Glorious gardens nestled in a charming landscape dotted with grand castles and heroic history are at the heart of this gentle walking tour. Visit Sissinghurst and Great Dixter as well as other gardens known as the very best in Britain as you amble on foot and by steam railway from inland slopes to the sea. Medieval history is ever-present in the timber framed architecture and on full show in the small town of Rye whilst epic castles abound with a final night’s stay in magnificent Hever Castle.
Straddling Kent and Sussex, this area known as the High Weald has a history of horticulture be it farming, viticulture, gardens or now a vibrant locally produced food and drink scene. Ever beautiful and tranquil and sometimes remote, the High Weald is dotted with woods, beguiling hamlets and haphazard field patterns and embraces a laid back sometimes quirky culture of small holdings and independent businesses. We love its authenticity!
With several two night stays in characterful inns and hotels, and easy distances and walking you will have time to enjoy vineyards, local beers and exceptional food over and above the magical gardens, castles and scenery. This is a blooming good trip!
Holiday details
Price
- Classic
-
from £2,185 per person
- Luxury
-
from £3,270 per person
Based on two people sharing a room
Duration
9 nights
Start & Finish
Starts Staplehurst station ends Hever Station. Both are 1 hour from central London. Starts Wednesday or Thursday.
Hotels
- Classic
-
5 inns and a small hotel
- Luxury
-
A castle, 3 inns and 2 boutique hotels
Holiday type
Self-guided so you are free to explore at your own pace. More info...
Activity level
Gentle walking (2) More info...
Mileage
6 days of walking 2.5-10 miles (4-16 km) per day and 2 days of optional walks
Terrain
Gentle ups and downs or flat
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. Guidebook or OS maps. Protection of your funds. Advice, help and guidance planning your trip.
Entry to all the castles and gardens on this tour. A private guided walking tour of Rye. Read About Our Trips for further details
Options
- Play golf at the Nick Faldo designed Chart Hills Club near Sissinghurst or at Rye Golf Club
- Book an exceptional dinner at a Michelin green starred restaurant near Ticehurst
- On the classic tour upgrade to stay at Hever castle
Itinerary day-by-day
Classic
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1. Day one
Arrive Staplehurst
We meet you off the train at Staplehurst and transfer you the short distance to Sissinghurst village where you stay 2 nights in the village inn. Relax in the garden or enjoy a short circular walk to the nearby small town of Cranbrook known as the capital of the Weald. With many buildings dating from the 15th Century, its a characterful place to explore.
Optional 4 miles (6.5 km)
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2. Day two
Enjoy Sissinghurst
A short walk sees you at Sissinghurst Castle Garden. As one of England's foremost loved gardens, it's many 'rooms' show wonderful colour and shape combinations with both formal and informal areas. Enjoy its history and romance and relax over a leisurely lunch. An inspirational day to start your trip.
2.5 miles (4 km)
-
3. Day three
Sissinghurst to Tenterden
From your inn, wander tranquil footpaths today through dotted homesteads typical of the High Weald known for its pretty rolling landscape with small holdings, scattered woods and higgledy piggledy fields. Stop for a tour and tasting at Kent's oldest vineyard or at a hop farm with its own craft brewery - vines and hops being a vital feature throughout this trip. Enough quirky refreshment stops will keep you going until you reach the beautifully preserved Georgian and Victorian High Street of charming Tenterden, lined with independent boutique shops and inns. You stay overnight here.
10 miles (16 km)
-
4. Day four
Tenterden to Great Dixter and Rye
What a great day ahead! Find a keep sake or two in Tenterden's unique shops before boarding the mid morning steam train. Hissing and puffing it will stop at Bodiam for you to alight. A mere stone's throw away you can opt to explore moated and ruined Bodiam Castle built in the 14th Century for a heroic knight who had fought in France. A short walk then leads you to the innovative gardens and medieval hall at Great Dixter. Our words are inadequate to describe this extraordinary place and we leave you to enjoy it and draw your own conclusions! After your visit, we transfer you to another medieval gem - the town of Rye where you enjoy a 2 night stay.
3.5 miles
-
5. Day five
Enjoy Rye
The historic Cinque Port of Rye, no longer on the coast, is stuffed with medieval buildings, tales of smugglers and cobbled alleys and streets. So what better after a leisurely breakfast than to enjoy a private walking tour of the town with your Guide to fill you in on its intrigue and history. After lunch, explore on your own or enjoy a walk to the coast taking in wetlands, bird hides, the harbour and the River Rother.
Optional 6 miles (9 km)
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6. Day six
Rye to Batemans, Pashley Manor and Ticehurst
Heading inland this morning through the lovely Wealden landscape we will transfer you to Batemans, the gorgeous 18th Century house and romantic garden, working mill and waterside setting that Rudyard Kipling made into his retreat. Here he wrote several of his books and the poem If and today it remains almost unchanged. A pretty walk away finds you in the stunning 11 acre gardens at privately owned Pashley Manor. Their variety and beauty exhibit 40 years of creativity and inspiration by the family. A short walk on you find your stay for the next 2 nights.
6 miles (9 km)
-
7. Day seven
Scotney Castle
Moated and ruined 12th Century Scotney Castle is a rural idyll which you can explore along with the Victorian mansion, a later addition which abuts it. Margaret Thatcher had an apartment here whilst in office. Enjoy the various magical gardens and parkland with ancient woods and views to die for over the Wealden countryside. A lovely walk leads you back to Ticehurst across Bewl Water after your visit - we transfer you to the castle in the morning. If you didnt make Pashley Manor yesterday (and its not to be missed!) you can also visit here today.
Optional 6 miles (9 km)
-
8. Day eight
Ticehurst to Tunbridge Wells
Your final day's walk is a cracker, up and down through woods, nature reserve and forest tracks, past ponds, across rivers with vistas and barely a hamlet all day until you reach the spa town of Tunbridge Wells and its Georgian Collonade The Pantiles. Walk on to your hotel in the heart of the town where you stay one night.
7.5 miles (12 km)
-
9. Day nine
Enjoy Hever Castle
After a leisurely breakfast we transfer you to Hever Castle and gardens. Worthy of a full day's exploration, the spectacular moated castle embodies 600 years of history and was the childhood home of Anne Boleyne. Inside are impressive collections, outside there are 125 acres of award winning gardens and grounds. Its grand and breath-taking and a wonderful finale to this glorious gardens and heroic history trip. Your overnight stay is less than a mile's walk from the castle. You can upgrade to stay at Hever Castle if you wish.
0.7 miles (1 km)
-
10. Day ten
Depart Hever
We transfer you after breakfast to Hever Station for your onward journey.
Luxury
-
1. Day one
Arrive Staplehurst
We meet you off the train at Staplehurst and transfer you the short distance to your inn close to Sissinghurst where you stay 2 nights. Relax in the peaceful garden or enjoy a short circular countryside walk to a nearby village and pub for a refresher. Your inn serves dinner every night if you wish to eat here - It comes highly recommended!
Optional 5 miles (8 km)
-
2. Day two
Enjoy Sissinghurst
A short walk sees you at Sissinghurst Castle Garden. As one of England's foremost loved gardens, it's many 'rooms' show wonderful colour and shape combinations with both formal and informal areas. Enjoy its history and romance and relax over a leisurely lunch. An inspirational day to start your trip.
3.5 miles (5 km)
-
3. Day three
Sissinghurst to Tenterden
From your inn, wander tranquil footpaths today through dotted homesteads typical of the High Weald known for its pretty rolling landscape with small holdings, scattered woods and higgledy piggledy fields. Stop for a tour and tasting at Kent's oldest vineyard or at a hop farm with its own craft brewery - vines and hops being a vital feature throughout this trip. Enough quirky refreshment stops will keep you going until you reach the beautifully preserved Georgian and Victorian High Street of charming Tenterden, lined with independent boutique shops and inns. You stay overnight here.
8 miles (13 km)
-
4. Day four
Tenterden to Great Dixter and Rye
What a great day ahead! Find a keep sake or two in Tenterden's unique shops before boarding the mid morning steam train. Hissing and puffing it will stop at Bodiam for you to alight. A mere stone's throw away you can opt to explore moated and ruined Bodiam Castle built in the 14th Century for a heroic knight who had fought in France. A short walk then leads you to the innovative gardens and medieval hall at Great Dixter. Our words are inadequate to describe this extraordinary place and we leave you to enjoy it and draw your own conclusions! After your visit, we transfer you to another medieval gem - the town of Rye where you enjoy a 2 night stay.
3.5 miles
-
5. Day five
Enjoy Rye
The historic Cinque Port of Rye, no longer on the coast, is stuffed with medieval buildings, tales of smugglers and cobbled alleys and streets. So what better after a leisurely breakfast than to enjoy a private walking tour of the town with your Guide to fill you in on its intrigue and history. After lunch, explore on your own or enjoy a walk to the coast taking in wetlands, bird hides, the harbour and the River Rother.
Optional 6 miles (9 km)
-
6. Day six
Rye to Batemans, Pashley Manor and Ticehurst
Heading inland this morning through the lovely Wealden landscape we will transfer you to Batemans, the gorgeous 18th Century house and romantic garden, working mill and waterside setting that Rudyard Kipling made into his retreat. Here he wrote several of his books and the poem If and today it remains almost unchanged. A pretty walk away finds you in the stunning 11 acre gardens at privately owned Pashley Manor. Their variety and beauty exhibit 40 years of creativity and inspiration by the family. A short walk on you find your stay for the next 2 nights.
6 miles (9 km)
-
7. Day seven
Scotney Castle
Moated and ruined 12th Century Scotney Castle is a rural idyll which you can explore along with the Victorian mansion, a later addition which abuts it. Margaret Thatcher had an apartment here whilst in office. Enjoy the various magical gardens and parkland with ancient woods and views to die for over the Wealden countryside. A lovely walk leads you back to Ticehurst across Bewl Water after your visit - we transfer you to the castle in the morning. If you didnt make Pashley Manor yesterday (and its not to be missed!) you can also visit here today.
Optional 6 miles (9 km)
-
8. Day eight
Ticehurst to Tunbridge Wells
Your final day's walk is a cracker, up and down through woods, nature reserve and forest tracks, past ponds, across rivers with vistas and barely a hamlet all day until you reach the spa town of Tunbridge Wells and its Georgian Collonade The Pantiles. Walk on to your hotel where you stay one night. It has a spectacular position!
6.5 or 9.5 miles (10 or 15 km)
-
9. Day nine
Enjoy Hever Castle
After a leisurely breakfast we transfer you to Hever Castle and gardens. Worthy of a full day's exploration, the spectacular moated castle embodies 600 years of history and was the childhood home of Anne Boleyne. Inside are impressive collections, outside there are 125 acres of award winning gardens. Its grand and breath-taking. So too is your overnight stay here: a wonderful finale to this glorious gardens and heroic history trip.
-
10. Day ten
Depart Hever
After breakfast fit for a knight, we transfer you to Hever station for your onward journey.