Bespoke luxury travel outfitter Black Tomato, widely renowned as one of the industry’s top innovators, is at it again—this time, with one of its most ambitious rollouts to date.

Unveiled on February 13, The Pursuit of Feeling (PoF)–an AI-powered platform that uses leading-edge technology and Black Tomato’s two decades of top-tier travel planning to recommend trips based on the wide range of emotions they evoke–marks the company’s full-fledged entrée into our increasingly AI-infiltrated world.

But as company cofounder Tom Marchant takes pains to point out, the initiative, which dovetails with the company’s 20th anniversary this month, goes far beyond the seemingly ubiquitous chatbots populating online travel agencies and other industry websites.

“When we started the company in 2005, we had this perspective that often we didn’t know where we wanted to go, but we knew how we wanted to feel,” he explains. “On the first iteration of our website, we actually listed experiences according to the emotional need they’d fulfill. So when we started discussing this platform 18 months ago, we knew we wanted to create something that celebrates and reinforces the power of feelings, and brings travel’s ability to move you back to the fore.”

PoF’s pièce de résistance: the aptly monikered Feelings Engine–an augmented-AI-powered search engine, developed with the help of Ragu AI–that uses your wishlist of emotional outcomes to generate trip recommendations. Unlike many AI solutions that canvass and gather information from vast swaths of the internet, every modicum of information used to build and fuel the Engine–some 400 itineraries, seasonal travel recommendations, and suitability profiles, among myriad other data points–comes directly from Black Tomato’s experience and expertise.

“You’re basically getting the best of this technology to create a conversation based on all of our proprietary data that we’ve curated, researched, and tested over two decades,” Marchant says.

Of course, Black Tomato isn’t the only travel provider to factor feelings into the luxury travel equation. In findings released in August 2024 detailing travel trends and insights for the year ahead, Virtuoso, a network of 20,000 luxury travel agents in 58 countries, highlighted a shift in focus from itinerary-driven checklists to feelings in its most recent poll, with 65% of US travelers seeking “joy and happiness,” 57% angling for “awe and wonder,” and 51% looking for “anticipation and excitement.”

That said, based on a test run, Black Tomato’s Feelings Engine has set a high bar for the industry by making the process of discovering soul-quenching adventures user-friendly, seductive–and perhaps most of all, addictively fun.

The PoF platform invites travelers to approach planning from five emotional pillars–Revitalized, Freedom, Distraction, Challenged, and Contentment–and Black Tomato has created 100 new trips and five pull-out-all-the-stops, “spotlight” itineraries–ranging from eagle hunting in Mongolia to foraging in Greeland–tied to these pillars. You can literally shuffle through these singular adventures on the platform website, where they’re snazzily presented as cards you flip and expand to explore.

But the real fun begins when you hunker down for a conversation with the Feelings Engine. Enter an emotion in the white box, just as you would kick off an online search–there are (five-pillar) prompts like “I want to feel revitalized”–and let the engine go to work, as it sifts through the 400-odd itineraries tagged to a panoply of emotions. (While it’s thinking, charmingly hypnotic line drawings, all travel-themed and cleverly captioned, spring up to occupy you.)

At first pass, my search criteria–“I want to feel challenged and free”–returned the new PoF opportunity to become a lost explorer in Borneo by heading into the Sarawak Jungle to spend 10 days with the Penan tribe (one of the last remaining nomadic jungle tribes on earth) to learn how to set wild pig traps, make a blow-pipe dart, and identify edible plants, among other survival skills. After the tribesmen’s ten-day tutelage, you’ll be left to fend for yourself in the jungle for 48 hours (!), with a Penan guide on-hand for advice, but no hands-on help. (Suffice it to say that Black Tomato isn’t kidding around in the Challenged department.)

Notably, when I said I wanted to feel “cleansed” in another search, the same trip popped up again, but with a distinctly different spin: while the first description invited me to “imagine breaking free from the constraints of modern life in Borneo,” the next described the Borneo jungle immersion as “the ultimate cleansing experience for body and spirit.” Ever the canny marketers, Black Tomato designed the Engine to modify trip descriptions to satisfy different desired feelings, just as travel agents tweak their pitches to entice various kinds of travelers.

On the next go-round, I searched for a trip that would make me feel “pampered and well fed” (arguably my default desired emotional state). When the Engine offered an 11-night culinary journey in Thailand, I asked for “something in Italy,” curious to see if a feeling-less prompt would throw a wrench in the works. Instead, “The Young Pope: Italy”–another new PoF itinerary based on the hit TV series and laden with truly exclusive experiences in Rome (like a private tour of the Vatican Museum before it opens to the public), Verona, and Venice–appeared to entice my inner Italophile. Beneath each engaging trip summary, you can opt to “explore trip,” which takes you to the whole itinerary, or “get in touch,” which opens a form requesting basic information and parameters (where and when you’d like to go; how much you’d like to spend) so a Black Tomato travel advisor can contact you to continue the conversation.

Central to the Feelings Engine’s founding ethos is the idea that it strengthens, rather than replaces, the company’s human touch.

“Black Tomato has always been about celebrating the power of human insight and expertise, and finding ways to use technology to amplify that,” Marchant says. “Obviously I’m very biased, but for me it’s a beautiful representation of where technology and human insight can blend really effectively. Ultimately we’re still putting our customers into the hands of our brilliant travel experts, who are irreplaceable because the type of trips we design are so bespoke and so crafted.”

In keeping with this human connection, Black Tomato is also launching a new podcast series, in which Marchant interviews an array of luminaries–including artist Ashley Longshore, fashion icon Fern Mallis, and world-renowned bartender extraordinaire, Mr Lyan—about their most memorable trips and how they made them feel.

Like all technologies, the Engine has its limits. It doesn’t collect location data, which I discovered when searching for a “revitalizing getaway near me.” When prompted to enter my state or region, and how far I was willing to travel, I requested a “revitalizing getaway in the southeastern US.” To that, the engine apologetically replied that it currently didn’t have any itineraries there in its dataset, but that “Black Tomato specializes in creating custom luxury journeys and would be delighted to craft a revitalizing escape in the Southeast” just for me, that might include farm-to-table culinary journeys through Virginia wine country, or peaceful escapes in the Georgia Sea Islands. Then, when I searched for the same revitalizing southeastern US trip again the next day to see if I received the same reply, the Engine instead offered a Deep South experience in Kentucky and Tennesee–which I wasn’t in the market for, but upon review sounds like a blast.

And therein lies the Feelings Engine’s undeniable appeal: its ability to make travel planning–which can often feel overwhelming and unwieldy–not only interactive and personal, but also wildly entertaining. It feels almost like a game of wits, in which you’re challenging a (relatively) omniscient travel genie to grant your ultimate travel wish by surfacing the trip you’ve perhaps been searching for all your life­–because, well…you’re doing exactly that. And identifying that trip is exactly what Black Tomato has designed the Feelings Engine to do.

Its debut also seems incredibly timely, in light of the arguably fragile and angst-inducing state of our global society in this moment.

“The world has been in and out of darkness and in a state of flux for what seems like years and years,” replied Marchant, when asked if he agrees that the Pursuit of Feeling’s launch seems very of the moment. “I do think in the last couple years, there’s been growing recognition of the role that the search for feelings has taken on in people’s lives–not only in travel, but also in art and fashion–and the importance of finding ways to escape to immerse yourself in those feelings,” he continued, noting many clients’ requests since the year’s start for off-the-grid trips where they can go clear their heads in whichever way they choose.

“We normally launch a new marquee product line in September, but we held off last year because there was so much going into this one, and we didn’t want to rush it,” he said. “Now it seems like the stars are aligning with our timing, as it already feels like it may be a long year. Hopefully this particular launch will really resonate with people, and truly inspire them to get away.”



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