One of the things I find myself telling people is, “There are pros and cons to everything.” When people hear you travel a lot, they think of it like going on vacation a lot. Traveling is great. I love it. But that doesn’t mean it’s anything like going on vacation. Traveling can be exhausting. Being away from home for extended periods of time can make you miss privacy, sleeping in your own bed, and not living out of a suitcase. Being mobile day after day can make every day a little more stressful. It’s not for everyone.

That doesn’t mean a traveler will want to spend vacation cooped up at home!

I decided to take a couple weeks off work, after hitting a milestone on a project. It would be nice to unplug and get away from it all for a little bit. I was looking for a cheap getaway, but I still searched for international options. The best trip within my budget was Rome, but the timing wasn’t right (the friend I’d be staying with was in between apartments). I decided to think outside of the box, but not necessarily outside of the country.

Starting from my employer’s headquarters in the San Francisco area, I decided to hop on a train (thanks for the lift, Marcus! [SJ]) to Denver, CO to visit some friends in Boulder and Denver. The train ride on Amtrak along their California Zephyr route was quite a site-seeing experience, going through the Sierra Nevada Mountains in California, the Wasatch Mountain Range in Utah, and various canyons along the Colorado River (most notably Ruby Canyon and Glenwood Canyon).

In Denver, I was pleasantly surprised to find that the Amtrak station is at Union Station, with buses running to Boulder for $4.50 until about 1am (My train was 4 hours late, so I ended up taking the midnight bus). After spending a few days hanging out with my favorite Boulder peeps – Andrew Hyde [SJ], Jeremy Tanner [SJ], Matt Gist, Grant Blakeman, Rachel Ryle [SJ], Heather Capri, and I got to meet Michael Tseng. On day #4 of my vacation (Wednesday), I booked the next two segments on my trip: Denver to Chicago and Chicago to Washington DC. On my way to catch the train in Denver, I got to hang out with John Wilker and Aimee Giese.

In Chicago, I arrived just in time to go straight to the CHIRP Radio (Chicago Independent Radio Project) launch party with my friend Mike Gibson [SJ], who is a co-founder. Before I hopped back on a train, Mike and I had brunch with Chelsea Winkel, who was visiting from Los Angeles.

I arrived in Washington DC on February 1, day #9 of the vacation, completing a coast-to-coast train trip totaling about 72 train-hours at a cost of about $400. My goal had been to arrive by February 2, so I could attend Peter Corbett’s event, BIBA: Big Ideas, Big Action. The night before the event, Peter was running around taking care of stuff, so I checked out the International Spy Museum and had dinner with Melissa a.k.a. h0neyb. BIBA was a lot of fun, there were some great speakers, and I met some awesome people, including the rest of the iStrategy Labs team and Scott and Yoni from OPOWER.

Getting to DC was the extent of my “planning” for this vacation, so when I found out Peter (who was providing me with a couch) was leaving the country hours after the end of BIBA, I decided to hit the road that night, too. I ended up getting an $18 Bolt Bus ticket to NYC, which included power and wifi.

Arriving in NYC after midnight on about 12 hours of notice and hoping to find free lodging for the night is, well, not very practical. Fortunately, I have some awesome friends! Kroosh [SJ] was happy to let me crash at her place.

I don’t drink, yet this part of my trip is a bit of a blur. That’s the effect NYC can have on you. Life at 100 miles per hour.

In a few short days, I was able to pack in a lot of hanging out with some of my favorite NYC friends.

I went to Soho Haven, a shared office space for start-ups, for the first time to meet up with Jason Kende. Jason and I met up with Leo Newball [SJ coming soon] to grab dinner and go bowling at Brooklyn Bowl, a rad bowling alley with live music and excellent (albeit pricey) food!

The next day, Thursday, I met up with Michael Gruen for lunch/coffee at Stumptown / Ace Hotel (well, he’d already had lunch and he doesn’t drink coffee… so we met up so he could watch me eat lunch and drink coffee). Mike’s a smart guy and an excellent person to have a conversation with. I think this was our first one-on-one conversation, so it was great to sit down and exchange what each other was up to.

Thursday night involved attempting to go to a Sony event, then going to a punk show being put on by twin brothers who make coffee at my favorite NYC coffee shop. After that, I went to the Keen Kong launch party at New Work City, where I got to hang out with Jason, Tony Bacigalupo [SJ], Mark Burstiner [SJ], Stephanie Kibbe [SJ coming soon], Sukhjit, and @MissSomething.

Friday, I grabbed lunch with Mike Germano [SJ], who is always up to amazing and exciting stuff at Carrot Creative. I hung out at the Carrot office for a while with the rest of the Carrot crew (Sorry, Rob, Maury, Chris, and gang.. All these individual links are getting exhausting!).

For dinner, Mark & Kibbe introduced me to soup dumplings at Joe’s Shanghai. Holy crap. Most people know what dumplings are — a wad of meat, wrapped in dough. Well, combine that with a water balloon filled with ramen noodle broth and you’ve got soup dumplings. After that, I went out with Jason, Leo, and Erik Nygren (from co-founder of Soho Haven) to a couple of bars. Later that night, after midnight, Ana Hevesi, who introduced me to Code and Beats, joined us to help close out the night. Just in time, too! My flight was scheduled for 8am the next morning. Well, it was until it got canceled.

My return flight was canceled due to weather, and that turned out to be awesome. I was able to transfer to a different flight, leaving at 2:45pm, which is a lot easier to catch after you’ve been out until 3am. Not only that, I was able to fly first class!

Here’s why/how I flew first class for free:
When presented with over a dozen flight options at the same price, always choose one with a layover and the longest distance. On Star Alliance (US Airways, United, etc), you need 25,000 miles OR 30 segments to get Silver Preferred status. I got status last year by reaching 30 segments, though it’s easier to get it with miles if you fly cross-country a few times or overseas. I rack most of my miles up 651 miles at a time between PHX and SFO. With Silver status, you’re given complementary first class upgrades when available. Essentially, if they don’t sell all their first class seats, they pluck you out of the crowd and plop you into a 2-4x more expensive seat at no cost. My 8am LGA->BOS leg apparently wasn’t very popular, because a couple days before the flight, I got an email confirming a first class seat for that flight. However, the day before, the flight got canceled. When I called reservations, I was presented with my options for getting back to Phoenix. The representative noted that I had a first class seat on one of my legs and offered to look for flights with first class seats. We discovered that the 2:45pm flight with a layover in Charlotte, NC had first class seats available on both segments.

BAM! Just like that, I went from having coach-coach seats to first-coach seats to first first seats! $275 (with taxes and fees) for a short-notice one-way flight from NYC to PHX, first class, totaling 2,896 miles toward status and rewards (LGA->CLT = 543m; CLT->PHX = 1774m; + 25% bonus miles w/ Silver status). Remember: Having status makes it easier to keep status!

I’ve told a few people about how the flight situation worked out, and based on their responses, I figured I’d do a quick write-up on it. Some people find The Miles Game pretty interesting!