Stay in and explore legendary castles built by the Romans and Henry VIII on this gentle cycling trip, This is a remarkable ride through history covering seashore defenses at the Cinque Ports of Deal and Walmer, the forts of ancient coasts, Canterbury's Saxon castle and pilgrim roots with a stay in moated and grand, Leeds Castle as a finale to the tour.

Freewheeling through orchards and across downs, you enjoy leafy back lanes, the fun of fords and grand views. Discover Kent's clapper board villages, seaside cycling, oysters in Whitstable, the medieval gem of Sandwich and several stunning gardens. This is also a land awash with local produce - beers and seafood, soft fruit and vineyards all of which you will have plenty of time to enjoy!



Holiday details

Price

Classic

from £1,135 per person

Luxury

from £2,185 per person

Based on two people sharing a room

What’s included?

Entry to Leeds castle and grounds on days 6 and 7, dinner at Reads on the luxury tour.  See what’s included as standard

Duration

6 nights

Start & Finish

Starts Saturdays in Canterbury finishes Leeds Castle. Canterbury station is on the mainline from London, Leeds Castle is close to Maidstone and not far from Ashford stations

Hotels

Classic

Three small hotels, an inn and a stay within Leeds Castle grounds

Luxury

Two 4 star hotels, a very special boutique hotel, a restaurant with rooms and a stay within Leeds Castle grounds

Holiday type

Self-guided

This tour is priced without a guide and you are free to explore on your own.  If you would like a guide for part or all of your trip, we are happy to provide a knowledgeable, local guide

Activity level

Gentle cycling (4) More info...

Electric bikes

Available

Mileage

5 days of cycling 14-22 miles (22-35 km) classic and 14- 28 miles luxury (22-45 km) per day

Terrain

A few gentle slopes most days

Traffic-free

10%. Mostly country lanes with low traffic

Options

  • Add an extra day with a driver guide to Hever Castle and Sissinghurst Castle gardens


Itinerary day-by-day


Classic

  1. 1. Day one

    Arrive in Canterbury

    Arrive in Canterbury and check into your hotel in the heart of the city. There's so much to explore in this astounding heritage city with its Norman castle, magnificent cathedral, and many other historic buildings. Your bicycles will be waiting for you at the hotel so if you wish, you can enjoy the main sights by taking our city centre bike tour.

    3 miles (5 km)

  2. 2. Day two

    Canterbury to Sandwich

    Your host will meet you after breakfast to run through your itinerary before you pedal way to the coast. Your route takes you through orchards and a flattish landscape of clapper board villages to reach the ruined Saxon shore castle of Richborough Fort. Being of Roman construction is has huge walls and an amphitheatre. Close by is the characterful old port of Sandwich where you spend two nights. Explore the fascinating history of this Cinque port town, one of the best preserved medieval towns in Britain.

    17 miles (27 km)

  3. 3. Day three

    Sandwich to Deal and back

    This circular route gives you the opportunity of discovering two castles built by Henry VIII at the Cinque port towns of Deal and Walmer. The fascinating town of Deal with its pier and charm also has one of the finest Tudor castles in England. Cycle on adjacent to the shore to explore Walmer castle with its huge award winning gardens. Head back to Sandwich on a route through the dunes, quite different to your outward ride through tiny hamlets and along the old cycle path taken by the miners on their way to the former coal pits.

    14 miles (22 km)

  4. 4. Day four

    Sandwich to Chartham Hatch

    Flattish rural riding to start gives you wonderful views, woodland and the odd village. Take in a stop at a vineyard for a tasting and swan around the quite beautiful gardens of Goodestone Park with its cafe and quirky village inn. As you approach the Kent Downs and a few hills, the scene changes, ever rural and charming until you reach the banks of the Great Stour and your hotel for the night.

    22 miles (35 km)

  5. 5. Day five

    Chartham Hatch to Faversham

    You skirt around Canterbury, along the river briefly to pick up the Crab and Winkle Way and freewheel down to the coast, following the cart route which delivered seafood to London from Whitstable on a daily basis. Here you can spoil yourself with local oysters, eat chips on the beach, enjoy the town's arty vibe and quench your inevitable thirst with a cuppa in the gardens of 18th Century Whitstable Castle. It's flat pedalling then to reach marvellous Faversham with its barge lined creek, 300 listed buildings and maritime history - but no castle! .

    20 miles (32 km)

  6. 6. Day six

    Faversham to Leeds Castle

    This last day is another different scene with a very gradual and beautiful ride into the Downs along forgotten back lanes. Villages are well spaced amongst the orchards but there are some cracking pubs with The Ringlestone Inn a triumph. Tear yourself from lunch for a refreshing freewheel down to Leeds Castle where you spend your last magnificent night in the stable courtyard. Explore the castle and after the crowds have left, enjoy the grounds and a knight's dinner.

    18 miles (28 km)

  7. 7. Day seven

    Depart Leeds Castle

    After breakfast, enjoy this stunning castle, its fascinating history and magnificent grounds. We hope as you depart you will feel castel-(e)lated. Do let us know!

Luxury

  1. 1. Day one

    Arrive in Canterbury

    Arrive in Canterbury and check into your hotel in the heart of the city. There's so much to explore in this astounding heritage city with its Norman castle, magnificent cathedral, and many other historic buildings. Your bicycles will be waiting for you at the hotel so if you wish, you can enjoy the main sights by taking our city centre bike tour.

    3 miles (5 km)

  2. 2. Day two

    Canterbury to Sandwich

    Your host will meet you after breakfast to run through your itinerary before you pedal way to the coast. Your route takes you through orchards and a flattish landscape of clapper board villages to reach the ruined Saxon shore castle of Richborough Fort. Being of Roman construction is has huge walls and an amphitheatre. Close by is the characterful old port of Sandwich where you spend two nights. Explore the fascinating history of this Cinque port town, one of the best preserved medieval towns in Britain.

    17 miles (27 km)

  3. 3. Day three

    Sandwich to Deal and back

    This circular route gives you the opportunity of discovering two castles built by Henry VIII at the Cinque port towns of Deal and Walmer. The fascinating town of Deal with its pier and charm also has one of the finest Tudor castles in England. Cycle on adjacent to the shore to explore Walmer castle with its huge award winning gardens. Head back to Sandwich on a route through the dunes, quite different to your outward ride through tiny hamlets and along the old cycle path taken by the miners on their way to the former coal pits.

    14 miles (22 km)

  4. 4. Day four

    Sandwich to Bridge

    Flattish rural riding to start gives you wonderful views, woodland and the odd village. Take in a stop at a vineyard for a tasting and swan around the quite beautiful gardens of Goodestone Park with its cafe and quirky village inn. As you approach the Kent Downs and a few hills, the scene changes, ever rural and charming until you arrive at your wonderful manor house hotel for the night. Arrive in good time to fully enjoy this marvellous place.

    14 miles (22 km)

  5. 5. Day five

    Bridge to Faversham

    A few slopes at the start of the day before you skirt around Canterbury, along the river briefly to pick up the Crab and Winkle Way and freewheel down to the coast, following the cart route which delivered seafood to London from Whitstable on a daily basis. Here you can spoil yourself with local oysters, eat chips on the beach, enjoy the town's arty vibe and quench your inevitable thirst with a cuppa in the gardens of 18th Century Whitstable Castle. It's flat pedalling then to reach marvellous Faversham with its barge lined creek, 300 listed buildings and maritime history - but no castle! .

    28 miles (45 km)

  6. 6. Day six

    Faversham to Leeds Castle

    This last day is another different scene with a very gradual and beautiful ride into the Downs along forgotten back lanes. Villages are well spaced amongst the orchards but there are some cracking pubs with The Ringlestone Inn a triumph. Tear yourself from lunch for a refreshing freewheel down to Leeds Castle where you spend your last magnificent night in the stable courtyard. Explore the castle and after the crowds have left, enjoy the grounds and a knight's dinner.

    18 miles (28 km)

  7. 7. Day seven

    Depart Leeds Castle

    After breakfast, enjoy this stunning castle, its fascinating history and magnificent grounds. We hope as you depart you will feel castel-(e)lated. Do let us know!