Five-Star Four Seasons Hotel Toronto, chef concierge Harry Hollywood has been creating bespoke guest experiences for more than 10 years.
Starting as a guest services agent, he later joined the concierge team, where he learned under the tutelage of now-retired, legendary Four Seasons concierge Liloo Alim, the first woman to join the Canada chapter of Les Clefs d’Or, the leading international association for hotel concierges.
Having worked as a concierge for more than a decade, Hollywood has seen the rise of smartphones and the way they changed how people travel, research and even find their way around town. More recently, the Les Clefs d’Or concierge has also observed visitors leveraging AI engines like Claude, ChatGPT or Gemini to help in building their trip itineraries.
Four Seasons Hotel Toronto
With the massive shift of using AI to do the work of coding, writing, predicting, generating ideas or trip suggestions, what does it mean for the luxury hotel industry and hospitality professionals?
At Four Seasons Toronto, the concierge desk remains as busy as ever. For the team, using AI to help draft emails or responses gives it more time to spend with a guest. Every day, guests approach the concierges looking for advice or assistance with booking an attraction, experience or dining reservation. This is the moment that Hollywood and the team shine.
They know they have just a few moments to understand what a guest is looking for and give options personalized to the individual’s tastes.
“Are they looking for something romantic? Are they more interested in food or ambiance?” Hollywood says. There are considerations, like if a guest has arrived after a long flight, a three-hour tasting menu may not be the right recommendation. If the weather calls for snow, an outside walking tour or attraction would not be a great suggestion, and a concierge can pivot on the fly.
Four Seasons Hotel Toronto
“With a few guiding questions, within 20 to 30 seconds, I try to give three strong options for a guest to find the right fit and experience for them,” Hollywood says.
It’s this interaction that many Four Seasons guests are still very much looking for: recommendations tailored to their tastes and preferences, with that human touch. They seek the depth of experience that concierges can offer and a greater sense of certainty that their endorsement will hit the spot.
While AI can recommend what to see and where to dine, it relies heavily on information available online. This digital dependency often falls short of expectations: according to TravelAge West, while 56% of U.S. travelers used AI for at least one trip in the last year, only 8% felt that those AI answers alone were sufficient. The reality is that you can’t trust everything you read online. Business hours, especially during holidays, can be incorrect, and pricing for admissions or menus is frequently outdated.
Four Seasons Hotel Toronto
As local experts and de facto ambassadors to the city, concierges have their fingers on the pulse and can vet these for a guest. The breadth of knowledge and deep connections allow them to find, if not create, experiences that aren’t online and that go beyond what a guest may know is even possible.
Hollywood and the concierge team look to make a guest’s unique vision come to life. These one-of-a-kind itineraries or experiences can often tap into niche interests and hobbies, like a behind-the-scenes VIP experience during an athlete meet-and-greet, a tour of the city to find vintage luggage or a crawl of the best cocktail bars with only off-menu items.
The work of a chef concierge at the Four Seasons is not just a job, it’s a lifestyle, Hollywood says, and when he’s not on the clock, he’s researching the latest restaurants and neighborhoods. In a business where relationships are everything, guests at Four Seasons Toronto can essentially tap into the hotel’s rolodex to secure a hard-to-book spot. These bonds and tourism association connections can also mean savings on attractions or outings.
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Finally, while AI can do the work of building trip itineraries, for now, it still falls on a guest to buy show tickets or make reservations online. Whether in person or through the Four Seasons app, these are tasks the concierge team can handle, allowing a guest to enjoy the city rather than being stuck with the administrative work.
For now, we live in a world where luxury hospitality and AI are complementary and can enhance a guest’s experience. Avid travelers can certainly find efficiencies with AI-generated travel recommendations, saving time and effort in hours of research or planning.
For others, though, AI may not be enough. Luxury travelers with specific expectations are looking for personalization. They want to take the risk out of their limited time and ensure each experience hits the mark. And that’s precisely when top concierges like Hollywood spring into action.
