We are thrilled to offer this walking holiday which includes so much of what is magical about Kent. You will amble along wonderful sea shores with sand and pebble beaches, cliffs and sea wall, taking in 7 very varied and remarkable castles with an overnight stay in the grandest of all - Leeds Castle.
Your route through the 'Garden of England', as this area is known, leads across rare chalk down land and through ancient woods and a plethora of orchards to a string of small, fascinating towns packed with local gems - medieval buildings, arty shops and oyster shacks. And the historic city of Canterbury with its stunning cathedral and ancient buildings is a remarkable place in its own right. We have chosen overnight stays in these locations so that you can discover all they have to offer. And with easy distances and walking, you will have time to enjoy the abundance of local produce, from vineyards and fruit farms to seafood restaurants and local beers and ciders.
Holiday details
Price
- Classic
-
from £1,595 per person
- Luxury
-
from £1,995 per person
Based on two people sharing a room
Duration
7 nights
Start & Finish
Starts Saturdays at Leeds Castle finishes Dover. Leeds Castle is close to Maidstone and not far from Ashford stations. Dover has its own station.
Hotels
- Classic
-
3 small hotels, an inn and a stay within Leeds Castle grounds
- Luxury
-
One 4 star hotel, two 3 star hotels, a boutique hotels and a stay within Leeds Castle grounds. Option to stay in an 11th Century Tower within Dover Castle's walls
Holiday type
Self-guided so you are free to explore at your own pace. More info...
Activity level
Gentle walking (2) More info...
Mileage
5 days of walking 8- 11 miles per day (13 - 18 km) and 1 optional day of walking
Terrain
Mostly flattish or gently undulating
What’s included?
Ensuite accommodation every night with breakfast. The services of our friendly local Hosts. Luggage transfers between hotels. 24/7 phone contact number. Adventure Handbook with our local tips. GPS Routes on an App with waterproof phone holder. Guide Book or OS maps. Protection of your funds. Advice, help and guidance planning your trip.
Entry to Leeds Castle and grounds on days 1 and 2. Read About Our Trips for further details
Options
- Add an extra day with a driver guide to Hever Castle and Sissinghurst Castle gardens
- Stay in Dover Castle, in an 1th Century tower instead of in Deal
Itinerary day-by-day
Classic
-
1. Day one
Arrive Leeds Castle
This walking tour has a wow start with a full-on castle experience at Leeds Castle. Arrive in your own time and discover this magnificent 900-year-old moated castle and learn more about the 6 queens who lived here. Punt on the moat and swan around the beautiful gardens and lakes of this 500-acre estate. You will also have the chance to wander the grounds – in peace in the evening, when only residents remain. You stay the night in the stable courtyard and dinner is available too.
-
2. Day two
Enjoy Leeds Castle and Canterbury
Enjoy a Knight’s breakfast before we transfer you to historic Canterbury where there is much to explore. Your host will meet you on arrival to brief you on your itinerary. Our city centre walking tour leads you to the Norman castle, the famous cathedral and a host of other quite remarkable ancient buildings.
Optional 3 miles (5 km)
-
3. Day three
Canterbury to Whitstable
This glorious first day of walking takes you up into the rural and gently rolling Kent downs. These chalk downs house many rare habitats and much of the landscape is protected. Enjoy marvellous views and ancient woodlands before joining the old Crab and Winkle Way to trendy Whitstable on the coast. Oysters are big here, poke around the working harbour and enjoy arty and offbeat shops. You stay here 2 nights.
8 or 11 miles (13 or 18 km)
-
4. Day four
Whitstable to Reculver
Today's walk is literally adjacent to the beach and waves as you follow the sea wall for much of the time, there to protect the low cliffs along the coast. Take in big views, beach huts, cafes and working harbours, dog walkers and cliff top hide-outs until you reach the Roman fort at Reculver, standing proud and weather eroded. We meet you here and transfer you back to Whitstable for a second night there.
Optional 8 miles (13 km)
-
5. Day five
Upstreet to Sandwich
We transfer you after breakfast to Upstreet, a buzzy little place on the river. From here you walk inland, this once marshy and now reclaimed landscape being a hive of farming activity, with numerous orchards and often large fields. You amble along the Great Stour riverbank first and then weave through rural hamlets with the occasional inn and cafe. The castle of the day is at Richborough - a fort built by the Romans with vast walls and an amphitheatre that although ruined, is worth a visit. Not far beyond lies the gem of Sandwich, one of the best-preserved medieval towns in Britain. It's a Cinque port, that's no longer on the sea but on a river. You stay overnight here.
8.5 miles (14 km)
-
6. Day six
Sandwich to Deal and Walmer
Head off to the sea, a couple of miles away, to wander idyllic paths along the coast which has long sandy beaches most of the way. As if this wasn't enough for a walk, there are two remarkable castles enroute both built by Henry VIII and both Cinque ports. First up is Deal, one of the finest Tudor castles in Britain. The town is also a favourite of ours with an authentic high street, a pier and a pebble beach. Continuing along the coast briefly you reach Walmer Castle which also has superb gardens and evolved into a stately home, lived in by no less than the Queen Mother amongst others. It's a majestic place! Stay the first of 2 nights in Deal.
7.6 miles (12 km)
-
7. Day seven
Deal to Dover
Your final day of walking is the most dramatic as the cliffs deepen towards Dover and you climb to the ultimate height of Dover Castle, standing proud atop the white cliffs guarding the port and shore below. Take in stunning views across the English Channel, dip into beach cafes backed by vast walls of chalk and enjoy the impressive castle first imagined by Henry VIII and critically employed during WWII. If you fancy staying here in an 11th Century tower, see the options above. Otherwise, we transfer you back to Deal for a 2nd night.
Optional 8 miles (13 km)
-
8. Day eight
Depart Dover
We transfer you to Dover after breakfast for your departure. You may want to take time to enjoy Dover castle with all its turrets and war time tunnels as this is the jewel of all castles and the oldest surviving in England. Dover is on the rail network for onward connections to Canterbury, Ashford for Eurostar or London.
Luxury
-
1. Day one
Arrive Leeds Castle
This walking tour has a wow start with a full-on castle experience at Leeds Castle. Arrive in your own time and discover this magnificent 900-year-old moated castle and learn more about the 6 queens who lived here. Punt on the moat and swan around the beautiful gardens and lakes of this 500-acre estate. You will also have the chance to wander the grounds – in peace in the evening, when only residents remain. You stay the night in the stable courtyard and dinner is available too.
-
2. Day two
Enjoy Leeds Castle and Canterbury
Enjoy a Knight’s breakfast before we transfer you to historic Canterbury where there is much to explore. Your host will meet you on arrival to brief you on your itinerary. Our city centre walking tour leads you to the Norman castle, the famous cathedral and a host of other quite remarkable ancient buildings.
Optional 3 miles (5 km)
-
3. Day three
Canterbury to Whitstable
This glorious first day of walking takes you up into the rural and gently rolling Kent downs. These chalk downs house many rare habitats and much of the landscape is protected. Enjoy marvellous views and ancient woodlands before joining the old Crab and Winkle Way to trendy Whitstable on the coast. Oysters are big here, poke around the working harbour and enjoy arty and offbeat shops. You stay here 2 nights.
8 or 11 miles (13 or 18 km)
-
4. Day four
Whitstable to Reculver
Today's walk is literally adjacent to the beach and waves as you follow the sea wall for much of the time, there to protect the low cliffs along the coast. Take in big views, beach huts, cafes and working harbours, dog walkers and cliff top hide-outs until you reach the Roman fort at Reculver, standing proud and weather eroded. We meet you here and transfer you back to Whitstable for a second night there.
Optional 8 miles (13 km)
-
5. Day five
Upstreet to Sandwich
We transfer you after breakfast to Upstreet, a buzzy little place on the river. From here you walk inland, this once marshy and now reclaimed landscape being a hive of farming activity, with numerous orchards and often large fields. You amble along the Great Stour riverbank first and then weave through rural hamlets with the occasional inn and cafe. The castle of the day is at Richborough - a fort built by the Romans with vast walls and an amphitheatre that although ruined, is worth a visit. Not far beyond lies the gem of Sandwich, one of the best-preserved medieval towns in Britain. It's a Cinque port, that's no longer on the sea but on a river. You stay overnight here.
8.5 miles (14 km)
-
6. Day six
Sandwich to Deal and Walmer
Head off to the sea, a couple of miles away, to wander idyllic paths along the coast which has long sandy beaches most of the way. As if this wasn't enough for a walk, there are two remarkable castles enroute both built by Henry VIII and both Cinque ports. First up is Deal, one of the finest Tudor castles in Britain. The town is also a favourite of ours with an authentic high street, a pier and a pebble beach. Continuing along the coast briefly you reach Walmer Castle which also has superb gardens and evolved into a stately home, lived in by no less than the Queen Mother amongst others. It's a majestic place! Stay the first of 2 nights in Deal.
7.6 miles (12 km)
-
7. Day seven
Deal to Dover
Your final day of walking is the most dramatic as the cliffs deepen towards Dover and you climb to the ultimate height of Dover Castle, standing proud atop the white cliffs guarding the port and shore below. Take in stunning views across the English Channel, dip into beach cafes backed by vast walls of chalk and enjoy the impressive castle first imagined by Henry VIII and critically employed during WWII. If you fancy staying here in an 11th Century tower, see the options above. Otherwise, we transfer you back to Deal for a 2nd night.
Optional 8 miles (13 km)
-
8. Day eight
Depart Dover
We transfer you to Dover after breakfast for your departure. You may want to take time to enjoy Dover castle with all its turrets and war time tunnels as this is the jewel of all castles and the oldest surviving in England. Dover is on the rail network for onward connections to Canterbury, Ashford for Eurostar or London.