Singapore is a popular stopover destination for U.S. travelers going to Asia on long-haul flights, but most spend fewer than 24 hours in the small island country. Now, the Singapore Tourism Board is giving travelers a chance to stay longer—for free.
On March 18, the destination marketing organization launched a new Stopover, Do-Over campaign in partnership with Singapore Global Network, a community of Singaporeans living abroad and expats living in Singapore. The campaign includes a giveaway of 60 round-trip flights for U.S. travelers to commemorate Singapore’s 60th anniversary of independence on August 9, 2025. There is also one grand prize: a fully customized “do-over” trip designed to showcase Singapore’s hidden gems, from its buzzing hawker centers to lush urban green spaces and impressive craft cocktail scene.
In 2024, more than 692,000 American travelers arrived in Singapore, a signal of the destination’s appeal to long-haul U.S. travelers. Whether travelers had a quick taste of Singapore and left wanting more, have yet to visit, or would love the chance to explore the country at a slower pace, the tourism board wants to share that Singapore isn’t just a stopover—it’s a place worthy of deeper exploration, with a vibrant cultural heritage and history, world-class dining, lush nature, and dynamic cityscapes.
“You’ll never run out of things to do in Singapore—uncovering hidden speakeasies, taking in skyline views from the world’s largest rooftop infinity pool, or immersing yourself in a different cultural enclave each day—our city rewards curiosity,” says Eileen Lee, senior vice president, Americas at the Singapore Tourism Board. “The ‘Stopover Do-Over’ campaign is an invitation for travelers to slow down, stay a while, and truly experience the depth of Singapore.”
How to enter to win a free flight to Singapore
From March 18 through April 18, 2025, visit www.SingaporeStopOverDoOver.com and enter for a chance to win by submitting an essay detailing why you need a Singaporean “do-over.” One grand prize winner will receive a full trip, including airfare, accommodations, and activities in Singapore. Thirty more winners will each receive two round-trip flights (for themselves and a guest) to Singapore from the United States, for a total of 60 flights being provided.
What to do, eat, and where to stay while in Singapore
With a week in Singapore, visitors can do a deep dive of the destination, experiencing distinctive neighborhoods like the Civic District, Katong Joo Chiat, Little India, Mandai, and Tanjong Pagar, one of the oldest, with buildings dating back to the 1800s.
Other fun and interesting activities include riding the cable cars above the city, visiting Rainforest Wild Asia, and exploring the Peranakan Museum (where you can learn about Peranakan culture and history, an ethnic group comprised of people of Chinese, Malay, and Indonesian descent). Visitors can also dive into the impressive art collections of the National Gallery Singapore before ambling through Gardens of the Bay. For shopping, head to Orchard Road. And for temple hopping, head to Thian Hock Keng and Sri Mariamman Temple. With so much time, you can make it out to the island resort of Sentosa for some beach relaxation and to the Southern Ridges for hiking.
Singapore is filled with Michelin stars and incredible upscale dining options—make reservations at Kun for a Sichuan omakase and Candlenut for traditional Peranakan food. Still, you’ll also want to leave plenty of time to eat your way through the hawker stalls at Maxwell Food Centre, Tekka Market, Old Airport Road, and Joo Chiat. For a nightcap, settle in at Night Hawk, an Edward Hopper–inspired speakeasy.
As for where to stay, Afar has compiled a complete list of hotels we love in Singapore. You can never go wrong with the legendary Raffles Hotel Singapore, or for a thoroughly modern hotel, the Singapore Edition or Artyzen Singapore both offer design-forward options in central locations.
