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Kent & East Sussex, England 15-Day Trip Itinerary

Kent & East Sussex, England Trip - Sep 1, 2026 to Sep 15, 2026

Sep 1 - Sep 15

Embark on a captivating 15-day self-drive adventure through England, beginning via Eurotunnel in Folkestone, to discover a rich tapestry of history, nature, and culture. This immersive journey blends historical sites, castles, ancient ruins, and charming villages with breathtaking national parks and scenic coastal drives, offering ample opportunities for relaxation, local markets, and traditional pub experiences away from London.

Kent & East Sussex, England view
1

Arrival via Eurotunnel & Dover Castle

Tuesday, September 1
1.1
09:00 - 11:00

Travel to Folkestone

Drive from Paris to Calais and take the Eurotunnel Le Shuttle to Folkestone, England.

Enjoy the quick and convenient crossing under the English Channel.

Ensure you have your booking reference and passports ready. Arrive at least 30-45 minutes before your scheduled departure.

1.2
12:30 - 16:30
EUR 68 for 2 people

Explore Dover Castle

Discover England's largest castle, a strategic fortress for over 9 centuries.

Explore the Great Tower, secret wartime tunnels, and admire views over the English Channel.

Booking tickets online in advance is recommended, especially for specific time slots for the Secret Wartime Tunnels. Allow plenty of time as there's a lot to see.

1.3
19:00 - 20:30

Dinner in Canterbury

Enjoy a traditional English dinner in the historic city of Canterbury, known for its charming pubs and diverse restaurants.

Many restaurants offer pre-theatre menus if you're interested in an evening show. Consider 'The Old Weaver's Restaurant' for a scenic riverside meal.

2

Canterbury Cathedral & City Exploration

Wednesday, September 2
2.1
09:30 - 12:00
EUR 40 for 2 people

Canterbury Cathedral

Visit the magnificent Canterbury Cathedral, a UNESCO World Heritage Site and the mother church of the Anglican Communion.

Explore its stunning architecture and rich history.

Guided tours are often available and highly recommended to learn about its history, including the murder of Thomas Becket. Photography is usually allowed without flash.

2.2
13:00 - 15:00

St. Augustine's Abbey

Explore the ruins of St.

Augustine's Abbey, another UNESCO World Heritage Site, founded shortly after Augustine's arrival in Kent in 597 AD.

The site is managed by English Heritage. A combined ticket with Canterbury Cathedral is sometimes available, or entry may be included if you have an English Heritage membership.

2.3
15:30 - 17:00

Canterbury City Stroll

Wander through the charming streets of Canterbury, exploring its shops, quaint alleyways, and medieval architecture. Consider a punt tour on the River Stour.

Punt tours offer a unique perspective of the city and its history from the water, often with a knowledgeable guide.

2.4
19:00 - 20:30

Traditional Pub Dinner

Experience a classic English pub for dinner.

Enjoy traditional fare and local ales in a cozy atmosphere.

Try 'The Parrot' for a pub in one of the city's oldest buildings, offering a great selection of food and drinks.

3

White Cliffs & Medieval Rye

Thursday, September 3
3.1
09:00 - 11:30

White Cliffs of Dover Walk

Enjoy a scenic walk along the iconic White Cliffs of Dover.

Take in the breathtaking views across the English Channel and explore the visitor centre.

Wear comfortable shoes as paths can be uneven. The National Trust manages the area and has a visitor centre with facilities. Parking available (charge applies).

3.2
11:30 - 13:00

Scenic Drive to Rye

Embark on a picturesque drive through the Kent countryside towards the medieval town of Rye in East Sussex.

Enjoy the 'Garden of England' scenery as you drive. Consider a brief stop in charming villages along the way if time permits.

3.3
14:00 - 17:00

Explore Medieval Rye

Wander through the cobbled streets of Rye, exploring its charming boutiques, antique shops, and historic buildings like Mermaid Street and St. Mary's Parish Church.

Climb the tower of St. Mary's for panoramic views over Rye and the surrounding coastline. Don't miss the Landgate, one of the original town gates.

3.4
19:00 - 20:30

Dinner in Rye

Dine at one of Rye's excellent restaurants or historic pubs, enjoying fresh local produce, especially seafood.

The 'Mermaid Inn' on Mermaid Street offers a unique dining experience in a historic building with tales of smugglers.

4

Coastal Views & Garden Visit

Friday, September 4
4.1
09:30 - 12:30

Great Dixter House & Garden

Visit the renowned Great Dixter House and Gardens, the former home of gardener and gardening writer Christopher Lloyd.

Explore its unique and influential gardens.

Check opening times before visiting, as they can vary seasonally. There's also a nursery if you'd like to take home a plant or two.

4.2
12:30 - 14:00

Drive to Brighton

Enjoy a scenic drive along the coast and through the Sussex Downs towards the vibrant city of Brighton.

This route offers diverse landscapes, from the flat coastal plains to rolling hills. Consider a stop at Battle Abbey if you're interested in the site of the 1066 Battle of Hastings (requires more time).

4.3
15:30 - 17:00

Brighton Palace Pier

Stroll along the iconic Brighton Palace Pier, enjoy the traditional seaside atmosphere, arcade games, and perhaps a stick of rock or some fish and chips.

A quintessential British seaside experience, perfect for people-watching and enjoying the fresh sea air. Some rides may be closed in September depending on weather.

4.4
19:00 - 20:30

Dinner in Brighton

Explore Brighton's diverse culinary scene, offering everything from trendy cafes to fine dining.

Plenty of options for fresh seafood.

Brighton is known for its vegetarian and vegan options, as well as its many independent eateries in 'The Lanes' area.

5

Royal Pavilion & Brighton Lanes

Saturday, September 5
5.1
10:00 - 12:30
EUR 47 for 2 people

Royal Pavilion

Tour the magnificent Royal Pavilion, a former royal residence built for George IV.

Marvel at its Indo-Saracenic exterior and lavish Chinese-inspired interiors.

Audio guides are usually included and provide fascinating insights into the history and design. No photography allowed inside.

5.2
13:00 - 16:00

Explore The Lanes

Get lost in the famous Lanes, a maze of narrow alleyways filled with independent shops, antique dealers, jewellery stores, and charming cafes.

This is the perfect spot for unique souvenirs and exploring Brighton's bohemian side. Be prepared for crowds, especially on a Saturday.

5.3
16:00 - 17:30

North Laine District

Venture into the North Laine, a vibrant area north of The Lanes known for its quirky shops, street art, and independent businesses, offering a different vibe from the historic Lanes.

Great for unique finds, vintage clothes, and browsing record stores or artisan craft shops. Catch some street performers if you're lucky!

5.4
19:00 - 20:30

Farewell Brighton Dinner

Enjoy a final dinner in Brighton, perhaps by the seafront or in one of the lively areas like Kemptown.

Consider a restaurant with a view of the West Pier ruins for a memorable end to your time in Brighton.

6

Journey to the Cotswolds & Bibury Charm

Sunday, September 6
6.1
09:00 - 12:00

Drive to the Cotswolds

Begin your scenic drive from Kent/East Sussex towards the heart of the Cotswolds.

Enjoy the changing English countryside as you head west. Suggested arrival area is near Cirencester or Bibury.

From Kent/East Sussex to The Cotswolds

This is a driving day, so ensure your vehicle is ready for a longer journey. Take breaks as needed.

6.2
13:00 - 15:30
GBP 10 for 2 people

Explore Bibury Village

Often called 'the most beautiful village in England', Bibury is famous for its Arlington Row of weavers' cottages, the tranquil River Coln, and its charming Cotswold stone buildings.

Walk along Arlington Row, visit the local trout farm, and enjoy the serene atmosphere. Parking can be busy, especially on a Sunday.

6.3
16:00 - 17:00

Check into Accommodation

Settle into your hotel or guesthouse in or around Cirencester, known as the 'Capital of the Cotswolds'.

Cirencester offers a good base for exploring the central Cotswolds.

6.4
19:00 - 20:30

Dinner in Cirencester

Enjoy a traditional pub dinner or a meal at one of Cirencester's local restaurants.

The Fleece at Cirencester or The Old Brewhouse are popular choices for a classic pub experience.

7

Northern Cotswolds Villages & Views

Monday, September 7
7.1
09:30 - 12:00
GBP 24 for 2 people

Bourton-on-the-Water

Explore Bourton-on-the-Water, often referred to as the 'Venice of the Cotswolds' due to the River Windrush flowing through its centre under several low bridges.

Visit the Model Village or Birdland Park.

The Model Village is a popular attraction, an exact replica of the village itself.

7.2
12:30 - 14:00

Stow-on-the-Wold & Lunch

Head to Stow-on-the-Wold, the highest town in the Cotswolds, known for its ancient market square and antique shops.

Enjoy lunch at a traditional pub.

Don't miss the picturesque 'tree in the door' at St. Edward's Church.

7.3
14:30 - 16:30
GBP 12 for 2 people

Broadway Tower Visit

Climb Broadway Tower, an iconic folly offering spectacular panoramic views across 16 counties on a clear day. Explore the surrounding parkland.

Great photo opportunities and walking paths. Check opening times for the tower itself.

7.4
18:30 - 20:00

Dinner in Chipping Campden

Conclude your day with dinner in Chipping Campden, a beautiful wool town with an elegant High Street.

The Noel Arms Hotel or The Cotswold House Hotel offer lovely dining options.

8

Southern Cotswolds & Wye Valley Arrival

Tuesday, September 8
8.1
09:30 - 11:30

Visit Castle Combe

Discover Castle Combe, often cited as one of England's prettiest villages.

Admire its quaint houses, picturesque bridge, and the By Brook river. It feels like stepping back in time.

Parking is usually at the top of the hill, and it's a pleasant walk down into the village. Be respectful of residents' privacy.

8.2
12:00 - 13:30

Drive to Wye Valley

Embark on your journey from the Cotswolds towards the stunning Wye Valley, a designated Area of Outstanding Natural Beauty. The drive itself is very scenic.

From Castle Combe to Wye Valley (e.g., Chepstow)

Enjoy the shift in landscape as you head towards the Welsh border.

8.3
14:30 - 16:30
GBP 16 for 2 people

Explore Tintern Abbey

Visit the magnificent ruins of Tintern Abbey, one of the most iconic monastic sites in Wales, nestled dramatically on the banks of the River Wye.

It's an inspiring sight.

8.4
17:00 - 18:00

Check into Accommodation

Check into your accommodation in the Wye Valley area, perhaps near Chepstow or Monmouth, offering convenient access to local attractions.

These towns provide good bases for exploring both the English and Welsh sides of the Wye Valley.

8.5
19:00 - 20:30

Dinner in Chepstow

Enjoy dinner in the historic town of Chepstow, with its impressive castle and riverside views.

Try The Boat Inn for riverside dining or The Coach & Horses for traditional pub fare.

9

Wye Valley Views & River Activities

Wednesday, September 9
9.1
09:30 - 12:30
GBP 70 for 2 people

Canoeing on River Wye

Experience the Wye Valley from the water with a scenic canoeing or kayaking trip.

Options range from short hourly rentals to longer half-day adventures.

Several providers offer rentals; book in advance, especially during peak season. No experience necessary for gentle sections.

9.2
13:30 - 15:30

Symonds Yat Rock Viewpoint

Visit Symonds Yat Rock for breathtaking panoramic views of the horseshoe bend of the River Wye, the surrounding forest, and beyond.

This is a prime spot for nature photography.

Look out for peregrine falcons soaring above the valley. There's a café at the viewpoint for refreshments.

9.3
16:00 - 17:30

Explore Ross-on-Wye

Wander through the charming market town of Ross-on-Wye, famous for its picturesque setting and independent shops. Enjoy the riverside walks.

Visit the iconic Market House and browse local craft shops.

9.4
19:00 - 20:30

Dinner in Monmouth

Enjoy dinner in the historic border town of Monmouth, situated at the confluence of the Rivers Monnow and Wye.

The Misbah Indian Restaurant or The Punch House offer good dining options.

10

Castles & Countryside before Dorset

Thursday, September 10
10.1
09:30 - 11:30
GBP 20 for 2 people

Visit Goodrich Castle

Explore the impressive Norman ruins of Goodrich Castle, one of the best-preserved medieval castles in England, offering fantastic views over the Wye Valley.

Climb to the top of the keep for panoramic views and explore the various sections of the castle.

10.2
12:00 - 13:30
GBP 14 for 2 people

Raglan Castle Exploration

Discover Raglan Castle, a magnificent late medieval fortress known for its hexagonal Great Tower and grand architecture.

A true gem of Welsh history.

Offers fantastic photo opportunities and insights into 15th-century castle design.

10.3
13:30 - 14:30

Lunch in Usk

Enjoy a relaxed lunch in the small, attractive town of Usk, known for its floral displays and riverside setting.

The New Court Country House Hotel or local pubs offer good lunch spots.

10.4
15:00 - 17:00

Leisurely Drive South

Begin your gradual journey south, making your way towards the next segment of your trip in Dorset.

Enjoy the changing scenery as you leave the Wye Valley.

From Usk towards Dorset

This drive sets you up for an easier start to the Dorset Coast & New Forest segment tomorrow.

10.5
17:30 - 18:30

Check into Overnight Stay

Check into an overnight accommodation to break up the journey, perhaps in a town like Bristol or Bath, or further south to minimize travel time tomorrow to Dorset.

Booking a hotel slightly south of the Wye Valley will shorten tomorrow's drive to the Dorset coast.

10.6
19:30 - 21:00

Dinner & Relaxation

Enjoy dinner and relax at your chosen overnight stop, reflecting on your adventures in the Cotswolds and Wye Valley.

11

Jurassic Coast Wonders & Arrival in Dorset

Friday, September 11
11.1
09:00 - 12:00

Drive to Dorset

Begin your drive from the Cotswolds/Wye Valley region south towards the stunning Dorset coastline, an Area of Outstanding Natural Beauty.

Various routes to Dorset

Enjoy the scenic drive through the English countryside.

11.2
13:30 - 15:30

Lulworth Cove Exploration

Discover the iconic, perfectly almost-circular Lulworth Cove, a UNESCO World Heritage site known for its unique geology.

Enjoy a walk along the shore.

There's a car park nearby, and a short walk down to the cove. Wear comfortable shoes.

11.3
15:45 - 17:45

Visit Durdle Door

Walk from Lulworth Cove to the magnificent natural limestone arch of Durdle Door, offering breathtaking views of the coastline.

This is a must-see along the Jurassic Coast.

The walk involves some steep paths and steps. Parking available at Durdle Door Holiday Park (charges apply).

11.4
19:00 - 20:30

Dinner in Wareham

Enjoy a relaxing evening and dinner in the charming Saxon market town of Wareham, situated on the River Frome.

Explore local pubs and restaurants offering traditional English fare.

12

Corfe Castle & Purbeck Peninsula

Saturday, September 12
12.1
09:30 - 12:00
GBP 15 for 1 person

Explore Corfe Castle

Visit the dramatic ruins of Corfe Castle, standing majestically on a hill overlooking the village.

Learn about its thousand-year history as a royal fortress and family home.

Run by the National Trust. Check opening times and consider booking in advance, especially for a Saturday. Parking is available in the village.

12.2
13:30 - 15:30
GBP 20 for 1 person

Swanage Railway Ride

Take a nostalgic steam train ride on the Swanage Railway from Corfe Castle to Swanage, enjoying views of the Purbeck countryside.

Timetables vary; check their website for Saturday schedules. Return tickets are available.

12.3
15:45 - 17:00

Swanage Beach Stroll

Enjoy a leisurely walk along Swanage Beach, a beautiful sandy bay perfect for relaxing and enjoying the coastal air.

12.4
19:00 - 20:30

Dinner in Swanage

Dine at one of Swanage's many restaurants or traditional fish and chip shops.

13

Into the Heart of the New Forest

Sunday, September 13
13.1
09:30 - 10:30

Drive to New Forest

Depart from Dorset and drive into the enchanting New Forest National Park, famous for its ancient woodlands, heathland, and free-roaming ponies.

Wareham to Lyndhurst, New Forest

The drive itself offers beautiful scenery as you enter the national park.

13.2
10:45 - 12:45

New Forest Nature Walk

Take a refreshing walk or short hike to spot wild ponies, deer, and other wildlife.

Lyndhurst, the 'capital' of the New Forest, is a good starting point for various trails.

Pick up a map at the New Forest Centre in Lyndhurst for recommended trails. Wear appropriate footwear.

13.3
13:30 - 17:30
GBP 28 for 1 person

Beaulieu Estate Visit

Spend the afternoon at the Beaulieu Estate, home to the National Motor Museum, Palace House, and Beaulieu Abbey.

A fascinating blend of history and automotive heritage.

Allow ample time to explore all the attractions. Tickets can be purchased online for a discount.

13.4
19:00 - 20:30

Dinner in Lyndhurst

Enjoy dinner at one of the welcoming pubs or restaurants in Lyndhurst, soaking in the village atmosphere.

14

Maritime History & Coastal Charm

Monday, September 14
14.1
09:30 - 12:00
GBP 10 for 1 person

Buckler's Hard Maritime Village

Explore the historic 18th-century shipbuilding village of Buckler's Hard on the Beaulieu River.

Discover its role in naval history and enjoy the riverside setting.

Part of the Beaulieu Estate, but often accessible separately. Check for specific entry fees.

14.2
13:00 - 15:30

Lymington Town & Quay

Visit the Georgian market town of Lymington, known for its busy quay, independent shops, and connection to the Isle of Wight ferries.

14.3
16:00 - 17:30

Traditional Afternoon Tea

Indulge in a classic English afternoon tea experience at a quaint New Forest tea room or hotel.

Booking is often recommended, especially for popular establishments.

14.4
19:00 - 20:30

Farewell Dinner in New Forest

Enjoy a final dinner in the New Forest, perhaps at a traditional country pub, savoring local flavors.

15

Journey Back to France

Tuesday, September 15
15.1
09:30 - 11:30
GBP 12 for 1 person

Winchester Cathedral Visit

On your way east, make a stop in the historic city of Winchester to visit its magnificent cathedral, one of the largest in Europe and burial place of Jane Austen.

Check opening hours, especially for a Tuesday. Parking available nearby in Winchester city center.

15.2
12:00 - 14:30

Drive to Folkestone Eurotunnel

Begin the journey back east towards Folkestone, Kent, for your Eurotunnel crossing.

Winchester to Folkestone

Allow extra time for potential traffic on motorways. Grab a quick lunch on the way.

15.3
15:30 - 16:30

Eurotunnel Check-in

Arrive at the Eurotunnel terminal in Folkestone, check in for your pre-booked crossing, and prepare for boarding.

Aim to arrive at least 45 minutes before your scheduled departure. Have your booking reference and passport ready.

15.4
17:00 - 18:00

Eurotunnel Crossing to Calais

Enjoy the approximately 35-minute train journey under the English Channel back to Calais, France.

Stay in your car during the crossing. Refreshments and restrooms available at the terminal.

This 15-day itinerary for Kent & East Sussex, England can be customized using our AI travel planner. Chat with our AI assistant to modify activities, adjust timings, add personal preferences, and get recommendations for restaurants, hotels, and transportation.