Isle of Wight Itinerary

A road Trip Adventure in the Isle of Wight

Embarking on an Isle of Wight road trip is like stepping into a blend of picturesque landscapes, rich history, and coastal charm. As someone who lives on the road, the Isle of Wight offers a unique escape that combines serene countryside with the adventurous spirit of island life. This small island off the south coast of England is packed with scenic views, from its rugged cliffs to soft sandy beaches, making every mile driven an experience in itself.

We spent a delightful week in the Isle of Wight, exploring, walking, eating and generally having a relaxing week away. 

Isle of Wight Itinerary - Jump To...

Why Visit The Isle of Wight

The Isle of Wight is a haven for travellers seeking a mix of relaxation and exploration. Its compact size packs in everything from dinosaur footprints at Compton Bay to the historic Osborne House, Queen Victoria’s summer home. The island’s network of roads meanders through quaint villages, past ancient castles, and along dramatic coastlines, offering endless opportunities for discovery. You do have to watch some of the narrow roads in the Isle of Wight when you are doing your riad trip, but we managed OK in our 7m motorhome and we have been in much tighter spots in our time, that is for sure!

Best Time For Your Isle of Wight Road Trip

Choosing the best time to visit the Isle of Wight largely depends on what you’re looking to get out of your trip. The island offers a different charm for each season, catering to a wide range of interests from outdoor activities to cultural festivals. The one thing you can do all the time is walking! There are some amazing walks in the Isle of Wight, so make sure you take your boots!

Spring (March to May)

Spring is a beautiful time to visit the Isle of Wight as the island begins to bloom with flowers and the weather starts to warm up. This season is ideal for those who enjoy walking and cycling, as the island is not yet as busy as in the summer months, allowing for a more peaceful exploration of its natural beauty. Attractions like the Ventnor Botanic Gardens are particularly impressive during this time, with fantastic displays of plants and flowers. Ventnor was one of our favourite places to base ourselves. Milder spring weather also makes it comfortable for exploring outdoor historical sites like Carisbrooke Castle, but you don’t get the summer crowds.

Summer (June - August)

Summer is the peak season for the Isle of Wight, attracting visitors with its long, sunny days and a plethora of events and festivals, such as the famous Isle of Wight Festival and Cowes Week, one of the oldest and largest sailing regattas in the world. The beaches, like Shanklin, Sandown, and Ventnor, are perfect for sunbathing, swimming, and water sports. While this is the busiest time of year, the island’s infrastructure is well-equipped to handle tourists, offering a lively and vibrant atmosphere. However, it’s wise to book motorhome and campervan campsites and your ferry tickets in advance.

Autumn (September to November)

Autumn brings a quieter but equally charming experience to the Isle of Wight. The landscape is painted with golden and russet hues, making it a fantastic season for photographers and nature lovers. The cooler temperatures are ideal for hiking, particularly along the coastal paths where you can enjoy dramatic views of the sea and cliffs. While some attractions may have reduced hours, the less crowded sites allow for a more relaxed visit. Autumn also hosts events like the Isle of Wight Literary Festival, appealing to culture enthusiasts.

Winter (December to February)

Winter on the Isle of Wight is the least crowded season, offering a tranquil escape with crisp, cool days. Many of the island’s attractions remain open, including museums, castles, and indoor gardens like the Butterfly World. Pubs and restaurants offer a cosy refuge with fireplaces and hearty meals. Winter is also a special time for experiencing the island’s Christmas markets and celebrations. Though some outdoor activities may be limited by shorter days and colder weather, the island’s natural beauty still makes for enjoyable walks.  Do check that your preferred campsite is open, don’t leave it to chance as many of them do close. 

When is the Best Time to Visit?

The best time to visit the Isle of Wight depends on your personal preferences. For outdoor activities and the full vibrancy of island life, late spring to early autumn (May to September) offers the most favourable weather and the widest array of open attractions and events. If you prefer a quieter visit with fewer tourists and don’t mind a bit of chill, autumn through spring provides a more laid-back experience with the opportunity to engage with local culture and enjoy the natural scenery without the crowds.

No matter when you choose to visit, the Isle of Wight’s charm and variety of experiences make it a year-round destination for travellers seeking both adventure and relaxation.

How to Get to the Isle of Wight

If you plan on taking your motorhome, campervan, car or any other vehicle, you have to catch the ferry. It is the only way. Pound for mile, this is the most expensive ferry route from the UK. However, we booked it at the time, because it was actually the cheapest, because the Isle of Wight is so close and we wanted to explore somewhere different. The crossing time is less than an hour! 

The Ferry Operators for your Isle of Wight Road Trip!

 The Island is served by three independent ferry operators.

  • Wightlink – This is the option we took from Lymington, although you can go from Portsmouth too. 
  • Red Funnel – They operate car ferry and passenger route from Southampton. 
  • Hovertravel  – They have a passenger service from Southsea if you are planning to camp or rent a car when you reach the Island.

Wightlink Routes

Three routes travel to the Isle of Wight, but only two of them you can take your motorhome or campervan with you:

  • Lymington – Yarmouth (Vehicle and passenger – 40 mins)
  • Portsmouth – Fishbourne (vehicle and passenger – 45 mins)
  • Portsmouth – Ryde (Passenger only – 22 mins and hire a car when you are there. You can also take bicycles on this ferry)

Red Funnel Routes

Red Funnel gives you one vehicle option and one foot passenger option from Southampton: 

  • Southampton – West Cowes (vehicle and passenger – 55 mins)
  • Southampton – East Cowes – Passenger only – 28 mins) 

Hovertravel Routes

Three routes travel to the Isle of Wight, but only two of them you can take your motorhome or campervan with you:

  • Portsmouth – Ryde (Passenger only – 10 mins and hire a car when you are there)

Cheapest Ferry Operator to the Isle of Wight

For the purpose of this blog post, I am not going to include the foot passenger option on here as that would be like comparing apples with oranges! Of course it is more expensive to take your motorhome with you than travelling alone. 

The dates that I have used are Saturday 25th May – Friday 31st May (which is a half term holiday for those with school aged children) for one week. I am travelling in a 7m motorhome (which is what we have) and 2 adults. 

Wightlink – £278.50 (Lymington to Yarmouth return) 

Travelling ‘Standard Class’ it is almost £100 cheaper if you go early in the morning or late at night (£157.75 vs £205.00). Travelling Economy (£139.25 vs £179.50). As you would expect, the economy ticket is not flexible, so not able to move.  

Wightlink – £278.50 (Portsmouth – Fishbourne return) 

The prices for the Portsmouth route were identical when the search was carried out. There is a slight difference in the timings – you could leave from Portsmouth slightly later for the same prices – but it is still early in the morning at 07:20.  

Depending on your travel flexibility, for an extra £20 each way (approx.) you can change your tickets, which is what we ended up doing.  We changed our crossing which was returning us to the mainland, giving ourselves more time over on the Island. We found so many things to do we wanted to stay longer. If you have some flexibility, then I would recommend that you travel standard. 

If you book using the camping and caravan club, your tickets really are greatly reduced. £139.24 return! Yes - RETURN PRICE FOR THESE DATESWe always book via them as they have always been cheaper.

Your Isle of Wight Road Trip Useful Facts

Total Distance

*75 miles / 120 km approx.


4 - 8 days

Driving Time

*3 hours approx.

*Driving and milage depend on your exact route and places that you visit. These are rough guesstimates to help you plan your road trip to the Isle of Wight.

Isle of Wight Road Trip Itinerary

Using the map.  Our map for your Isle of Wight Road Trip Itinerary uses green hearts to show our stops. We have included loads of places to visit, lots of different motorhome campsite options as well as walks.  We mostly wild camped in the Isle of Wight, but of course, that is up to you! Easier out of season as usual. 
If you have a touch screen, use two fingers to increase the size or decrease. If you click on each of the stops, it will give you the name of the stop. Click on the other items to see the names of attractions and motorhome campsite stops.   

Isle of Wight Road Trip Itinerary

Road Trip at a Glance

Yarmouth ~ Needles ~ Chequers ~ Ventnor ~ Shanklin ~ Bembridge ~ Ryde ~ Cowes


Starting your Isle of Wight road trip in Yarmouth offers a blend of cultural and natural attractions. Dive into local history with a visit to Yarmouth Castle, perfect for a glimpse into the past. It was built by Henry VIII in the 1540’s so has some really interesting history behind it. It’s a great place to stop for a picnic too – so if you have taken the early morning ferry – this could be your breakfast stop.  Rustle up a bacon butty in the van with a flask of tea. It has great views across the solant.  Although its a castle, it’s definitely not a big one!  

Take a short stroll along Yarmouth Pier, just to take in the views of the channel that you have just crossed. Meander through the towns streets, stop to visit the Jireh House, which is a cute little gallery that shows off local art, which captures  the essence of the island. 

Have a browse through Harwoods of Yarmouth, which is a charming shop offering everything from handmade crafts to island souvenirs. Yarmouth is just the start to your road trip, but it manages to blend a little history, art and natural beauty in a compact, welcoming start to your Isle of Wight road trip..


Spending a day around the Needles on your Isle of Wight road trip gives a mix of natural beauty, history and adventure. Take a walk to the Needles Headland for some fantastic views of  the iconic chalk stacks and the lighthouse. This area, part of the National Trust, offers several walking paths that provide spectacular views of the coastline and a chance to immerse yourself in the island’s natural beauty.


After your walk, head over to Alum Bay, famous for its multi-coloured sand cliffs. Here, you can take the chairlift down to the beach for a closer look at the sand’s unique hues or embark on a boat trip for a different perspective of the Needles.

Next on your agenda should be a visit to Carisbrooke Castle, located in the heart of the Isle of Wight. This historic castle offers a glimpse into the island’s past, with its medieval walls, museum, and the famous donkeys that operate the water well. Explore the castle grounds and ramparts which gives a fascinating look back in time and also stunning views of the surrounding countryside.


This is more a campsite to stay at for the evening as you tick off a few things on your way there in your motorhome. The campsite is such a lovely place, and it sits right on the edge of the Isle of Wights AONB (area of natural beauty) so lots of walking if that is your interest.   On the way to your stay over in Chequers, there are several places to stop at. The Dimola Museum & Galleries, the Isle of Wight Pearl and the Dinosaur Expedition Centre.  The Dinosaur Expedition Centre run organised fossil hunts on 2 parts of the Island that dinosaur bones can be found freely which is a great, fun and educational  activity. 

If you need some chill time from all the rushing about, Compton Beach is the one to go to. Of course you may wish to  have a lazy beach day and stay there for the day, soaking up the suns rays, if your road trip is in the warm summer months.

If you don’t want to head inland to Chequers, there are plenty of campsites and motorhome and campervan stops on the way down towards Ventnor, which is your next stop on your Isle of Wight road trip itinerary anyway. 


Ventnor is a great place to visit! If you base yourself in Ventnor for a couple of days, you can visit the Botanical Gardens and then take a walk down to St Catherine’s Lighthouse. Or drive there afterwards which is a quick 15 minute drive away.  Have a walk on the seafront and be sure to stop for coffee. We had a coffee in a delightful café which had dogs running around that you could pet. 

Just a 10 minute drive from the Botanical Gardens is the Donkey Sanctuary, which I loved. As a horse lover, that could have skewed my view slightly, but it was a lovely thing to visit whilst we were in the Isle of Wight. 

Blackgang Chine is also worth looking into if you have decided to take a road trip to the Isle of Wight. Although it is classed as a Theme Park, which might not be your thing, they often have events on, which you may be more interested in. An example of this is Judge Jules, Ibiza Nights and Summer Festivals. It is open from late March to about late September. So check them out as part of your planning as it may change the dates you pick to visit. 

If you have decided to do your road trip to the Isle of Wight in the summer time, you may be in Ventnor when the fringe festival is on at the end of July. Ventnor Fringe Festival is hosted over several days and showcases rising talent in the arts. Talking of arts – if you fancy a little bit of pottery making whilst in the Isle of Wight, Tregear Pottery do classes of all sorts, from kids to adults, which you can book online if you are interested in a little creativity.  

Café in Ventnor with all the Dogs! Isle of Wight Road Trip


Your next stop is Shanklin during your Isle of Wight road trip, which encapsulates the quintessence of the island’s charm, blending scenic beauty with quaint village allure. A stroll along Shanklin Seafront, with its expansive views of the sandy beach and the English Channel might be something you want to check off. The esplanade is perfect for a relaxed morning, with cafes where you can enjoy a warm drink and watch the world go by. 

Next, venture into Shanklin Old Village, a picturesque setting with thatched cottages, tearooms, and gift shops offering local crafts and souvenirs. The village’s quaint atmosphere feels like stepping back in time, making it a must-visit spot for those looking to experience the island’s history and culture. There is a lovely walk to be had just around the village to see all the different cottages. 

Old Town of Shanklin on our Isle of Wight Road Trip
Old Town of Shanklin on our Isle of Wight Road Trip

Head to Shanklin Chine, a stunning natural gorge that offers a tranquil and shaded path through lush vegetation, leading down to the beach. The Chine is one of the Isle of Wight’s oldest tourist attractions, featuring waterfalls, woodland, and an abundance of wildlife. It’s a magical place just crammed natural beauty.

After exploring the Chine, grab lunch at one of Shanklin’s cute little cafes or pubs. They are big into creating dishes with local produce and fresh seafood. Spend the afternoon on Shanklin Beach, where you can relax on the sand, take a dip in the sea, or try your hand at some water sports. You can rent kayaks here if you want to actually get on the water.

If you still have some energy left after a hectic day, try a walk along the coastal path towards Sandown, which offers more stunning views and the opportunity to spot local wildlife. This stretch of the coast is perfect for those looking to extend their walk and experience more of the island’s natural landscapes.


The Garlic Farm in Newchurch is a great place to drop in on your way to Bembridge. You will spend money though…… they sell so many delicious garlic infused products you are bound to buy something. The aged black garlic is particularly delicious –  I ate it with cheese and it is just scrummy. We parked up here the night before and started our day with a visit here, but it was during the winter time.

It is eight minutes drive time to visit the vineyards on the Isle of Wight. Adgestone Vineyard is a delightful place to visit, but just make sure you are not the designated driver! They have music on over lunch time in June and July (check for the dates) and they have blue wine! The blue colour comes from extractions from the black grape skin apparently.

A further nine minutes driving gets you to Bembridge to  explore. The number one stop must be a visit to Bembridge Windmill, the island’s only surviving windmill and a fascinating glimpse into its agricultural past. It is managed by the National Trust, it offers a unique start to the day with its historic structure and educational displays.

Take a walk and head to the Bembridge Trails, where there are several routes around the village and its surroundings, including the Bembridge Fort Walk and the Culver Down Walk. These hikes have fabulous views of the coastline and rural landscapes. If you are lucky you may get to spot some of the local wildlife. The Culver Down Walk, in particular, will take you to a high vantage point with panoramic views of the sea and the mainland beyond.

Bembridge Windmill in the Isle of Wight
Bembridge Windmill in the Isle of Wight


Kick the day off with a leisurely walk along Ryde Pier, one of the oldest piers in England, enjoying the expansive views of the Solent. After soaking in the early morning tranquillity, head into town to explore its vibrant high street. Here, you’ll find a variety of interesting shops, from quaint boutiques offering unique gifts and souvenirs to vintage shops where you can hunt for treasures. 

Art lovers should not miss a visit to the Depozitory Art Gallery, a fascinating gallery housed in a former Wesleyan chapel, showcasing works by local artists and offering a glimpse into the island’s creative talent.  

As your time for exploring the Isle of Wight comes to a close, head off to Cowes which is your final stop on our Isle of Wight road trip. 

Osbourne House - Best Things To Do On The Isle of Wight


It is easy to spend a day in Cowes. I would suggest that the first thing to do that day would be to take a trip to the glorious Osbourne House in the Isle of Wight, a magnificent English Heritage house that was the home of Queen Victoria. You can even go and dip your toes in the water on her old private beach where her children learned to swim! 

For art enthusiasts, the Coast Gallery showcases stunning local artwork, offering a glimpse into the island’s vibrant creative scene. When it’s time for a decent lunch spot, stop off at The Garden. They do super food at a fairly decent price.

Spend your afternoon exploring the historic Cowes Castle, home to the Royal Yacht Squadron, enjoying the panoramic views of the Solent and doing a little shopping.  There are some great shops in Cowes selling all sorts of quirky little things. As the day winds down, meander along the seafront promenade, soaking up the last rays of sunshine before heading to one of Cowes’ cosy restaurants for a delightful seaside dinner. See our food stop for our recommendation – and the pictures below too! It was delicious! 

If you want to splash out a little on your road trip to the Isle of Wight, stop at The Smoking Lobster in Cowes. You will need to book as it is very popular. We had the most delightful meal there but it is more 'meal of the week' than budget grub.

Festivals in the Isle of Wight

Isle of Wight Festival: One of the UK’s most famous music festivals, the Isle of Wight Festival, has a storied history dating back to 1968. It gained legendary status in 1970 when it attracted over 600,000 people to see acts like Jimi Hendrix, The Who, and Joni Mitchell. After a hiatus, the festival was revived in 2002 and has since been a staple in the summer music calendar, drawing major international acts across various genres. Held in June, it offers a blend of rock, pop, electronic, and indie music, alongside a range of activities and entertainment options, making it a must-visit for music lovers.

Cowes Week: Cowes Week, held in August, is one of the oldest and largest sailing regattas in the world, dating back to 1826. This prestigious event sees thousands of sailors, from Olympic and world-class professionals to weekend enthusiasts, compete in over 40 daily races. The waters around the Isle of Wight become a spectacle of sails and competition, with races viewable from many coastal points. Beyond the sailing, Cowes Week is celebrated with a lively shore-side program that includes live music, parties, and family activities, making it an exciting event for both participants and spectators.

Garlic Festival: The Isle of Wight Garlic Festival, held in August, is a celebration of the island’s rich agricultural heritage, with a particular focus on garlic. Visitors can explore a vast array of garlic-infused foods, from garlic ice cream to garlic beer, showcasing the versatility of this beloved ingredient. The festival also features live music, cooking demonstrations, and a variety of stalls selling local produce and crafts. It’s a family-friendly event that offers something for everyone, whether you’re a foodie, a music lover, or simply looking for a unique day out.

Isle of Wight Literary FestivalTaking place in October, the Isle of Wight Literary Festival attracts authors, poets, and speakers from around the world to share their work, insights, and love of literature with audiences. Held in the historic and picturesque town of Cowes, the festival offers a range of talks, workshops, and panel discussions covering a wide variety of topics, from fiction and history to science and current affairs. It’s an intellectual feast for book lovers and those interested in the arts and culture, providing a platform for lively debate and learning.

Ventnor Fringe: Inspired by the famous Edinburgh Festival Fringe, Ventnor Fringe is a week-long celebration of the arts held in July. This eclectic festival transforms the seaside town of Ventnor into a vibrant hub of creativity, featuring performances by musicians, actors, comedians, and artists from across the globe. The festival embraces a spirit of adventure and experimentation, with shows and events taking place in unconventional spaces such as churches, bars, and even living rooms. It’s a testament to the island’s burgeoning arts scene and a fantastic opportunity to experience cutting-edge performances in a relaxed, informal setting.

Walking Festival: The Isle of Wight Walking Festival, held in May, takes advantage of the island’s stunning natural beauty and extensive network of footpaths. It’s one of the largest walking festivals in the UK, offering a program of guided walks suitable for all ages and abilities. From leisurely coastal strolls to challenging cross-island hikes, the walks are led by knowledgeable local guides who share insights into the island’s wildlife, history, and landscapes. It’s an excellent way to explore the Isle of Wight’s diverse environments and to meet fellow walking enthusiasts.

Does an Isle of Wight Road Trip Deliver?

Visiting the Isle of Wight was such a fantastic journey.  It is full of delightful places to go, bracing walks, fabulous people, delicious food and unspoilt beauty. 

This Isle of Wight road trip is one that I would recommend to everyone. Although it can be kind of expensive to get to, its a great trip to tag on to the end of a Dorset road trip, or just for a long weekend. 

From the historical depths of Osborne House to the natural beauty of The Needles, each stop brought its own unique flavour to our adventure.  To truly soak in all the Isle of Wight has to offer, I’d recommend at least a week in your motorhome. This gives you ample time to explore, relax, and immerse yourself in the island’s laid-back lifestyle. You could absolutely catch the key points of the The Isle of Wight road trip in a long weekend if you were rushed. The Isle of Wight is more than just a destination; it’s a journey through history, nature, and culture, making every moment spent here a really wonderful part of the whole trip. 

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