2025: AI-Powered Itinerary Personalisation Becomes the New Battleground in Travel

Personalisation in travel planning has evolved beyond targeted emails and “recommended for you” packages. In 2025, the new frontier is AI-powered itinerary personalisation, where generative AI and behavioural models curate hyper-specific, moment-by-moment experiences. Whether for leisure, business or bleisure travel, LLM-backed platforms are now capable of building travel itineraries that adjust dynamically in real-time, understand individual travel histories, and prioritise user goals such as relaxation, exploration or wellness. As consumer demand for seamless, tailored journeys skyrockets, this has become the battleground for OTAs, DMCs, hospitality brands and even DMOs.

According to a report by Skift, 74 % of travellers now expect itineraries to be personalised based on both real-time data and past preferences (skift.com), while Google research shows users are 60 % more likely to book when presented with adaptive, AI-curated day plans (blog.google).

Why 2025 Is a Tipping Point for Personalised Itineraries

LLM advancements. GPT-4o, Gemini 1.5 and Claude 3 Opus now support trip planning with deeper contextual memory, reasoning and regional nuance.
Cross-platform data unification. Providers like Amadeus and Hopper now aggregate flight, accommodation, weather, events and consumer behaviour into unified traveller profiles (amadeus.com).
API-powered ecosystems. AI engines are now interoperable across booking engines, calendar apps, ride-hailing, loyalty systems and more, enabling true “life-aware” travel plans (phocuswire.com).
Demand from Gen Z and Millennial travellers. These groups expect curated experiences, not generic packages. 68 % say AI-generated trips feel more “in tune” with how they travel (booking.com).

What Personalised AI Travel Looks Like in 2025

1. Real-Time Reactive Itineraries

Plans now adjust in the moment — when it starts raining in Florence, the AI reschedules the walking tour, rebooks a gelato class indoors and pings you a map to the venue, all while alerting your hotel you’ll be late for dinner.

2. Hyper-Specific Daily Plans

AI-generated itineraries can accommodate constraints like “low-impact travel,” “gluten-free meals,” “15-minute rest breaks” or “Instagrammable stops every hour.”

3. Goal-Based Trip Design

Instead of just inputting cities and dates, users describe goals like “recharge from burnout” or “history-heavy 4 days with local food focus,” and receive itineraries reflecting those intents.

4. Memory Across Trips

Platforms like TourGuides.ai and Airbnb’s AI Concierge now remember user styles, accessibility needs, and loyalty perks across multiple trips (tourguides.ai, airbnb.com).

Case Studies

Trip.com’s TripGenie. Offers daily re-routing suggestions based on real-time crowd data, air quality, and weather. Customises for solo travellers vs. families with children (trip.com).
Expedia’s AI Assistant. Integrates with user Gmail and calendars to pull in events, recommend hotel timing and pre-book dinner reservations (expedia.com).
Google SGE Travel Mode. Builds interactive maps with itinerary items layered in, colour-coded by type and time (techcrunch.com).

Implications for the Industry

Stakeholder	Opportunity	Risk
DMOs	Power AI agents with local datasets to own discovery layer	Get bypassed if experiences aren’t API-accessible
Tour Operators	Offer ultra-flexible modular tours	Rigid packages will appear outdated
OTAs	Upsell smart bundles like “skip-the-queue plus airport lounge”	Fail to differentiate if personalisation feels generic
Hospitality Brands	Inject unique offerings (e.g. chef meet-and-greet) into agent feeds	Lose guest mindshare to OTA-owned journeys

How to Get Ahead of AI Itinerary Expectations

Enable live inventory feeds for tours, classes and events via standardised APIs (e.g. Viator, Bokun).
Tag experiences semantically (e.g. wellness, sensory-friendly, LGBTQ+-friendly) to improve relevance.
Ensure listings are machine-readable by submitting to agents or schema.org-enhanced directories.
Encourage feedback loops so agents learn what travellers liked — and disliked — post-trip.

Looking Ahead

AI-generated itineraries are evolving from simple day planners to dynamic, multi-modal life companions. In the coming 12 months, we’ll see cross-border continuity (e.g. rebooking transit during strikes), emotion-aware adjustments (“suggest slower pace after poor sleep”), and multimodal exports to wearables or in-car voice assistants. Those in the travel industry who embrace data-sharing, open APIs and AI-native thinking will thrive. Everyone else risks becoming invisible.

2025: AI-Powered Itinerary Personalisation Becomes the New Battleground in Travel