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Planning your next getaway might be as simple as sliding into Expedia’s DMs. The global travel giant has launched Trip Matching, an AI-powered feature that lets Instagram users send a public Reel to @Expedia and get back a customized travel itinerary within about 60 seconds.

For today’s social-first travelers, who often find inspiration on Instagram, TikTok, or YouTube, Trip Matching bridges a crucial gap: turning visual content into real-world travel action.

In this post, we’ll explore what Trip Matching is, how it works, why it matters, and how you can use it effectively.

🔍 What Is Expedia’s Trip Matching?

Trip Matching is a new feature currently in beta in the U.S., built by Expedia’s in-house AI team.

The idea is simple:

1. You find an Instagram Reel featuring a travel destination.
2. You DM it to @Expedia.
3. Expedia’s AI scans the video using computer vision and language models.
4. Within about 60 seconds, you receive a personalized itinerary, including:
   • Destination highlights
   • Recommended hotels and stays
   • Activities and local experiences
   • Suggested timeline
   • Booking links you can click to reserve immediately.

You don’t need to follow @Expedia to use the feature, and everything happens right within Instagram’s DM interface.

🌐 Why Is Expedia Doing This?

Expedia’s Chief Marketing Officer, Jon Gieselman, explained the strategy clearly.
80% of millennials use social media as a key source of travel inspiration. Yet the path from “wow, that looks cool” to booking a trip can be long and fragmented.

Trip Matching compresses this path. It lets Expedia meet users where they already are, on Instagram, then seamlessly transition them from discovery to booking.

The move also fits into Expedia’s broader push to integrate AI across its services. The company is partnering with OpenAI and Microsoft to bring conversational AI booking to platforms like Copilot and Operator. Trip Matching is a preview of how that kind of integration can reshape travel planning.

📝 Real-World Feedback: Testing Trip Matching

Several journalists and influencers have tested Trip Matching already. Here’s what they’ve found.

Thailand Trip Test

A Condé Nast Traveler editor sent a Reel showcasing a trip to Thailand.

• The AI returned a basic two-week guide including Bangkok, Chiang Mai, and Krabi.
• The itinerary listed general attractions but lacked deeper local recommendations.
• Some details were incorrect (for example, a typo “Koholananta” instead of Koh Lanta).
• Verdict: Useful as a starting point, but not yet highly detailed.

Edinburgh Foodie Trip Test

A Reel featuring Edinburgh’s food scene produced a more effective result.

• A three-day itinerary with:
  • Top dining spots.
  • Hotel recommendations (such as The Balmoral).
  • Sightseeing suggestions.
  • Clickable booking links.
• The AI also offered DM buttons to refine the plan (for example, “show more cafes” or “add whisky tasting”).
• Verdict: Stronger performance when the Reel contained clear, structured information about a destination.

🛠️ How to Use Trip Matching Effectively

If you’d like to try Trip Matching, here are some tips.

1. Choose the right Reel.
   Reels that name locations, attractions, or experiences tend to yield better results than abstract “vibe” videos.
2. Be patient.
   The feature is still in beta, so not every Reel will produce a perfect itinerary.
3. Use the DM buttons.
   After receiving the first itinerary, you can click suggested buttons to refine or adjust it.
4. Cross-check details.
   Verify hotel names, spelling, and dates before booking.
5. Expect ongoing improvements.
   Expedia plans to update and refine the tool as user feedback rolls in.

⚖️ Pros and Cons

Pros Cons Transforms social inspiration into bookable trips Some itineraries may lack depth Works directly in Instagram DM Occasional errors or misspellings No extra apps required Currently limited to public Reels Booking links provided Refinement sometimes needed

💡 Why It Matters for Travelers

For social-first travelers, particularly Millennials and Gen Z, Trip Matching removes friction from travel planning. It lets them go from watching to booking in one fluid flow.

It also reflects a larger trend. Visual media is becoming increasingly interactive. AI is shortening the loop between seeing and doing. Social platforms are evolving from passive discovery tools to active transactional spaces.

Trip Matching shows how this dynamic is playing out in travel, a space where social media inspiration is particularly powerful.

🔮 What’s Next?

Expedia’s marketing chief has stated that this is only the beginning. Future plans include:

• Integrating Trip Matching with Expedia’s own app and web experience.
• Extending the tool to other platforms beyond Instagram.
• Adding more sophisticated AI personalization.
• Exploring monetization models that might one day involve content creators.

📌 Key Takeaways

• Expedia’s Trip Matching turns Instagram Reels into personalized, bookable itineraries within Instagram DMs.
• It targets social-first travelers and reflects a shift toward blending content and commerce.
• The tool is in beta, with strong potential and some early limitations.
• For influencers and content creators, it opens both opportunities and questions around revenue sharing.
• For travelers, it offers a fun, fast new way to turn travel inspiration into reality.

Conclusion

Expedia’s Trip Matching is one of the most innovative new AI travel tools of 2025. It shows how companies are using generative AI not just to answer questions, but to drive meaningful actions.

For travelers, it offers speed and convenience. For creators, it prompts a conversation about the value of influence in commerce. And for the travel industry at large, it marks a glimpse into an AI-powered future where every Reel, TikTok, or post could become a booking engine.

If you’re curious, try it yourself. Find a Reel that inspires you, DM it to @Expedia, and see where your next adventure might take you.