It occurred to me as I was writing some blog posts that as much as I talk about various individual hacks, I’ve never actually detailed a real set of redemptions I made, how I constructed a trip, and the final costs. I think it’s because they aren’t the most fun to write (because usually they’re not all that novel), but they can actually be pretty fun to read because they demonstrate what’s really possible with travel hacking.

There were a huge range of strategies I employed on my trip to Europe (Milan, Nice, Zurich), so I figured this would be as good a time as any to share how I think about trip-planning as a travel hacker and what I ended up getting for my money.

Let’s start with the transit.


Leg Cost Cost of Miles Net Cost
SFO-MXP 50,000 AS + $23.70 on AA 0.1 cent / AS $73.40
Milan-Nice (train) 12.40 GBP on Thello 1 GBP = $1.45  $17.97
NCE-ZRH 108.37 EUR on Swiss 1 EUR = $1.14  $123.61
ZRH-SFO 50,000 AS + $79 on AA 0.1 cent / AS $129

Whenever I plan a trip, I always deal with the endpoints first and fill in the middle as I go, as they typically are the harder ones to secure. My constraints were that I wanted to meet my sister where she was studying (in Milan) and spend a week in Europe before heading back home. That afforded me a ton of flexibility, because not only did I not have exact dates already in mind, but I could actually construct my trip itinerary around where I could find award availability.

Since I had a lot of Alaska (AS) miles, most of which came from sign-up bonuses and real flying (well, some of it was real anyway) (which gives my near-zero cost of 0.1 cent per mile), and it has numerous partners that fly to Europe (British Airways, KLM, Air France, AA, and even Emirates (EK)), redeeming them seemed like a good bet.

Because of fuel surcharges BA and EK were pretty much off-limits, and AF/KL have fairly limited availability, so in practical terms, I’d be flying AA. I was particularly keen on flying in business class, so I wanted to make sure that I could fly one of the newer, lie-flat business class products. This effectively restricted me to connecting in Miami or New York (AA flies a lot of ex-US Airways planes out of Philadelphia and its older fleet out of Chicago and Dallas). Obviously I preferred flying out of New York since I could take a stopover there and visit my family.

That out of the way, the next question was where AA flies direct out of JFK. The answers: Milan, Barcelona, and Zurich. Since I was booking in October, I had a pretty good slate of availability, and I found a Saturday redeye that would get me into Milan Sunday morning. Sold.

(If you’re curious, I wrote trip reports for my first class flight from SFO-JFK and my business class flight from JFK-MXP).

For the return, I didn’t mind flying through Miami, so that expanded my options a bit, but I didn’t want to have to get back to Milan since I’d lose a lot of travel time. Ideally I could do Barcelona, since I had wanted to make my way down the Southern coast of France anyway, but the only availability for the return flight was ex-Zurich, so I went ahead with that.

Note that at this point, I hadn’t figure out where I was actually going to visit outside of the endpoints, and this is almost always how I plan my trips nowadays. Flexibility is your most powerful ally when travel hacking, and I try to use it whenever I can.

By the time I settled on visiting Nice (Zurich was obviously forced), I compared flight and train costs (Rome2Rio is a fabulous resource) and booked the legs listed above. Since intra-Europe cash fares tend to be cheap, miles bookings are usually suboptimal, which is why I paid for them out-of-pocket.


Accommodations tend to be easier to deal with than flights, because most bookings are refundable and allow you to speculatively make them before you’ve locked in your plans. Here were mine for this trip:

Stay Where Cost Cost of Points Net Cost
Milan (2 nights) Sister’s apartment FREEEEEE Putting up with my sister 😉 $0
Nice (3 nights) La Malmaison 36,000 Choice Points $155 via Daily Getaways $155
Zurich (2 nights) Courtyard Marriott Zurich North 93.40 Orbucks + $7.89 + 109.50 CHF $0.25/1 Orbuck; 1 CHF = $1.03 $144.37

Since I was visiting my sister, Milan was taken care of, but I had plenty of choices for Nice and Zurich, respectively. I wanted to treat my sister to something nice, since was the first time we had ever traveled together, and I like spoiling her, so initially, I had planned for us to stay in the Hyatt Regency Nice.

The rack rate for 3 nights at the Hyatt was 315 EUR / night, which I would never would have paid were it not for the fact that I shopped around and made a best rate guarantee claim (Hyatt offers 20% off whatever rate you can find from reputable travel agencies, if the other room details match, although it’s gotten more stringent recently), which allowed me to lower the price to 177.50 EUR / night. Combine that with my Diamond Suite Upgrades (complimentary, confirmed upgrades to the lowest-level suite for those holding Diamond status), and it was sure to be a great stay.

This is where flexibility and having options comes in. Since the rate was refundable, I was able to take advantage of the Daily Getaways deal on Choice Privileges points that I had blogged about (alas, I couldn’t get the 40,000 point offer at 0.4 cents per point, but I was able to lock in two, 36,000 point packages for $155 each), and then immediately redeem the points for three nights at La Malmaison Nice. Because I bought the points for 0.43 cents/point, I got a nearly $250 hotel room (complete with top-floor balcony, and a jacuzzi bathtub with mood-lighting):

View from my balcony

View from my balcony

Too bad I wasn't traveling with my girlfriend ;)

Too bad I wasn’t traveling with my girlfriend 😉

…for a mere $51.67 a night! That was too good to pass up on relative to the $220/night I’d be paying at the Hyatt, so I cancelled the Hyatt reservation without hesitation.

Lastly was Zurich, which, to say the least, is expensive as $*^&#@%&! Even compared to San Francisco, the prices are absurd ($10-$20 for a meal at Burger King!). I wasn’t particularly willing to shell out for the top-tier hotels, even on points, so I needed a slightly different strategy. At my disposal were some Orbucks, some Marriott and IHG points, and obviously, cash.

There weren’t any reasonable redemptions in the downtown area, so I needed to widen my search a bit. I stuck to main tram lines between the downtown area and the airport, and came up with the Courtyard Marriott Zurich North, which had rates for about $100/night.

Here is where strategically paying cash comes in handy. When I say strategic, I don’t mean paying cash when redemption rates are bad; I mean paying cash when there are outsized benefits to doing so. In this case, my ace in the hole was a Marriott promotion I had signed up for offering me a free night certificate after just TWO stays (one of which I was already planning to complete in Alaska). Paying cash was therefore a no-brainer, but why pay for both nights when I could get away with paying for one of the two? No reason at all, so I made a second booking for the other night using my Orbucks (which I had acquired for about 25 cents on the dollar through best rate guarantees I had submitted last year). I wouldn’t earn any loyalty points for the Orbitz night, but it was fairly easy to have the hotel link two reservations so I wouldn’t have to check in and out twice, and it cut my cash outlay in half.


In total, I paid $643.35 out of pocket for what are normally the most expensive parts of a trip (and flew in business class, no less!), freeing me up to do all sorts of amazing things (mostly related to food :P) and really just not have to worry about money during the trip (I’m pretty strict about budgeting, as you know). That’s the real ‘value’ I get out of travel hacking. Not only did I not have to think twice about visiting my sister in the first place, but also I didn’t have to think twice about the experiences I wanted to have when I was actually on the ground. Doesn’t get much better than that.

Happy hacking!