7 Night Isle of Wight Family Walking Adventure

Distance: 3 miles (4.5km)

Ascent: 350ft (100m)

We’ll follow the Shepherd's Trail through the fields and along an ancient trackway to Carisbrooke Castle. If you’d like to visit the castle (payable locally), please check out the English Heritage website as they often run special events in the summer, some of which you will need to prebook. We haven’t included the cost of entrance as we know many of you are English Heritage members already and will benefit from free or reduced-price entry.

What your kids will love: The fairytale-feel of exploring mighty Carisbrooke Castle. Have fun dressing up as Norman soldiers, walk the battlements to discover how cannons are fired, and relive an age of knights, broadswords, and battles.

Distance: 6 miles (9.5km)

Ascent: 700ft (220m)

This option is slightly longer and sees us cross the island's central hills from the picturesque village of Shorwell to the impressive medieval castle at Carisbrooke. If you’d like to visit the castle it is payable locally (see above). 

What your kids will love: Meeting Carisbrooke Castle’s resident family of donkeys. A supply of fresh water was essential for a well defended stronghold and for hundreds of years these friendly animals were used to turn the treadmill and raise water from the well.  Fun fact, all the donkey’s names begin with the letter J. See if you can guess them all.

Distance: 7½ miles (11.5km)

Ascent: 1100 feet (340m)

Starting from Brighstone we’ll pass through Shorwell before crossing open countryside until we arrive at Carisbrooke Castle (payable locally).   

What your kids will love: Spotting the small ships carved into the chalk blocks on the walls of Brighstone – these were once used as secret codes and signals for smugglers delivering contraband to the island. There’s time to explore the Carisbrooke Castle, too.

Distance: 12½ miles (20.5km)

Ascent: 1,600ft (480m)

Challenge yourself to this fantastic walk along the spine of the island from Carisbrooke Castle to Freshwater Bay. We’ll cross the hills to Shorwell then pick up the Tennyson Trail which runs along the top of the chalk downs.   

What your kids will love: The bragging rights of being tough enough to take on the challenge. Although this is our longest walking option of the day, there’ll be plenty of fun, excitement, and adventure along the way.

Distance: 3½ miles (6km) 

Ascent: 550 feet (180m) 

Stroll along the coast path to Tennyson Down and the Needles. We'll return on the open-top bus and be back to enjoy plenty of time to play in the pool at Freshwater Bay House.   

What your kids will love: Riding the world-famous Needles chair lift (payable locally). Test your bravery with a chair lift trip from the top of Alum Bay cliffs down to the beach below. There’ll also be time to paddle in the sea and make a game out of how many colours you can spot in the multi-coloured cliff face. Check out videos of the chairlift on YouTube.

Distance: 7 miles (11km)

Ascent: 1,200ft (360m)

A fabulous walk over the chalk cliffs of Tennyson Down to the Needles and Alum Bay; one of England's finest coastal walks.   

What your kids will love: Discovering what was once a secret rocket testing range and finding out about the Isle of Wight’s role in the space race. Don’t forget the code word: Project Black Knight.

Distance: 8½ miles (13.5km)

Ascent: 1,300ft (400m)

Head to the coast at Totland Bay then soak up glorious sea views as you round the Needles headland and return over Tennyson Down.   

What your kids will love: Imagining what it was like to be one of the island’s ancient tribal chieftains with a visit to the ruins of a bronze age burial mound.

Distance: 12 miles (19km)

Ascent: 1,550ft (480m)

Our longest walking option is a circuit of the western tip of the island. We’ll follow the Yar Valley to Yarmouth, then take the coastal path to Alum Bay, before a glorious finale over Tennyson Down.   

What your kids will love: Stopping at the Needles viewing platform – the perfect spot for selfies.

Distance: 4 miles (7km) 

Ascent: 490 feet (150m) 

From Godshill the Stenbury trail takes us to the romantic ruins of Appuldurcombe House (free entrance), a great place for hide & seek. Our trails then lead us to the Isle of Wight Donkey Sanctuary (free entrance), home to over a 100 donkeys and Shetland ponies. There’ll be plenty of time to meet the residents before walking back to Godshill where, if time allows, there’s the model village and museum to explore (payable locally).    

What your kids will love: There are over 100 donkeys and ponies in residence at the Isle of Wight Donkey Sanctuary. Can you spot a donkey with the same name as you?

Distance: 5 miles (8km)

Ascent: 500 feet (160m) 

With this option we’ll walk from Niton to the village of Whitwell and on to Steephill Cove. Enjoying great views of the English Channel, we’ll reach the island’s highest point and pass by both its oldest inn and what’s arguably one of its prettiest beaches. We’ll round off with a stop at Ventnor Botanic Garden (payable locally).   

What your kids will love: Rock pooling at Steephill Cove and reaching the medieval lighthouse that marks the highest point on the island. Look closely. Can you see why it’s nicknamed the “Pepperpot”?

Distance: 8 miles (13km)

Ascent: 1,200 feet (360m)

Soak up sea air and views of the English Channel on a walk through the Undercliff from Niton to Shanklin Old Village. At the end of the walk there’s the chance to visit the historic waterfall-splashed gorge of Shanklin Chine (payable locally). Alternatively, simply relax on Shanklin beach and enjoy an ice cream or two.

What your kids will love: Searching for dinos and their eggs hidden in the undergrowth around the beautiful waterfalls of Shaklin Chine or playing a game of crazy golf. Be sure to pay a visit to Jurassic Jim in Shanklin town centre – it’s the perfect place to start any fossil collection.

Distance: 9½ miles (15km)

Ascent: 1,250ft (380m)

This walk encompasses all the best bits of options 2 and 3 but extends the journey along the length of Undercliff. Starting at the coastal path after Whale Chine, we'll round St Catherine's Point before picking up the coastal path through Ventnor to Shanklin.   

What your kids will love: Exploring over 9 miles of beaches, rock pools, and fossil-rich sands - more than deserving of an ice cream or two, right? 

Distance: 3 miles (5km)

Ascent: 320ft(100m)

Take a trip on the Isle of Wight steam railway before following a trail that takes us onto Brading Down for fabulous views. It’s also home to one of the best-preserved Roman sites in the UK - Brading Roman Villa (payable locally).  

What your kids will love: Riding a real steam train and finding out how good the Romans were at art with a visit to Brading Roman Villa. You can top it all by popping on a toga and dressing up as one of the ancient Romans that once lived here, too.

Distance: 6½ miles (10km) 

Ascent: 600 feet (180m) 

Bring your binoculars for a chance to spot dragonflies, lapwings and more in Brading Marshes Nature Reserve. Continuing to Bembridge, there’s time to explore the island's last surviving windmill (payable locally) before some superb coastal walking that ends in Sandown and the chance to play on the beach or explore Dinosaur Isle (payable locally). Please note, we haven't included entry to the windmill as we know many of you are members of the National Trust, and are eligible for free entrance 

What your kids will love: Climbing to top of a windmill, playing in its mud bakery, or stepping back in time at Dinosaur Isle – home to almost every newly discovered dinosaur in the British Isles.

Distance: 8 miles (12.5km)

Ascent: 550ft (180m)

Enjoy excellent views from Brading Down before we head to the historic village of Brading village where we’ll join the same route as the option 2 walk.   

What your kids will love: Reaching Yarborough Monument. Why not make a race of it and see who can be first to the finish line?

Distance: 10½ miles (17km)

Ascent: 950ft (280m)

Our longest option of the day is a walk along the valley before climbing up onto Brading Down. We’ll walk along the chalk ridge, enjoying the views across the Solent to the mainland, before continuing over Culver Down and along the coastal path to Sandown.   

What your kids will love: Looking out over the blue-green waters of the Solent. How many sailing yachts can you spot?

Distance: 3½ miles (5.5km)

Ascent: 100ft (20m)

A gentle walk from Freshwater Bay House that follows the Yar Valley through a nature reserve. We’ll walk along a disused railway line to the old harbour town of Yarmouth before an open-top bus ride back to Freshwater Bay.   

What your kids will love: Keeping an eye out for red squirrels scurrying through the trees and raven, kestrel, buzzard, and barn owl soaring overhead. There’ll also be plenty of time to explore Yarmouth where you can play on the green and visit the castle (free to English Heritage members or payable locally).

Distance: 7 miles (11km)

Ascent: 350ft (120m)

We’ll walk beside the tidal River Yar to the historic town of Yarmouth with its bustling harbour and Tudor castle. We’ll return on the opposite side of the river back to Freshwater Bay.

What your kids will love: Making a game of who can spot the most wildlife as we walk through the salt marsh, reedbeds, and mud flats of the Yar Estuary.

Distance: 8½ miles (13.5km)

Ascent: 1000ft (300m)

Get that on-top-of-the-world feeling as we traverse the high point of the Downs east of Freshwater Bay. We’ll then head to the beach and follow the coastal path back to Freshwater Bay House.   

What your kids will love: Paddling at the beach and getting selfie-worthy views of the island's south-west coast as we walk over the chalk cliffs of Compton Down.

Distance: 11½ miles (18.5km)

Ascent: 1200ft (380m)

Our longest option is a walk over the Downs to the Neolithic Longstone. We’ll then descend to the coast and follow the coastal path all the way back to Freshwater Bay.   

What your kids will love: The Neolithic Longstone. According to legend this 13ft stone was thrown here by a giant. Keep your eyes peeled for fossilised forests and dino footprints at Hanover Point, too.