On our guided cycling holiday in Kent, return to nature and discover the ‘Garden of England’, from the stunning White Cliffs of Dover along the coast to the famous Canterbury Cathedral at Kent’s heart, we visit Churchill’s home at Chartwell, the picturesque foody heaven of Whitstable, as well as many incredible castles, gardens and vineyards along route!
Flexible Cycling Distance Options Each Day
Journey on two wheels to rediscover the English countryside and coast by joining our groups, as a solo traveller, couple or bringing family and friends to cycle with you and return to nature. Don’t feel obliged to cycle the full distance each day. There are shorter options for guests, with opportunities to spend more time at the iconic castles, manors, gardens, beaches and in the towns for those wishing to cycle fewer miles each day.
Kent Guided Cycling Itinerary
Day 1Whitstable, Faversham, Canterbury Cathedral and St Augustine’s Abbey
The tour starts at London St Pancras where we pick up all guests. We travel out to Canterbury by high speed train (in 45 minutes) and give guests a full safety briefing before heading out on the bikes along a disused railway line, brilliantly name the Crab and Winkle Way, to the foody heaven of Whitstable for lunch. We visit Faversham, home of the oldest Brewery in England – Shepherd Neame, before returning to Canterbury for a tour around the Cathedral and St Augustine’s Abbey, dating from 597 AD.
Mileage: 10-20 miles
Day 2The Turner Contemporary gallery, Coastal Cycling to Castles and Ports
We bike from Canterbury, up to the North Kent coast, past the Reculver Towers, visiting the Turner museum in Margate and then hug the coast past the wonderful seaside towns of Broadstairs and Ramsgate and along the off road coastal path onto the Cinque Ports of Deal and Sandwich, with their castles and trading history spanning back to the Norman Conquest of 1066. Mostly traffic free, the routes are flat and suit cyclists of all abilities. We return through gentle but beautiful countryside to Canterbury for the evening.
Mileage: 20-33 miles
Day 3Dover Castle, The White Cliffs, The Battle of Britain Memorial
We cycle through the beautiful Kent countryside and stop at the Battle of Britain Memorial, just outside Dover, for coffee. In Dover we visit the magnificent castle with its rich history dating from before Roman times, keeping England safe against Napoleon, Hitler and all who tried to invade through the ages. We also visit the iconic White Cliffs of Dover, the first land to be seen by travellers returning to our shores. A day for the history buffs, Dover is unsurpassed as destination and is a favourite iconic location for our guests.
Mileage: 20-30 miles
Day 4Leeds Castle, Lakes and Estate, onto Tunbridge Wells
We leave Canterbury and head for the iconic Leeds Castle, approaching 1000 years old, frequented by Henry the VIII and Catherine of Aragon and more recently the American heiress Lady Baillie. With its stunning architecture and famous lake which surrounds the castle it is an iconic visit not to be missed. The afternoon ride is gentle and into the Spa town of Tunbridge Wells, where many opt for an early finish or a day off the bike totally.
Mileage: 23-30 miles
Day 5The Garden of England, Sissinghurst and Kentish Wines
Right in the heart of the Garden of England, the route immerses guests in Kent’s magnificent gardens, be they in the quaint villages along the route or the magnificent Sissinghurst, with a number of different gardens, set out by Vita Sackville-West and her husband in “rooms” each with their own distinct flavour. From Sissinghurst we visit one of England’s premier vineyards where we challenge guests not to love both the award winning white and sparkling wines. We return in the afternoon to your hotel in Tunbridge Wells.
Mileage: 15-25 miles
Day 6Hever Castle home of Anne Boleyn and Anne of Cleves, Churchill’s home at Chartwell
Once again we bike through the beautiful Kent countryside to the magnificent Hever Castle, home to Anne Boleyn and Anne of Cleves (wives two and three of Henry VIII) and more recently the Astor family, before making the short journey to Chartwell, home to Winston Churchill, with the wonderful rose gardens, lovingly curated by his wife Clementine. The visit to Chartwell heralds the end of the tour when we will transfer guests back to London by train, a journey of 40 minutes.
Mileage: 15-25 miles
Download Detailed Intinerary
For full information about this tour and to find out all you need to know, download your copy of the detailed itinerary by clicking the button below.
International Flights and travel to and from the start/end of the tour
Items of a personal nature
Lunches and café stops
Gratuity for your local guide
Where is Kent?
Kent is to the south-east of London, a gorgeous lowland county with a long coastline. Rural Kent has long been known as the ‘Garden of England’ for its orchards, hop gardens and vineyards. It is one of the top coastline cycling destinations as its bordering the English Channel and North Sea.
Why choose a guided cycling holiday?
Join a group of like-minded people, looking for an active cycling holiday exploring Kent. Led by our team of exceptional guides, we know every turn in the road, every pub, trail, café and castle. Dine together some evenings, share the stories of the day and fully enjoy the magical experience of cycling the Kentish coastal roads and inland trails. On our guided trips, all of our routes can be tailored for those wishing to cycle less or further, just ask your guide and they will be able to extend or shorten the planned routes to suit you and your group.
Where to visit in Kent?
We visit Kent’s most iconic places, including Canterbury and its Cathedral. Kent is famous for its historic coastline; its trading and raiding history stems back beyond the Norman conquest, and the coast is dotted with castles, including Dover Castle, over the White Cliffs of Dover, and Leeds Castle, approaching 1000 years old! Kent is also famous for its vineyards and its award-winning white and sparkling wines.
What is the weather like in Kent?
Kent has a mild climate, with July being its hottest month with an average high of 21 degrees Celsius. Because of its coastline and location in the Southeast, Kent is often warmer and drier than other parts of the UK; this has been vital to the success of its orchards and vineyards.