PACK IT UP
In the winter months, days can be chilly and possibly rainy. Like most islands, the weather is mercurial. Give it an hour or two, and it's guaranteed to be a different sky. So being prepared and flexible in wardrobe is key. Pack a variety of leggings, jeans, and other warm clothing that can be paired with other layers. Since you'll be traveling in a rental car and walking most places, consider comfortable shoes that can be at home on a beach, at a pub, or on dirt paths. Style on Isle of Wight is country chic comfort heavily influenced by the weather. Forego the stilettos for some long leather boots with a short heel or some water-resistant sneakers. If you have some extra room in the suitcase, bring some wellies (rainboots) for the many walks you're bound to take!
Want even more packing ideas? Be sure to check out our special Editor's Picks for a UK Honeymoon. We already did the research for you on the most essential things to get in that suitcase of yours before you hop across the pond!
PREPARING TO DRIVE IN THE UK
While trains are most always the perfect way to get around in the United Kingdom, adventuring to the Isle of Wight is best done by car so you can get the full experience of the island. As most Americans know from BBC television shows and movies, the UK drives on the opposite side of the road than the US does. Make sure you are comfortable with this before booking anything! Most vehicles are also manual transmission. If you don't know how to drive manual, that's okay! You can rent an automatic car, but it must be done in advance and will cost a bit more than a manual car. It's not so scary as it might seem; it's all about preparation with a spirit of adventure.
Plan Ahead: Unlike some European countries, you do not need an International Driver's Permit (IDP) to drive in Great Britain (England, Scotland, and Wales) before you go. However, if you are planning to drive over to France or another European country after your Isle of Wight trip, check their local laws. IDPs are easy to get; you just need to go to your closest AAA office to get more information and apply.
GETTING TO THE ISLAND
Isle of Wight is a must visit in conjunction with your UK vacation. Once you arrive in Portsmouth, England, WightLink is your smooth sailing ticket to a stress-free island trip. This modern ferry allows not only walk-on passengers, but also your car and crew. Unlike some local Virginia ferries we have experienced, this transportation service by WightLink is efficiently cozy from the very first moment you drive into its port area. Cars park in dedicated lines until ready for departure, and once on the ferry, you leave your car to relax in the comfortable lounges on the upper decks of the ferry for the 45 minutes' ride. These clean and contemporary lounges include cafés, free WiFi, and an outdoor observation deck so you can watch the smaller local boats go by as you cross the Solent strait.
For the Portsmouth to Fishbourne route we took, prices vary depending on day and time, but you can budget somewhere around $80 USD for a roundtrip ticket at its most expensive quote. It is best to make a reservation ahead of time online so you are guaranteed a spot for your preferred time because you want to make the most out of Isle of Wight!
STAYING ON THE ISLE OF WIGHT
When so many lodging options are available on Isle of Wight, you need a local expert to help find your perfect accommodations without the stress and endless Google searching from the States. Whether you love a beach view or prefer a cozy cottage, we found that Annabel of HB Holiday Lettings, a local vacation home rental concierge and fabulous owner behind this special niche business, was just that expert. Unlike large online homestay marketplaces, HB Holiday Lettings knows each and every property they offer inside and out. Envision a dreamy estate for a destination wedding or girls' trip? Westcliff is literal Georgian manor perfection. Want a gorgeous beachside cottage? The Old Boat House is stuff of romance. Or fancy a charming higgledy piggledy modern home? 19 Lower Green Road is a personal favorite and where we stayed for this visit -- it is attached to an old book shop overlooking England's largest public village green!
Beyond the actual accommodations, Annabel is your local wealth of knowledge. From pub recommendations to memorable experiences, she can connect you to make the most of your Isle of Wight visit. To have a wonderful concierge at hand is essential for a seamless vacation because no matter how much internet searching you do, nothing beats a human who knows the island and its residents!
THE QUICK OVERVIEW
The compact size of Isle of Wight is part of its charm because you don't have to skip one thing over the other. It only takes about 2 hours to get from one side to the other, so for one week on the island, plan your journey based on the areas: North, East, South, and West. From coastal views to scenic fields, there will be many moments where you will want to stop for spontaneous photos and building in that extra cushion of time will only elevate your experience.
ISLE OF WIGHT: NORTHERN REGION
The north region of Isle of Wight is home to two of the most iconic historical sites the island offers: Osborne House and Quarr Abbey. Famous for being Queen Victoria's holiday home (as seen most recently in one of our personal favorites, Victoria & Abdul), Osborne House is everything one looks for when visiting England: timeless elegance, gardens for days, and a look into royal life of the past.
Fun Fact: If you're looking for the epic of all epic wedding venues, you can even get married at Osborne House! Not many can say they walked the hallways of Queen Victoria as they say I Do, so if destination wedding is on your bucket list, this is a beautiful one to consider!
Just five miles down the road from Osborne in the town of Ryde is Quarr Abbey, a stunning active Catholic Benedictine monastery that is home to practicing monks and English wildlife. Surrounded by farms of lifestock, you'll be greeted by a plethora of animals on your walk from the parking lot to the abbey. Be on the lookout for blackbirds, robins, and other birds as they hop around the property's gardens.
While the brick architecture is memorable in of itself, it is the little tea shop that makes Quarr Abbey a special stop. Partake in traditional English cream tea (which consists of a pot of brewed tea, two scones, clotted cream, and your choice of jam) in a rustic dining room filled with eclectic wooden chairs and tables. Their gift shop also has local treats made on Isle of Wight such as Mermaid Gin and Isle of Wight Cheese Co.. (If you have dietary restrictions or allergies, you'll be happy to know England is overall very progressive in that sense! Gluten-free scones were readily available without reservation at the abbey tea shop.)
ISLE OF WIGHT: EASTERN REGION
From quiet beaches to thatched cottages to animal sanctuaries, the eastern side of the island will be your most diverse day of adventure. With villages like Shanklin and Godshill, you get a look into charming English history, tea shops with scones and other delectable baked goods, and everyday life for these islanders.
Thanks to the chalky south-facing slopes and generally mild climate of Isle of Wight, there is a special kind of English wine made here unlike any other, and couples can find a taste at Adgestone Vineyard in the town of Sandown. Since 1968, this local winery has been growing a variety of grapes for their wines which appeal to a wide range of preferences: reds, white, sparkling, and even liqueurs. Adgestone Vineyard also is home to some adorable farm animals to make you smile during your tasting visit. Looking for a truly unique wedding beverage? Their naturally-occurring sparkling blue wine, Something Blue, is visual wedding day perfection!
Nearby the winery are fields and barns of 97+ precious hoofed creatures living out pampered retirement surrounded by love and care. To tie in a charity and "giving back" aspect to your vacation, Isle of Wight Donkey Sanctuary will steal your heart with their docile residents who came to the sanctuary for many reasons. Some were abandoned, some rescued, some whose owners passed away. Admission is always free, and the sanctuary is open seven days a week. Various events throughout the year also give visitors the ultimate donkey care experience by grooming one of their mini-donkeys and taking some new furry friends for a walk around one of the paddocks. During your honeymoon, you can give back by donating money and shopping the café or gift shop, but the most memorable is by "adopting" or sponsoring one of the beloved donkeys that you meet.
Editor's Experience: The staff at Isle of Wight Donkey Sanctuary gave such a wonderful media tour during our visit, and it only took seconds watching these sweet donkeys and hearing their stories to make me want to do anything I could to support this local gem as a short term visitor. Before going for a walk with lead in hand, I got to give a good ole brush down to Miss Geraldine, a petite donkey with the sweetest disposition and coarse gray fur. Much like a horse, necessary grooming is always needed, and it's a special way to bond with these donkeys.
Granted, when any animal was once unwanted, that lodges an automatic lump in my heart and creates the mission of "Love all of them!" no matter where I go. So I took my experience one step further and adopted a sweet donkey named Myra! I asked which one wasn't sponsored as often, and Myra was top of the list, so I spotted her in one of the female paddocks, said hi, and was able to make a one-time payment to support this non-profit that gives a forever home to British donkeys and provides community education through their care.
SOUTHERN REGION OF ISLE OF WIGHT
It's not every day that a prehistoric palm plant blooms for the first time in 60 million years due to climate change, but on the Isle of Wight, it happened! On the southern coast, Ventnor Botanic Garden is home to this Jurassic palm tree called the cycad and many other gorgeous plants and scenery that otherwise could not grow in the UK because of the varying temperatures. From workshops to grand gardens to even centuries old donated trees by Queen Victoria herself, this beautiful destination is a must visit for any horticulturist or plant lover.
Looking for a fun twist? Ventnor Botanic Garden actually encourages people to go off the path to explore through their many "secret gardens" or hidden areas that enhance the experience. Talk about being an approved rebel and even have a little romantic spot to steal a kiss!
Fun Fact: If you're looking to elope during your travels, you can absolutely say I Do surrounded by these wild, yet lovingly curated gardens at Ventnor Botanic Garden. Welcoming to all couples, make sure to ask about their Signal Point Cottage overlooking some of the garden for a perfectly memorable honeymoon!
Leave your car at Ventnor Botanic Garden and take a short walk to the idyllic Steephill Cove off of Love Lane. As the name implies, it is literally a steep hill to descend into the cozy cove area. Rocky beaches, thatched vacation cottages, and a gorgeous view of the Isle of Wight's southern coastline await at the bottom. A seasonal restaurant and a coffee shop may be closed if you visit during the winter, but the charm of an intimate getaway is here all year round.
ISLE OF WIGHT: WESTERN REGION
If you've seen a photo showing Isle of Wight in England, chances are very likely that the photo is of the famous red lighthouse and the Needles, a trio of chalk stack "islands" jutting out into Alum Bay. Once upon a time, there were four stacks but the sea reclaimed the fourth in the 18th century, but nonetheless, it remains a very popular destination for visitors to the island. A large parking lot allows you to leave your car for the 20 minutes' walk towards the national park of The Needles Old Battery and New Battery. The view is spectacular, and because like all things wonderfully English, hot tea and delicious scones await (gluten-free available, too!) at the end in the Old Battery that has been converted into a 1940s-inspired tea room. Everything is made fresh daily in their tea room's kitchen and served on eclectic vintage china. If you are fascinated by the style and history of the World War II era, you'll fall in love with this perfect afternoon spot.
For the ultimate coastline experience, driving along the west coast on Military Road will show off the best landscapes of Isle of Wight. England is known for public footpaths/pathways that people can walk for a refreshing tour in the countryside, and Freshwater Bay has plenty of them. Along the cliffs, getting out of your car is a must as this affords the most breathtaking views you'll ever see of the turquoise waters and ancient cliffsides that immediately drop. White houses and buildings contrast against the emerald green fields, and you will feel like you have been instantly transported into a period drama on BBC. Imaginary picnic and gentlemen in knee breeches included.
Once you have soaked up the landscape, head to The Buddle Inn in Niton to continue the history with a warm lunch. This 16th century pub overlooking the English Channel was once popular with smugglers and gives an incredible step-back-into-time vibe with its giant open fireplace encased in dark wooden beams. If you are obsessed with flagstone floors and historic details, the pub's atmosphere will charm the socks off of you as the food does your stomach.
Whether you are a coastal lover or a cozy cottage connoisseur, the original Isle of Wight is full of quintessential vacation vibes. With so much to do no matter the time of year, you will soon understand why the British love this spot for their own local weekend getaways. Easy to get to, charming people, and beautiful scenery everywhere you go, this special island will nestle into your heart for endless memories in years after.
- Chelsea
TRAVEL GUIDE CREDITS
Photography & Article: Chelsea LaVere for Tidewater and Tulle | Host: Visit Isle of Wight | Accommodations: HB Holiday Lettings | Transportation: WightLink Ferries | Tour Providers: Isle of Wight Donkey Sanctuary, The Needles Old Battery and New Battery (National Trust), Ventnor Botanic Garden, Adgestone Vineyard
Disclosure: Some transportation, accommodations, and activities were provided so we could better experience Isle of Wight. All love and opinions for what's been mentioned in this feature are our own. Some of the above product links are affiliate-linked and purchasing through these links helps support Tidewater and Tulle and its wonderful partners! You can find our full disclosure policy here.
