Expedia Trip Matching turns Instagram Reels into bookable itineraries
With its AI-powered Trip Matching tool, Expedia doesn’t just identify hotels, restaurants and destinations featured in Instagram Reels, but makes them effortlessly bookable, too. Robbie Hodges reports
There has been plenty of recent buzz around the potential of generative AI when it comes to planning travel itineraries – mainly with regards to curating personalised journeys from a single prompt. But Expedia is applying AI in a different way by using computer vision to translate Instagram reels into a series of bookable products, services and experiences.
The technology is long overdue, and promises to revolutionise influencer and social media marketing, a key driver of travel booking. A Phocuswright survey published in September 2024 reported that almost three quarters of international travellers who used social media for trip planning made a purchase or visited a destination based on content they’d viewed on the feed.
While many travel brands have toyed with Instagram Shopping and many platforms aim to help travel influencers monetise their content (TrovaTrip, for example), Trip Matching promises to make video content seamlessly bookable – connecting users not only with big brands but also less established, independent restaurants or hotels listed on Expedia.
The way Expedia’s tool works is simple. If an Instagram reel piques curiosity – whether published by an influencer, brand or a friend – users send it to Expedia’s Instagram account via direct message. Then, Expedia’s AI assistant analyses the content and matches scenes spotted in the video with images and resources available via the company’s internal database and Google Data – a process that takes roughly 60 seconds.
Once complete, users are presented with a series of travel tips, a potential itinerary and destination information along with Expedia booking links.
In the accompanying press release, the OTA is clear to highlight that AI might be prone to hallucinations and recommendations could be misguided, though early tests suggest that the tool is effective in converting more typical, listicle-style reels into itemised itineraries. It’s less successful at making more evocative, atmospheric content bookable.
For example, Globetrender did trial the tool with our own reel that was filmed during the May 2025 Globetrender Retreat in Norway, but the assistant was unable to offer suggestions. Instead, it responded: “For help with your itinerary, please contact us via Facebook Messenger, or visit Expedia service for the latest travel info and booking support”.
Of course, the tool is faced with ethical challenges. As is true of many AI-powered platforms that draw on publicly available data sets, Trip Matching consolidates revenue in the hands of a large booking platform with no reward or reimbursement for the creators supplying the itineraries.
Regardless, the translation is impressive and points to a future in which brand search and discovery is increasingly multimedia – traversing not just text, but image, video and sound, too.