Isle of wight heritage driving trail

Your Isle of Wight history adventure starts as you drive aboard one of our iconic Red Funnel ferries at our terminal in Southampton, before cruising with us across the Solent. 

The Red Funnel brand is named after our ships’ iconic, black-topped red funnels. Although the origins of Red Funnel date back to 1820, it wasn't until 1935 that the trading name "Red Funnel Steamers" was first adopted. It was in this year that the famous red funnel and black top was uniformly adopted across the entire fleet, marking the very beginning of ‘Red Funnel’.

Once we’ve crossed the Solent, you’ll arrive at the picturesque marine town of East Cowes, where your road trip to unearth the island’s historical gems begins. If you have time, it is worth stopping here for a short time to explore the town’s idyllic seafront and historic streets.

If you're visiting between 29 July and 4 August this summer, you may want to stop for longer to absorb the atmosphere of Cowes Week and take in the sight of hundreds of sailing boats cruising across the Solent. Now nearly 200 years old, Cowes Week is the oldest and biggest sailing regatta in the world.

Address: York Ave, East Cowes PO32 6JX (approx. 5 minutes’ drive).
Travelling Southbound along the A3021, it takes about five minutes to drive from East Cowes to Osborne House. An English Heritage Site, Osborne House is well-known for being the former home of Queen Victoria and Prince Albert, as well as the late Monarch’s favourite royal residence.

2024 marks 181 years since the royal couple first moved into the estate. Although Queen Victoria and Prince Albert did not officially purchase Osborne House until 1845, the family first moved into and leased the property in 1843 as a seaside retreat for their growing family. Osborne House was also the location of the UK’s first long distance telephone, which took place at Osborne House 140 years ago this year.  In 1878, Scottish inventor Alexander Graham Bell demonstrated the telephone for the first time to Queen Victoria from Osborne House by calling Cowes, Southampton, and London. Queen Victoria liked the telephone so much she wanted to buy it.

At Osborne House, visitors can discover the royal couple's grand State Rooms, Family Rooms, Queen Victoria's beach, as well as the garden and grounds. There is also a plethora of family-friendly activities at Osborne House, such as a Family Tree Trail and two playgrounds.

Castle Hill, Newport PO30 1XY (approx. 17 minutes’ drive).
Driving southbound from Osborne House towards Newport will take you to Carisbrooke Castle, the oldest castle on the island. Here, visitors can explore the castle buildings, its chapel, idyllic gardens, enjoy the tearooms, and discover plenty of royal history.

Carisbrooke Castle is well-known as the location where, following the end of the First English Civil War, King Charles was held for 14 months prior to his execution in 1649. However, there is also a wealth of other history to discover here too, including Carisbrooke Castle Museum, which was opened by the daughter of Queen Victoria, Princess Beatrice. Founded as a memorial to Princess Beatrice’s husband, Prince Henry of Battenberg, following his passing in the Anglo-Ashanti wars in 1896, it remains Britain's only public museum founded by a member of the Royal Family.

44 Scarrots Ln, Newport PO30 1JD (approx. 7 minutes’ drive).
Having worked up an appetite after all that driving, you'll want to stop by Scarrots Lane Bakery in Newport. A short 7-minute drive into Newport town from Carisbrooke Castle, Scarrots Lane is a popular traditional bakery that has been serving locals delicious treats baked from scratch for years. A range of delicious delicacies can be purchased from Scarrots, including a variety of breads, savouries, pastries, and cakes. 

Railway, Havenstreet Station, Isle of Wight Steam, Main Rd, Havenstreet, Ryde PO33 4DS (approx. 16 minutes’ drive).
Take the A054 eastbound towards Havenstreet for the Isle of Wight Steam Railway. The island’s heritage Steam Railway, visitors can jump aboard for an idyllic journey through 5.5 miles of picturesque island countryside.

Starting at Smallbrook Junction to Wootton station, the journey is ideal for adults and families alike, and this year the Isle of Wight Steam Railway are celebrating the 100th anniversary of their historic Southern Railway line.

The Pier, Ryde, PO33 2HF (approx. 13 minutes’ drive).
Take the A3054 towards the seaside town of Ryde on the island’s north-east coastline, where you will find a historic town and Britain’s oldest pier. Just down the road from the Pier, you’ll also find Appley Beach, famed for its golden sands and warm water. This year the town’s pier has an important birthday, as it was 110 years ago in June 2023 that the first foundation stone was laid to construct Ryde Pier.

Now in its 135th year, Ryde Carnival - the UK’s oldest carnival celebration - will also take place in the town between 26 August - 2 September. In addition to the usual colourful floats and marching bands will be an illuminated procession with a spectacle of light and music designed to see off the summer season in style.

Sherborne Street, Bembridge PO35 5XW (approx. 16 minutes’ drive).
Driving southbound on the A3055 and B3395, it will take you about 20 minutes to reach the scenic village of Bembridge from Ryde. Well worth the drive for travellers looking to unearth some of the island’s lesser-known attractions, the village is unique because it houses the UK’s oldest working telephone box on its main street. 

Turning 102 years old this year, the classic K1 telephone box was first introduced to the UK’s streets in May 1921. Sadly, this model of telephone box has now been largely removed from service, with only a few K1 telephone boxes still in existence - most of which currently sit in museums or are out of operation.  However, the K1 telephone in Bembridge is still in operation and open to the public - ideal if you need to make a call and for photo opportunities! 

Adgestone Vineyard, Upper Road, Brading PO36 0ES (approx. 10 minutes’ drive).
Drive West for approximately 10 minutes along Sandown Rd/ the B3395 to discover the UK’s oldest continuously operating vineyard. Turning 55 years’ old in 2023, Adgestone features over 10 acres of breath-taking vineyard overlooking the sea and is open to the public between Wednesdays and Sundays until December. Producing a wide range of delicious English wines, including the UK’s only blue sparkling wine, the site is home to original Seyval Blanc vines from 1968 - the oldest commercial vines in the UK.

Adgestone offers guests audio and guided tours of the vineyard, as well as wine tasting sessions, live music, and the opportunity to stay overnight at the site in a charming holiday cottage.

Culver Parade, Sandown PO36 8QA (approx. 6 minutes’ drive).
Drive 6 minutes’ South along the B3395 to Britain’s first ever dinosaur attraction in Sandown where families can explore the fascinating history of how dinosaurs roamed the island over 125 million years ago. Turning 22 years’ old in 2023, Dinosaur Isle is a purpose-built dinosaur museum designed by Isle of Wight architect Rainey Petrie Johns in the shape of a giant pterosaur (a type of flying dinosaur).

Home to one of the UK's most important collections of dinosaur remains, Dinosaur Isle offers family-friendly exhibits and the opportunity to see, hear, touch, and smell ancient remains, learn stories about how the dinosaurs lived millions of years ago, and discover fossils, rocks, minerals, and other historic artefacts found in the islands' waters.

3 Chine Ave, Shanklin PO37 6BW (approx. 10 minutes’ drive).
Drive roughly 10 minutes South bound along the A3055 to Shanklin Chine, the island’s oldest tourist attraction and one of Britain’s most impressive geological wonders. A truly breath-taking site with plenty to discover, Shanklin has inspired many, including the likes of English Poet John Keats and the renowned novelist Jane Austen.

Although the Chine itself is over 10,000 years old, the site is also now the island’s oldest tourist attraction, having first opened to the public in 1817. Visitors are invited to meander through the Chine to discover breath-taking waterfalls, significant geological formations, an abundance of local wildlife, and a diverse ecosystem of wild and rare plant species. There is also a Tea Room and Antiques Centre onsite, as well as The Fisherman’s Cottage Inn - a local pub located at the bottom of the Chine.

Blackgang Rd, Ventnor PO38 2JB (approx. 20 minutes’ drive).
Taking the A3055 south bound along the island’s southern coast will lead you to St. Catherine's Oratory after about 20 minutes. Built in 1313, St. Catherine's Oratory on St. Catherine's Down is Britain’s oldest surviving mediaeval lighthouse. Turning 710 years old in 2023, the small lighthouse is affectionately known as ‘the Pepperpot’ by islanders and offers spectacular sea-views. On a clear night, the site is also a fantastic location for a spot of stargazing.

Ventnor, PO38 2HN (approx. 1 minute drive).
Blackgang Chine, the UK's oldest theme park, is celebrating a major milestone in 2023. Having first opened its doors to visitors in 1843, the iconic theme park is celebrating its 180th anniversary this year. Still run by the same family who originally built the theme park, Blackgang Chine offers a plethora of exhilarating rides, family exhibits, live performances, and colourful characters. New this year, the park’s ‘Extinction’ ride is a hair-raising experience as visitors are strapped to a pendulum that swings to heights of 18 metres.

Newport, PO30 4ED (approx. 15 minutes’ drive).
Taking around 15 minutes to drive from Blackgang Chine via the A3055, this picturesque drive along the coast will take you to the idyllic village of Mottistone. Known for its historic buildings and gardens, Mottistone is also home to St Peter and St Paul's Church. Dating back to the 12th century, the church offers stunning architecture and was also where Hollywood actor Benedict Cumberbatch and theatre director Sophie Hunter tied the knot back in 2015.

Alum Bay New Rd, Alum Bay, Totland Bay PO39 0JD (approx. 20 minutes’ drive).
Needing no introductions, the Island’s ‘The Needles’ near Alum Bay is an iconic Isle of Wight attraction and one of the most photographed groups of rocks in the world. From here, visitors can discover the famous chalk rocks by boat or via the site’s spectacular chairlift. Picking up visitors from the top of the Alum Bay cliffs, the chairlift - which turned 50 years old in 2023 - takes visitors out to discover The Needles and stunning views across the English Channel. You can also see the historic red and white lighthouse here. First completed in 1859, the lighthouse turns 165 years old next year. 

Yarmouth, PO41 0QN (approx. 25 minutes’ drive).
Driving for around 25 minutes from The Needles northbound along the A3054 will take you to Yarmouth, the oldest town on the island. Over 1,000 years old, Yarmouth boasts an unusually long, lively, and rich history.

Although there is evidence of Roman activity in the area, the first proof of a fixed settlement at Yarmouth dates back to 991 AD. Home to charming, cobbled streets and an array of great local cafes, pubs and restaurants, you’ll find no shortage of things to do here. Discover the shops and galleries in the main square, which overlooks a stunning 17th century church, explore Yarmouth Pier, or get active with excellent cycling along the town’s flat paths, which run beside nature reserves.

Newport Rd, Calbourne, Newport PO30 4JN (approx. 15 minutes’ drive).
With a history going back 1000 years, the Water Mill & Rural Museum in the picturesque village of Calbourne was first mentioned in the Domesday Book in 1086 AD. Calbourne is accessible via the A3054 and takes about 15 minutes to drive to from Yarmouth. Having supplied flour and animal feeds to the people of the Isle of Wight for centuries, the historic mill here uses grit and burr stones to produce up to sixty tons of flour and oats each year. From here, visitors can explore the old Mill and museum, enjoy the tea rooms, and stroll the site's spectacular grounds.

East Cowes Ferry Terminal, PO32 6RA
Taking about 25 minutes to drive along the B3401 from Calbourne, take in the Island’s countryside while heading on to East Cowes for your return voyage with us back to Southampton.