The Perfect Isle of Wight Itinerary for a Long Weekend

When it comes to weekend getaways, the Isle of Wight perhaps doesn’t immediately spring to mind. But I am here to tell you that this little Island in the heart of ‘The Solent’ just off the south coast of England, is a true hidden gem for anyone who wishes to get away from London to relax near the seaside.

And if you are anything like me you will be glad to hear that there are plenty of things to do on the Isle of Wight too. From learning about the Island’s medieval history associated with Carisbrooke Castle to enjoying the natural beauty of its landscape as you walk across the Needles in Alum Bay, you will be spoilt for choice when it comes to activities to partake in.

Gary and I visited the Isle of Wight last October for a three-day weekend getaway. This was my second visit to the Isle of Wight, whilst it was Gary’s very first time. My experience was tinged with childhood memories of our theatre excursion to the Island, whilst Gary saw everything with fresh eyes.

Either way we had an extremely pleasurable long-weekend, and would whole-heartedly suggest you familiarise yourself with this spectacular part of England. I have outlined our three-day itinerary for the Isle of Wight down below. You can either follow it word for word or use it as inspiration – as always the choice is yours.

ABOUT THE ISLE OF WIGHT

The Isle of Wight is actually classified as a county of England and is located about 10 miles from the famous sea port of Southampton in the South East of England.

This island is known for its summertime festivals, exceptional local produce, and its fairly relaxed outlook on life.  Many visit to have some fun with their family on the beach, go surfing or bike along the island’s nature trails.

The Isle of Wight Music Festival is held annually in June. With legendary artists such as Bryan Adams, David Bowie, The Who, and Coldplay having featured on the stage, it’s no surprise that this festival is one of the most popular attractions associated with the island. Indeed the music festival attracts visitors from all around the world.

The Isle of Wight Garlic Festival is another iconic festival held annually on the Island. It is held outside of Newchurch and offers an opportunity for locals and visitors alike to show off their most impressive garlic collection, celebrate the summer season and just have a little fun!

HOW TO GET TO THE ISLE OF WIGHT 

The Isle of Wight is easily accessible with one of the car ferries from a variety of ports on England’s mainland.

There are currently three different ports from which you can depart in order to reach the island, namely Southampton, Portsmouth and Lymington. And to make things more complicated they all dock at different spots on the island including Cowes, Ryde and Yarmouth.

The good news is that the Isle of Wight is relatively small and it will take you a maximum of an hour and a half to drive from what end to the other.

Your choice of ferry will most likely be determined by your geo-graphical starting point. The most popular departure point from England is Southampton.

Red Funnel’s ferries operates daily between Southampton to West Cowes. Depending on whether you have a vehicle or simply traveling by foot, you have two alternatives to choose from.

The high speed ‘Red Jet’ ferry service is for foot passengers only and makes a swift crossing in only 25 minutes.

Those that are taken their own car or prefer the cheaper option can take the vehicle ferry and will reach the Isle of Wight within an hour. There are crossings throughout the day and night that generally leave every 90 minutes.

An alternative method of crossing the Solent, and our personal choice, is to take a Wightlink vehicle ferry departing from Portsmouth.

From Portsmouth, you can reach both Fishbourne and Ryde and the reality is that either is a viable option depending on the location of your accommodation on the island. Either way, the journey takes approximately 45 minutes and ferries depart every half hour.

If you would rather get across to the Isle of Wight in the shortest amount of time possible, Lymington will likely be your port of call given that you can make the crossing in under 35 minutes.

Wightlink also services this port and although it may not have the same glamour as Southampton or Portsmouth, it is certainly a viable choice given that it offers the shortest ferry route.

In total, our journey from London to Shanklin, should have taken approximately 5 hours, but as luck would have it there were some issues at the ferry terminal that day and we were delayed by two hours.

WHERE TO STAY ON THE ISLE OF WIGHT

The Isle of Wight is well-known for being a writers retreat and numerous noted authors and poets have spent at least some time on the Island.

So in keeping with our literary weekend, Gary and I sought out a hide-away to inspire our creativity.

Our choice fell upon Keats Cottage, formerly Eglatine Cottage, a boutique B&B located at the top of the Old Village in Shanklin. 

The B&B was named after John Keats, an English Romantic poet who stayed at the Cottage in the summer of 1819 and wrote some of his most famous poems at this very property. His poetry, as well as Blake’s, Shelley’s, Byron’s and Tennyson’s after who further rooms are named, is readily available at Keats Cottage.

Steeped in history and with parts of the building over 400 years old, Keats Cottage has been lovingly refurbished. No surprise then, that our room was beautifully appointed and quintessentially English.

David and Ewa, our hosts were utterly charming throughout our visit, and I cannot recommend this Bed and Breakfast enough as a base for your Isle of Wight getaway.

DAY 1 ON THE ISLE OF WIGHT – EAST WIGHT

In order to make the most of our weekend trip to the Isle of Wight, Gary and I left London on Friday afternoon after work.

After a seven hour journey, and severe delays caused in part by stormy weather conditions at the ferry port, there wasn’t much time left to explore the island that same day.

Nonetheless Gary stopped in several locations along the East coast of the Island, as we made our way down from Ryde to Shanklin.

A STROLL ON THE BEACH IN SANDOWN

Sandown was one of these locations. Situated half-way between Ryde and Shanklin, in a beautiful sheltered bay, Sandown is a seaside resort with a healthy tourist population owed in part to its many sea front hotels.

It is famed for its long golden sandy beach and traditional British seafront and pier.

Sandown has a great selection of attractions, including a Zoo housed in an old fort and a purpose built interactive Dinosaur Museum.

If unlike us you have a little time on your hands, spend some quality time strolling along Sandown Beach which stretches along the Esplanade until it meets Yaverland Beach.

And if you are planning a family beach vacation make sure to check out these tips to enjoy the beach with your toddler.

Yaverland Beach is one of the island’s most beautiful beaches and is particularly popular for watersports, including windsurfing, kayaking or many other activities.

As you make your way down the beach, keep an eye out for fossils, this area has one of the highest concentrations of dinosaur fossils anywhere in the world.

Then follow your stroll up with an ice cream or refreshments at one of Sandown’s licensed beach cafés.

One of the town’s most well-known features is the traditional Sandown Pier. Here you will find a range of traditional amusements and arcade games, which will keep both adults and children entertained for hours.

In addition to this Sandown features a large assortment of pubs and restaurants, perfect for an evening meal.

DINNER IN NEWPORT

Newport, located in the heart of the island, is the capital of the Isle of Wight. Indeed it is easy to access other all parts of the island from this hub.

Newport combines a rich sense of history with modern architecture and this is very typically seen in the array of buildings available.

At one extreme is the “Roman Villa” settlements that are still visible while the modern era is identified by the new bus station that are clearly pursuing the eco-friendly approach of public transportation.

If you are a bit of a shopaholic, you are going to want to visit Newport’s main high street, packed with some of Britain’s most popular shops, as well as lesser known brands.

Newport is the perfect location to grab dinner, if it isn’t served back at your hotel or accommodation. There is a myriad of dining options available for all taste buds so I am sure you will find something that you will enjoy!

DAY 2 ON THE ISLE OF WIGHT – NORTH WIGHT

THE ISLE OF WIGHT LITERARY FESTIVAL

On Saturday morning Gary and I woke up extra early, in order to attend Jane Thynne’s lecture on her book series the Real Housewifes of Nazi Germany.

We were in fact visiting the Isle of Wight specifically and just in time to take part in the Isle of Wight sixth Literary Festival.

This event for major bookworms takes place every year in October, and gathers some of the biggest names in fiction and non-fiction, as well as journalists, actors and historians.

This time the festival was hosted by Northwood House, a magnificent Grade II* listed late Georgian manor house set in a 20 acre park. Purchased by George Ward in 1793 and extended and improved by his heir, George Henry Ward, the House has a varied and interesting past including hosting elaborate entertainments for royalty and Victorian history, serving as a convent and acting as a convalescent VAD hospital in the First World War. 

Jane Thynne’s lecture wasn’t just enlightening, it was very entertaining too. Neither of us had ever learned about Germany’s past from this particular perspective. And I couldn’t help but feel common grounds with the main heroine of the fictional Clara Vine  series, who just like me has dual nationality.

FUN AT OSBORNE HOUSE

One of our favourite activities on the Isle of Wight was visiting Osborne.

Built between 1845 and 1851, in the Italianate style, this magnificent bright yellow stately home was Queen Victoria’s summer residence.

Osborne House accurately reflects Queen Victoria and Prince Albert’s passions, tastes and style. Ornate furnishings and artefacts from The Royal Collection fill rooms and corridors where Victoria entertained heads of state, inventors, princess and princesses and ruled the vast British Empire.

And the Durbar Room is perhaps the most incredible feature of this vast stately home. Designed by Lockwood Kipling, father of Rudyard Kipling, the room reflects Queen Victoria’s status as Empress of India (although she never had a chance to visit the country in her lifetime).

Queen Victoria loved her palatial summer home, spent many summers here and wrote the following about it: “It is impossible to imagine a prettier spot”.

Gary and I couldn’t agree more. Indeed we had a fabulous time exploring Victoria and Albert’s private apartments, strolling through the garden terrace with its beautiful views across the Solent and then walking hand-in-hand along the royal families’ private beach.

The children’s Swiss-chalet-style play-cottage gave us an intimate glimpse into the royal families’ private life and we even learned a couple of tricks on how to raise our own future children.

I would recommend you schedule at least 2-3 hours to see the entire grounds. (Indeed we were personally a little crunched for time).

Note that Osborne House is open daily from 10am – 6pm and the last admission to the house is at 4.30pm as it closes at 5pm.

THE PORT OF EAST COWES

We couldn’t have visited the Isle of Wight without popping into its main port.

Cowes has gained an international reputation for it’s sailing races and regattas. The town has good views over the busy shipping lanes of the Solent and is famous as a yachting center.

Cowes is divided into two distinct communities, East and West Cowes. Situated on either side of the estuary of the River Medina, they are linked by a chain ferry.

Gary and I visited East Cowes and went for a little walk along its promenade, enjoying the fine views across the mouth of the river and the bustle of ships in the harbour.

ADVENTURES (OR NOT) AT CARISBROOKE CASTLE

Being English Heritage members, Gary and I hoped to follow up our visit to Osborne House with one to Carisbrooke Castle, one of the most fortified and historic castles in the United Kingdom.

Unfortunately, our membership card was out-of-date and our new cards had been delayed in the mail. Nonetheless, I would recommend, you add Carisbrook Castle to your Isle of Wight itinerary.

Whilst the exterior of this castle isn’t especially striking, this fortress near the town of Newport offers layers of history instead.

The remains of an ancient Roman fort, Anglo-Saxon strongholds, and arrangements from the modern era all come together to reveal the island’s impressive historical and cultural heritage.

DINNER AT KEATS COTTAGE

After a fun but exhausting day, Gary and I spent the rest of the evening at Keats Cottage.

This local Bed and Breakfast doubles up as a restaurant in the evening and serves delicious food.

I was pleasantly surprised, when I found out that Keats Cottage dinner could easily rival that of many London restaurants.

The starter of fresh smoked salmon with horseradish puree and roasted beetroot , in particular, was beautifully presented and tasted fabulous.

For the main course I opted for roast beef on a bed of potato mash with roasted carrots and beetroot, whilst Gary chose the ever popular Schnitzel.

I couldn’t help myself and succumbed to my sweet tooth, enjoying a New York cheesecake for desert.

All this was washed down with some fresh dry white wine, just as I like it.

DAY 3 ON THE ISLE OF WIGHT – SOUTH WIGHT TO WEST WIGHT

THE OLD TOWN OF SHANKLIN

Our second day on the Isle of Wight, was spent exploring the island’s bountiful South coast.

We started the day off with a tour of Shanklin.

This wasn’t the first time I found myself in this adorable British Village. Indeed as a youngster, I had participated in a week long theatre programme organised by my school. It is thus fair to say that my sense were flooded with old memories.

Shanklin, our base for the entire trip, is a quaint village located on the Easter coastline of the Isle of Wight, with a very picturesque village center.

We had a fantastic time wandering around the Old Town of Shanklin, exploring it’s thatched cottage lined street and traditional sweetie shop.

The Crab Inn is a great little English pub with a beer garden of substantial size and thus the perfect place to relax for a couple of hours in summer with a cold beer.

EXPLORING SHANKLIN CHINE

If you are visiting Shanklin, then you should definitely take a gander down through Shanklin Chine, the Isle of Wight’s oldest tourist attraction and this Victorian oddity still has appeal today.

Shanklin Chine is a tree lined gorge, formed by a river (well perhaps more of a stream now), which cuts from Shanklin Old Village down to the beach and seafront. It’s lush gardens created to surround the pathway down the gully are wonderful.

And at night the gorge it is creatively lit up, which makes it quite a magical experience.

During the war, Shanklin Chine was taken over and used as an assault course by the commandoes which were based at the Upper Chine School.

40 Royal Marine Commandos trained at the Chine in preparation for the Dieppe raid in 1942. You can walk down a set of stairs to see the waterfall.

Observe the birds and wildlife, then head to the deck for elevated views across Shanklin beach.

Entrance to Shanklin Chine cost £4.30 for Adults and £2.50 for Children over 5.

FRESH BREEZE ON SHANKLIN BEACH

If beach life is more your thing, then Shanklin beach offers a stretch of glorious golden sand that is well worth a visit.

Shanklin is situated on a hill and while the beach is at the very bottom of it, there is a lift available to take locals and tourists from the town to the beach and back.

Shanklin is one of the most popular seaside resorts on the island and Shanklin Seafront is packed full of amusements, activities, soft plays, trampolining, bouncy castles and much more. It’s a bit busy and full on but also lots of fun.

THE OLD CHURCH OF BONCHURCH

From Shanklin, Gary and I took a road trip along the southern coastline of the Isle of Wight, from East to West.

On the way we stopped in a couple of quaint villages. One of which was Bonchurch.

Bonchurch is a small village located to the East of Ventor, and one of the oldest settlements on the island. It is certainly picturesque and it is said that Charles Dickens spent a couple of days here.

Stooped in history Bonchurch offers some great walks, and there is also a fantastic secluded beach.

Make sure to pop across to the Old Church. The Saxon patron saint, St. Boniface, is believed to have visited the Isle of Wight, and possibly the area where Bonchurch is now located, in the 8th century.

According to legend monks from Lyra in Normandy erected a building in his honour, where the Old Church now stands.

BRIGHSTONE OLD LIBRARY

The charming village of Brighstone is situated a mile from the sea, on the southern coast, between Shorwell and Mottistone, about halfway along the coastal route between Ventnor and Freshwater.

It’s history dates back to the ninth century when it was given to the Bishop of Winchester by King Egbert.

It is a pretty village with an old church, traditional farmhouses and thatched cottages built from local “clunch” stone.

At the village centre stands the iconic ‘North Street’, a row of attractive traditional cottages owned by the National Trust which now house Brighstone Library and a small Village Museum.

Whilst Brighstone offers a number of pleasant walks, we only stopped long enough to take a couple of pictures of it’s thatched cottages and old library, before we were back on our way to Freshwater.

POPPING INTO VENTNOR

Ventnor is the most southern town of the Isle of Wight and especially renowned for its mild climate.

Sheltered from the north winds by St. Boniface Down, Ventnor is a sunshine trap. With its sheltered beach, esplanade and traditional seaside attractions, it is a popular destination for family holidays.

Developed in Victorian times, the resort is built on a series of terraces, giving it a distinctive continental feel. This is why Ventnor is sometimes dubbed The English Madeira.

FRESHWATER BAY

Freshwater Bay is located about Three miles east from the famous landmark known as The Needles.

This town become a popular residential area during the 19th century when the poet Tennyson took up residence in the locality.

Although the Church of All Saints in the village of Freshwater is the more ancient one, it’s charming counterpart St. Agnes Church has the distinction of being the only thatched church on the island. Constructed in the style of a barn, long and low, it was built in 1908 to serve the growing community of Freshwater Bay.

Situated on a spectacular stretch of the island coastline, Freshwater is very popular with holidaymakers. The beach looks out across a little horseshoe-shaped cove which has been eroded out of chalk cliffs by the action of the wind and waves, leaving distinctive isolated stacks standing offshore. Behind the bay, Tennyson Down rises to an impressive height of 482 feet.

PHOTOGRAPHY EXHIBITION AT DIMBOLA MUSEUM

Located in freshwater, Dimbola Lodge was once home to the celebrated Victorian photographer Julia Margaret Cameron. Today it is a Museum and Gallery dedicated to her life and work, which also showcases contemporary exhibitions from photographers around the globe.

In 1860, while her husband and son were in Sri Lanka inspecting their new coffee plantations, Julia Margaret Cameron bought two cottages in Terrace Lane, as the family’s new home. The two cottages were joined together with a central tower in the then fashionable Gothic style in 1870 and renamed Dimbola Lodge.

Julia Margaret Cameron was an incredibly prolific photographer and came into contact with some of the most famous people of her time, including Charles Darwin.

A woman ahead of her time, she was ambitious and freethinking when most Victorian women were passive and demure. She took on the challenges of handling large cameras and dangerous chemicals at a time when photography was known as ‘The Black Art’. Ignoring conventions, she experimented with composition and focus.

Being a woman she was sadly often the subject of amusement. Nonetheless, her photographs were gradually accepted as the work of the most influential pioneer of perhaps the most important art form of the 20th century.

Today she is credited with creating the first photographic close-up portraits and influencing the subsequent Pictorialism movement with her use of diffused focus.

It was at Dimbola that Julia Margaret Cameron took most of her photographs, so I don’t think there is a better place to enjoy her photographic collection.

A HIKE UP TO THE NEEDLES

Located in Alum Bay, the Needles is one of the most beautiful spots on the Isle of Wight and perhaps its most famous landmark.

The Needles is a row of three distinctive stacks of chalk that rise out of the sea off the western extremity of the island and is a must-see for all visitors to the Island. Actually, there used to be four stacks, but one of them collapsed during the great storm of 1764. One of the tallest needles in the famous rock formation, all that is left of it today is a large gap.

There are a few ways to see famous this landmark. You could take a chair lift down to Alum Bay then board a boat that takes you right up close to the rock formation. Alternatively, you can walk for a mile up to the top of the cliff and look down onto the Needles.

If you are going to take only one walk during this weekend getaway then I would suggest you make it this one. It is incredibly picturesque and we were even blessed with a rainbow. If you have a bit of spare time, you could start your hike at Freshwater Bay.

In this case, the journey should take around 3 hours.

Once you’ve had a good look at the lovely rock stacks take some time to visit the National Trust Needles Battery, a former military installation where rockets were once secretly tested. The museum offers a number of fascinating exhibitions about the role the Battery played in the second world war and there are also plenty of activities for children.

If you are visiting the Isle of Wight by car, you can park at Alum Bay car park for £5 per day.

COTTAGES IN GODSHILL

Godshill is a bustling yet timeless village where neat thatched cottages cluster in the shadow of the 15th century Church of All Saints.

This was the final stop on our Isle of Wight Itinerary before we drove back north to catch the ferry.

Perched on a hill above the village, the church dates from the days of Edward the Confessor, although it was largely rebuilt in the 14th century.

Many visitors are attracted to Godsill by the charming groups of ancient cottages. With their thatched roofs and delightful gardens, they give the impression of having altered little since they were first built.

OVERVIEW OF OUR FULL ISLE OF WIGHT ITINERARY

The Isle of Wight truly represents England in miniature form, from its majestic landscape to its quaint villages and grand estates.

The pace of life and local culture are best described as laid back and nostalgic.

The island’s landscape changes dramatically from cliffs to rolling hills to forested valleys and flat fields. And there is no shortage of great towns, museums, castles, and Palaces to explore.

Nonetheless if like us you enjoy a busy itinerary, you should easily be able to cover a vast majority of its sites in a long weekend.

Note that I tend to pack our itineraries full activities. Total cost of this trip was 366£ or 183£ per person

PLEASE NOTE: Visit Isle of Wight kindly helped us organise this weekend and our two-night stay at Keats Cottage. But as always all opinions expressed in this article are my own.