An Isle of Wight Weekend

Date Posted: October 11, 2019
Posted in: Travel Tales

This page may contain affiliate links, for which I could earn a small commission. You can review my full disclosure here.


An Isle of Wight weekend can refresh the soul. I, honestly, knew next to nothing about this English island when I decided to go. But I was visiting Portsmouth for house and cat sitting, so this nearby isle offered a perfect additional getaway.

Read: 11 Lessons Learned House Sitting with TrustedHousesitters

Luckily for me, an Isle of Wight weekend break was absolutely perfect to utterly unwind. First of all, it’s an island! The sea has magical abilities to relax the soul. But island life also just brings that extra little bonus of slower pace and friendly folks.

I used to think it was the heat of the tropics that induced Island Time. But it might just be the very nature of its separation from mainland speed and demands that allows an island anywhere to relax.

So it is with the Isle of Wight: Slow down, walk more, have a good long chat, and get yourself on Island Time.

Where is the Isle of Wight?

First, let’s set the scene.

I had no idea where the Isle of Wight was before moving to Scotland, so don’t worry if you’re in the same boat. (Although, if we’re in the same boat not knowing where an island is located, we probably shouldn’t have been entrusted with a boat!)

The Isle of Wight is a tiny island just off the southern shore of England, resting in the English Channel.

Here you can see the southern English coastline with the Isle of Wight just offshore:

Isle of Wight location map

For scope, reference the size of greater London and then the small Isle of Wight just separated from the mainland.

It’s not very big at all!

My weekend on the Isle of Wight was spent in the northern part of the island entirely. While it is small, that doesn’t mean I was about to rush around just to “see” it all without enjoying any of it!

Marked on this map are my stops and a few other recommendations for Isle of Wight attractions. Those are listed at the end of this article.

My Isle of Wight Weekend

“You know that’s a bitter, right?” he asked me incredulously as I sat with my pint of ale. While I wasn’t 100% sure I enjoyed bitter ales, I’m always game for trying something new – and I’m also fond of acting overly confident, for some reason. 

“Of course! Don’t you like bitter ales?” I nonchalantly replied as I pulled out my notebook while simultaneously snapping a photo in the island-themed bar

Yates brewery bitter ale in Saltys bar Yarmouth

We chatted for quite a while, this local guy sitting casually at the bar with a pint and his wife working behind the bar. A few other patrons came and went along the way. It was an island-themed bar on an island, to be sure, with the same familiarity and friendly conversation I’ve come to expect from any such locale.

Check out my island homes in the Caribbean and Mediterranean.

He asks why I’m taking notes, which turns into the three of us establishing common ground.

Their niece married a Scottish guy (I got married and live in Edinburgh). They moved to Boston (where I’m from), but now they live in Texas where she’s a successful blogger (hi! This is my blog!). Her name is also Amanda (ahem, also my name).

Yep, it’s a small, funny world! And islands just seem to reinforce that fact at every turn.

When it was time for me to leave, I received a big ole bear hug and well wishes for a wonderful visit. This island is indeed just like all those other islands. That small-town vibe coexists with the understanding that tourists will come and go as part of the lifeblood of the community. 

I’m rather addicted to that island way of life, it feels.

Feeling at Home in Yarmouth

While this island isn’t tropical – it’s in the English Channel, after all – I still feel a kinship with its residents and its general lifestyle. A walk along England’s longest wooden pier in Yarmouth offers a glimpse into that wonderfully familiar sense of community.

Read next: My island life wasn’t normal

I witness multi-generational fishing endeavors, a timeless passage of skills and experience. They’re standing beside the neighborhood kids lapping ice cream cones. And those omnipresent neighborhood dogs wait underfoot, hoping to catch a delicious drip.

Elderly men haltingly stroll along the planks; I imagine they’re chatting about the old days together. I silently observe, unintentionally still walking at mainland speed, making my way past them all to the very end of the pier.

Looking back across the distance toward shore, I have a dark feeling that many ships filled with many men headed off to war would have had this same view in years past.

Yarmouth Harbour Pier IOW

It’s a beautiful pier. It’s been recently, lovingly preserved by the local community through fundraising and the purchasing of individual planks for oneself or for loved ones.

The names create a step-by-step who’s who of Yarmouth and its surrounds. Not that I recognize any names, being such an outsider to this island. But I’m certain that locals could walk along this extensive pier and bring to life the memories of so many of these individuals and families.

What a lovely way to center the community, both physically and emotionally.

Heading Toward Fort Victoria

I walk away from the traditionally quaint town of Yarmouth heading toward my guest room by the sea at Fort Victoria.

And I mean “quaint” in every stereotypical cliche version possible. Its Tudor style pub is a focal point, surrounded by local sea-themed art shops and fish-and-chips shops, plus all manner of residences that have been inhabited for centuries.

Yes, it’s quaint and it feels like it’s been this way for countless generations.

Fort Victoria itself isn’t much to behold, although families with young kids might find entertainment among its offerings. I prefer the stretch of beach beside the fort and the utterly dilapidated dock in front of my room.

My room has quite the view, actually.

I sit on my patio sipping a glass of wine with my box of fish and chips from The Blue Crab in hand. A lone sailboat glides by easily in this swift current. The sun glistens upon the surface of the sea as two women zig-zag along the surf seeking perfect seashells. Their intermittent laughter mirrors the occasional clanging buoy bell as the waves shift its weight.

Two men leave their fishing poles resting against the rock wall as music drifts out from their open truck windows. Their cans echo a slow crack to tell me it’s beer o’clock.

Apparently, I didn’t leave the cliches behind back in Yarmouth.

A small biplane flies overhead toward the mainland of England. My mind drifts, again, to the scenes of war that would have been present here.

I imagine those island kids would’ve sat on this spot counting all the planes that left, flying towards mainland Europe. And they might have counted just how many managed to make it back later on. It must have been a simultaneously encouraging and terrible sight to see.

Read next: My visit to the D-Day Story Museum in Portsmouth

Things to Do on the Isle of Wight

The Isle of Wight has much to offer, so I’ve learned through a bit of research but mostly through conversations with locals and regular visitors.

At the mention of an impending trip, everyone who knows anything about a place will offer as much insight as possible. I always readily accept recommendations, hoping for some hidden gem or view that I otherwise might not have found on my own.

Sometimes I luck out. Other times, I just politely listen as folks recommend the same top 10 destinations found on TripAdvisor.

Historic Homes

I skipped Osbourne House, much to the chagrin of those who offered their own tips. Apparently, it’s a “must-see” for any who visit the Isle of Wight, yet I felt absolutely no pull to visit at all.

I did, however, visit Farringford, the historic home of Alfred, Lord Tennyson. I didn’t go in, but I did admire it architecturally and wandered the paths and grounds for a bit. The walled garden was particularly lovely, despite the miserable weather.

I arrived there via the Coastal Path, a 72-mile route that encircles the entire island. The Coastal Path offers walkers and cyclists a beautiful, historical, and well-equipped series of paths to follow.

Certain accommodations advertise specifically to those people, as do pubs and restaurants and historical attractions. It must be incredibly popular in good weather, but I managed to visit during a particularly terrible day with sideways rain and winds whipping across the island.

Yet I still managed to walk to the house via a bit of Coastal Path that was well-sheltered with trees. Instead of walking the long route back to get my bags, as intended, I opted to retreat for a hot lunch and a pint before getting completely soaked.

The Piano Cafe was ideal, with its diverse menu and local beers to add to my list of local options I’d sampled. Look how the chips (locally known as crisps) match the salad (which can sometimes just mean lettuce and tomato on a sandwich…local lingo can be confusing!).

The bus back towards Yarmouth was easy to find from there. In fact, the buses all around the Isle of Wight are easy and convenient! The only slight struggle is that all buses converge in central Newport, which might not be directly en route to your destination.

Cowes Week on the Isle of Wight

The day before had been sunny and beautiful, a perfect way to arrive by slow ferry from Southampton to East Cowes. And – coincidentally – I arrived in the middle of Cowes Week itself.

The annual regatta lasts a week and includes street vendors, boat races, evening parties, fireworks and more. I knew what I was walking into, but I still felt surprised by the sheer volume of blue and white stripes worn to show off that yacht connection.

People-watching was fantastic, as was the view as I climbed the hill toward Northwood House from Cowes Bay. That grassy hilltop area simply begged for a nap, so I happily obliged.

Being awakened by two sniffing labradors as I was splayed out on the warm grass under an ancient pine tree was nothing short of heaven, in my book. 

Cowes itself was also fun to wander. Plenty of shops, window shopping for ships and local real estate, plus ample choice for bars and restaurants.

I chose Gastronomy for its intriguing menu and large windows from which I could continue my people-watching and stripe-counting. It did not disappoint!

table setup at Gastronomy restaurant in Cowes on the Isle of Wight with Island Visitor magazine and a beer

Isle of Wight Transportation Options

I had wandered that way from the “floating bridge” ferry across the estuary that had followed the slow ferry from Southampton.

Isle of Wight car ferry terminus from the floating bridge departure point

That was all after I’d taken the bus from the train station after taking the train from the airport after flying down from Edinburgh at 7am.

Car, plane, train, ferry, boat, bus, walk along the beach: that was my full day of Isle of Wight transport. Not bad, in terms of covering all the bases!

But the transport that beat them all was the one I took from the Isle of Wight toward Portsmouth, where a house sitting gig awaited me. I took a hovercraft from Ryde to Southsea.

A HOVERCRAFT.

You may now call me a Jedi, please and thank you.

We boarded the hovercraft on land. Once we were all seated, the tubes inflated to raise us up even higher off the ground. The interior looks like a plane, with rows all facing forward toward a large screen up front, where a safety video was shown.

And – just like a plane – we rumbled backward to turn around at the water’s edge and begin the 10-minute journey over the sea. Literally over the water.

While I could see whitecaps all around us (this was the same day of whipping winds and sideways rain), there was no familiar rocking like a boat. Instead, I felt as if I were traveling by train, feeling the movement more than a plane but not swaying like a boat.

It was fascinating!

To be sure, I was the only one on board demonstrating any child-like wonder at this contraption. Others were obviously more local and far too familiar with this sorcery.

Other Isle of Wight Attractions

I didn’t do everything on my Isle of Wight weekend because – well – I was only there for a weekend!!

But, if you’re interested, these are some of the top things to do on the Isle of Wight that I purposefully or accidentally didn’t do:

Just because I don’t go somewhere doesn’t invalidate it. We can all have different interests!

You can easily find details for the Isle of Wight Coastal Path if you intend to walk more of it. And there is ample information for the very popular Isle of Wight Festival that attracts visitors to the island every summer.

When I travel, I love chatting with locals, slowing down, and trying (often failing) to fit in and act like a local.

If your travel style is different, that’s fine, too! But I hope you enjoyed my experience.

My Isle of Wight weekend was absolutely lovely and just what I wanted and needed to unwind for a short break. It led me perfectly into a week of house and cat sitting in Portsmouth!


If you’re new here, feel free to check out my expat timeline for some highlights.

We housesit and petsit our way around the world. You can learn all about TrustedHousesitters (our preferred housesitting website) here.

You can follow along on our adventures by subscribing to my newsletter below, and join me on social media, too! I’m on FacebookInstagramTwitter, and Pinterest. See you there!

This page may contain affiliate links, for which I could earn a small commission. You can review my full disclosure here.


An Isle of Wight weekend can refresh the soul. I, honestly, knew next to nothing about this English island when I decided to go. But I was visiting Portsmouth for house and cat sitting, so this nearby isle offered a perfect additional getaway.

Read: 11 Lessons Learned House Sitting with TrustedHousesitters

Luckily for me, an Isle of Wight weekend break was absolutely perfect to utterly unwind. First of all, it’s an island! The sea has magical abilities to relax the soul. But island life also just brings that extra little bonus of slower pace and friendly folks.

I used to think it was the heat of the tropics that induced Island Time. But it might just be the very nature of its separation from mainland speed and demands that allows an island anywhere to relax.

So it is with the Isle of Wight: Slow down, walk more, have a good long chat, and get yourself on Island Time.

Where is the Isle of Wight?

First, let’s set the scene.

I had no idea where the Isle of Wight was before moving to Scotland, so don’t worry if you’re in the same boat. (Although, if we’re in the same boat not knowing where an island is located, we probably shouldn’t have been entrusted with a boat!)

The Isle of Wight is a tiny island just off the southern shore of England, resting in the English Channel.

Here you can see the southern English coastline with the Isle of Wight just offshore:

Isle of Wight location map

For scope, reference the size of greater London and then the small Isle of Wight just separated from the mainland.

It’s not very big at all!

My weekend on the Isle of Wight was spent in the northern part of the island entirely. While it is small, that doesn’t mean I was about to rush around just to “see” it all without enjoying any of it!

Marked on this map are my stops and a few other recommendations for Isle of Wight attractions. Those are listed at the end of this article.

My Isle of Wight Weekend

“You know that’s a bitter, right?” he asked me incredulously as I sat with my pint of ale. While I wasn’t 100% sure I enjoyed bitter ales, I’m always game for trying something new – and I’m also fond of acting overly confident, for some reason. 

“Of course! Don’t you like bitter ales?” I nonchalantly replied as I pulled out my notebook while simultaneously snapping a photo in the island-themed bar

Yates brewery bitter ale in Saltys bar Yarmouth

We chatted for quite a while, this local guy sitting casually at the bar with a pint and his wife working behind the bar. A few other patrons came and went along the way. It was an island-themed bar on an island, to be sure, with the same familiarity and friendly conversation I’ve come to expect from any such locale.

Check out my island homes in the Caribbean and Mediterranean.

He asks why I’m taking notes, which turns into the three of us establishing common ground.

Their niece married a Scottish guy (I got married and live in Edinburgh). They moved to Boston (where I’m from), but now they live in Texas where she’s a successful blogger (hi! This is my blog!). Her name is also Amanda (ahem, also my name).

Yep, it’s a small, funny world! And islands just seem to reinforce that fact at every turn.

When it was time for me to leave, I received a big ole bear hug and well wishes for a wonderful visit. This island is indeed just like all those other islands. That small-town vibe coexists with the understanding that tourists will come and go as part of the lifeblood of the community. 

I’m rather addicted to that island way of life, it feels.

Feeling at Home in Yarmouth

While this island isn’t tropical – it’s in the English Channel, after all – I still feel a kinship with its residents and its general lifestyle. A walk along England’s longest wooden pier in Yarmouth offers a glimpse into that wonderfully familiar sense of community.

Read next: My island life wasn’t normal

I witness multi-generational fishing endeavors, a timeless passage of skills and experience. They’re standing beside the neighborhood kids lapping ice cream cones. And those omnipresent neighborhood dogs wait underfoot, hoping to catch a delicious drip.

Elderly men haltingly stroll along the planks; I imagine they’re chatting about the old days together. I silently observe, unintentionally still walking at mainland speed, making my way past them all to the very end of the pier.

Looking back across the distance toward shore, I have a dark feeling that many ships filled with many men headed off to war would have had this same view in years past.

Yarmouth Harbour Pier IOW

It’s a beautiful pier. It’s been recently, lovingly preserved by the local community through fundraising and the purchasing of individual planks for oneself or for loved ones.

The names create a step-by-step who’s who of Yarmouth and its surrounds. Not that I recognize any names, being such an outsider to this island. But I’m certain that locals could walk along this extensive pier and bring to life the memories of so many of these individuals and families.

What a lovely way to center the community, both physically and emotionally.

Heading Toward Fort Victoria

I walk away from the traditionally quaint town of Yarmouth heading toward my guest room by the sea at Fort Victoria.

And I mean “quaint” in every stereotypical cliche version possible. Its Tudor style pub is a focal point, surrounded by local sea-themed art shops and fish-and-chips shops, plus all manner of residences that have been inhabited for centuries.

Yes, it’s quaint and it feels like it’s been this way for countless generations.

Fort Victoria itself isn’t much to behold, although families with young kids might find entertainment among its offerings. I prefer the stretch of beach beside the fort and the utterly dilapidated dock in front of my room.

My room has quite the view, actually.

I sit on my patio sipping a glass of wine with my box of fish and chips from The Blue Crab in hand. A lone sailboat glides by easily in this swift current. The sun glistens upon the surface of the sea as two women zig-zag along the surf seeking perfect seashells. Their intermittent laughter mirrors the occasional clanging buoy bell as the waves shift its weight.

Two men leave their fishing poles resting against the rock wall as music drifts out from their open truck windows. Their cans echo a slow crack to tell me it’s beer o’clock.

Apparently, I didn’t leave the cliches behind back in Yarmouth.

A small biplane flies overhead toward the mainland of England. My mind drifts, again, to the scenes of war that would have been present here.

I imagine those island kids would’ve sat on this spot counting all the planes that left, flying towards mainland Europe. And they might have counted just how many managed to make it back later on. It must have been a simultaneously encouraging and terrible sight to see.

Read next: My visit to the D-Day Story Museum in Portsmouth

Things to Do on the Isle of Wight

The Isle of Wight has much to offer, so I’ve learned through a bit of research but mostly through conversations with locals and regular visitors.

At the mention of an impending trip, everyone who knows anything about a place will offer as much insight as possible. I always readily accept recommendations, hoping for some hidden gem or view that I otherwise might not have found on my own.

Sometimes I luck out. Other times, I just politely listen as folks recommend the same top 10 destinations found on TripAdvisor.

Historic Homes

I skipped Osbourne House, much to the chagrin of those who offered their own tips. Apparently, it’s a “must-see” for any who visit the Isle of Wight, yet I felt absolutely no pull to visit at all.

I did, however, visit Farringford, the historic home of Alfred, Lord Tennyson. I didn’t go in, but I did admire it architecturally and wandered the paths and grounds for a bit. The walled garden was particularly lovely, despite the miserable weather.

I arrived there via the Coastal Path, a 72-mile route that encircles the entire island. The Coastal Path offers walkers and cyclists a beautiful, historical, and well-equipped series of paths to follow.

Certain accommodations advertise specifically to those people, as do pubs and restaurants and historical attractions. It must be incredibly popular in good weather, but I managed to visit during a particularly terrible day with sideways rain and winds whipping across the island.

Yet I still managed to walk to the house via a bit of Coastal Path that was well-sheltered with trees. Instead of walking the long route back to get my bags, as intended, I opted to retreat for a hot lunch and a pint before getting completely soaked.

The Piano Cafe was ideal, with its diverse menu and local beers to add to my list of local options I’d sampled. Look how the chips (locally known as crisps) match the salad (which can sometimes just mean lettuce and tomato on a sandwich…local lingo can be confusing!).

The bus back towards Yarmouth was easy to find from there. In fact, the buses all around the Isle of Wight are easy and convenient! The only slight struggle is that all buses converge in central Newport, which might not be directly en route to your destination.

Cowes Week on the Isle of Wight

The day before had been sunny and beautiful, a perfect way to arrive by slow ferry from Southampton to East Cowes. And – coincidentally – I arrived in the middle of Cowes Week itself.

The annual regatta lasts a week and includes street vendors, boat races, evening parties, fireworks and more. I knew what I was walking into, but I still felt surprised by the sheer volume of blue and white stripes worn to show off that yacht connection.

People-watching was fantastic, as was the view as I climbed the hill toward Northwood House from Cowes Bay. That grassy hilltop area simply begged for a nap, so I happily obliged.

Being awakened by two sniffing labradors as I was splayed out on the warm grass under an ancient pine tree was nothing short of heaven, in my book. 

Cowes itself was also fun to wander. Plenty of shops, window shopping for ships and local real estate, plus ample choice for bars and restaurants.

I chose Gastronomy for its intriguing menu and large windows from which I could continue my people-watching and stripe-counting. It did not disappoint!

table setup at Gastronomy restaurant in Cowes on the Isle of Wight with Island Visitor magazine and a beer

Isle of Wight Transportation Options

I had wandered that way from the “floating bridge” ferry across the estuary that had followed the slow ferry from Southampton.

Isle of Wight car ferry terminus from the floating bridge departure point

That was all after I’d taken the bus from the train station after taking the train from the airport after flying down from Edinburgh at 7am.

Car, plane, train, ferry, boat, bus, walk along the beach: that was my full day of Isle of Wight transport. Not bad, in terms of covering all the bases!

But the transport that beat them all was the one I took from the Isle of Wight toward Portsmouth, where a house sitting gig awaited me. I took a hovercraft from Ryde to Southsea.

A HOVERCRAFT.

You may now call me a Jedi, please and thank you.

We boarded the hovercraft on land. Once we were all seated, the tubes inflated to raise us up even higher off the ground. The interior looks like a plane, with rows all facing forward toward a large screen up front, where a safety video was shown.

And – just like a plane – we rumbled backward to turn around at the water’s edge and begin the 10-minute journey over the sea. Literally over the water.

While I could see whitecaps all around us (this was the same day of whipping winds and sideways rain), there was no familiar rocking like a boat. Instead, I felt as if I were traveling by train, feeling the movement more than a plane but not swaying like a boat.

It was fascinating!

To be sure, I was the only one on board demonstrating any child-like wonder at this contraption. Others were obviously more local and far too familiar with this sorcery.

Other Isle of Wight Attractions

I didn’t do everything on my Isle of Wight weekend because – well – I was only there for a weekend!!

But, if you’re interested, these are some of the top things to do on the Isle of Wight that I purposefully or accidentally didn’t do:

Just because I don’t go somewhere doesn’t invalidate it. We can all have different interests!

You can easily find details for the Isle of Wight Coastal Path if you intend to walk more of it. And there is ample information for the very popular Isle of Wight Festival that attracts visitors to the island every summer.

When I travel, I love chatting with locals, slowing down, and trying (often failing) to fit in and act like a local.

If your travel style is different, that’s fine, too! But I hope you enjoyed my experience.

My Isle of Wight weekend was absolutely lovely and just what I wanted and needed to unwind for a short break. It led me perfectly into a week of house and cat sitting in Portsmouth!


If you’re new here, feel free to check out my expat timeline for some highlights.

We housesit and petsit our way around the world. You can learn all about TrustedHousesitters (our preferred housesitting website) here.

You can follow along on our adventures by subscribing to my newsletter below, and join me on social media, too! I’m on FacebookInstagramTwitter, and Pinterest. See you there!

About the author

Amanda Walkins

Serial expat Amanda Walkins is a freelance writer & blogger. She has lived in 7 countries, traveled to many more, and loves helping people explore the world through slow travel (like house and pet sitting!) and living overseas.