How a local travel company designed American actress Drew Barrymore’s Singapore itinerary within a week

On Oct 1, Hollywood A-List actress Drew Barrymore uploaded a TikTok video of herself eating popiah off a tray in Maxwell Food Centre. The clip instantly went viral, with Singapore fans proclaiming they didn’t know she was in town. 
What they also didn’t know was her visit to the hawker centre was a completely spontaneous decision during her family’s four-day visit in early August. The popular lunch spot in central Singapore wasn’t on the itinerary planned by travel company Blue Sky Escapes, its founder and director Krystal Tan revealed. 
Barrymore was “very attentive” and observant, Tan recalled. During a food walk that took the family past Maxwell, she pointed out the food centre looked “really interesting” and asked if they could eat lunch there instead. 
So the Blue Sky Escapes team “shifted gears”, largely thanks to Pei Shyuan or PS as she’s better known – the guide they’d roped in from local agency Everyday Tour Company which specialises in walking tours around Singapore’s “less-touristy” spots. PS managed to immediately secure them a table, “even though it was the peak of lunch (hour)”, said Tan.
Maxwell Food Centre ended up being the only hawker centre where Barrymore’s family ate during their stay in Singapore – although it wasn’t the only unplanned activity.
Barrymore, a fan of flowers, also wanted to visit the Botanic Gardens at the last minute. “Thankfully”, said Tan, former CEO of Bollywood Veggies Manda Foo, who’s part of the Blue Sky Escapes team, was available to be her guide.
Nifty turnarounds to accommodate such requests on a whim might seem super stressful, requiring not only quick thinking and nuanced knowledge of a country’s culture at any one point, but deep respect and genuine understanding of the unique travel needs high net worth guests might have. 
But that was precisely the reason Blue Sky Escapes was asked to plan Barrymore’s itinerary.
A week before Barrymore and her family were due to land in Singapore, the team at Marina Bay Sands – where the family would stay – learnt their guests wanted a ground handler to curate “bespoke and interesting activities” for their trip. 
The timeline was tight. But the luxury hotel had previously worked with Blue Sky Escapes and knew they’d be able to deliver as “a specialist in this realm of bespoke travel”, Tan said.
Founded by the 37-year-old in 2017 with her business partner and now-husband Chervin Chow, the Singapore-based boutique travel firm specialises in crafting “luxury, bespoke journeys” in over 60 destinations from Bhutan to the Faroe Islands.
Their itineraries ensure immersive, “extraordinary experiences” off the beaten track without skimping on comfort – which means the luxury properties and local guides they partner must be “able to service the kind of guests that are basically fitting our own profile”, explained Tan. 
Travel requests come in every other week from a clientele that includes celebrities, politicians and prominent business personalities among other high net worth individuals.
But experiences “are not limited to the well-heeled”, according to the Blue Sky Escapes’ website. Costs typically start at US$300 (S$392) per person, excluding flights, depending on the size of the group and nature of the journey, and the team does their best to work with many budgets.
It is also common for them to be directly approached by hotels where such high-profile individuals stay, like in Barrymore’s case. The company is part of Virtuoso – a leading global consortium of luxury and experiential travel providers whose membership is by-invite-only.
Still, the initial buzz from being appointed to host famous personalities probably doesn’t get old. After receiving the call from Marina Bay Sands about Barrymore’s visit, Tan’s team was “of course, very, very thrilled”, she laughed. 
“But we couldn’t sit around long and just be happy about it. We had to spring into action immediately (and) check on availability for all the different experiences that we were looking to propose.”
The first thing Tan’s team did was a “profiling call” with Barrymore’s agent to understand what the actress and her family were going for, as well as their likes and dislikes. This call is done with any guest.  
“We always ask things like, what are the sensations they’re going for? Do they want to recharge or are they (looking for) active and invigorating (experiences)? How much privacy do they need? Any special, particular interests?” she said.
Typically, when the guest is “more high profile”, such as a celebrity or politician, her team places a host with them throughout their stay, she added. “But there have been times where they’re also high-profile yet prefer their privacy. Usually, you just sense (what they prefer), and get clearance upfront from their agent or personal assistant (if you’re going to constantly have someone by their side).”
Compared with other requests, Barrymore’s team outlined a “pretty relaxed” and “down-to-earth” brief that wasn’t difficult to execute.
“They didn’t need to be shielded from the crowds; they just wanted to blend in. They wanted something that’s special, family-friendly, fun, (where they could) go to chic places to people-watch and really feel the heartbeat of a culture, but it didn’t need to be fancy. They’re also happy with different cuisines,” Tan said.
She knew Barrymore loved flowers and meditation, and her two daughters loved ice-cream.
At the same time, Marina Bay Sands had generously proposed a few activities for her team to consider including in Barrymore’s itinerary, such as a private tour led by directors of the ArtScience Museum.
Barrymore’s personal assistant had also mentioned the actress “wanted to be able to get on a boat” – a wish that was eventually fulfilled. 
One of the shortlisted activities was a private ride in a traditional bumboat down the Singapore River with a guide who shared about Singapore’s history. 
Barrymore and her family also visited the Museum of Ice Cream in the Dempsey Hill area, where the Blue Sky Escapes team surprised the actress with an ice-cream flavour named after her: Drew Berry. 
In another activity, she did a walkabout in the Bukit Brown Cemetery, ending it with a contemplative session with a qi gong master – which the team had designed based on her interest in meditation.
“Personally, I like to show Singapore in a different light, where instead of going to a museum to understand more about the history of Singapore and who built the country, why don’t you go to Bukit Brown and have a historian take you to the grave sites… of pioneers who built Singapore?” said Tan.
“It’s such a different way of looking at Singapore. You also see the real super trees too in the wilds of Bukit Brown.”
But the activity that seemed to leave the most lasting impression on Barrymore was a ride in a sidecar along a “curated route” on Singapore’s roads. Tan’s team had surprised her family in their suite before the ride with a rack of upcycled silk kimonos by two local designers, from which Barrymore and her daughters could choose an outfit paired with a flower headband.
“We had the sidecars show up in the car park as a surprise for the girls. The kids went down to the car park expecting to just get into a (regular) car for the next activity, then they saw the sidecars. And that moment, Drew said… brought tears to her eyes,” Tan shared. 
“She asked me if I’d watched Inside Out but I hadn’t. She told me that sidecar experience we designed for the family was a ‘core memory’ for her. And after I watched the movie, I felt very touched by (her words).”
Barrymore’s experience is not the exception. Striving to meet a guest’s emotional needs, beyond their travel requirements, seems to be why the Blue Sky Escapes team spends time understanding each individual. 
Tan remembered a burnt out lawyer, who’d shared during the profiling call: “I don’t care where you put me, just anywhere that is remote, as long as I cannot be contacted.”
Her team sent him to Mongolia, where they put him in a ger, or yurt, with a nomadic family. “There was no Wi-Fi. He spent the days living as a nomad. He was collecting water, shovelling cow manure, herding animals – and he just loved it,” she recalled fondly.
Perhaps it also helps that Tan and her husband, once in law and investment banking respectively, empathise with such needs. They’d started their travel company, after all, from their own desire to “escape the mundane and wanting to get as far away as possible, where we couldn’t be contacted because of our gruelling work schedules”, she said. 
“So we already had (access to) the kind of clientele who were working in these professions and at a level where they’re able to spend on holidays… but they’re also time-poor.” 
For instance, there was a guest who’d told the team to “stick me in a helicopter” for any drives longer than two hours.
Then they have guests so well-travelled that their requests are uber specific. One, in particular, was returning to Tanzania in East Africa despite having previously been there during the Great Migration. Witnessing the year-long phenomenon, which sees constant movement of over a million wildebeest and hundreds of thousands of zebras and gazelles across the Serengeti-Mara ecosystem, is one of the most sought-after experiences for wildlife and nature enthusiasts. 
The guest had said, “I’m only going back to Tanzania because I need to see the animals crossing the river. I don’t want to see them running about in the fields. They need to be crossing the river”, Tan recalled in amusement.
“It’s a very specific request, so we had to stick them at a lodge that’s right by the Mara River, and you have to time it in such a way that you know the animals are going to be there crossing the river at the time they’re staying there.”
In Singapore, one of the most “puzzling” requests they received was from a guest who wanted to replace the mattress in the presidential suite of an ultra-luxe heritage hotel in the city centre, whose name Tan requested to withhold. He’d found it “too hard” due to his back issues. 
“The problem is the mattress was made specifically for the custom-built bed frame. You can’t just switch it out with any other mattress,” Tan said. The repeated attempts by the butler team to use mattress toppers to soften the mattress were unfortunately futile.
So she’d initially apologised, unable to see any way her team could fulfil the request, even as they’d worked quickly with the hotel’s butler team to try and resolve the concerns. Then, unexpectedly, a solution presented itself.
“While (the client) was in the spa, we worked with the hotel’s butler team, who managed to source a softer mattress from a partner property that was able to fit the suite’s custom bed frame. The hotel’s housekeeping team of about six to eight people then transported the replacement mattress by foot, hand-carrying it across the road and switching it out whilst the client was in the spa.”
Admittedly, it takes a distinct personality type to find such requests a thrilling challenge, instead of ludicrous demands.
Tan seems to have cracked the code to attracting the right hires, including freelance travel designers who may already hold full-time jobs but simply yearn to share their in-depth knowledge about a certain country.
“My team is constantly travelling, trying out new things and not being afraid (of doing so). They are genuinely passionate about travel… about helping people access these insider experiences. It’s about having a growth mindset, to be constantly hungry for new explorations and experimentation,” she said. 
They also design lifestyle and corporate events, bringing the “programming and curatorial aspect in events” to a guest’s travel itinerary. But the essence of every experience, it seems, remains the same.
“Have the mentality, when you craft somebody’s trip, that you’re going to spend this person’s money like it’s yours. It’s about remembering that we have a very important role to play – we are the safekeepers of people’s time,” Tan believes.
“And I feel that especially so because I came from being a lawyer. Just having that one week off, I wanted it to be a super special week. Trusting somebody with that time, where I eat, how long it takes me to get to one place, where I sleep, was such a big responsibility.”