Creative Deals: Winter Break in 4 Cities for 42,500 Miles + $195

Several people have told me that I keep coming up with amazing deals in both travel and life, and suggested that I share my process with others. This is an experiment in doing so…let me know what you think!
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Those of you who know me know that I don't often stay in one place for long when I travel, and this winter is no exception. I'll be spending time in four cities between December 16 and January 4, and the whole trip is costing me a total of 42,500 Alaska Airlines miles and $195. (I could probably have done this for even cheaper had I been able to plan further ahead). This was booked as three separate tickets, as follows:

Ticket One: Graduation Party in Western Massachusetts
One of my best friends is graduating with honors from community college next month, and he invited me to his graduation celebration. Unfortunately, his party is scheduled for Saturday, December 20, right in the peak of the Christmas travel season. By doing a flexible date search and leaving a few days early, I was able to find a one-way redeye flight from San Francisco to Boston for $180 - which would be a decent price even if it wasn't so close to the holidays. Using a Delta 5% meeting discount code I found online earlier this year knocked the price down to $173. I'll earn roughly 4,600 Alaska Airlines miles for this flight because I have MVP status with Alaska.

Ticket Two: Christmas in Oregon and New Year's in Alaska
I've always gone up to Anchorage for Christmas, but since my mom passed away right before Christmas in 2012, things haven't been as festive. I don't get to see my extended family in Oregon too often, so I thought I'd change things up this year and go see them for Christmas. I'll be spending five days in Oregon and then flying up to Anchorage the night of the 27th.

Alaska Airlines is very flexible about letting you have stopovers in connecting cities, so I was able to book Boston-Portland and Portland-Anchorage (via Seattle) as a single ticket. Low-level award space was completely sold out (no surprise on a transcontinental route, especially three days before Christmas), but since I'm getting a lot of bang for my buck I felt okay with spending 30,000 miles for a fully refundable ticket (plus $11.20 in federal security fees).
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Ticket Three: Back to California, with a Weekend in Seattle
After spending so many miles on that ticket, I wanted to get the cheapest possible award flight to get back to Oakland. Since Alaska has so many flights up and down the West Coast, there were a handful that still had availability for 12,500 miles (the standard price for low-level Continental US awards), but trying to do a straight shot from Anchorage to Oakland or San Francisco would have required a long layover in the middle of the night. I enjoy Seattle and have friends there, so I decided to leave a couple of days early and spend the weekend down there, taking advantage of the aforementioned stopover option again. This flexibility allowed me to spend a weekend in Seattle and get myself back to Oakland in time to start work again on Monday for just 12,500 miles + $11.20.
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Lessons Learned
Flexibility is the name of the game in travel, whether you're looking for paid tickets or award flights. I'm fortunate that the work that I do allows me to do a lot of things remotely – if I didn't have the ability to leave a few days early for Boston, that same ticket could easily have cost $300 or more. Similarly, if I'd insisted on getting back from Anchorage to the Bay Area in a single day, I would have had to shell out 20,000 miles instead of the 12,500 I actually spent.

If I were planning this trip again, I would have definitely tried to start earlier, so that I would have a chance to get a cheaper ticket out of Boston (12,500 or 20,000 miles one-way). However, given the time constraints and the busy holiday travel season, this worked out very well. If I hadn't had miles to use for this trip, it simply wouldn't have happened - these tickets could have easily cost $1000 had I been buying them with cash.

Getting Started
If you don't have any Alaska Airlines miles, a good place to start is signing up for the
Alaska Airlines Visa Signature Card from Bank of America, which gives you $25,000 miles for signing up, or one of the Starwood Preferred Guest cards from American Express, which gives you 25,000 Starpoints that can be transferred 1:1 to Alaska Airlines miles (plus you get a 5,000 mile bonus for every 20,000 miles transferred).
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