Getting Good At Cities II


(I’m writing something every day for #100days. This is post 24/100.)


Every time I travel somewhere new in North America, I use this system to figure out where to go.

It’s a system that will lend itself to obsessives, to analysts, to researchers — more so than it will give you an immediate shot of what you need.

But it’s worked for us in Portland, Seattle, Bozeman, Missoula, Jackson, Santa Cruz, Ojai, Russian River, San Luis Obispo, Tampa, Bend, Boulder, New Mexico (Santa Fe) and Sea Ranch.

1 — TripAdvisor

>> Search by place, sort by ‘Top Rated Things To Do’.

This is always my first stop. The lowest common denominator of what people like to do in a place.

TripAdvisor isn’t a to-do list in order. In fact, it might be more useful as a ‘not-to-do’ list.

Take San Francisco for example. According to TripAdvisor, the #3 BEST thing you could do in San Francisco is take a Segway tour.

But TripAdvisor sets the baseline.

It’s a rough map of everything available. The first data set you can use to triangulate the best places.

In a separate file, make a list of anything that jumps out at you as interesting from this first Trip Advisor view.

2 — Yelp

>> Find field empty, full zoom out on the city, sort by most reviewed, then highest rated.

At a finer level of granularity is Yelp.

This is the second data set for your triangulation.

The ‘most reviewed’ filter is going to give you a similar list to Trip Advisor, with a heavier bias to restaurants.

Anything that jumps out at you, note it down in your text doc.

Switching your sort to ‘highest rated’ will give you more signal. Again, its not a perfect filter, but it’s a good third data set to build out your mental model.

For example, San Francisco’s highest rated Yelp submission is ‘BYOBW- Bring Your Own Big Wheel Race’ a once-a-year event.

This isn’t the last we’ll see of Yelp, but by now, you should have 10–20 interesting things.

There are 3 final great filters to layer on to Yelp.

In the places that jump out at you, dive in and look at the photos.

They’ll tell you a lot about whether a 4-Star place is really worth all 4.

Finally, search for something obscure, that only a place that really cared would have.

So if you love coffee, search for ‘pour over’ because it’s unlikely in 2015 that it can both be a great coffee shop and not have pour over coffee.

You could also search for ‘IPA’, or ‘wood-fired oven’ to see what emerges.


3 — Airbnb

>> No dates selected, full zoom out on the State.

We used this technique to find an Earthship in the middle of New Mexico to visit. It’s why we went to Sea Ranch. We’re going to Joshua Tree in a few months based on this search.

Airbnb will surface you the best places to stay, and sometimes that will be enough to guide your trip to somewhere new.

It’s also a great way to assess whether you’re visiting the best parts of the place you’re going. Great houses are strong proxies for great neighbourhoods.


4 — Foursquare

>> foursquare.com, empty ‘I’m looking for’ field, max zoom, then add the ‘places my friends have been’ filter.

The next level of granularity down from Yelp, Foursquare is the final data set you’ll in the triangulation for your initial list.

If you found it on TripAdvisor, Yelp and 4Sq through the filters I mentioned, that’s a very strong signal.

You’ll now have a very strong list, 20–25 items long of good things to do.

Rerun the search but filter by ‘places my friends have been’ for an additional layer of insight.

5–36 Hours In

>> Search Google for ’36 hours in <city name>’

If you’re in luck, the NY Times will have given you the gold of a ’36 Hours In’ review. If it’s in the ‘36 hours’ list and on your 20–25er, it gets bolded.

6 — Strava Heatmap

>> Find your location here: http://labs.strava.com/heatmap/

In my experience, good places to run correlate really highly with good places to have a picnic, a coffee and a baked good.

The Strava heatmap is a really accurate guide of good places to run in a city.

7 — Facebook/Twitter

>> Tweet/Facebook out a call for recommendations.

A simple, but often overlooked source of great tips and insights to act as a final filter set is just to ask people in your network.

Look for the repeats, the things that keep popping up. If it’s highly rated on Yelp, a friend has been there, another friend on Facebook recommends it, the images look good and it’s in the NY Times ’36 Hours’ list, you’re probably in good shape.

Finally, and these are my personal preferences here, in any place you go, you can’t go too far wrong looking for the best:

  • sports store
  • bakery
  • cheese plate
  • trail run
  • farmer’s market
  • dessert
  • gallery
  • local beer
  • bookstore; and
  • park.

The Final List

The final step is to take your 20–25 list, and based on amount of time you have somewhere, figure out how many of the things you can realistically do. Take that final list, and add each location to Google Maps.

Look for experiences clustered geographically, and then build your days around them. You can then start to connect up all these experiences in the most frictionless sequence possible.

Good samaritans will then turn these into Foursquare lists for others to test, review and improve.

Getting good at cities is an excellent way to spend a life.

This is an update to Getting Good At Cities, a post about how to uncover the gold in cities, originally written in August 2011.

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