Ten years ago a trip usually started on a flight‑search site and ended on a beach. We booked flights and hotels in separate tabs, printed our reservations and hoped nothing went wrong. Today’s travellers expect much more – not just a place to sleep, but inspiration, planning, activities, safety and support. online travel agencies with AI

Digital travel platforms are answering that call. Giants like Expedia, Booking.com and Trip.com are no longer mere booking engines; they are becoming full‑service experience platforms that combine AI‑driven trip planning, immersive tours and activities, and embedded insurance, all inside a single app. Here’s how they’re doing it.

The tipping point: travellers want a concierge, not a search engine

Modern consumers are flooded with options. Social media shows us hidden waterfalls and rooftop bars, but the sheer volume of information can be paralysing. Platforms realised that to keep users engaged, they need to guide them all the way from inspiration to in‑trip support. This trend isn’t just about convenience; it’s a fight for loyalty. Travellers who can plan an entire trip within one ecosystem rarely stray to competitors, and their data helps companies refine services even further.

Expedia Group: bundling cars, activities and insurance with AI fairy dust

Expedia started as a flight‑and‑hotel marketplace. Recently it has positioned itself as an AI‑driven travel operating system. At the company’s Explore event in May 2025, it unveiled a suite of new tools and APIs designed to make travel more seamless. On the business‑to‑business side, Expedia’s Private Label Solutions now offers APIs for cars, activities and insurance, giving partners access to over 170,000 experiences worldwide and enabling trip protection during booking. These APIs complement a forthcoming air API so partners can package flights, hotels and car rentals in one booking flow. A new reservation management API promises to save hotels millions of hours by automating changes, payments and data recovery.

On the consumer side, Expedia has embraced generative AI. Its Trip Matching tool turns Instagram reels into personalised itineraries; travellers can share a reel and receive destination suggestions, hotels and activity ideas in real time. The company also launched an AI agent on Hotels.com that merges discovery and service into a single conversational interface. Users can ask about destinations, see dynamic pricing and photos, and modify existing bookings. Expedia is integrating this agent with OpenAI’s Operator platform and Microsoft Copilot, bridging the gap between AI inspiration and actual bookings. Behind the scenes, its Artificial Creative Intelligence system optimises and creates short videos, moderating over 400 videos per day to keep content fresh. In short, Expedia is weaving AI into every stage of the trip – from inspiration to booking modifications – while giving partners the tools to add cars, activities and insurance to their offerings.

Booking.com: connecting stays, experiences and peace of mind

Booking.com once focused on lodging; now it wants to be travellers’ digital companion. In late 2024 it rolled out a trio of AI‑powered features: Smart Filter, Property Q&A and Review Summaries. Smart Filter lets travellers describe their dream accommodation in natural language (for example, “a honeymoon hotel with a rooftop bar and canal views”), and the system applies relevant filters automatically. Property Q&A pulls answers from listing information, photos and guest reviews so users can ask specific questions such as whether a property has EV charging or accepts large dogs. Review Summaries condense key points from dozens of reviews, highlighting what matters most – accessible parking, good Wi‑Fi or wheelchair accessibility – and will be rolled out after further experimentation. These features shorten the research phase, letting travellers spend less time comparing and more time dreaming.

Another headline is Booking.com’s AI Trip Planner, which launched in the US in June 2023 and expanded to multiple countries in 2024news.booking.com. Travellers can ask broad or specific questions and receive itinerary suggestions that include attractions, accommodation and on‑trip recommendations. For example, you might ask, “What’s the best way to spend three days in Kyoto?” and the planner will propose temples, food tours and hidden cafés. The company has hinted that this AI will become even more proactive, helping travellers navigate disruptions such as flight cancellations.

Yet perhaps the biggest shift is the insurance layer embedded into every Booking.com stay. According to an industry webinar summarised by Hostaway, every Booking.com reservation now includes liability coverage of up to $1 million for hosts and neighbouring properties. Damage protection up to $1 million is slated to roll out later in 2025. The insurance is automatic – hosts don’t need to opt in or pay extra – and covers bodily injury and property damage claims. This offering positions Booking.com not just as a booking site but as a risk‑management partner, which is especially appealing to vacation rental owners worried about liability.

Booking.com is also expanding beyond stays with attractions and tours. The company’s attractions platform allows travellers to reserve tickets for tours, museums and theme parks with instant confirmation and free cancellation on many options. The inclusion of attractions is part of Booking.com’s Connected Trip strategy, which aims to combine flights, stays and experiences under one umbrella; in 2025 the company reported that attractions bookings more than doubled year‑over‑year. As attractions become a new battleground among travel companies, Booking.com is building the payments and infrastructure to support a full journey.

Trip.com: a super‑app approach with TripGenie and Travel Smart

Trip.com, the global arm of Chinese travel giant Trip.com Group, is pursuing a super‑app strategy. Its home page already offers hotels, flights, trains, cars and attractions in one place. The company’s AI assistant TripGenie takes that integration further. The TripGenie landing page promises over one million attractions across more than 180 countries and offers advice for every step of the trip. Users can ask it to plan a four‑day itinerary in Thailand, find a boutique hotel near the Eiffel Tower or locate family resorts in Hong Kong. TripGenie creates custom itineraries, provides flight and hotel bookings and remains a companion after booking; travellers can ask follow‑up questions and get real‑time support.

An interview with Trip.com executive Wei in PhocusWire reveals how integral TripGenie has become. Wei noted that travellers using TripGenie spend about 20 minutes or more in the app, double the time of users who don’t engage with itphocuswire.com. The tool has transformed from a basic Q&A bot into a versatile virtual assistant that can handle conversations, book services, generate itineraries and even assist after the trip. This evolution increased order conversion and user retention; TripGenie now handles reservations, itinerary planning and post‑sale queries, effectively covering the entire travel journey.

Trip.com also embeds insurance deeply into its ecosystem. On its US site, the company sells AXA Travel Insurance with two plan options. The Vacation Package Plan offers 100 % trip cancellation coverage, $50,000 in emergency medical expenses and baggage protection up to $1,500us.trip.com. The Post‑Departure Plan includes $10,000 in emergency medical expenses and baggage cover. Trip.com emphasises that it has protected over 1.9 million customers in the past two years. For travellers outside the US, Trip.com’s partnership with AXA Hong Kong & Macau introduced Travel Smart, an exclusive program with one‑click purchase. Travel Smart plans cover medical expenses up to HKD 1.5 million, personal liability up to HKD 2 million and compensation for trip delays and cancellations. The partnership integrates insurance purchase seamlessly into the booking flow; users can manage policies and claims via AXA’s app. Trip.com’s vice president Zhe Wang said the goal is to provide peace of mind while keeping booking frictionless.

Trip.com’s super‑app also emphasises activities. TripGenie has access to over one million attractions, and Trip.com’s tours and tickets section offers theme parks, city passes and unique experiences. The TripGenie upgrade announced in 2024 (which was accessible earlier this year) added collaborative editing, enabling friends to co‑plan itineraries, integrate booked flights and hotels into daily schedules, and receive real‑time flight status and hotel check‑in alerts. Data showed that travellers using TripGenie were 30–40 % more likely to return, with order conversions doubling and users spending 20 extra minutes in the app (information noted in earlier Trip.com releases). These numbers underline how integrated experiences drive loyalty.

What it means for travellers

So why should any of this matter to a traveller planning their next vacation? There are several implications:

1. Less planning fatigue: You no longer need to juggle multiple sites or spreadsheets. AI‑powered planners like TripGenie and Booking.com’s Trip Planner can digest your preferences and build an itinerary, complete with flights, hotels and attractions. Expedia’s Trip Matching even turns your Instagram mood board into a plan.
2. More personalised experiences: By analysing past trips and real‑time preferences, these platforms suggest experiences you might not have discovered yourself. Smart Filter or TripGenie might nudge you toward a rooftop bar with canal views or a secret stargazing tour when you told them you’re into noctourism.
3. Embedded safety net: Insurance isn’t an afterthought anymore. Booking.com’s automatic $1 million liability coverage protects hosts and guests, while Trip.com’s AXA plans cover trip cancellations and medical emergencies. This reduces the anxiety associated with “what if something goes wrong?”.
4. Integrated experiences: Adding tours, theme‑park tickets and local activities into the booking flow means you can lock in sold‑out experiences in advance and often get better prices. Expedia’s activities API boasts 170,000 experiencestravelandtourworld.com, and Booking.com’s attractions bookings have doubled.

Is the journey over?

The race to become an end‑to‑end experience platform is far from over. Competitors like Airbnb are reviving their experiences product, while Google and Meta continue to integrate travel research into search and social feeds. Privacy concerns, algorithmic bias and the risk of “walled garden” travel where options outside the platform are hidden also loom. Nonetheless, the direction is clear: travel platforms want to be with you from the moment you dream of a destination until you’re posting beach photos – and even after.

For travellers, this evolution offers convenience and personalisation at the cost of surrendering more data. Whether you’re comfortable with that trade‑off is a personal decision. But if there’s one silver lining, it’s that the next time your friend sends a sun‑drenched reel from Bali, an AI might transform it into your own paradise itinerary before you can type “jealous.”