TripHobo: For When You Know Where You’re Going But Need Help With An Itinerary

by SharonKurheg

When you’re planning a trip, it’s easy to decide where you want to go. Paris! Capetown! Beijing! San Francisco! It’s figuring out what you’re going to do once you get there that can be the problem.

A lot of people will ask for advice on forums, groups or message boards, and it’ll often look like this:

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I’m all like, “Really?” (Joe: Those requests are definitely from aliens)

That request is SOOO open-ended. It makes me want to ask:

  • Who is “we?” Age of the people who are going?
  • How long are you staying?
  • Have you been there before? If so, what did you see? Do you want to see any of those again, or no?
  • What do you like and dislike? How do you feel about history? Walking tours? Broadway shows? Other kinds of shows? Museums? Shopping?
  • Are you comfortable taking the subway or would you walk and/or take taxi/Lyft/UBER everywhere?

But kindhearted people will give every sort of answer, from the Statue of Liberty to Harlem and everywhere in between. And the sad thing is, most of the suggestions won’t even be 2nd tier considerations for some people because of reasons.

OR you can go to a website that’s specifically made to work with you for itineraries that are custom made for the needs and likes of you and your party.

It’s called TripHobo and it touts itself as the “World’s Smartest Vacation Planner.”

Well, that’s quite a self-made moniker. I don’t know if I would go THAT far, but it’s certainly helpful.

TripHobo’s home page gives you a chance of Plan Your Next Vacation and Find Tours & Activities. We’ll save the tours and activities for another time and just focus on building your own vacation…

First, you tell TripHobo where you’re going and when you’re going to be there:

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Then you can tell the website how important specific categories are you to, and who the travelers will be:

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After that, you can add your arrival/departure info and accommodations, if you’d like, which will help TripHobo organize what you should see when. However, it’s not mandatory. Heads up that the search function is not super intuitive. For example, it found the New York Marriott Marquis but couldn’t find it as Marriott Marquis New York, which, I’m sure, would be a common mistake.

Next up, you’ll see a LONG list of places that may or may not be on your wish list of places to go. Stuff like the Empire State Building, Statue of Liberty, Rockefeller Center, Times Square. The Metropolitan Museum of Art, the High Lines, Children’s Museum of Manhattan, etc. Lots of off the beaten path stuff, too. As you choose each location, you have an option to add a tour or not.

Once you’ve chosen what you’d like, TripHobo gives an overview of an itinerary for you:

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They also offer an editable view that includes how long it’s recommended to stay, how long it will get from Point A to Point B, a space for notes, what else is nearby whatever location, etc.

Overall, I think the site is moderately helpful, at least in terms of learning some of what’s available in a given city, and perhaps in making an itinerary based on your interests.

The website does have one relatively big drawback in that you’re limited to the cities it has available. So while New York City has a lot of options, Mondsee, Austria has 9 places listed and then starts adding sites in Salzburg, which is almost an hour away. Bithlo, FL has nothing listed (which, in all fairness, is accurate). But as long as you’re looking at major or even moderate-sized cities, you should be fine.

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This post first appeared on Your Mileage May Vary

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