Signal 003: How Brand Trips Became Immersive Campaigns

In 2015, a group of beauty creators boarded flights to Turks and Caicos under the banner “Trippin’ with Tarte.” The guest list reflected the early days of influencer culture, made up largely of YouTube beauty creators. They filmed “get ready with me” videos from hotel bathrooms, documented group dinners, and posted tutorials featuring the latest palette launch. Over time, Tarte’s trips would expand to destinations like Bora Bora, Costa Rica, and Dubai, becoming a defining part of the brand’s marketing playbook. What looked like a vacation was, in fact, a marketing experiment. Founder Maureen Kelly conceived the trips as a workaround when the brand couldn’t afford to compete with traditional advertising, focusing instead on building real-life relationships with creators. The strategy worked: according to the brand, the trips regularly generated hundreds of millions of #trippingwithtarte impressions, and one trip reportedly drove more than $7 million in exposure.

Before this, brand trips were largely the domain of traditional media. Editors were flown to destinations around the world on tightly scheduled itineraries, where the expectation was clear: in exchange for access, there would be coverage. The trips were often lavish, but fundamentally transactional. Product was the focus, whether a collection preview, a hotel opening, or a beauty launch, and the destination itself functioned as logistics. Where you stayed mattered less than what you were there to see, and press hits ultimately measured the value of the trip.

Those excursions haven’t disappeared, and for many brands, they still function as a core part of the press strategy. Today, editors and creators often attend the same trips, but the roles they play differ. These trips are no longer built solely around influencers, but around a broader group of tastemakers, Substack writers, creative directors, and cultural curators whose value lies in how they interpret and shape a point of view.

Creators offer something traditional media cannot: direct access to an audience and a defined perspective. What unfolds is a stream of Instagram Stories, trending audio TikToks, and in-between moments that feel closer to watching a group vacation than being served a campaign. As a result, brands now design trips not just for exposure, but for the kind of storytelling that can be told organically (or as organically as a brand-hosted, all-expenses-paid experience can be) and in real time.

But what once felt novel now risks feeling interchangeable if not hosted with clear intention. As brand trips have multiplied, simply flying creators somewhere beautiful isn’t enough to stand out. The trips that cut through are the ones that build a world, where the setting, the people, and the product come together to tell a cohesive story.

That difference is already visible across trips hosted in the last year. J.Crew brought a cast of tastemakers to Puglia to celebrate a collection developed in partnership with Masseria San Domenico, where every detail, from what guests wore to where they gathered, contributed to the visual world. Every post functioned as both aspirational travel content and campaign imagery. Matteau staged a trip to Hôtel Les Roches Rouges, aligning its minimalist beachwear with the quiet luxury of the Côte d’Azur. Even smaller brands are adopting the model: ski equipment brand Yardsale organized a trip where the surrounding experience, from the slopes to the spa, became the primary content.

Photos via Comme Si

To launch Comme Si’s Sport line last June, the brand took ‘friends of the brand’ to Bio-Hotel Stanglwirt. “The setting was incredibly intentional,” says Founder, Jenni Lee, referring to a backdrop of tennis courts, alpine air, and wellness programming that were all part of the product story. “It allowed the collection to live in its intended context, moving from tennis to swimming to a long lunch, then into the evening… it didn’t feel like we were placing a product somewhere, but rather revealing it in the right setting.”

That framing extends beyond the experience itself to how it’s perceived by those watching from afar. As Lee puts it, “People are not just buying an object—they’re buying into a way of living. The destination provides context. It helps answer what the product is for, and how it should feel to wear it.”

For creators, these trips function very differently from the usual campaign. Earlier in her career, Margot Lee approached brand trips with a defined set of deliverables, often completed and approved after the fact (she notes, now having been on 15-20). Now, she describes a shift toward looser structures and more self-directed storytelling, where “it doesn’t feel like everyone there is competing to create the same exact content.”

That shift is closely tied to the environment itself. “My bread and butter is lifestyle content… the world around me essentially becomes my set,” she explains. On a recent trip with Yardsale, that meant focusing less on the product in isolation and more on the surrounding experience. “The hotel, the spa, and the product all told one coherent story. The experience was the content.” 

For Lee, this is where these trips become most effective. “I love when brands worldbuild,” she says, noting that aligning a product with a physical place or experience allows it to be understood in context. Rather than asking creators to manufacture a scenario, the setting does the work, making the content feel more natural and, as a result, more compelling to an audience.

ShopMy’s data around Comme Si’s June 2025 brand trip points to a distinct pattern in how these experiences translate into purchase behavior. During the four-day trip window, creator linking activity more than doubled, marking the highest-volume linking period in the surrounding five-week window.

While sales saw a more modest lift during the trip itself, the more meaningful shift came in the weeks that followed. In the two weeks after the trip, conversion rates increased significantly, with click-to-order improving by more than 60% and link-to-order by more than 30% compared to the two weeks prior. Notably, this occurred even as overall clicks declined, suggesting that the audience engaging post-trip was smaller but more intent-driven.

Rather than driving immediate spikes, these trips appear to create a wave of discovery that translates into more qualified demand over time.

These trips reflect a shift in what brands are selling. Where they were once designed to generate coverage, and even early creator trips were built to drive awareness, today’s iterations are designed to immerse both those in the room and those following along in a world. The destination is no longer incidental to the story; it is the story, showing not just what something is, but what it feels like to live with it.

Though the immediate output may appear less structured, the impact is no less intentional. As the data suggests, these activations don’t just drive visibility; they shape perception, creating a slower, more considered path to purchase. In this way, the brand trip has evolved from a marketing tactic into a narrative tool–one where the world is no longer just aspirational, but shoppable.