History & Heritage of Kent

Suggested Itinerary

Day 1 – Hever Castle & Gardens

Board our private executive coach at your preferred pick up points – stop at a convenient property en route such as Hever Castle and Gardens, the childhood home of Anne Boleyn and dating back as far as 1270 – check in at the 4* Bridgewood Manor on the outskirts of Chatham.

Day 2 – Canterbury, Canterbury Cathedral & Leeds Castle

Guided tour of the UNESCO listed city of Canterbury taking in the city walls – Canterbury Cathedral, dating back to 597AD when St Augustine established his seat in Canterbury, was the site of Archbishop Thomas Becket’s murder in 1170 and ever since the Cathedral has attracted thousands of pilgrims, as told famously in Geoffrey Chaucer's ‘Canterbury Tales’ – Leeds Castle, set in 500 acres of beautiful parkland and offering over 1,000 years of history, has Norman foundations, a medieval gatehouse, a Tudor tower and a 19th century country house, all of which were substantially refurbished in the 20th century by the last private owner of the castle, Lady Baillie, the heiress to an American fortune.

Day 3 – Sissinghurst Castle Garden, Great Dixter House & All Saints’ Church, Tudeley

The National Trust’s Sissinghurst Castle Garden is developed around the surviving parts of an Elizabethan mansion and provide outstanding design and colour throughout the season – Great Dixter House and Gardens was once the family home of the late Christopher Lloyd who devoted his life to creating one of the most experimental, exciting and constantly changing gardens of our time – All Saints’ Church in Tudeley is internationally famous for its twelve stained glass windows by the great Russian artist Marc Chagall.

Day 4 – Dover Castle & Walmer Castle

Guarding the Straits of Dover, English Heritage’s Dover Castle occupies a site that has witnessed more than 2,000 years of history and its Secret Wartime Tunnels played an important role in World War II – English Heritage’s Walmer Castle and Gardens was transformed from a Tudor castle into the elegant home and residence of the Lord Warden of the Cinque Ports.

Day 5 – Ightham Mote Stop at a convenient property en route home such as the National Trust’s Ightham Mote, a superb moated manor house and garden dating from 1330 whose main features span many centuries and include the Great Hall and Tudor Chapel with painted ceiling – return to our original departure points with comfort stops en route.

Tour Features

4* hotel

Half board accommodation

All excursions & guided tours included

Blue Badge guide in Kent

Executive coach throughout

One free place per 10 paying passengers

Hever Castle & Gardens

UNESCO listed Canterbury - guided tour

Canterbury Cathedral

Leeds Castle

Sissinghurst Castle Garden

Great Dixter House & Gardens

All Saints’ Church, Tudeley

Dover Castle & Secret Wartime Tunnels

Walmer Castle

Ightham Mote


Four nights on half board basis at the 4* Bridgewood Manor on the outskirts of Chatham. Ideally located for the itinerary, facilities at the hotel include a restaurant, bar and swimming pool. All rooms are en suite.

Tailor-make this tour

Your tailor made tour

Here are some more suggested places of interest you might like to include:

  • Chartwell - the family home of Sir Winston Churchill from 1924, the rooms remain much as they were when he lived there
  • Kent Battle of Britain Museum -  the most comprehensive and longest serving Battle of Britain museum in the United Kingdom
  • Turner Contemporary, Margate - more than 100 of Turner’s works, including some of his most famous seascapes, were inspired by the East Kent coastline
  • Smallhythe Place - an early 16th century half-timbered house that was home to renowned Victorian actress Ellen Terry from 1899 to 1928

Tour Reviews

Reviews for History & Heritage of Kent

Date of Tour: July 2019

Thank you so very much for organising such a successful and wonderful trip for our club. The organisation and attention to detail was superb, it ran like clockwork. The hotel was in a great location, and our guide could not have been kinder or more helpful. He kept us all entertained with many an anecdote; and his knowledge of the local history and geography was astounding, very much appreciated. Once again, thank you for all the time and effort you put into the organisation.
SO, Cork 

Date of tour: October 2018

We had a lovely time in Kent - everything worked like clockwork as it always does under Tailored Travel’s expert organisation! Our blue badge guide entertained and looked after us in his own inimitable way. We enjoyed our choice of venues and the weather was fantastic - the 5 days just flew by.
GC, Watford

Date of tour: May 2017

Our trip went so well. All in the party enjoyed themselves hugely both the locations we had chosen but also each other’s company. The coach and driver were excellent. Our hotel was good, comfortable rooms and good food. The Blue Guide knew his brief extremely well and information poured out all the time. He was friendly and courteous but the party found him over fussy. The three guides at the Watts Gallery, Tudeley Church and the Pallant House Gallery were all that we could have wished for. They knew their subject very well, picked out pictures/windows and talked in the detail and at the level at which we are used to and had a clear love and enthusiasm for their subject. Tudeley impressed especially, only one had been there before, and I was so pleased we included something that they are not likely to see anywhere else! They all loved Sissinghurst. The pace was just right, the only tiredness arose from Sunday’s early start but the Watts Gallery and Chapel made that worthwhile. Your own itinerary, the timings, the paperwork and arrangements with all our locations were all first-rate, so we experienced no hiccups to our programme. I congratulate you and thank you on behalf of our party.
PH, Chulmleigh

Date of tour: July 2014

Five lovely days in Kent, a county most of us from up here in the frozen North may only have seen en route to Dover! So many interesting and beautiful houses and castles, none more so than Churchill’s home, Chartwell, or Anne Boleyn’s home, Hever Castle, or the wonderful Leeds Castle. Our day out in Canterbury with its magnificent cathedral was definitely a highlight for the group. That was followed by a quieter day at Sissinghurst, amongst the beautiful gardens designed by Vita Sackville West. And every day the sun shone! In addition our guide, Wilf, expertly and with much humour, fed us the history of the places visited. Add to all this a first rate hotel and it is easy to see why we are all ready for our next holiday with Tailored Travel.
JT, Anlaby

Date of tour: October 2014

Just to let you know that everyone who recently went on the trip to Kent which you organised, thoroughly enjoyed it and wished me to thank you and Louise. The itinerary was well chosen and very interesting. Wilf our guide was very knowledgeable and entertaining and Cynthia, our driver, was excellent so much so that members asked if we could have her again. Finally the hotel, food and staff were ‘much better than usual’ I was told by some regulars on these trips. We were blessed with constant sunshine. So a great success and we look forward to many trips with you in the future.
GE, Stevenage

Date of tour: June 2014


Dear Damian, we all enjoyed our holiday in Kent. All your hard work, and that of Louise, of course meant we had a great time.
JD, Durham

Date of tour: October 2013

I have just returned from the WI sortie to Kent. Everything about it was great. Our wonderful coach driver, Brian, the super hotel, a brilliant guide and marvellous itinerary. It all went well and I look forward to future WI holidays. Next autumn to the Lake District, can’t wait!
CB, Totnes

Date of tour: April 2013

On behalf of all 33 members who went on this trip, a big thank you for the excellent arrangements you made for us. Simon, our driver, was conscientious and amusing and very efficient in planning ahead for each venue (we all thoroughly enjoyed his tin of sweets!). Wilf, our BBG, was a gem and extremely knowledgeable about so many things. Our venues were so popular with everyone, and the hotel was very good with several members making use of the leisure facilities. I would like to thank you personally, Louise, as I felt confident you were on the ball and thinking about little details which made me rest assured. Having organised for so many years, it can be difficult to let go - but I was delighted that everything ran so smoothly.
JS, Kent

Date of tour: June 2010

We all enjoyed the visit to Kent. Very lucky with the weather. The driver, Malcolm, was excellent. Everything went off without problem. Thank you for all your service.
CC, Pershore

Call us on
020 7064 4970
to tailor this tour
for your group

Tailor make your group tour

Remember this itinerary is just our suggestion. Tailor make this tour exclusively for your group to suit your members’ budget or preferences. You could:

  • stay at a 3* hotel
  • with fewer dinners included
  • for more (or fewer) days
  • include different excursions – see ‘Tailor-make this tour’ tab for suggestions
  • bring a specialist lecturer
  • include all entrance fees & gratuities

Call us on
020 7064 4970
to tailor make the perfect tour
for your group