Embark on a 10-day self-drive tour through the rolling hills of the English countryside. Amid its verdant forests and wild moors, you'll discover vast treasures in the form of medieval villages and ruggedly beautiful coastline. This adventure includes stops at some of the gems of England, like Canterbury, the castles of South Downs, Devon, the Isle of Wight,  Cornwall, and Oxfordshire.


  • Tour ancient Canterbury
  • Visit the fairy-tale Arundel Castle
  • Explore Cornwall’s rugged coastline and sandy coves
  • See Queen Victoria's Osborne House, on the Isle of Wight
  • Learn about the history of Glastonbury

Brief Itinerary

Day Highlights Overnight
Days 1-2 Arrive in Kent & Explore Kent
Day 3 West Sussex & Portsmouth Arundel
Days 4-5 New Forest District & Isle of Wight New Forest
Day 6 Explore Devon Devon
Day 7 Explore Cornwall St Mawes
Days 8-9 Tour Somerset County & Castle Comb Bath
Day 10 Explore Oxfordshire & Depart Oxford

Detailed Itinerary

Days 1-2: Arrive in Kent & Explore

Garden of England

Welcome to the county of Kent! Your journey begins in this southeast region of the country, which is known as the "Garden of England." It earned this moniker centuries ago due its beautiful landscapes that include rolling green hills, castle parklands, fertile valleys, fruit orchards, strawberry fields, and downs peppered with villages and windmills. Upon arrival you'll check into your accommodation and will have the next two days free to enjoy the region however you please. 

Optional activities include: 

  • Shepherd Neame Limited brewery: Kent is also known as the "Beer Garden of England." Find out why when you stop for a tasting at Shepherd Neame, one of the country's oldest breweries (it was founded in 1698).
  • Canterbury: Marvel at ancient Roman walls in the city that inspired Chaucer's masterwork and where Marlowe penned Elizabethan plays like "Doctor Faustus." 
  • Rye: Explore the town's cobbled streets and see the region where William the Conqueror first engaged the Saxons in 1066.
  • White Cliffs: Follow a coastal path along the famous White Cliffs of Dover.
  • Brighton: Wander through narrow lanes of this seaside resort destination and visit the 18th-century Royal Pavilion, known for its iconic onion-domed roof.  

Day 3: West Sussex & Portsmouth

Arundel Castle

Your grand tour of southern England continues. In the morning, you'll travel west from Kent to the county of West Sussex. From there you'll continue on to neighboring Hampshire County and the coastal city of Portsmouth, a major naval stronghold. Some of the sights you'll be able to stop at along the way include:

  • Arundel: Come to this market town to witness the majesty of its fairy-tale castle, which is the ancestral home of the Duke of Norfolk. 
  • South Downs: The range of chalk hills running along England's southeast coast is one of the most stunning landscapes in the country. For a fun adult outing here, take a wine tour at Nyetimber, a historic estate and vineyard. 
  • South Downs Way: Venture down this long-distance footpath and equestrian route that cuts through scenic river valleys and ancient woodlands.  
  • Fishbourne: Tour this village's famous Roman Palace, which dates to 75 AD, and witness its intricate mosaics.
  • Chichester: Discover a town encircled by ancient Roman walls and visit its 11th-century Anglican Cathedral, which overlooks the plains between the South Downs and the sea.
  • Portsmouth Naval Port: Learn about the rich maritime history of Lord Nelson's flagship HMS Victory, and the Mary Rose, a ship in Henry VIII's navy. 

Driving time: 1 hour and 30 minutes
Driving distance: 75 miles (120 km)

Days 4-5: New Forest District & Isle of Wight

Osborne House, Isle of Wight

For your next adventure you'll travel to the rich woodlands of the New Forest District, in Hampshire. You'll also visit the Isle of Wight, which is located just offshore of Portsmouth and is accessible via ferry. You can choose from a mix of outdoor adventures and cultural activities that might include: 

  • Winchester: Immerse yourself in more than 900 years of history in this former capital of Saxon kings that was also a seat of power for bishops in the Church of England. Marvel at its 11th-century Cathedral, which features an eclectic mix of architectural styles including Norman crypts, Renaissance chapels, and a Gothic nave.
  • New Forest: Venture deep into this national park that abouds with beautiful heathlands, wild ponies, and forest trails.  
  • Beaulieu: Tour a once medieval abbey that is now famous for its National Motor Museum and collection of vintage cars.
  • Buckler's Hard: Step back in time with a visit to this charming, 18th-century shipbuilding village on the banks of the Beaulieu River, in the county of Hampshire.
  • Isle of Wight: Take a ferry from the port town of Lymington to the Isle of Wight, where you can visit Queen Victoria's Osborne House and the Norman fortress Carisbrooke. You can also enjoy a sailing trip on The Solent, a straight that separates the Isle of Wight from the English mainland.

Driving time: 1 hour
Driving distance: 50 miles (80 km)

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Day 6: Explore Devon

Devonshire coast
The Devonshire coast

Today you'll travel further west to Devon County, in southwest England. This area is known for its beautiful coastline and postcard beaches. Devon is also famous for its rich culinary tradition, which includes tea served with scones and clotted cream. Sights you can visit on today's itinerary include:

  • Exmoor National Park: Head to north Devon and explore the hilly moorlands and dramatic coast of this national park that covers 267 sq. miles.
  • Dartmouth: Thread your way through the elegant Georgian coastal towns of the "English Riviera" to the harbor of Dartmouth, where you'll enjoy Devonshire tea, scones, strawberry jam, and clotted cream.  
  • Dartmoor National Park: Explore vast moorlands, fertile river valleys, and marvel at wild ponies galloping across wildflower meadows.
  • River Tamar: Try your hand at fly-fishing and reel in some salmon and sea trout.
  • Buckland Abbey: Tour the 700-year-old home of Sir Francis Drake.
  • Plymouth: See the sights in this historic coastal city and visit The Hoe, which offers stunning views over Plymouth Harbour. There's also Barbican, the old port section of town known for cobbled streets and 16th-century warehouses. Take in the history of the Mayflower Steps, where pilgrims set off for America in 1620. 

Driving time: 2 hours
Driving distance: 91 miles (146 km)

Day 7: Explore Cornwall


In the morning make your way to Cornwall, located at the westernmost end of southern England. Here you'll enjoy beautiful coastal views, walk near wildflower-lined cliffs, discover hidden coves, visit gorgeous harbor towns, and taste Cornwall's culinary delights, like crumbly Yarg cheese and ice cream famously made with clotted cream. Other highlights include: 

  • St. Michael’s Mount: Visit this small island in Mount's Bay that is linked to the town of Marazion by a man-made causeway. Notable landmarks include a Norman church and a medieval castle perched atop a hill. 
  • The Minack Theater: Tour this cliffside, open-air theater in the village of Porthcurno and take in views of the Celtic Sea. The 750-seat theater opened in 1930 and still hosts regular performances.
  • St. Mawes Castle: Learn about the history of this artillery fort constructed by Henry VIII between 1540 and 1542, which helped protect against invasion from France and the Holy Roman Empire.
  • Saint Just-in-Roseland: This village, which enjoy AONB (Area of Outstanding Natural Beauty) status, was founded around 550 CE and is known for its 13th century Church of England parish Church.
  • Lost Gardens of Heligan: The Lost Gardens are located on the grounds of a 13-century Cornish estate and are regarded as some of the most beautiful botanical gardens in the country. Its impressive group of camellias and rhododendrons are part of a national collection. 

Driving time: 1 hour and 45 minutes
Driving distance: 95 miles (152 kilometers)

Days 8-9: Tour Somerset County & Castle Comb


Today you'll journey north and spend the next couple days touring historic cities and learning about some of the most famous British English legends. The areas and sights that you'll visit will include: 

  • Glastonbury: Learn about the town's Arthurian legends and visit religious landmarks, like the Chalice Well, a sacred garden and natural spring where some people believe the cup used at the Last Supper is buried. Afterward, be sure to head to the impressive ruins of an abbey which was founded in the 8th century. You can also climb Glastonbury Tor, a green hill that offers panoramic views of the English countryside.
  • Wells: Visit this medieval city whose name originates from the three wells dedicated to Saint Andrew. You can also explore the grounds of the Bishop's Palace and 13th-century Cathedral
  • Bath: Explore this historic spa town in the valley of the River Avon, which is the setting for two Jane Austen novels. You'll have time to visit the city's ancient Roman Baths and thermal springs, plus snap photos of its impressive Georgian architecture.
  • Castle Combe: Tour this 14th century village, which has been the location for countless films and is part of the Cotswolds Area of Outstanding Natural Beauty.

Driving time: 3 hours and 45 minutes
Driving distance: 200 miles (321 km)

Day 10: Explore Oxfordshire & Depart

Blenheim Palace, Oxfordshire

This county in southern England is best known for its prestigious Oxford University, which was established in 1096. Today you can tour the university as well as the area's other sights.

One can't-miss highlight is Blenheim Palace. The seat of the Dukes of Marlborough, this is one of the United Kingdom's finest manor homes. Explore its landscaped gardens, admire its collection of art and artifacts, visit the Butterfly House (home to butterfly species from around the world), and meander through the Marlborough Hedge Maze.

At the end of the day, you'll conclude your epic 10-day sojourn to southern England. Until next time!

Driving time: 1 hour and 30 minutes
Driving distance: 78 miles (125 km)

More Great England Itineraries

Looking for more inspiration for your trip to England? Check out these other UK itineraries, with outdoor adventures and best-of tours that cover the highlights. 


Map of Explore Historic Southern England - 10 days
Map of Explore Historic Southern England - 10 days