Our Perfect Southern England Itinerary: A Road Trip Guide

(Last Updated On: August 12, 2023)

Discover the perfect Southern England itinerary and plan the perfect trip in England today.

Medieval castles, coastal paths with epic sea views, pretty towns and villages, beautiful landscapes, culture, and history are just some reasons why you might think about doing a southern England road trip in the near future.

The South of England is full of gems that most travelers and even locals have no idea about, but we decided to change that. We set out on this epic 10 day South England road trip itinerary that turned out to be full of magic, colour, and quintessentially British culture and we’d like to encourage you to do the same.

I should probably warn you that our road trips tend to be quite full-on, starting early and ending late and this itinerary reflects that so if you fancy something a little more relaxed feel free to change parts and miss out certain destinations altogether.

Equally, this southern England road trip can easily be extended to 11 or 12 days.

This itinerary is best done in spring, summer or early autumn when days are longer and allow for more sunlight. It is possible to do in the winter but you’ll be pushed for time when trying to get to certain recommenced places for sunset.

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We do recommend doing this southern England itinerary as a road trip to allow for the most possible flexibility. Cars can be rented in London and rates are competitive.

However, it can also be done by public transportation, a mixture of train and bus but you will have to allocate more time for getting from place to place.

Also, make sure to book your tickets for attractions, gardens, and castles in advance. Ticket sales are controlled to limit visitor numbers so make sure you do so in advance. 

Before You Set Off on the Southern England Itinerary

Car Rental

While you can do this southern England road trip itinerary by public transportation, it will take you much longer so I highly recommend you use a private car or rent one. Cars are very easy to rent in England. You’ll need your driving license and valid credit card to secure the booking.

Driving in London can be challenging with all the traffic, bicycles and especially if you aren’t used to driving on the left side of the road. To make things easier, consider taking a train to Oxford and renting a car from there and then returning your car to London at the end of the trip, or even leaving it in Canterbury.

I always use Rental Cars for the best value car rental deals in the UK. Check rates and availability for your dates below:

Accommodation

Southern England is full of amazing accommodation options for all travel budgets at each of these destinations. Personally, I always use either Booking.com or VRBO when booking accommodation as they are the most reliable and have the most amazing options.

Feel free to use the form below to search for the best hotels at each itinerary location.

Do you prefer luxury top-quality rentals over hotels? Have you heard about the Plum Guide? It’s like Airbnb but so much better! Check out all the luxury rentals in Southern England on the Plum Guide website today.

Southern England Itinerary: 10 Days Road Trip

In summary, here’s a quick breakdown for each day of this Southern England Itinerary road trip. Make sure to scroll down further for what to see in each place and where to stay. You can also use the Google Map below to help you plan your trip.

Day One- Oxford, Stratford Upon Avon

Oxford is a university town, rich in history, culture, students, and fun things to do. The best way to see Oxford is on foot, exploring and popping into various colleges, cafes and restaurants along the way.

Most colleges are open for visitors and for a small fee, you can visit some of the most famous such as Christ Church, Magdalen, and Trinity College.

Make sure not to miss the famous Bridge of Sights and while it’s probably not as impressive as the one in Venice, it’s still worth a look.

Also, don’t leave without seeing the iconic Radcliffe Camera, a circular Neo-classical building now used as a reading room, and the Bodleian Library, one of which was used as a filming location for Harry Potter.

A quintessential part of Oxford and Cambridge student culture, don’t miss punting on the river- floating downriver in specialized rowboats while relaxing with a beverage- the best way to do it.

If you get peckish check out Organic Deli Cafe, for delicious cafe classics like salads, soups, sandwiches, and the British jacket potato. 

For the full guide check out Oxford in One Day Itinerary

Next, make your way north-west to Stratford-upon-Avon, the birthplace of England’s most famous writer William Shakespeare.

A self-guided walking tour is a perfect way to enjoy this city, filled with dozens of spectacular Tudor buildings, historic pubs, and buildings notable to Shakespeare’s life.

You can also take a boat tour down the River Avon.  If you’re a fan of the writer, you can visit the house in which he was born, see his old school, and visit his wife’s (Anne Hathaway’s) cottage.

Of course, you can also see a play at the Royal Shakespeare Company and enjoy his work in action.

For some incredible Tudor-inspired night, stay at Mercure Stratford Upon Avon Shakespeare Hotel or the White Swan Hotel. Both hotels are listed Tudor buildings and offer beautifully preserved wooden beam architecture and finishings.

They are the perfect place to grab a drink in the evening and get a peaceful night’s rest, all while transporting you back to the times of Shakespeare.

Check availability and rates for Mercure Stratford here | booking.com | hotels.com

Check availability and rates for White Swan Hotel here | booking.com | Agoda

Day Two: Cotswolds

On the second day of your southern England road trip, continue south into the Cotswolds Area of Outstanding Beauty where rolling green hills are punctuated by delightful little towns of pretty stone cottages, flower-filled gardens and the smallest streets imaginable.

The Cotswolds are spread out over quite a large area so, start exploring from the north, making your way south through the day.

Enjoy your day driving through and exploring villages like Stow-on-the-Wold, Bourton-on-the-Water, and Upper and Lower Slaughter to start.

These villages are compact and can be visited fairly quickly if you’re short on time- walk around and admire the hundred-year-old stone cottages and bridges and the calming canals, creeks, and waterways.

For more on the Cotswolds make sure not to miss The Prettiest Cotswold Villages | 5 Unmissable Villages You Have To Visit and The Ultimate Cotswold Itinerary for the Perfect Weekend Trip (including Oxford and Bath) for a great Cotswolds itinerary idea.

After lunch, make your way south along the A429, with a quick detour to the popular Cotswolds village of Bibury.

Bibury seems to be extremely popular in the morning but in the afternoon tourist buses seem to have died down making it a great time for the perfect Instagram photo.

After marveling over the history and beauty of this village travel south through the larger market towns of Cirencester, Tetbury and finally the stunning village of Castle Combe.

Explore the village itself and Manor House nearby too, a beautiful period house with lovely gardens and if you’re feeling peckish, it’s the perfect stop for a traditional English afternoon tea. 

Stay the night at Manor House (pictured) if your budget stretches that far, but if not, don’t worry. I recommend The White Hart, located in the nearby village of Ford, this is a beautiful typical British pub/inn with co