Trip planning has more headstones in the travel tech startup graveyard than most other sectors.
But some survivors are learning from the past, making the most of today’s tech landscape to create fit-for-purpose planning and booking tools for today’s travelers.
There are various reasons why many of the first wave of trip planning sites failed - from customer acquisition costs to supply and technology limitations.
In the end, finding a viable commercial model proved tricky for many startups.
And not just for startups. None of the global giants have managed to create the go-to planning tool, despite access to IT budgets and a talent pool most startups could only dream of.
Live and inclusive
Transactional planning tools represent an addressable, global market worth billions.
As a result, investors haven’t entirely deserted the sector while the world’s biggest online travel agencies are thinking how to gate-crash the Trip Planning 3.0 party.
Today’s travel tech ecosystem is open, characterized by APIs, platforms and partnerships.
In the Trip Planning 1.0 era, less technology was available and product supply was constrained. Verticals were standalone, unable to connect.
Travel planning startups failed to deliver what the investors wanted – returns! –because they couldn’t deliver what the customers wanted – everything in one place.

None of the global giants have managed to create the go-to planning tool, despite access to IT budgets and a talent pool most startups could only dream of
Manuel Hilty - Nezasa
Personalization, albeit basic, took trip planning into the 2.0 stage, a holding pattern of sorts. But without sophisticated and integrated booking capabilities, plans proved hard to monetize.
The progression of trip planning towards 3.0 has happened as the buzz around the “travel super-app” has increased - a single customer touchpoint where all travel details are held in the same place and from where all elements can be serviced, pre-departure and post-arrival, in real time.
Customers want this. A Booking.com study from late-2018 found 57% of the 12,500 travelers from nearly 30 different countries wanted “a single app for all their planning, booking and travel needs.”
By developing proprietary systems to work with available APIs, travel planning tools can get creative with new, targeted features, all held in the same place.
Merchandising and retailing are ideas more usually associated with airlines, but are now part of the Trip Planning 3.0 playbook.
Upselling to existing customers is better than chasing new ones.
Travel firms with access to the end-to-end live itinerary can work on targeted upselling and generate truly incremental revenue streams by offering new and personalized inventory which fits into the existing itinerary.
But what happens if one element of the itinerary changes, such as a delayed flight or a re-arranged meeting?
Brands attempting to corner this space should consider this as part of their focus – bringing everything together to create a live itinerary which can automatically adjust in real-time when a single component changes.
As part of this shift from static to live itineraries, the platform needs to be able to handle any disruption seamlessly so that rebooking the transfers, or cancelling the lounge access, or adding another room night, can be taken care of by the platform.
They also need to allow travelers to manually adjust their own itineraries in a similarly seamless way.
Takeaway
Transactional planning sites are competing against OTAs and other intermediaries in a land grab to capture bookings across the entire journey, from the initial search phase to the increasingly important post-arrival in-destination business.
But the OTA’s ability to offer travelers a one-stop-shop for personalized total trip planning is limited by their not knowing what the traveler has purchased outside of their walled gardens.
Unless the traveler buys the flight and hotel at the same OTA, there will be gaps in their knowledge of the traveler’s itinerary, a rare chink in their armour.
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Many planning sites are able to aggregate feeds from different suppliers into a static holding page.
But without booking capabilities and targeted up-sell options, based around a live itinerary, the graveyard still casts its shadow.
Let's face it: today’s travelers expect more than a static PDF page timetabling their day.
The often-overlooked reality is that travel plans are fluid. They can change in advance or in the moment.
Itineraries are, or should be, fluid, able to manage any disruption to any component of the trip, in real-time, through a single point of contact.
The technology, the demand, the inventory is all here.
The next wave of travel planning – hyper-personalized, with booking, live itineraries and in-destination capabilities – should be arriving soon.