Example Itinerary

WWII: Journey through the Battle for Singapore

4 days / 3 nights
Price Per Person

Singapore was once called the “Gibraltar of the East” by the British, then renamed “Syonan-to” by the Empire of Japan after its surrender on 15 February 1942. An important Southeast Asian stronghold of the British Colony during WWII, the seemingly impenetrable city’s fall was dubbed the “worst disaster” in British military history by Winston Churchill. Relics of the fall and consequent occupation still stand amongst today’s skyscraper landscape, an indelible imprint left by 3.5 years of Japanese Occupation. See where it happened, learn what the British did wrong, and what the aftermath and consequences were of the Battle of Singapore.

This itinerary is an example. It’s designed to inspire you and provide you with thoughtfully curated ideas. You can choose to do this exact itinerary or completely personalize it. All trips are 100% bespoke.


• Battlebox: Inside Fort Canning Hill is a monument to the British surrender almost eight decades ago. There are many commemorations to the battle for Singapore, but none more apt than this secret bunker that was only relatively recently unearthed.

• Kranji War Memorial: A serene and poignant hideaway in northern Singapore, the Kranji War Memorial and Cemetery is the site of a former POW camp and hospital. The memorial has 24,000 names of fallen servicemen and women inscribed on the 13 walls.

• Fortress Singapore: On Sentosa island, Fort Siloso features a coastal gun battery which was part of the "Fortress Singapore." Here, travelers will squeeze into a preserved pillbox, inspect the remains of gun emplacements, and view displays of the British surrender at the Surrender Chamber.


Day 1


Arrive at Changi Airport and meet your guide for your private transfer to your hotel. Relax and unwind from your flight for the rest of the day.

Hotel Options
Why We Love This Hotel

Location: Strategically placed at the centre of Singapore's business district, the Singapore Fullerton Bay is the newest hotel along the stunning Marina Bay waterfront.

History: The Fullerton Bay is relatively new, but within its short history, it has managed to pick up the Best New Business Hotel Worldwide by Business Traveller UK magazine.

Service: Business guests can take full advantage of this hotel’s long list of business-oriented services, while those looking to explore Singapore will appreciate the complimentary shuttle service provided for guests.

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Fullerton Bay Hotel Preferred Hotel

Day 2


Stroll through Fort Canning Park, a respite of quiet greenery in the city, and come upon the Battlebox, where it all began. This bunker was the largest underground military operations complex in Singapore and the very place where British decided to surrender on that fateful day in 1942. Virtually forgotten for decades after the war and left derelict, today it is a museum that educates visitors on the true causes of the “worst disaster and largest capitulation in British history.” Throughout its history, the Former Ford Factory assembled motorcars for the Singapore public, fighter planes for the Royal Air Force, and finally military vehicles for the Japanese war efforts. Tour this historic site, now a museum housing photos, archival records and exhibitions presenting the events and memories surrounding the British surrender, the occupation, and the legacies of the war. See the Hong Lim Complex where a memorial stands to commemorate the taken lives of thousands of Chinese men who reported to the site during occupation. Head to Sentosa island to see Fort Siloso, a restored coastal gun battery which was part of the ‘Fortress Singapore.’ Squeeze into a preserved pillbox, inspect the remains of gum emplacements, and view displays of the British surrender at the Surrender Chamber.    


Day 3


Today visit the moving Changi Museum which is devoted to Singapore’s history during WWII, particularly the interment of the POWs and civilians at the infamous Changi Prison during the occupation.  See a replica of the chapel built by Allied POWs, a display of daily life in Changi prison, and artwork created by prison inmates. In the surrounding area are other historical sites such as old Changi Jail and Selarang Barracks. Visit Reflections at Bukit Chandu, a colonial bungalow honoring the fallen soldiers of a heroic last stand against the Japanese army, reminding its visitors the price of peace and sacrifice of patriots. The Kranji War Memorial and Cemetery is a serene and poignant hideaway in northern Singapore, located at the site that was a POW camp and hospital. The memorial has 24,000 names of fallen service men and women inscribed on the 13 walls. Singapore also honored its fallen civilians by erecting the Civilian War Memorial, declared a national monument, where a memorial service is held annually on February 15th.

Day 4


Depart for your flight onward and take with you the story of Singapore’s fall and its many lessons.

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