Travel Planning nightmares
Shared by AndyDent-Touchgram · 94d ago · 6 comments

I've met a few travel-oriented startups here on Pioneer and wanted to highlight what's one of the biggest pains for us, as my wife has started planning a holiday. I would love to hear of someone with a realistic solution. We would pay at least $200 pa for something that made this easier than my spreadsheets.

We're trying to plan a multi-week EU holiday including visiting family in the far North of Scotland.

Just to start with, considering that leg, we are juggling ferries, choice of airport, how to get from one to the other.

Holiday planning is often not about planning optimal routes but looking for most enjoyable and that often makes things much more complicated.

For example, the amazing Seat61 says this is the "World's best train journey"

So now I am trying to work out if we could include that. A viable option is to do a one-way car hire from Fort William to Inverness, keeping the car for the entire duration of visiting my brother (sometimes it's a lot cheaper to do a single one-way hire and have a car sitting idle for 2-3 days than to incur the cost of two one-way penalties).

We would at least have to align times for flight arrival, transfers, train, car hire and ferries. That's just in the first 2 days!

Just putting this out there in case anyone amazing is working on it and has something usable within the next few months.

I don't think this necessarily needs to be a scraper - it could be something where I just drop a bunch of proposed legs in and it does the juggling for me. Or, even better, prompts "you need a way to get from X to Y within this time frame".

kendsouza · 93d ago

Check out includes trains, buses, ferries, cars, flights etc

AndyDent-Touchgram · 90d ago

Thanks, Ken, rome2rio has come up with some interesting suggested connections.

ashwinsk · 93d ago

I'm an avid traveler myself (albeit a lot of solo journeys) and I have pretty much staved off travel agencies, apps and aggregators entirely as they always recommend the same boring locations with really tight schedules. But I have a personal system which worked for me during my trips across Europe and the Middle East.

In the case of my 4 day long trip to Italy which I went with my friend, we decided to randomly choose an initial spot and move from there. I had a budget of 400 euros for the entire trip including activities, hotels and travel, none of which was booked in advance. The only things we booked were the flight tickets to our first location (Lake Como) via Milan. In spite of this, we managed to go to Bellagio, Brunate, Milan and even Venice where we managed to visit a few museums, eat at decent restaurants and even attend a private art exhibition by an American collective out of Marfa, Texas (it was a bit grunge for my taste). All of this was kept under budget and we were back on time to attend classes for the following week.

For the travel, we used Trainline, Vueling & Ryan Air; For the hotels, we used A & O and some good ol fashioned google searching. For the activities, we resorted to asking the locals what to do (even though we didn't speak the language) either by speaking to them on the street or through meetups hosted by groups on Meetup and Couchsurfing (I highly recommend these.)

My point here is that it is best to travel off the beaten path using local suggestions rather than pre planning a trip. An app or an agency are built for optimization and for people who want a token trip rather than an experience. The best experiences often comes from places that are hidden from the eyes of tourists. I personally plan my trip along the way and never really think about pre-planning. A little dangerous for sure, but it has worked out well for me so far.

Now coming to the building of a solution, I agree with you ideas on auto planning your trip as it is definitely useful for people who don't have time to micro plan everything. Maybe if there was a local-powered aggregator (perhaps a service to meet locals either virtually or physically in order to find and create a journey map of the best things you could do from a more informed perspective) coupled with a service such as the Isochrone API ( for adjusting the number of places you can go to in a given amount of time. Maybe someone will implement this here. Who knows?

AndyDent-Touchgram · 93d ago

The Isochrone API is interesting. I'm now putting it away on a list of cool stuff to play with one day as I have way too much to do in my little time. I've enough geospatial processing experience that I could get seriously distracted playing with it.

AndyDent-Touchgram · 93d ago

I'm married to someone who plans trips to pretty much every single day of an 8 week itinerary. My only input is being the planning assistant ensuring things are feasible, and driving. I've found myself doing 150km/hr on Slovenian highways under construction to get between two bookings on a day as a result.

Have been to a lot of the places you mention and that kind of relaxed lifestyle is something we envy Europeans. When holidays start with 26-35hrs of airline travel it's a bit more pressure to plan.

ashwinsk · 93d ago

That airline travel time must be a menace! As for the speeding, I can understand that as cancellations are quite the mess on any budget. Still... must've been fun ─=≡Σ((( つ◕ل͜◕)つ