Self-Drive Holidays
9 Nights
  • Fully customisable itinerary
  • Prices from: £1335 per person
  • Best time to go: April - October
  • Transport: Rental car included (optional)


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The historic hometown of Oxford University, ‘The City of Dreaming Spires’ is a wonder to behold. The medieval city centre and side-streets of Oxford are characterised by their elegant architecture, vibrant culture and wealth of historic intrigue.

The Cotswolds
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The Cotswolds is a designated Area of Outstanding Natural Beauty – a series of enchanting and picture-perfect villages situated amid rolling limestone hills.

Seemingly untouched by modern society, spending time exploring the charming villages of Bibury, Bourton on the Water, and Upper and Lower Slaughter is like looking through a window to times gone by.

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The English wine industry has flourished in the last decade and the South East has become the focal point of production due to its warmer, drier climate.

There are a multitude of vineyards operating in Surrey, Sussex and Kent, and with many of these offering tours and tastings, you can spend an afternoon sampling some of these now world-renowned wines. 

South East coast
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As well as being home to some of the UK’s most popular blue flag beaches and seaside towns, England’s ‘Creative Coast’ is known for its unmissable cultural attractions.

These include world-class galleries such as the Turner Contemporary in Margate and the Towner Art Gallery in Eastbourne, alongside unique museums like Dickens House in Broadstairs. 

The White Cliffs of Dover
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A visit to the South-East would not be complete without a trip to Dover. Escape the bustling port for a serene walk along the famous White Cliffs, complete with panoramic views and an abundance of wildlife and history.

Dover Castle is equally impressive, and it is worth setting time aside to explore this iconic fortress. 

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Immortalised by Geoffrey Chaucer’s Canterbury Tales, Canterbury is a city with a rich cultural and historical heritage. Home to a UNESCO World Heritage Site, Canterbury boasts some of England’s greatest examples of medieval architecture and one of its oldest cathedrals.

The Beautiful South: History, Culture and Stunning Coastlines

The South East is a region with a fantastic amount to offer. Shaped equally by its sites of historical importance and its contributions to contemporary culture, there is an incredible variety of things to see and do.

Your journey between Oxford and Canterbury will celebrate this marriage between England’s past and present, by taking you to picturesque rural villages, vineyards at the forefront of the blossoming British wine trade, and the bohemian ‘Creative Coast’. 

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Your journey begins in the famous university town of Oxford. A romantic city steeped in history, this is the perfect place to begin your journey through the South East and provides an excellent base to explore the rest of Oxfordshire and The Cotswolds.

After exploring the city, you will journey through The Chilterns, an AONB, and Surrey. This drive will take you past Windsor, where you can make a detour to visit Windsor Castle – the oldest and largest occupied castle in the world.

Brighton, the next overnight stop, is a seaside resort located on the South Coast. People have been flooding to Brighton for hundreds of years for restorative purposes, and today the town is full to the brim with independent restaurants, vintage shops and a cultural quarter which could rival that of a much larger city.

The drive along the South East coast is breathtaking and provides the opportunity to stop and explore the seaside towns of Eastbourne, Hastings and Rye. It also allows for a visit to one of the most iconic landscapes in the UK: the White Cliffs of Dover. Clear away the cobwebs with a brisk walk along the clifftops, an immersive way to experience the ‘gateway to England’.

From Dover, it is a short drive to Canterbury, your final overnight location. This beautiful, small city is home to a UNESCO World Heritage Site and was a place of pilgrimage in the middle ages. You can spend time exploring Canterbury Cathedral and St Augustine’s Abbey, as well as paying a visit to one of the city’s many excellent museums.

From Canterbury it is only a stone’s throw to the Kent coast, with the pastel-coloured seafronts of Whitstable, Margate and Broadstairs readily accessible, for a final day at the beach, to draw your adventure through the South East to a close.

Suggested Itinerary

The holiday ideas on our website are just examples of the amazing trips we offer. Think of this itinerary as a starting point which can be tailored into something completely unique to you by our award-winning specialists.

We love the opportunity to use our first-hand knowledge and experience to design and deliver the perfect, bespoke holiday experience for you.

Day 1: Arrive in Oxfordshire
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Your journey through the South East begins in Oxfordshire. Before making your way into Oxford, you could visit some of the impressive manors of North Oxfordshire.

With over 300 years of history, spectacular Blenheim Palace, a World Heritage Site and birthplace of Winston Churchill, is one not to miss.
Overnight – Oxford

Day 2: Oxford Sightseeing
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A full day to explore this most famous and beautiful city. Oxford is a fantastic city to wander, with many of the university colleges and iconic landmarks such as the Bodleian Library, Radcliffe Camera, and the Sheldonian Theatre located in the compact city centre.

There are many superb museums as well as walking and bus tours. To see the city from a different perspective, you could try punting on the River Thames – an archetypal Oxford experience.
Overnight – Oxford

Day 3: The Cotswolds Sightseeing
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From Oxford, it is a short drive to The Cotswolds, an Area of Outstanding Natural Beauty famed for its picturesque chocolate-box villages set amid rolling green countryside.

The villages of Bourton-on-the-Water, Bibury, Lower Slaughter and Chipping Norton are excellent examples of these quintessentially English villages – full of winding lanes, cosy pubs and tearooms.
Overnight – Oxford

Day 4: Oxford to Brighton
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On the way to Brighton, make a stop at Windsor Palace – this striking residence has been a royal home and fortress for over 900 years.

You could also make a detour to visit Guildford, located in the Surrey Hills in an area synonymous with producing outstanding wines. Albury Vineyard, Greyfriars Vineyard and Denbies Wine Estate all offer fantastic tours and tastings.
Overnight – Brighton

Day 5: Brighton Sightseeing
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A full day in Brighton to immerse yourself in everything that the bohemian coastal town has to offer. Visit the Royal Pavilion, an exotic seaside palace built for George IV, explore the independent boutiques and cafes in The Lanes, and take a walk through English seaside history on Brighton Palace Pier, a 1722 ft long Victorian pier which has stood since 1899.
Overnight – Brighton

Day 6: South Downs Sightseeing
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Today you could choose to escape into the tranquillity of the South Downs, England’s newest national park, for a day walking the South Downs Way.

Alternatively, you could visit Fishbourne Roman Palace, an archaeological museum preserving the ground floor of a supply fort or Arundel Castle and its magnificent Gardens.
Overnight – Brighton

Day 7: Brighton to Canterbury
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Your journey will continue along the coast to your final overnight stop, taking you through the towns of Eastbourne, Hastings and Rye – each with their own distinct charm.

You could choose to travel via Dover, to take in the world-famous White Cliffs – the dramatic limestone cliffs have been considered a symbol of hope and freedom for many centuries.

To learn more about Dover’s strategic importance, you could visit Dover Castle – an impressive fortress overlooking the channel.
Overnight – Canterbury

Day 8: Canterbury Sightseeing
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A day to spend exploring Canterbury, a cathedral city and UNESCO World Heritage Site that was one of the most important centres of pilgrimage in Medieval England.

There is so much to see in this incredibly beautiful and historic city, including Canterbury Cathedral, St Augustine’s Abbey, Westgate, and St Martin’s Church, which is the oldest in the English speaking world.
Overnight – Canterbury

Day 9: Kent Coast Sightseeing
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On the final day of your adventure through the South East, make the short journey from Canterbury to the Kent coast.

The towns of Whitstable, Margate and Broadstairs ooze old school seaside charm: Whitstable is famous for its fresh seafood, Broadstairs boasts two Blue Flag beaches and Margate is the home of Dreamland and the Turner Contemporary Gallery.
Overnight – Canterbury

Day 10: Depart Canterbury
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After breakfast, it’s an hour and a half drive to London where your South of England Road Trip will come to an end. 

What's Included?

Your holiday includes:

  • Carefully selected en-suite accommodation for 9 nights including traditional English breakfast
  • Comprehensive information pack
  • Personalised itinerary with our recommendations for the best places to eat and drink and sightseeing suggestions
  • Map of England with our recommended driving route
  • 10 days rental of an Economy car (other vehicle categories available) including comprehensive insurance
  • 24-hour emergency contact number
  • Full financial protection

Your holiday doesn't include:

  • Travel insurance
  • Flights
  • Lunches and evening meals

Accommodation & Prices

Special Places to Stay Special Places to Stay
Special Places to Stay Special Places to Stay
Premium Premium
Premium Premium
Standard Standard
Standard Standard

We know that after a busy day of sightseeing an exceptional place to stay makes all the difference. That’s why all of the accommodation we select is hand-picked using our first-hand knowledge of the best places to stay.

Our discerning team has a wealth of experience, and we extensively research and regularly review all of the accommodation we select for our clients.

Please choose from one of our accommodation categories below. If you wish to combine these categories or perhaps upgrade for a special occasion let us know in your enquiry.

Accommodation type
Price per person
4* Guest Houses and 3* Hotels
From £1335

A collection of quality 4* Guest Houses and 3* Hotels often located in beautiful locations which provide an excellent standard of accommodation.

Tastefully decorated and furnished, these properties are generally owned and operated by locals who have a genuine passion for their region which they are keen to share with you. Their warm hospitality is sure to be a highlight of your experience.

Boutique Guest Houses and 4* Hotels
From £1630

Our Premium category includes a unique collection of luxurious and stylish boutique Guest Houses and small 4* Hotels. These are wonderfully charming and intimate and run with great flair by their owners.

It also comprises larger 4* Hotels selected for their high standard of accommodation, exceptional service, and great location. These range from traditional luxury to contemporary Hotels.

Special Places to Stay
Exceptional Hotels and luxury Resorts
Please enquire

From award-winning luxury Hotels to unique country retreats, all of which offer exceptional accommodation with superb facilities and outstanding service.

These are truly magical places and amongst the best England has to offer. The perfect choice when you would like somewhere really special which can be a treat for the night or for your entire holiday.

Car Hire

Our packages include car rental and comprehensive insurance for the duration of your holiday. Absolute Escapes has an excellent relationship with a number of car hire operators and we are able to offer quality vehicles and great value for money.

If you plan to bring your own vehicle, we are also able to offer this itinerary without a rental car.

All our packages include:

  • Collision Damage Waiver
  • Super Damage Excess Waiver
  • Third Party Insurance
  • Theft Waiver
  • Tax
Vauxhall Corsa or similar
  • Good for 2 people
  • Maximum of 4 passengers
  • 2 large suitcases
  • Manual or automatic transmission
Ford Focus or similar
  • Good for 2 – 4 people
  • Maximum of 5 passengers
  • 2 large suitcases
  • Manual or automatic transmission
Volkswagen Passat or similar
  • Good for up to 4 people
  • Maximum of 5 passengers
  • 3 large suitcases
  • Manual or automatic transmission
VW Sharan or similar
  • Good for 5 people
  • Maximum of 7 passengers
  • 3 – 4 large suitcases
  • Manual or automatic transmission

Make an enquiry

South of England Road Trip

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