she shares detailed travel itineraries, helpful travel guides and inspiring blog posts about the places she's been to. When she's not travelling overseas, you'll find her joining her husband, Scott on various day trips, weekend getaways and walks within the UK, which she also writes about on Wanderers of the World. Aside from travelling and writing, she also loves reading, crafting and learning about nature.

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