The Perfect 5-Day Isle of Wight Itinerary


From jaw-dropping majestic coastlines awash with stunning white chalk ridges, to some of the most unique wildlife, serene countryside, award-winning beaches, attractions and some of the best eateries in UK, the Isle of Wight just off the south-coast of England makes for an inspiring holiday destination with this Isle of Wight itinerary.

Located at just 2 hours from the city of London, this stunning island is bursting with so many things to experience that 5 days on the Isle of Wight may not be enough. However, here is the best of the best of this island to ensure you make the most of your vacation here. The Isle of Wight itinerary for 5 days is easily adaptable to suit your schedule for 3 days, if required.


1 | Isle of Wight Bucket List

2 | Where to Stay

3 | The Victorian Love Affair

4 | The Needles Rocks & Trinity Lighthouse

5 | Best Viewing Points of the Needles


The Isle of Wight is a splendid choice for a beach holiday in the UK. This inspiring island offers a range of stunning beaches, from pretty sandy shorelines to rolling cliffs and breathtaking coastal views. The beaches offer a little of everything on an unassuming scale. The weather has a Mediterranean feel and is generally better than the rest of the UK. With great outdoor activities and nature walks, the island is a fantastic destination to get away to.

The Isle of Wight is a great destination for everyone — singles, couples and families, especially families. I would go as far as to say that the Isle of Wight is the best UK island destination for kids.


The Isle of Wight is a small island, measuring 37 kilometres by 20 kilometres and you could circle the entire perimeter in three hours. However, the beauty of this enchanting island is in the pictureque villages, bustling small towns, miles and miles of walking routes that offers some amazing views along with the fresh seafood of the day. To experience all or most of what the island has to offer, you will need more than three hours!

The Isle of Wight has plenty to offer all visitors and is an island full of attractions. This itinerary offers several ideas for making the most of your visit. You could choose to spend any length of time on the island, from one day to five days or more. The Isle of Wight is a great destination to get away for a day from London. With the quick train connections from London, along with a good local transportation on the island means you will certainly see a lot in a day. A minimum of 3 days is highly recommended and if you can, make it 5 days. I spent 5 days with my family and it was brilliant. There was so much to do and so little time was spent in the car or indoors.


Isle of Wight Itinerary | timelesstravelsteps
Isle of Wight map data Google

The Isle of Wight is one of England’s best havens and is located in the English Channel, separated from the mainland by the Solent. Boasting popular holiday resorts since the Victorian times, the island is known for its mild Mediterranean like climate, epic coastal scenery, green and leafy landscape, along with ravines and falls. Historically part of Hampshire, and is a designated UNESCO Biosphere Reserve, this beautiful island is home to wild-life conservation, some of the richest cliffs and quarries of dinosaur fossils in the world.

Besides playing an important role in the defence of the country against the enemy approaches in both the World Wars, the Isle of Wight was home to the famous poets, Charles Swimburne, and Alfred, Lord Tennyson along with Queen Victoria who made her summer residence at Osborne House.

The island has been host to the Isle of Wight Festival, one of the most popular rock music events in the world. An annual event, the one-day Isle of Wight yacht race takes place, racing anticlockwise around the island starting at Cowes.

The Isle of Wight is a popular tourist destination throughout the year and for UK travellers, especially during summer holidays and end-of-term holidays for families, when kids are on holidays.

This Isle of Wight itinerary for 5 days offers suggestions, tried and tested tips for you to have amazing times on the island. While public transportation on the island is good, we found having our own transportation to be invaluable. For this particular itinerary, having your own transportation is highly recommended. This very special island can be accessed by ferries, catamarans and hovercraft, an overview is offered below.

Check availability and book your ticket to visit Osborne House, Isle of Wight


The Isle of Wight can be reached by ferries, catamarans and hovercraft, from Britain’s mainland ports of Portsmouth, Southampton and Lymington. A beautiful and peaceful retreat, the island can be reached easily and relatively quickly. It takes about two hours from London to reach the ferry ports and a 45-minute ferry crossing, available regularly throughout the day.


Departure ports for the Isle of Wight and Arrival points on the Isle of Wight

You can depart from Portsmouth, Southampton or Lymington and arrive at Fishbourne/Ryde, Cowes or Yarmouth. Popular ferry operators are Wightlink and Red Funnel. There are more than 15 ferry crossings a day offered by each of the operators, so there are plenty of options for you to choose from for your Isle of Wight itinerary.

The ports you choose to depart from determine the arrival point on the island. Regardless of where you arrive on the island, you could easily drive to your destination relatively quickly. For most travellers, the popular departure point is Southampton, England.

1 | From Southampton to East Cowes and West Cowes:

From Southampton to East Cowes

The route from Southampton across the Solent to East Cowes is a vehicle ferry service operated by Red Funnel Ferries. Red Funnel ferries operate daily and offer choices for travellers travelling with a vehicle and on foot. This crossing takes one hour and has a capacity to carry up to 200 cars.

Check Red Funnel ferry times from Southampton to East Cowes.

From Southampton to West Cowes

The crossing from Southampton to West Cowes is operated by Red Funnel Ferries and offers a means for foot passengers only. The Red Jet Hi-Speed Passenger Service catamaran crosses the Solent in 28 minutes, which makes it an ideal option for both business and leisure travellers alike.

Check for the Red Jet Hi-Speed Passenger Service schedule here >

2 | From Portsmouth to Fishbourne and Ryde:

From Portsmouth, you could take either the vehicle ferry to arrive at Fishbourne or take the catamaran to arrive at Ryde. Both are viable options depending on the location of your accommodation.

From Portsmouth to Fishbourne:

The crossing from Portsmouth to Fishbourne is offered by Wightlink and takes 45 minutes. Ferries depart every half-an-hour. Arriving at Fishbourne provides easy access to the towns of Ryde and Newport.

Check ferry times from Portsmouth to Fishbourne by Wightlink

From Portsmouth to Ryde:

Portsmouth Harbour to Ryde Pier Head route is most suited for foot travellers. The journey across takes just 22 minutes, connecting easily to transportation within the island. The route is managed by Wightlink aboard their FastCat catamarans and comes with spacious lounges, bike racks and sun-decks to take in the beautiful views.

Check crossing times from Portsmouth Harbour to Ryde Pier Head by Wightlink

Book your hovercraft ride from Portsmouth to Isle of Wight

3 | From Lymington to Yarmouth

The ferry service from Lymington in New Forest to Yarmouth in West Wight is offered by Wightlink. Lymington to Yarmouth ferry route is the quickest route and takes 30 minutes. This route is favoured by most travellers for the views of the coastline and it is less busy during the off-peak season.

Check Lymington to Yarmouth ferry service


Accommodations on the Isle of Wight are plentiful — from camping and caravan sites to holiday parks along with the very best in hotels and resorts.

Take a look at the 26 best places to stay on the Isle of Wight


It was an early start on day 1 as we made the 8:00 a.m. Red Funnel vehicle ferry from Southampton to East Cowes. Our stay was in Bembridge, and the journey from East Cowes to Bembridge was just a little over half-an-hour. There was plenty of time to settle in and we were eager to explore this haven, which some often regard as a place where you are never quite alone!

From mornings spent in nature or exploring the picturesque coastal towns, to afternoons on the beach or rockpooling, and everything in between, here is my guide to the best of Isle of Wight itinerary for 5 days.


Due to our early start to the day, we arrived at Bembridge, our home for the next 5 days well before midday. Our first activity was, of course the beach then we headed to the village and the surroundings.

1.1 | Bembridge

Bembridge is a village on the most easterly point on the Isle of Wight and is situated behind the picturesque headland of Culver. The village has a harbour, three beaches and an airport. Bembridge. Described as a “wonderful coastal setting”, Bembridge is a perfect base for exploring the Isle of Wight.

> Things to do in Bembridge

The three beaches, Lane End, the Ledge and Bembridge Beach offer distinctive coastlines, rock pools and incredible panoramic views out to sea.

Whitecliff Bay, a sheltered cove beneath Culver is one of the best places to explore. The Bembridge Lifeboat station offers free tours and is worth visiting. A short distance away at the outskirts of Bembridge village is the 500 year old Bembridge Windmill, cared for by the National Trust. You can climb to the top of the windmill and learn how the mill worked. There are plenty of walks to choose from that offer stunning views of the surrounding areas, of cliffs, Sandown and Culver Down. The Earl of Yarborough Monument is prominent atop the cliff and is worth the climb.

> Where to eat at Bembridge:

There are several small restaurants with high reputations for food. Culver Haven Inn is perfect for ice-creams; Crab and Lobster Inn is an award winning pub, offering a wide range of tasty meals and seafood dishes; Ganders Restaurant in nearby St Helens serves locally sourced meat and fish, with a setting ideal for quiet family meals.

1.2 Brading

Located at just ten minutes drive from Bembridge, Brading is reputed to be one of the oldest towns on the Isle of Wight, with King Alfred being the founder in the 7th century. Surrounded by rolling green hills that drop down towards the sea, numerous footpaths and a variety of distinctive wildlife.

> Things to do in Brading

Brading offers a mix of heritage and environment along with a vibrant community. Our highlight was the surviving 3rd century Roman Villa with some of the best preserved mosaics.

> Where to eat in Brading

There are a variety of pubs, restaurants and cafes in this historic village which is a former sea-port that offers great places to sample local ales on tap. For an authentic experience, you may want to visit The Bugle Inn, one of the most famous pubs in Brading Isle of Wight for traditional home cooked foods, using locally sourced ingredients which is also a pet-friendly inn.

1.3 Ryde

Ryde is a fun seaside town with long stretches of sandy beach, a flourishing shopping scene, numerous eating out, and framed by Victorian architecture. Ryde was a joy to explore. Ryde offers the first view of the island for anyone coming in on the catamaran from Portsmouth.

> Things to do in Ryde

Appley Beach is one of the best beaches on the Isle of Wight. The fine golden sandy beach comes with a small playground and a lush green park, which is perfect for family time out. The thriving shopping scene is worth exploring for souvenirs and there is also a Christmas store all year round. Explore the adventurous scene of tree climbing, and Go karting. Hop onto the Isle of Wight Steam Railway, located at just 4.8 km (3 miles) from Ryde.

Quarr Abbey is an interesting venue to visit. Quarr Abbey is nestled between Ryde and Wootton and is within a beautiful natural landscape. An ancient monastery has been here since 1132, and presently is home to a small group of Benedictine monks. Quarr Abbey offers a Farm shop of local produce and a Tea Shop where you could relax.


Our cottage was located by the sea, and waking up to the sound of the sea waves and seagulls were extraordinarily beautiful.

2.1 | Parkhurst Forest

In the morning of the second day, a visit to Parkhurst Forest, made for a great start. Walking and exploring Parkhurst Forest was a perfect way to discover some of the island’s beautiful landscape. Parkhurst is a site of Special Scientific Interest and consists partly of ancient woodland and plantation woodland. The Isle of Wight is one of the few places in England that is home to red squirrels, a protected species, and you can find them here in their magnificent log cabin ‘hide’. Red squirrels are generally shy and rather cute compared to their grey cousins. Parkhurst has wide forest roads and numerous footpaths and you could easily spend a couple of hours here.

2.2 | Cowes

Cowes Isle of Wight England |

After Parkhurst, drive to Cowes, a sailing town, located about fifteen minutes from Parkhurst and explore both East and West Cowes.

Visit Osborne House, Queen Victoria’s favourite home. Get an intimate glimpse into royal life while experiencing the opulence and grandeur of this sumptuous house, that has remain intack for over 100 years. The gardens and the beach gives Osborne House that special must visit status on any itinerary. Close to Osborne House, is St Mildred’s Church. This charming church was used by Queen Victoria and her family whenever they were in residence at Osborne House.

While in Cowes, walk along Cowes Yacht Haven. There are a number of eateries here that make a perfect stop for lunch. If you are into maritime, the Cowes Maritime Museum and Sir Max Aitken museum are well worth a quick stop. Later, take a walk along the esplanade to Gurnard and watch a sunset while you savour on some of the island’s delectable cuisines.

Read > The Victorian Experience on IOW

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A day for West Wight requires an early start. There is so much to do here for memories that will last a lifetime and you may be blown away by some of the amazing sights across the sea.

3.1 | The Morning at West Wight

> Start at Alum Bay, before the crowds! and Visit the historic Batteries

The Needles Isle of Wight England |

Alum Bay is renowned for its multi-coloured sand cliffs and the stunning views across the Solent, along with The Needles landmark attraction.

Alum Bay beach is one of the most picturesque beaches on the Isle of Wight at the most westerly point of the island. It is framed by the iconic chalk stacks known as The Needles. The chalk stacks have a historic lighthouse at the end looking out towards the sea. Sometimes known as Trinity Lighthouse, the Needles Lighthouse is a 19th century lighthouse and is fully operational to this day.

The cliffs are world famous for the coloured sands of 21 different shades. The sight is picturesque, natural and dramatic, all at the same time. From the beach, take a boat ride for an up-close view of the Needles Rocks and Trinity Lighthouse.

> The Needles Attraction

Above Alum Bay beach is The Needles Attraction. The Needles Attraction centre offers a range of attractions and activities for the whole family. These include glass blowing, sweet making and sand filling, a traditional family carousel along with a wide variety of catering facilities. There is a chairlift which you could take to the beach below. It offers another point of striking views of the chalk stacks and the Solent.

**Entry to the Needles Attraction is completely free, but charges apply for the activites offered.

> Historic Needles Batteries

After the Needles, make your way to the Needles Old Battery and New Battery. Steeped in history, the Old and New Batteries are a National Trust attraction and well worth a visit.

Read: The Complete Guide to the Historic Needles Batteries

Alum Bay and the Needles Attractions along with the historic batteries will typically take up the whole morning, taking you past noon. You may want to break for a quick bite at the Needles Attraction. Alternatively, if you have brought a picnic along (weather permitting, of course), you may wish to carry on, following one of the best walks on the IOW, and take a break amidst a spectacular horizon.

3.2 | The Afternoon at West Wight — Tennyson Trail, Freshwater and Totland Bay

From the historic batteries, we began on the Tennyson Trail, and headed towards Tennyson Monument. We did not do the full trail but did up to Tennyson Monument, Freshwater and Totland Bay, and returned to our car park in the evening.

> Tennyson Trail: From Alum Bay to Tennyson Monument

Isle of Wight itinerary |
Tennyson Trail: From Old Battery (Alum Bay to Tennyson Monument) credit: map data Google

The hike up to the Tennyson monument from Alum Bay (Old Battery) is just 3.3 km (2.1 miles) and took us about an hour with many stops. The trail offers breathtaking views of the Solent, the rugged coastline, white cliffs and the somewhat surreal views of the Needles and lighthouse landmark. Hiking this trail can be tiring, and at times a little challenging but it is an absolutely splendid experience to have.

TTS pro tip: Tennyson Trail Isle of Wight is a 22.5 km (14 miles) walk from Carisbrooke to the Needles on West Wight. The route goes through Bowcombe Down, Brightstone Forest, Mottistone Down, Brook Down, Afton Down, Freshwater Bay, Tennyson Down and West High Down through to Alum Bay. You could break the route up to suit your itinerary.

Tennyson Trail is one of the top walks in the United Kingdom. It offers several splendid coastal walks to suit an individual’s ability and time.

> Tennyson Trail: Tennyson Monument to Freshwater

Isle of Wight Itinerary |
From Tennyson Monument to Freshwater Bay credit: map data Google

Extend your walk to nearby Freshwater Bay, then to Freshwater. The route from Tennyson Monument to Freshwater Bay is 2.25 km (1.4 miles).

Freshwater Bay is a picturesque small crescent bay framed by high chalky cliffs stretching over 16 km (10 miles), offering fantastic views. The beach is of flint and chalk pebbles, along with some sandy areas, making it ideal for rock pooling. Freshwater Bay is away from the town, making it a tranquil escape and there is a little teashop for a quick stop.

Isle of Wight itinerary |
Tennyson Trail: From Freshwater Bay to Freshwater credit: map data Google

Freshwater has an extensive shopping area and good eateries, including a Tesco superstore. The route from Freshwater Bay to Freshwater is about 2 km ( 1.4 miles) and takes about 30 minutes.

TTS pro tip: If you wish to do the Tennyson Trail from Freshwater towards the Needles Headland, Freshwater Bay makes a great starting point for walks along Tennyson Trail.

> End your day at Totland Bay

Isle of Wight Itinerary 5 days |
Tennyson Trail: From Freshwater to Totland Bay credit: map data Google

End your day at Totland Bay before heading to the car park at the Needles. From Freshwater to Totland Bay is 3.7 km (2.3 miles) and takes about an hour to complete this trail.

Totland Bay Isle of Wight is a scenic sandy beach and offers expansive views over mainland England. The clear waters are suitable for swimming and there’s a row of pretty beach huts as well. The beach backs onto a seawall, and some parts of the coastline are rocky, dotted with trees and greenery. A narrow lane leads to the seafront where there is a pub/restaurant (The Waterfront) with large windows offering great views over the horizon. It’s a great place to catch the sunset.

For the latest on Totland Bay weather, check the BBC Weather.

For the latest on Totland Bay tide times, check the official web of the Metoffice before you go.

> Where to eat at Totland Bay

If you are looking for places to eat, there are several Totland Bay restaurants that offer Asian dishes and the island’s famous fish and chips. By far the best restaurant is the Totland Bay Waterfront.

The Waterfront at Totland Bay is the best place to be to watch the sunset on the west of the Isle and to have a fabulous meal at the same time. Hidden away towards the end of Totland Bay and sitting atop the sea wall, it looks out to sea and offers views of Hurst Castle on the mainland.

Where: The Beach, Madeira Rd, Totland Bay PO39 0BQ

Totland Bay to Needles Attraction is a fifteen minute walk. There is a car park here which was ideal for our day out at West Wight.

TTS pro tip: Park at the Needles Attraction Landmark car park. It costs £6.00 for an all day parking between April 1 through to October 30. At all other times, parking is free.

> Yarmouth

Yarmouth — The picturesque Yarmouth Harbour is situated on the Estuary of Western River Yar and is home to a unique 700ft long timber pier. The pier is a Grade II listed structure. There are some good small shops, cafes, restaurants and traditional pubs here. The Bugle Coaching Inn, is a 16th century inn situated in the centre of the market square and offers wholesome traditional home cooked foods.

Day 4 | South East ( Sandown and Shanklin) and Central Wight (Newport, Godshill and Carisbrooke)

Our fourth day on the island was another full-on day as we wanted to explore as much as possible on our last full day. We covered the main areas on the south east and central of the island.

On day 4, we began our day at Godshill, Isle of Wight. Godshill is a postcard perfect English village boasting old architecture and delightfully charming thatched-roofed cottages. The winding street offers traditional tearooms and the model village here is a popular destination. Our stop here was a brisk one as we headed to Newport next.

Newport is the main city for the Isle of Wight and is geographically located in the centre of the island. The town has plenty of shops, is pedestrianised and offers a variety of options for food. After a late breakfast and a quick stroll, we headed to neighbouring Carisbrooke.

> Carisbrooke | Carisbrooke Castle

I looked forward to our one and only destination at Carisbrooke, the historic Carisbrooke Castle, which is presently managed by English Heritage.

Carisbrooke Castle is famous for its role in British history from Saxon times in particular its association with Charles I and his execution. His youngest daughter also died here in 1650. Carisbrooke Castle has a strong connection to Princess Beatrice, the youngest daughter of Queen Victoria and Prince Albert.

> What not to miss at Carisbrooke Castle

Princess Beatrice founded the Carisbrooke Castle Museum which is located within the medieval castle. The museum makes for a great visit with its 35,000 items connected to the island.

When visiting Carisbrooke Castle, ensure you meet the castle’s donkeys. These resident donkeys have been drawing up water in the well-house for hundreds of years. Explore the castle grounds, Norman keep and the wall walk. Experience the tranquility of the castle chapel along with Princess Beatrice Garden.

The Castle Tearoom is a lovely place to rest your weary feet after ‘conquering’ the castle and to enjoy a light lunch.

A visit to Carisbrooke Castle will typically take two to three hours.

Read > The Complete Guide to Carisbrooke Castle.

Check availability and book your entry ticket/s to Carisbrooke Castle

> Robin Hill Isle of Wight

Make a quick stop at Robin Hill. Robin Hill Isle of Wight is an exceptional country park with rolling hills, beautiful gardens and adventure rides. You could spend the whole day here but we couldn’t as we headed to Shanklin and Sandown next.

> Shanklin Isle of Wight

Set against the dramatic chalk cliffs, Shanklin is a fascinating attractive beach town that will tug at your heart strings long after you leave the island. Visit the Old Thatch Teashop. This pink teashop is the most surprising, delightful and fabulous tearoom on the island for some Afternoon Tea. The Isle of Wight is popular for its cream teas, so you gotta have one on the island. You can’t really say you’ve been to the island unless you’ve had one 🙂

Shanklin offers one of the best beach walks to experience on the island.

Take the Isle of Wight Coastal Path from Shanklin to Sandown. The route is about 4.9 km (3 miles) and the path is generally moderate with clear signs. The walk can be done by following the flat sea wall of the more scenic undulating clifftop coastal path. Though it was windy, we preferred the clifftop route for spectacular sea views. The clifftop path follows a route that is clearly signposted and there is a set of steps that leads down onto Sandown Esplanade.

> Sandown Isle of Wight

Sandown sits on a beautiful sheltered bay on the south east coast of the Isle of Wight. Famed for its beautiful sandy beach, Sandown Bay is a fun place for fossil discovery. There is an interactive Dinosaur Museum nearby that tells the story of the pre-historic creatures and the fossil discoveries on the island. You could access the beach at low tide and make your own discoveries. If you are an ardent fan of dinosaurs, head to Compton Bay, Freshwater on the southwest of Isle of Wight, where you could see dinosaur prints made millions of years ago.

Check tide times for Sandown Bay

Sandown offers many things to do for all ages — from gardens, mini golf, a zoo, to long walks along the Esplanade where it meets Yaverland Beach, another beautiful beachfront. One of the main features at Sandown is the traditional British seafront pier, Sandown Pier. There is no shortage of places to grab an ice-cream or places to eat. It is worth spending some time here.

TTS pro tip: Park at the pay and display car park near Old Shanklin. The Coastal Path is easily reached from the car park. To return to the car park from Sandown, take the bus Line 3 from centre of Sandown. The bus is a convenient option as the journey is about 10 minutes and the bus stops near the car park in Old Shanklin.

You could also take the train or a taxi but the train is less frequent and the taxi is more expensive than the bus/train.

Check timetables and maps for the island buses.

DAY 5 | South Wight — The last day on the island and …

Our ferry ride back was not till 4:00 pm. This meant we still had the whole morning to explore and grab some late lunch before catching our ferry. We went south, to Ventnor.

> Ventnor Isle of Wight

Ventnor Isle of Wight England |

Ventnor is the southernmost holiday spot on the Isle of Wight and has been traditionally well-known as a health resort because of its unique climate. There are plenty of shops and eateries along with a traditional arcade with a variety of amusements on the main promenade. This popular seaside resort is home to Ventnor Botanical Garden offering a vast subtropical grounds covered with plants. The Japanese Garden has an interesting collection from the far eastern climate.

Overlooking Ventnor’s splendid coastline is the renowned Royal Hotel. The Royal Hotel is one of Isle of Wight’s best kept secrets. This historic, elegant and luxurious accommodation is one for the discerning travelller. A stay at the Royal Hotel may require a booking well in advance of your travels. If you can’t get availability here, the next best thing is to enjoy lunch, dinner or their famous Afternoon Tea while experiencing their hospitality.

> Appuldurcombe House

5 days on the Isle of Wight itinerary |
Isle of Wight itinerary

A short drive up the road from the Royal Hotel is Appuldurcombe House. Appuldurcombe House is the ruins of an 18th century English country house belonging to the Worsley family. The house is open to the public and is managed by the English Heritage.

> Garlic Farm

On the return journey towards the ferry terminal, make a quick stop at the Garlic Farm. Buy as much garlic as you desire or have lunch. The Garlic Farm restaurant is one of the most popular restaurants on the Isle of Wight.


We had a fabulous time on the island! I sincerely hope that you find this article helpful in designing your Isle of Wight itinerary. If so, share your thoughts and experiences. I would love to hear from you.

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