Tripsy’s iOS 27 update includes smarter imports, on-device AI insights, more

The travel planning app Tripsy has released an update this week, enhancing its compatibility with the latest version of iOS, iOS 27. The update introduces several new features, including iOS 27’s extra-large widget support, a new Smart Import tool, and AI-powered functionalities. At Apple’s showcase event, the app was mentioned briefly alongside iOS 27’s Siri AI advancements. Apple followed up with an official press release, highlighting Siri’s upcoming ability to directly add restaurant recommendations to Tripsy trips.

Tripsy version 3.10, the updated version, offers users several AI-driven tools and compatibility with iOS 27 features. Among these, the Smart Import feature stands out, allowing users to transform a variety of content types—links, documents (including PDFs), saved emails, screenshots, Instagram and TikTok posts, and pasted text—into places and reservations within the app.

Smart Import also supports the importation of lists and guides from Google Maps and Apple Maps. Users can then select which suggested items they wish to include in their trip itinerary.

Additionally, the update brings Smart Insights into the mix, leveraging Apple’s Foundation Models to analyze attachments such as documents and emails on-device. This feature can surface useful trip details like baggage allowances, breakfast options, parking, cancellation policies, and costs. It’s worth noting that both Smart Import and Smart Insights are accessible through a Pro subscription, which costs $59 per year or $299 for lifetime access.

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