In my continuing credit card churning escapades, I managed to kind of accidentally end up qualifying Denisa for Southwest’s Companion Pass for a year. This means that for this entire year, anywhere Denisa flies on Southwest, I can fly with her for free. (If I’d been doing this the right way, I would have qualified her at the beginning of this year, which would have meant the free flights would have gone through this whole year and then all of next year, but . . . I goofed. C’est la vie.)
That’s a pretty great perk, and after talking it over some, Denisa and I decided to see just what we could do with all these points we’ve been accumulating. At first I wanted to go to Hawaii, but getting to Hawaii on Southwest when you live in Maine turns out to be more hassle than we were willing to deal with. So then we turned our eye to the Caribbean. Why not someplace that needed a passport to get to?
From there, it was a matter of finding out which flights were the easiest to manage all along the way. For example, Southwest technically flies to the Grand Caymans or Costa Rica, but actually getting there from Portland was going to be a beast, so I crossed the off the list of potentials. This narrowed my list of candidates to the Bahamas, Cancun, Puerto Rico, the Dominican Republic, Jamaica, and Aruba.
The next step was to figure out where we might stay. I’ve got a war chest of Marriott points, so I decided to focus on Marriotts for now. Ideally, I wanted a place that felt luxurious. Like we were really living it up. Flying off for a romantic getaway at a Residence Inn? Not quite what I was going for. But I also didn’t want to blow all my points at once. I wanted value luxury, if that existed. Cancun and Jamaica either had hotels that were Fairfield Inns or Ritz Carltons. Nothing in the sweet spot. The Bahamas had a nice candidate, until I realized taxes for the room were going to be $556. Paying that much in taxes doesn’t really make it feel free, you know?
At that point, it was down to Puerto Rico, the DR, or Aruba, and in the end, we went with Aruba for a couple of reasons. First, this is going to be a trip with just Denisa and me. Puerto Rico was really appealing, but we might head there with the kids sometime. It’s pretty easy to get to and navigate. Why not try something a bit more adventurous for this trip? In that case, Aruba sounded more exotic than the Dominican Republic, and it’s technically part of the South American continent, which means I could cross an entire continent off my “visited” list. Sold!
In the end, it cost 38,000 Southwest points (plus $180 in taxes) and 135,000 Marriott points (plus $25 in taxes) to book a five night stay in Aruba at a hotel with its own private island. It’ll cost more than that to go, of course, once we pay for parking and food and activities. But considering the flight and hotel have only going to set me back a grand total of $205, I think we can spend a bit on living it up while we’re down there. What will we do? Maybe scuba diving? Snorkeling? Horseback riding? If any of you have been and have suggestions, I’d love to hear them.
Still very glad I started churning. It takes some coordination and some research each time I need a new credit card (which I need to do again now), but I love how it’s been giving me the extra push I’ve needed to go out and try doing some different things that I wouldn’t have done otherwise. Money and time well spent.
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