Castles of Kent & Cliffs of Dover

Day 1: Arrive at Leeds Castle
Day 2: Leeds Castle and Canterbury, 3 mi. (5 km)
Day 3: Canterbury - Whitstable, 8 - 11 mi. (13 - 18 km)
Day 4: Whitstable - Reculver - Whitstable, 8 mi. (13 km)
Day 5: Whitstable - Upstreet - Sandwich, 8.5 mi. (14 km)
Day 6: Sandwich - Walmer - Deal, 7.6. mi. (12 km)
Day 7: Deal - Dover - Deal, 8 mi. (13 km)
Day 8: Departure

Day 1: Arrive at Leeds Castle
This walking tour has an impressive start with an authentic castle experience at Leeds Castle. Arrive here on Sunday at your leisure to discover this magnificent 900-year-old moated castle. It is especially pleasant to wander the grounds in the evening when only those staying at the castle remain out and about. You stay the night in the stable courtyard and dinner is available too.

Sample accommodations:
Classic: Leeds Castle (standard room in Stable Courtyard)
Luxury: Leeds Castle

Day 2: Leeds Castle and Canterbury, 3 mi. (5 km)
After enjoying a knight's breakfast you can spend the morning discovering more about the life of the six queens who lived at Leeds. Punt on the moat and stroll around the beautiful gardens and lakes of this 500-acre estate if you like.  After lunch, you will be transferred to historic Canterbury where there is much to explore. A city center walking tour leads you to the Norman castle, the famous cathedral, and a host of other quite remarkable ancient buildings. Your host will meet you early in the evening to brief you on your upcoming days.

Sample accommodations:
Classic: House of Agnes
Luxury: The Falstaff Canterbury 

Day 3: Canterbury - Whitstable, 8 - 11 mi. (13 - 18 km)
This delightful first day of walking leads you into the serene, gently rolling Kent Downs. These chalk hills are home to rare habitats, with much of the area under protection. Along the way, soak in stunning views and explore ancient woodlands before transitioning to the historic Crab and Winkle Way, which takes you to the vibrant coastal town of Whitstable. Known for its oysters, Whitstable boasts a bustling working harbor, quirky shops, and a creative, artsy vibe.

Sample accommodations:
Classic: Marine Hotel (standard room)
Luxury: Marine Hotel 

Day 4: Whitstable - Reculver - Whitstable, 8 mi. (13 km)
Today's walk hugs the coastline, keeping you close to the beach and the soothing sound of the waves as you follow the sea wall, built to safeguard the low cliffs. Along the way, enjoy expansive views, colorful beach huts, cozy cafés, bustling harbors, and scenic cliff-top hideaways. Your journey concludes at the striking ruins of the Roman fort at Reculver, standing weathered and majestic against the sea. From here, you’ll transfer you back to Whitstable for a second night.

Sample accommodations:
Classic: Marine Hotel (standard room)
Luxury: Marine Hotel 

Day 5: Whitstable - Upstreet - Sandwich, 8.5 mi. (14 km)
After breakfast, you'll transfer to Upstreet, a lively little village by the river. From here, your walk takes you inland through a once-marshy landscape now transformed into a thriving hub of farming activity, dotted with orchards and expansive fields. Begin by strolling along the peaceful Great Stour riverbank before winding your way through charming rural hamlets, complete with the occasional inn or café. The highlight of the day is Richborough Castle, a Roman fort featuring impressive ruins of vast walls and an amphitheater. A short distance further brings you to the historic gem of Sandwich, one of Britain’s best-preserved medieval towns. Though no longer by the sea, this Cinque Port rests along the river, offering a perfect setting for your overnight stay.

Sample accommodations
Classic: The Bell 
Luxury: The Bell 

Day 6: Sandwich - Walmer - Deal, 7.6. mi. (12 km)
Set out for the sea just a few miles away, where idyllic coastal paths lead you along stretches of long, sandy beaches. Along the way, you’ll encounter two remarkable castles, both built by Henry VIII as part of the Cinque Ports. First is Deal Castle, one of the finest Tudor fortifications in Britain. The town of Deal itself is a true gem, featuring an authentic high street, a charming pier, and a pebble beach. Continuing along the coast, you’ll come to Walmer Castle, known for its stunning gardens and its evolution into a stately home, once graced by residents such as the Queen Mother. It’s a truly majestic spot! Return to Deal where you'll stay for the next two nights. 

Sample accommodations
Classic: The Royal
Luxury: The Rose

Day 7: Deal - Dover - Deal, 8 mi. (13 km)
Your final day of walking is the most dramatic as the cliffs rise steeply toward Dover, culminating in the magnificent Dover Castle perched high atop the iconic white cliffs. From this vantage point, take in breathtaking views across the English Channel. Along the way, enjoy charming beach cafés nestled beneath towering chalk walls. Dover Castle, initially envisioned by Henry VIII and playing a vital role during WWII, is an impressive highlight of the journey. For an unforgettable experience, consider staying overnight in an 11th-century tower. Otherwise, you'll transfer back to Deal for a second night.

Sample accommodations:
Classic: The Royal 
Luxury: The Rose

Day 8: Departure
After breakfast, you'll transfer back to Dover for your departure. If time permits, consider exploring Dover Castle, a true gem among England’s castles, featuring majestic turrets and fascinating wartime tunnels. It is the oldest surviving castle in the country and a must-see for history enthusiasts. Dover is well-connected by rail, offering convenient onward travel to Canterbury, Ashford for the Eurostar, or London.  

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This tour is offered with two levels of accommodations, Luxury or Classic. You decide.
Luxury: You will be accommodated in a 4 star hotel, a 3-star hotel, a boutique hotel, a restaurant with rooms, and a stay within Leeds Castle grounds.
Classic: You will stay in 3 small hotels, two inns and within Leeds Castle grounds
On the day to day details, you will find the name of the preferred hotels for the luxury accommodations. Classic accommodations are based on availability but we will provide the preferred hotel list on request as a sample. Please note, that the final hotel list is based on availability and is subject to change!