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Road Trip Around South East England: A Travel Guide

Updated: Apr 12, 2023

In February 2020, just before the pandemic put an abrupt stop on all our travel plans, I went on one last road trip around South East England. Not being very familiar with Great Britain, I was excited but did not really know what to expect. Our expectations were exceeded: We LOVED our time on the island. It was filled with the most picturesque little towns, tea time all the time, and great accommodations. Join me on this journey as I share my South East England road trip itinerary.


Canterbury is a charming little town that is home to Canterbury Cathedral and its gardens. Stay at Pilgrims Hotel, eat at Zizzi or ASK, and don't forget to visit Canterbury Cathedral.

Leeds Castle

Leeds Castle, southeast of Maidstone, Kent, is a great place to learn about English history and about Henry VIIIs six wives.

Entry: £28 (grants repeat entry for 15 months).


Oxford is a beautiful city, home to Christ Church College, Carfax Tower (great views of the city), and The Divinity School. Look into Airbnb or hotels close to the city center for accommodation.

Stow-on-the-Wold in the Cotswolds

The Cotswolds are known for their charming small villages and honey-colored stone houses in the midst of rolling hills and meadows. Stay at The Lime Guesthouse, eat at Sheep on Sheep Street (Dinner & Bar), Huffkins Stow (Tea Time), Lucy's Tearoom (Tea Time), and take at least two full days here to just slow down, indulge in tea time and go on a hike.

Highclere Castle

(the Downton Abbey Castle)

Highclere Castle, the Downton Abbey Castle, is a must-visit for all Downton Abbey fans. Unfortunately, the castle was still closed for the season so the only peak we got of it was from a little hilltop surrounding the castle grounds. It was a bit disappointing to us, as we had really wanted to visit the castle. So be smart and do the research beforehand, if this is an important destination for you on your England trip.


Stonehenge is a breathtaking place to visit. Spend the money, go to the museum, and walk around the mysterious part of the Worlds Heritage that is said to date back to 2000 to 3000 years BC.


We randomly picked this town to be our last stop before going down to the coast. We are glad we did, our night at the Norfolk Arms Hotel was by far the best. It was very affordable but the interior in both rooms and common areas is beautiful. Upon check-in, we decided to add the breakfast and are so glad we did - it was not buffet-style but British breakfast à la carte and so delicious!

Stay at The Norfolk Arms, eat at The Black Rabbit (Fish & Chips and one original Harry Potter boat), and enjoy a British breakfast à la carte.


Eastbourne is known for its lazy beach days and ice-cream strolls down the boardwalk. When it's raining, walk around and drive up to Beachy Head which has views over the Seven Sisters cliffs. Early the next morning, go a second time to see the cliffs in a different light. Stay at The Pier Hotel, eat at The Ship (Burgers and Fish & Chips), Black Cat Tearooms (breakfast), Patisserie Valerie (Tea Time), and don't forget to visit Eastbourne Pier.

Cliffs of Dover

On the ferry ride back from Dover to Calais, we got spoiled with beautiful sunshine and spectacular views of the famous cliffs of Dover and its castle on the hill. I remember standing on the ferry and just feeling so peaceful. We knew that Covid-19 had already arrived in Italy and that it was only a matter of time before it reached Germany. I guess part of me knew that I should enjoy the moment while it lasted because I might not feel this free and alive for a long time.

I already look forward to returning to the island one day soon. Until then, I'll be trying to finally master baking scones that are somewhat comparable to what I had during our countless British tea times.

Safe travels!

Love, Lena

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