The Problem With Planning A Trip To NYC…Or Any City For That Matter

17 Jan 2011 in Startups & Technology

Addicted To Travel Teephoto © 2010 Jorge Quinteros | more info (via: Wylio)













Yes, I am a travel addict.

There are a million cool things to do in New York City. Tons of great restaurants to dine out at, lots of places ‘you just have to see’, shows to watch, stores to shop at….and on and on the list goes. Without question, “travel” was something that stands out as a theme of 2010 for me personally. My last trip of the year was to New York City to watch the ball drop on New Year’s Eve. Looking back on it (and since I love studying how technology can make life easier), I started thinking: I really wish there was a site that had specific daily itineraries to choose from for cities.


My friends and I were in Times Square for 3 full days. It was my best friend Stephjee from the Washington Semester Program, her twin sister Pauline from Holland, and me. Of course, we had a lot of decision making to do. There are so many options that we spent a lot of time just wondering what to do on New Year’s weekend. In general, we wanted to visit the must-see sights of Manhattan, go shopping, go to dinner, and have fun.

There was no easy way to plan this. In my research, I’ve only come across sites that listed scores and scores of tips or really long lists of great places to eat, for example. We decided to go shopping up and down 5th Avenue on Saturday, do some sight-seeing on Sunday, and use Yelp to find good restaurants for dinner. While I’d like to think of myself as a somewhat savvy early adopter of new technologies, I could not find the perfect site that made planning out a single day easy. Frankly, I was craving a site that recommended decisions for me. Think of marrying Hunch‘s personalized recommendation technology with Dopplr‘s extensive knowledge of cool things to do in cities around the world.


As I see it, the problem at large is that there are a bunch of long laundry lists of great things to do, great restaurants for dinner, etc. But they are mostly unorganized and too lengthy to sift through. To continue with NYC as an example, I couldn’t find any ‘pre-selected day itineraries’ that logically plan out a step-by-step agenda to assemble the killer weekend in Manhattan.


So, I started to deepen my research. There are some services that attempt to solve parts of this problem. You can try to leverage the recommendations that are available on Foursquare, Yelp, various blogs, etc. You could start with a Google search for “top 10 things to do in NYC” and then make your own agenda for a few days in Manhattan.

If you’re looking for something more specific to put on your agenda – for example, the highest rated clubs in NYC – you can do a Yelp search for “clubs” near “Manhattan” and then filter based on such factors as distance, price, if the club has a coat check, etc. Once you’ve arrived at a physical location, you can also check-in and read the Foursquare tips for that location (assuming that there are in fact tips…not all locations have some).


Recently, a company called Nextstop tried to tackle this problem with a more complete solution. They came pretty close. In this post, TechCrunch pitched Nextstop as a service that “mixes social recommendations with search and adds a reputation system and elements of gameplay.” Nextstop started with the goal “to make it dramatically easier to discover great things to do anywhere in the world” before getting acquired by Facebook for a cool US $2.5 Million in cash. However, the site was shut down this past September and is no longer available.

So, what other travel planning sites are trying to solve at least part of this problem? Well, there’s the huge site Lonely Planet that I like to think of as the ‘classic veteran’ in the space. But for NYC alone, they have a list of 124 sights you need to see, 135 restaurant options, and 150 choices for entertainment. It is hardly what I would call an ‘automatic agenda creator’. And with so many options, it certainly does not make deciding on a day plan any easier. I also found a blog called “Travel Plan Idea” that has a sizable list of cool plans they’ve assembled from over the years.

But using either of these sites requires a bit of tinkering on the site, and there are just so many choices. So, how would I fix this problem?


To continue with the NYC example, I thought of something like a recommendation engine for a day in Manhattan. In my dream world, I would be able to visit this site, filter by city, type in a starting address, and then choose from a set of maybe 5-7 of the highest rated “day plans” for what to do on a day-to-day basis in the city.

The kicker would be if ‘well known’ people or ‘city experts’ posted their “perfect day/weekend in Manhatten”. Imagine being able to see what Foursquare’s Co-Founder/CEO Dennis Crowley’s perfect 3 days in NYC would be. Since Dennis is an expert on the nooks and crannies of what I consider to be the greatest city on earth, his ‘ideal weekend’ would be something I’d love to replicate for myself and a few friends the next time we go to NYC. From where to eat breakfast to recommending that last post-clubbing-meal after going out, being able to see every detail of the day planned out would make the trip that much easier to organize.

Right now, Dennis has 4 pages of “tips” on his Foursquare profile. That means he’s written over 50 tips for different places he’s checked in at. But they aren’t organized into an easy-to-consume list, and they certainly don’t make the process of choosing between an abundance of options for what to do in NYC any easier. As for other Foursquare users, although Twitter’s creator and Co-Founder Jack Dorsey (who told Kevin Rose recently in an interview that he is addicted to understanding cities) is an expert on cities like San Francisco, he has only 15 tips for places he’s checked in at.


So, how would the ultimate travel site be set up? Would it be best to crowdsource this? Instead of one company focusing on filtering through all the great things different cities offer and creating specific day plans, could uber users just create their perfect trip and classify it under different categories of trips (with the best/most popular itineraries getting voted to the top)? One such category might be “the perfect weekend for a shopper-centric-tourist”.

What would using the site feel like? Would you be able to choose between type of trip (e.g. walking-oriented, museum-heavy, great food, etc.), or something different? Would you be able to answer a list of questions and then have the perfect weekend trip automatically assembled and then recommended for you?


In a couple days, I will profile 5 startups in the ‘social travel space’ that are working on solutions to parts of this problem. I hope you will check it out and tell me which one you prefer to use, and why!

I have to leave on this note: New Year’s Eve was something like my 10th time in NYC, and I still would find a site like this very useful. So, any recommendations? If a site exists that you think solves this problem, please share it in the comments!

  • Info

    Hey, I am coming to New York City this week. I get in on Wednesday afternoon. Are you going to show me the sights and sounds? Heck, you might not even be in NYC by then! You travel as much as I do. And I LOVE IT!

  • JohnExley

    RICKY. Ahhh, no kidding you are headed to NYC? So appropriate, right as I publish this post on NYC…hahaha.

    Just last night I was talking with my parents about this. I was actually wondering if there might be a way to get out to NYC tomorrow night. But, ultimately I can’t make it happen. I’m saving money right now and planning a trip there next month. Would have been impeccable timing though, right? I’ll be up there soon enough, and with your travel-holic lifestyle I know we’re bound to cross paths!

    What are you doing in NYC? Would you use a site/feature like the one I described here in my post…something that would automatically create a ‘day itinerary’ instead of just feeding you somewhere between 20-5,000 cool things to do/see/eat?

  • Brittany Laughlin

    Great post John – the travel search and planning experience is still super fragmented and requires a ton of digging. It’s surprising because we now live in a world with more data than ever before. At gtrot our core component is sharing travel with friends – from this social layer we’re working to create context and serve up the best travel recommendations based on what you like and what people you trust (ie: Dennis Crowley, Jack Dorsey or Anthony Bourdain recommends). I’d love to get your thoughts on the site and see if we’re getting closer to making your trip planning easier.

  • JohnExley

    Brittany, it is really great to see a founder jump into the comments. Pumped to meet you. I was clued into gtrot on Twitter yesterday by a friend Chris LoRusso (!/lorusso), but have not checked it out in depth yet! I too agree that it’s surprising how ridiculously unorganized a lot of the data is…seriously, a list of 100 cool things to do in a particular city does not help me make decisions too well.

    Because you took the time to leave me a comment, you have my word – I will check out gtrot, and I’ll let you know my thoughts. Keep hustling Brittany, you’re involved in a pretty exciting space IMO.

  • traviskatz

    Hey John – this is one of the more thoughtful posts I have seen on the topic. Thanks for posting! When traveling, I think most of us want to make every moment count, and want to really soak up the best of what a city has to offer. The challenge is that every person is different, and that as a result the kind of things I like to do may be very different from yours, depending on all sorts of factors from age, interests, budget, whether I am single or married, with kids or without. Like you point out, most travel sites focus on gigantic laundry lists full of reviews from people I don’t know and am not sure I really trust.

    We started a site called Gogobot to try to help filter out the noise and get me to the information I need by tapping into my friends through Facebook and Twitter. I actually spent 3 days in NY in December and asked my friends for tips on good bars and restaurants in the Village and the Meatpacking district. I got more than 40 responses, all of them spot on for what I like. You can check it out here: ( It was really mind-blowing. Would love to invite you to check it out as part of your research.

    Not sure we deliver 100% on what you are looking for, but I think its a step in the right direction ;)

  • JohnExley

    Travis, wow – I had an affinity for Gogobot already after playing with it a little and reading Arrington’s praise for your company. But, now? After having the founder himself stop by and dive into the comments?

    Even more so.

    Saying all that, your example is certainly ideal but not necessarily something that every Gogobot user can experience – yet. I imagine you have won over a bunch of your friends to contribute and use the site, so when you as the founder ask for tips, you will get some really amazing data.

    If you and I have the same preferences, then that data from your friends is probably useful to me as well. However, as you point out – every person is different. So, I need to get my trusted friends using Gogobot before I will have a similar experience to yours.

    Right? And while it does not directly solve the problem I have highlighted here IMHO, I cannot disagree with you that Gogobot is most definitely a step in the right direction. I’ve been a user for about 6 weeks I believe.

    Kudos to you for executing and helping to solve problems like this. As an aspiring entrepreneur, I look up to people like you. Keep chasing the dream bro.

    And: Travis, I published my follow-up piece yesterday with the 5 companies to watch in this space. Yours was on my list before this comment from you. I included part of your comment here, extending my review.

    This comment mattered to me. Thank you man, best of luck with Gogobot. Stay hungry. ~ John X