The Life and Times of Winston Churchill

The Life and Times of Winston Churchill

Led by Historian Dane Kennedy

April 14-19, 2023
October 13-18, 2023

Grand Bridge, Blenheim Palace


World War II is one of the most important events in modern history, as it posed an existential threat to the basic principles of civilization. During that tumultuous time, Winston Churchill stepped onto the world stage as a voice of courage and statesmanship, and his influence and leadership remain relevant today. On this unique trip, delve into Churchill’s role as a war leader and peacetime politician in London, as well as his early life in Oxfordshire. Explore Churchill’s childhood home, considered one of England’s greatest treasure houses, and see the preparatory school where he spent his formative years. Travel underground to view the bunker complex Churchill used to orchestrate his war machinations and visit Bletchley Park, where crucial work was done to decrypt enemy communications and help end the war.  End the trip with a firm understanding of how this towering historical figure’s spirit still lives on in present-day England.


  • Enjoy a concentrated focus on Winston Churchill, from his early life through his time as Prime Minister 
  • Visit key sites related to WWII in England, including Bletchley Park—home of the crucial codebreaking work that shortened the war, and RAF Biggin Hill Station, which was responsible for protecting the southeast of England during the Battle of Britain
  • Tour the archives of Cambridge University’s Churchill College, which contain a priceless collection of documents (over a million!) written by or belonging to Churchill
  • See Harrow School, the prestigious boys’ school Churchill attended, as well as the room where he gave his iconic ‘never give in’ speech 
  • Visit Chartwell, Churchill’s family seat, and catch a glimpse of a different side of Churchill – as a painter and garden designer
Headshot of Dane Kennedy, trip historian

Trip Historian

Dane Kennedy

Dane Kennedy is the Elmer Louis Kayser Professor Emeritus of History and International Affairs at George Washington University, where he taught British, British imperial, and world history for 20 years.  Prior to that, he was professor and chair of the University of Nebraska-Lincoln history department.  He has also served as director of the National History Center and president of the North American Conference of British Studies. He is the author of seven books and editor or co-editor of three more. His most recent books are The Imperial History Wars: Debating the British Empire (2018) and Decolonization: A Very Short Introduction (2016).


Upon arrival in London, transfer independently to the Leonardo Royal Hotel, your home in London for the next three nights. Gather as a group this afternoon and take a step back in time with a visit to Churchill’s Cabinet War Rooms. It is from this top-secret bunker beneath Whitehall, still pristinely preserved, where Churchill and hundreds of men and women conducted the war during the London Blitz.  Walk in Churchill’s footsteps through the Map Room, his bedroom, and past the Transatlantic Telephone Room, which was disguised as a private toilet.  Continue to dinner as a group at a nearby restaurant.

Included Meal: Dinner
Accommodations: Leonardo Royal Hotel 

Depart this morning for  Cambridge University, home of Churchill College. Churchill College is the official British memorial to Churchill and it houses the Churchill Archives Centre. Spend the morning exploring the Churchill Papers Archives, which comprise a total of 2,185 boxes containing more than a million documents. The archives hold not only Churchill’s most famous wartime speeches, but personal items such as his high school history notebook and Christmas gift lists. Enjoy lunch at leisure among the charm and ambiance of historic Cambridge.

This afternoon, travel to Bletchley Park for an in-depth perspective on the first machines designed to break German code. These machines, the Bombe and the Enigma, are credited with shortening WWII by two years, by successfully deciphering the encryption used by the Wehrmacht to safeguard its messages. (The actions of the inventor Alan Turing were dramatized in “The Imitation Game”). Churchill called the Enigma decrypts his “golden eggs”, and Eisenhower credited the information from Bletchley Park as saving thousands of American and British lives during the campaign to liberate Europe. Your evening is at leisure.  

Included Meal: Breakfast 
Accommodations: Leonardo Royal Hotel 

Depart this morning for Chartwell, a Victorian brick manor house which served as Winston Churchill’s country retreat for more than forty years. Here, the rooms are decorated exactly as they were in his lifetime, with treasured belongings reflecting his personal interests and political career. In the study, see the mahogany desk where speeches were penned, and visit the parlor where the Prime Minister might have been found engaged in a game of bezique. Stroll the hillside gardens and enter the art studio to admire the canvases that reveal Churchill’s artistic skill and his dreams and love of landscape and nature.

After lunch at a local restaurant, visit the Biggin Hill Heritage Hangar, formerly the RAF Biggin Hill Station, which was responsible for protecting the southeast of England during the Battle of Britain and guarding approaches to the capital. Meet with a guide and see the World War II-era Spitfires being restored while hearing about the plans put in place by Churchill that helped protect London.

Included Meals: Breakfast, Lunch 
Accommodations: Leonardo Royal Hotel 

Start this morning with a visit to the Royal Air Force (RAF) Museum, featuring dozens of WWII-era aircraft, including the Sikorsky R-4, the world’s first production helicopter and the Supermarine Spitfire, regarded as Britain’s champion warplane. Continue on to Harrow School, the boys’ school Churchill attended from 1888 to 1892. Take a guided tour to include the speech room where Churchill addressed the boys during World War II. Churchill was not a particularly good student, but he demonstrated keen ability for memorization for which he won a Harrow competition by reciting a 1,200-line epic poem. This afternoon, travel to Oxford and check in to your centrally-located hotel. 

Included Meal: Breakfast
Accommodations: Courtyard Oxford City Centre

Spend the day exploring  Blenheim Palace  in Oxfordshire. The family seat of the Churchills, it was designed for the first Duke of Marlborough by architect Sir John Vanbrugh in the early 18th century and is considered one of England’s great treasure houses. See where Winston Churchill was born and visit a newly reinvigorated permanent Churchill exhibition and a trail taking you to some of Churchill’s most cherished places on the estate. Before returning to Oxford, pay your respects at Churchill’s grave in nearby Bladon. Toast the trip during your farewell dinner as a group at a local restaurant.  

Included Meals: Breakfast, Dinner 
Included accommodations: Courtyard Oxford City Centre

This morning, transfer from Oxford to London Heathrow for individual flights home. 

Included Meal: Breakfast 


Available Dates & Pricing

April 14-19, 2023

$ 4,750
Single supplement $750
  • $500 deposit to reserve your space

October 13-18, 2023

$ 4,995
Single supplement $850
  • $500 deposit to reserve your space
  • Comprehensive educational program by professional on-site guides
  • Accommodations and meals as outlined in the itinerary
  • Sightseeing and visits, including entrance fees, as specified in the itinerary
  • Ground transportation within the itinerary
  • Gratuities to porters, drivers, and guides
  • The assistance of an ATA tour manager for comprehensive logistical and customer service management on the trip
  • The assistance of an ATA professional travel team to assist with pre-trip questions, travel arrangements, including flights, extra hotel nights, and other services
  • Comprehensive pre-departure information about the destination and what to expect on the trip, including a suggested reading list
  • Fully vetted program that meets COVID-19 health and safety protocols
Leonardo Royal Hotel
Courtyard Oxford City Centre


Leonardo Royal Hotel | London

The Leonardo Royal Hotel London City is a luxury 4-star superior accommodation with superb river views. A smart, modern interior and unbeatable transport connections make this hotel in London ideal. Modern luxury is key, in contrast to the many fascinating heritage sites that surround the hotel. Large double-glazed windows frame cinema-style views of the city at night, while soft fabrics and ambient lighting make your spacious room the perfect place to wind down.

Courtyard Oxford City Centre | Oxford

Courtyard Oxford City Centre is in the heart of Oxford. Enjoy beautiful views of Oxford Castle from the hotel’s rooftop terrace. The hotel is equipped with a restaurant, bar, air-conditioned rooms and complimentary Wi-Fi. 

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