High Weald Gardens and Castles
United Kingdom
9 days (Bike: 7 days)
161 mi (~23mi per day)
Leisure
Quiet roads, Some hills
Self-Guided
Semi-Supported
New tour for 2026 with weekly self-guided departures available
Straddling Kent and Sussex, this High Weald cycling trip is packed with wonderful gardens and grand castles spread across a charming landscape.
Visit Sissinghurst and Great Dixter as well as other gardens known as the very best in Britain as you pedal ups and downs 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.
The High Weald has a history of horticulture be it farming, viticulture, gardens or now a vibrant locally produced food and drink scene. The ever beautiful rolling terrain with its short steepish hills, and a maze of back lanes and traffic free bridleways is one where E-bikes will be appreciated! 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 E-bikes which we recommend, you will have have time to enjoy vineyards, local beers and exceptional food over and above the magical gardens, castles and landscape.
Not so gentle cycling.
5 days of cycling 11- 25 miles (18 - 40 km) per day with 2 further days of optional cycling. Terrain: Many short steep slopes - 15% traffic free on cycle paths and bridleways, the rest on quiet back lanes
Tour Information
From
Staplehurst
To
Hever
Cost From
Self-Guided £ 2455
Departure(s)
Starts Friday
Inclusions
- Ensuite accommodation every night with breakfast
- The services of our friendly local Hosts
- Luggage transfers between hotels
- Touring bikes and accessories
- 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
- Train ticket from Rye to Three Oaks
Exclusions
- Airfares
- Travel to and from the trip start and finish points unless specified
- Entrances to attractions unless specified
- Boat fares unless specified
- Lunches and dinners unless specified
- Alcoholic beverages, mini bars and meals pre and post the trip
Options
- E Bikes
- 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
- Upgrade to stay at Hever castle
Additional
Starts Staplehurst station ends Hever Station. Both are 1 hour from central London. Staplehurst is also 15 minutes by train from Ashford International with direct trains to mainland Europe.
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