Journey-rative AI: How can LLMs generate the most perfect itinerary?

I have been thinking a lot about how Generative AI will impact my life and recently when i was away for vacation, I found something that excites me and other travelers who enjoy planning for their trip - THE PERFECT ITINERARY! Folks would probably have tried putting together personal itinerary on Google My Maps (as in the Image above) - While that is a really good tool, the effort one has to put in navigating the tools might not be the best part of the trip.

When swapping stories & itineraries with other travelers, it struck me that there is a wide range of itineraries even when everyone is traveling to the same place. Everyone might have followed the same few ‘Suggested Itinerary’ but the things that people actually do vary so much. Depending on how many people you have in your party, who they are, what they enjoy doing, fitness level, the possible permutations increase quickly. Take kids-friendly as an example, every kid is at different development milestones, with different interests - so the broad kids-friendly activities are usually not sufficient. I find myself envying families where the kids are slightly older and could go on longer hikes or not having to stop for nap ??

Lonely Planet/Rough Guides of the world, Suggested Itinerary/Things to do in (insert location) will be able to give a rough idea of the various points of interest, but things like how many days to stay, how to split time between the different things to do, special opening hours, activities requiring additional planning… are not (yet) as easily planned for in advance. This is especially true if one is looking for authentic, local experiences after ticking off the “must-do” checklists.

The best way to maximize your time there is still the old-school way - rocking up to the local tourist information office and talking to locals, going through the brochures and making plans on the fly. While this exudes old-world charm, I wonder if some of this research could be done in advance so that the planning could have been more seamless.?

There have been multiple instances where we wished we could have spent more time than we had planned for in certain places or even simply reordered our itinerary to be able to catch local festivals, markets etc. In hindsight, it is very easy to dismiss it as “We’ve booked too many nights in town A” but the real dilemma is knowing that in advance and the fear of not spending enough time in that place. And if you are someone greedy like me, who wants to see and do as much as possible in 2-3 weeks, you would probably understand this ‘traveler’s remorse’.

There is a growing demand for truly-personalized itinerary planning, especially as ‘revenge travel’ coincides with macroeconomic headwinds. The traditional resources discussed above are good starting points, but insufficient to meet increasingly higher expectations from travelers. Organizations that could provide tailored planning at scale will likely be able to gain share and loyalty with travelers.

Google Search results are illuminating in that the key theme across most industry predictions in 2023 is personalization. These are some examples of the growing macro travel trend, most of which require tailored and bespoke planning, especially if the traveling parties have different interests. These are not necessarily niche trends either, with up to 50% of travelers indicating interest in some of them (Guesses, anyone?)

1. Transformation Retreats: Deeper & more meaningful experiences to overcome grief, identify life’s meaning, learn (architectural, wildlife conservation, environment…)
2. Sustainable/Eco-conscious Tourism: Hybrid flight-light travel, Electric road trips (Planning around public transport schedules, terminal/platform changes, charging stations…)
3. Well-being Retreats: Identify destinations with amenities offering Adaptogenic (Active Ingredients in plants/herbs) menus, Psychedelic (Mental Health), Sleep (Itinerary that maximizes well-restedness, instead of taking additional 2 days off to recover from your 1-month travel) or Silence (Remember the blissful peace & quiet during CoVid?)
4. Set-jetting + Art/cultural festivals: Combine filming locations with nearby locations or multiple TV shows/movies into one itinerary
5. Indigenous/Aboriginal/At-risk communities: Integrate into and learn about different ways of living, maximizing the impact to local communities (not intermediaries)
6. Bleisure: Instead of tacking on a few days at the end of a business trip, remote working enables a holiday-first mindset with work around it. Hence, requiring flexibility in planning things to do around work hours, going beyond the usual tourist attractions (that needs more planning)
7. Travel More, for less: Macroeconomic headwind means that every dollar has to stretch more. The other headwind is demand far outstripping supply, putting upward pressure on popular destinations. Increasingly, I know more and more people who pick a destination that is likely to fit within their budgets, not the other way round, due to these 2 headwinds.

Independent travelers are still the biggest (80%) & growing segment in the travel rebound. Even within package holidays, the fastest-growing and most lucrative segments are likely within the segments such as wellbeing and indigenous travel. Hence, the quest in finding the perfect itinerary is still relevant for most travelers.

This is where Generative AI might be able to curate tailored itineraries at scale. After that, the other large opportunity is definitely integrating across booking surfaces & things to do and bringing the planning to actual experiencing.

What are the key metrics that are relevant for you when planning for your trip? Please comment so anyone building a product out of this could have the right parameters to design the right user interface.

Thank you for reading!