You don’t need to be Bill Bryson* to fall head over heels in love with England on a cross country trek or UK road trip. I’ve personally travelled England lots and these are my recommended stops for an England itinerary, especially for first-time visitors.
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What Do I Know of England?
Did you know that for a while I lived in England? It was during my university exchange when I was a student in an obscure and unloved little place called Preston.
If you’re wondering (and many people either do or are shocked and feel sorry for me), Preston is near Manchester and Liverpool in the North West of England. Definitely travel Lancashire and do some activities in Manchester. There are quite a few gems around and it’s by the coast.
Preston itself is not particularly a must see place. It’s best part is Avenham Park with a little Japanese garden in its midst. So while I wasn’t studying, I made extensive use of my Young Persons Railcard and explored Lancashire and the rest of England as much as I could.
Here are some of the coolest places in England I’ve discovered along my England itinerary.
But besides awesome student times and terribly frustrating phases with big culture clashes, the time was mostly a lesson about foreign lands and strange people.
And I learnt my lesson so well that I am now travelling the world to get more of it! Meetings interesting people and learning from them is one of the best parts of travel, don’t you agree? And the chocolate. I cannot get enough of Cadbury milk chocolate* and Cadbury flakes*, ever!
The Isle of Wight – The Sunniest Place in England
To kick this off, why not head over to the sunniest part of England, which is the Isle of Wight. It is super cute, very old-fashioned and has a charming atmosphere with nice people.
While the whole island has many noteworthy attractions, I especially recommend visiting Victoria and Albert’s Osborne House and Carisbrooke Castle where King Charles I was captured, which led to the short period that England was actually a republic.
For more sad stories, check out the history of Godshill (Christianity versus heathens), but let’s move on over to Shanklin Shine, Sandown, the Needles and finally over on the ferry to Southampton.
However, this little town not a particularly attractive place. All there is to see are a couple of old city walls, a casino and the harbour, so move on pretty quickly and go to Brighton.

Brighton – The Perfect Seaside
In Brighton you can see lots of the quaint and typically British coastline promenades and houses. Unfortunately, you cannot walk along the old piers anymore (I was lucky to have seen one) as they all burnt down.
Never mind that now as the actual highlight is the Royal Palace, which looks very much Indian in style and extravagantly the-British-are-colonising-the-world on the inside. It is very much worth a visit! All in all, Brighton is excessively cute.
And you can even take a bus to explore some beautiful ancient woodland and see bluebells in May in Hancrosse.
What’s it like to live in Brighton? Check out this interview I did with a local artist.

London – A Capital Time
I don’t need to tell you there is so much to see in London. It would require a whole series of articles to cover it all. Planning a four day visit to London is a good idea to get to know the city.
You can visit the many free museums and galleries, stroll through the parks, visit a show on West End, reside in a fancy city apartment or sample the best London street food.
And yes, the typical attractions in London, like the Tower, the Dungeon or the Tates, should totally be on your list. They really are fascinating and not just a tourist trap.
In case you want to learn more about local history and curious anecdotes, check out these fun facts about Tower Bridge.
Two of my favourite times to visit London are for the spectacular Christmas lights around Oxford Street and the bluebell and wisteria season in Holland Park and Notting Hill.

Oxbridge – Nerdy in Many Ways
If you stay a little bit longer you should make a visit to both Oxford and Cambridge as a day trip each. They are extremely amazing in their own right and a definite must see not only for all fans of Harry Potter.
I actually did a series of Potter themed videos around England (and yes, the WB Studios as well). Check them out here:
- Visiting the Harry Potter Studios Part 1: The Forbidden Forest
- Visiting the Harry Potter Studios Part 2: Fighting a Death Eater
- Hermione going back to Hogwarts
If you want to save some money I say book a Megabus in advance and they can take you there for a single pound!
Just don’t rely too much on the London transport as I did back then when a train track burned down and announcers did not tell us passengers. Instead, my train went back to my starting point instead of towards the bus and I consequently missed it. So never have a too tight schedule.

Stratford-upon-Avon – A Shakespeare Fan Must
If you even have a little bit of a heart for British literature or are a massive fan of Shakespeare like me, then you absolutely must go to on a day trip to Stratford-Upon-Avon.
Attend a play at the Royal Shakespeare Company, check out Trinity church and look for to the little bust of the playwright inside (it used to be colourful). If you fancy a walk, you can also stroll through the pretty garden of his wife Anne Hathaway’s family cottage.
Read also: How to plan a Shakespeare-themed trip through England

Chester – Quintessentially Tudor
In case you need an extra dose of medieval British architecture and particularly if you are German and have learnt English from text books that were set in Chester, then you should drop by said town.
Just stay within the city centre as the suburbs are nothing special. Walking along the old cobblestone streets, you will feel as if thrown back in time to the Tudor era.
Anyway, for more beautiful architecture with old Tudor houses, church ruins and castles, check out both Coventry and Warwick. I promise you that you will fall in love with the latter!

Lancashire – Roughin’ It
And now it’s not a long drive over to the heart of North West England with Liverpool, Manchester and Preston being super near.
Places you can safely avoid visiting are Lytham (you can’t even find the ocean at the promenade!), Blackpool (only if you are into theme park promenades and clubbing) and maybe Southport (it has nice buildings but otherwise is boring).

Manchester – Industrial Chic
Manchester, the huge Primark near the train station is already an attraction as are the many events going on in the square. But that’s not it (or it would be sad).
Watch out for the many art installations across the city centre, visit the museum and library for some great British architecture and exhibits. If you like to chill on green grass by the water, do it like the locals and head to the canal district.

Liverpool – Beatle Tunes and Harbour Vibes
In Liverpool, the harbour is a must with the Three Graces and the Beatles Museum. Just across you can reach the big shopping district or walk all the way past the university buildings to the old cathedral and the small China Town. You might even stumble upon the artworks that are stone suitcases. You can easily spend an entire day in this harbour city.

York – The Prettiest Town?
After that, make your way to my absolute favourite town in England, York. It has everything you want from a typically English town: an old city wall, cathedral, medieval streets (the Shambles!), Tudor houses and modern quirky shops.
You can walk around easily in this town and see so many different faces of it, canals, a hill with a castle tower, the list goes on. Another tip are the university houses.
And if you’re a fan of the Bronte Sisters, so check out the Yorkshire moors and their little cottage. I wrote a little post about the key places for a Bronte Tour in Yorkshire in case you’re curious.
Just walking on their grounds you can imagine a nice student life here and in December, the York Christmas market is utterly charming.
Conclusion
And since all this talk about England and its wonderful sights has created quite the yearning for another visit as well as its food (hey, British food might have a bad rep but it can be really nice), I am making myself baked beans* in a baked potato with cheese on top and take a look at my old photo books. Hope to see you on the island soon!
Tell me: What would be your favourite part in this England itinerary?
More England trip tips
- Where to find the best bluebell spots in England
- How to find beaches in and around London
- Where to find iconic Jane Austen Filming Locations
- Why a visit to Dartmoor National Park in South England is a must

Ryan Biddulph says
I’d have to see and enjoy the sunniest place in England Annemarie. I’ve no clue in hell how folks live in places that stay cloudy almost 300 days a year, like many regions in the UK, Scotland, etc. No thanks. I dig clouds for some contrast but sun makes me feel alive. Kinda sustains life too ;)
Thanks for sharing :)
Ryan