Meals: Breakfast 

Prepare to transform your leadership mindset as you dive deep into the genius of Winston Churchill. This day is designed to show you how to inspire unwavering loyalty, unite your team under a single mission, and lead with a clarity of purpose that withstands even the most daunting challenges. By the end of the day, you’ll walk away with insights that can revolutionize the way you lead your organization. 

The day begins with an exclusive, private visit to the Churchill War Rooms before they open to the public. Your private driver will take you to this extraordinary WWII time capsule, where an expert curator will guide you behind the glass to uncover the treasures and stories that defined Churchill’s wartime leadership. 

Following this immersive experience, an expert guide will lead you on a private tour of London, highlighting hidden gems and iconic landmarks tied to Churchill’s legacy. You’ll visit the Imperial War Museums of London, enjoy stunning views, and gain rare insights into the man who inspired an entire nation to persevere and triumph.  

Through this journey, you’ll explore how Churchill’s ability to rally people with a single-minded purpose can be applied to your own leadership challenges—whether it’s building unity in your team, overcoming obstacles, or leading with confidence in the face of uncertainty. This is more than a history lesson; it’s a blueprint for transformational leadership. 

Overnight London: The Milestone Hotel or similar 

Meals: Breakfast, Lunch 

Get ready to sharpen your ability to think and react with precision under pressure as you step into the dynamic, chaotic world of air combat. This day is more than an adventure—it’s a chance to cultivate the calm, cool mindset required to make decisive moves in high-stakes environments, a skill that translates directly to leadership in the boardroom and beyond. 

After breakfast, you’ll leave the city behind and journey south to the Goodwood Estate. This 11,000-acre estate, home to the Dukes of Richmond for over three centuries, offers a stunning backdrop of Regency interiors and one of the country’s finest art collections. Just a few miles away lies RAF Tangmere, a key Allied airfield during World War II, known for its role in supporting Spitfire missions and its clandestine wartime operations. 

Following a light lunch, you’ll take to the skies for an unforgettable Top Gun Combat Mission. Flying in a Slingsby T67 Firefly military training aircraft, you’ll experience the thrill of air combat firsthand. Under the guidance of an ex-military flying instructor, you’ll begin with formation take-offs and close-formation flying. From there, you’ll progress to aerobatic maneuvers, tail chasing, and head-to-head air combat against a fellow expedition member. 

This epic 40-minute flying experience—25 minutes of which are airborne—is not just about adrenaline; it’s about learning to maintain clarity and focus in the heat of battle. By the end of the day, you’ll leave with newfound confidence and the ability to stay composed and decisive, no matter how turbulent the circumstances. 

The rest of the evening is at leisure.  

Overnight West Sussex, Goodwood Hotel or similar

Meals: Breakfast, Dinner 

Discover the secrets of transformative leadership as you explore the very epicenter of the Allied victory in Europe. This day will reveal how General Eisenhower’s ability to learn from past mistakes and adapt under pressure made him one of the most beloved and successful leaders of modern times—a skill set every modern leader can aspire to master. 

After breakfast at the hotel, you will check out and begin your journey to Southwick House, the Supreme Headquarters of Allied Expeditionary Forces in Europe and the heart of Operation Overlord’s planning. It was here that Eisenhower and his team meticulously refined the Normandy Invasion, drawing on hard-earned lessons from earlier campaigns to ensure its success. Together, we’ll unearth the leadership strategies Eisenhower used to overcome challenges, foster unity among diverse forces, and execute one of history’s most pivotal operations. 

Next, you’ll visit Poole, a coastal town instrumental in providing the boats and materials critical to the D-Day war effort. From Poole, we’ll take a ferry to Guernsey (approximately three and a half hours), where you’ll transfer to your accommodations at the Old Government House Hotel. This five-star property, originally built in the late 18th century, exudes history and elegance, having served as the official residence of the Lieutenant Governor before becoming a hotel. 

In the evening, you’ll enjoy a special dinner in the private Doyle Room, formerly the dining room of Lieutenant General Sir John Doyle, a prominent figure in Guernsey’s history. To enrich the experience, the current Lieutenant Governor, Lieutenant General Richard Cripwell CBE, will join us to share insights from his distinguished military career and his role as the Crown’s personal representative in the Bailiwick of Guernsey. 

This day is not just about reliving history—it’s about applying timeless leadership principles to modern challenges, equipping you to grow, adapt, and lead with confidence in your own professional battlefield. 

Overnight: The Old Government House Hotel & Spa or similar 

Meals: Breakfast 

Explore the leadership lessons of resilience, adaptability, and integrity as you delve into the unique history of the Channel Islands—the only part of the British Isles occupied by German forces during World War II. This day offers a powerful look at how the citizens and provisional government of Guernsey navigated sudden and profound disruption, balancing survival with the ethical challenges of occupation. For modern leaders, this journey provides invaluable insights into how flexibility, ethical decision-making, and clear communication can maintain integrity while securing stability in times of crisis. 

After breakfast, embark on a full day of exploration with a private local expert guide. Your journey begins in St. Peter Port, where you’ll pass the Liberation Monument and visit Fort George, built as the island’s main military headquarters and British Army garrison. From there, you’ll continue to Jerbourg, stopping atop a WWII bunker to take in panoramic views of the neighboring islands and walk out to the cliffs opposite the Doyle Monument for stunning vistas. 

Next, visit the German Occupation Museum, a private collection curated by Richard Heaume, whose childhood passion for collecting WWII artifacts grew into one of the most comprehensive displays of original occupation items and rare documents. This guided tour provides a firsthand look at life under occupation, shedding light on the choices and challenges faced by those living under harsh conditions. 

You’ll then tour either Batterie Mirus or Batterie Scharnhorst, WWII fortifications located on private land, before continuing to Pleinmont to view Batterie Dollman and the towering MP4 structure. Standing next to this massive installation, you’ll gain a true appreciation for the scale of these wartime defenses. The tour concludes along the west coast with a stop at Le Guet, offering breathtaking views over Cobo, a location prized for its strategic vantage during the war. 

This immersive day will leave you with not only a deeper understanding of the Channel Islands’ extraordinary history but also the leadership strategies needed to face unforeseen challenges with courage, integrity, and adaptability. 

Dinner at leisure to explore the beautiful town of St. Peter Port. 

Overnight: The Old Government House Hotel & Spa 

Meals: Breakfast, Dinner 

After breakfast at your hotel, you will take a ferry or flight back to London, where the final chapter of your expedition begins. The day includes a leadership workshop (timing TBD), offering a focused opportunity to consolidate the lessons you’ve gained and explore actionable strategies to implement them in your own leadership challenges. 

In the evening, we’ll convene for a formal debrief and farewell dinner at Raffles, Britain’s historic Old War Office. This magnificent Grade II* Edwardian Baroque building in Whitehall, once the epicenter of British Government, is steeped in history. Designed by British architect William Young, the War Office occupies the site of the Palace of Whitehall, home to English monarchs like King Henry VIII. The building also served as a hub for iconic figures such as Winston Churchill and Lord Haldane, and inspired Ian Fleming, creator of James Bond, with many scenes from the 007 films shot on location. 

Over dinner, we’ll engage in a structured after-action review, anchoring the insights and transformations from the expedition. This dynamic session will help you crystallize the leadership principles you’ve learned, ensuring they are ready to be deployed in your professional life. It’s not just a celebration—it’s the final, crucial step in equipping you to lead with purpose, resilience, and clarity in the face of modern challenges. 

Overnight London: The Montague on the Gardens Hotel or similar