How Testing Directions On The Apple Watch In Aspen Colorado Led Me To NBA Superstar Dwight Howard

Hey, I’m Chris. I wrote this article and I’m also the founder and Editor of DailyTekk. Lets connect on Twitter, Instagram, Snapchat and YouTube. Check back daily!

I’d never been to Aspen Colorado before this weekend which made it the perfect place to test getting both walking and driving directions on the Apple Watch. I’m happy to say that using the Apple Watch to navigate a new town was very convenient, despite a few minor quirks which, as it turned out, led me to a chance encounter with Houston Rockets center Dwight Howard. Here’s what happened.

Aspen, like New York or LA, is one of those ritzy places where you’ve got a decent chance of spotting a celebrity while you’re seeing the sights. Like the recognizable faces that can sometimes be seen popping out of the local Gucci store, Aspen itself is famous (the omelet chef at my hotel used to cook for Will and Jada Smith and their kids and toured with the Rolling Stones — and that was the best omelet I’d ever eaten). It’s known for being a naturally beautiful, swanky destination where you can ski and ride, shop and eat lots of good food.

For me, heading to Aspen meant driving through Denver. Denver is the gateway to Colorado’s most popular ski towns: Breckenridge, Vail, Beaver Creek and the like. And, as still happens even though this is 2015, there are patches along the Rockies’ major travel arteries that still don’t get the best mobile coverage (or any at all). So I knew I wanted to start my directions dialed in before I left Denver.

Just to make sure I was going to get the best, most-direct route I decided to enter the address on my iPhone. Once I hit start in Apple Maps, the directions immediately showed up on my Apple Watch as well. As the weekend went on, I found the opposite to be true as well: directions begun on the Apple Watch opened on the Apple Maps app on my iPhone simultaneously.IMG_0132

From my experience this weekend, it appears that as long as directions are started while in-service, moving out-of-service won’t halt them. That said, you’re maps might not be as detailed as when you are in service. Good to know.

After settling into the hotel it was time to do some exploring. But what to see? Siri time. The entire weekend, whether in a quiet hotel room or out on a busy street, pressing and holding the digital crown to activate Siri didn’t work well at all. It would activate Siri but then the wavy lines on the bottom of the screen signaling Siri is listening for a command abruptly ceased waving leaving a black screen with the text, “What can I help you with?” at the top. After multiple start and stop attempts to communicate with Siri, I finally tried the, “Hey, Siri,” approach — and that worked perfectly every single time.

And so, “Hey, Siri, give me walking directions to Aspen Dry Goods Company,” which was a clothes store I spotted on Foursquare. After a pause that was a bit too long, the directions showed up. I had to wait a few seconds longer for the start button to turn the correct shade of blue signifying I could press it. I did and I was off — and here’s where I had a lot of fun.

One complaint about Siri on the Apple Watch is that it has a tendency to misspell words every now and then which can be frustrating because you then must open Maps on your iPhone to input the correctly spelled destination. If I had to put it into a fraction, I’d say this happens once every six to nine times.


Whether walking or driving, the Apple Watch will tap you on the wrist and, as long as it’s not muted, issue a short set of beeps that remind me a bit of a car’s turning signal just ahead of when you need to make a turn.

While directions are active on the Watch, there are two screens you can view. The default is the next action: if you’re going to be turning left it show a left turn sign with the distance. Once you make that turn, it will bring up the next action. You can also swipe to the right to view a map view. On the map view, you can use your finger to scroll around a limited amount (as far as your finger can go from edge to edge on the screen) — but when you remove you finger, the map resets to center on your current position.

I particularly love walking directions with the Apple Watch. You never have to look at a map (i.e. look like a tourist). Instead, just continue on your way, wait for a tap, take a quick glance and keep going. This is awesome.

Using the Apple Watch while driving, however, feels dangerous; more so than looking at a screen on your car’s dash. Not advisable. But great if you’re a passenger.


So while using your Apple Watch to guide you by foot around a new city is really great once you’ve got your designated loaded up, figuring out which way to start walking is sort of quirky. The experience I want is to be able to just have the Watch tell me which way I need to go, but in reality getting started means getting oriented or just plain starting out in a direction to see if that’s the right way. Once you get your bearings, though, it’s very smooth sailing. I think the problem is that the Watch (and your iPhone that it relies on) still has a bit of a hard time telling which way you are actually facing.

The worst thing about using the Apple Watch for directions is that is drains the crap out of your iPhone battery (as any app that relies heavily on GPS is prone to do). For this reason I recommend having a portable power back on-hand just in case. Depending on where you are and what you’re doing, that may not always be feasible, so here’s hoping Apple packs the next iPhone with more juice (because I, for one, am pretty happy with how thin the device is at the moment).

Now here’s the final quirk I’m going to mention. The Apple Maps app on the iPhone (and the Apple Watch by extension), does a bad job at recognizing shortcuts that humans would take while walking in real life. For instance, I was walking toward a store in a small strip mall in Aspen and the directions given to me by the Apple Watch made me walk all the way around the mall and then cut back to get to the store I was heading to. This was a bit of a waste of time given that I couldn’t walked across a bit of grass and a parking lot to get there about 3 or 4 minutes faster. But…

Had I not followed my quirky Apple Watch’s directions that day — had I taken the shortcut a normal person would’ve taken — I wouldn’t have arrived just in time to see Dwight Howard and a couple friends of his discovering that the store we were apparently both heading to was closed this particular Sunday afternoon.

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On a side note, Dwight seems like a very nice guy. I walked up and, after realizing he was on a phone call, asked his friend if Dwight would be cool with a selfie. He said to wait a minute since he was on the phone. I considered leaving so as not to bother him, but after just a few seconds I heard, “Are you ready?” Dwight was nice enough to take a few seconds out of his downtime to pose for a picture (even though I’m pretty sure he might have still been on the phone) and to tell me to have a nice day. Cool guy.

Everyone is always saying that the Apple Watch doesn’t have a “killer feature” that will compel people to buy it. I think navigation on the Apple Watch is one of the many little features that people think, “Ya, so?” about; but when added together, all those little, “Ya, so?” features make for a really great, really useful experience.

Plus, who knows who you might run into while relying upon it for directions…

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