Every parent knows that Walt Disney World is a great vacation destination, and they also know it is an extremely expensive one. So, what's this "free flights and stay" stuff? Glad you asked …
Recently, Marci and I realized that our soon-to-be 9-year-old daughter last experienced Disney at age 4, and she does not remember much of it. So, we made a decision: 5 nights at Disney World in Spring 2016!
Being the cost-minded guy I am, the first thing I thought was "the tickets are going to absolutely slay me, and there are no awesome discounts on those, so what can I get for free?" Air and hotel instantly leaped to my mind. And this is where having a diversified points and miles strategy really comes into play. Let me explain.
The two cards that made this whole trip possible (Chase Sapphire Preferred and Starwood American Express), both earn flexible points, which are the best kinds of points to have. I can redeem Chase Ultimate Rewards points for a fixed rate of 1.25 cents per point toward travel (through the Chase website), but I can also transfer my points to the loyalty programs of Chase partners such as Southwest, United, Hyatt, and others ( hence the "flexible" part). When I transfer my points, I can get greater value out of them (for example, Southwest is typically going to yield somewhere between 1.4 and 1.6 cents per point, which is obviously better than the 1.25 cents per point I just mentioned). For our trip, we will fly Southwest to Orlando from Atlanta, and we won't need a ton of points to do so (since Atlanta to Orlando is a low fare and southwest bases the points required on the fare), for the four of Us, we are probably looking at around 45,000 – 50,000 Southwest points to get there and back. So, our airline is covered with Chase points after we transfer them to my Southwest account. Incidentally, Starwood points can be transferred to over 30 different airlines, hence their placement in the "flexible" category. They can be used both at Starwood hotels and for a wide variety of flights.
For this Disney trip, Marci and I wanted to stay somewhere fairly nice and close to the parks without having to a) spend a ton of money or b) commit to Disney's "Deluxe" hotels, which easily run $ 300- $ 500 a night during busy seasons. As many of you Disney aficionados already know, Starwood owns the Dolphin and Swan hotels, which are on Disney property and are incredibly close to EPCOT and Hollywood Studios, but they are not actually owned by Disney. As such, I can use Starwood points toward my stay at either of these two hotels. The Swan and Dolphin hotels are Category 4 hotels, which means they cost 10,000 points per night. If I had to rely on just my points earned from my everyday spend, it would take me forever to save enough points for 5 nights one night. But, when I signed up for the card, I got 25,000 points after meeting the spend requirement. After putting $ 15,000 total on the card, I have 40,000 points, and that is enough for 5 nights … wait, I thought you just said it was 10,000 points per night, Jim! Ah, the even better part. With Starwood stays paid with points, your fifth night is free! So, 40,000 points gets me 5 nights rather than just 4.
Now, how much is this really saving me? Well, the flights (as priced today) are around $ 900 for the four of us. The hotel would be about $ 300 a night, but I also do not have to pay the tax since there is nothing to tax. So, that's between $ 1600 and $ 1700 in hotel savings right there. Note: we do have to pay a resort fee and parking (for our rental car), but to save that much for that hotel? It's a no brainer. All totaled, that's around $ 2500 in savings, which for us working families is a life saver. But as I always say … when I have saved this much on the trip, I will put some of that back into the other aspects of the vacation, eg dining, souvenirs, and tickets. I'm not looking to be a cheap skate … I am looking to live large without spending large! And so can you!
My tip for couples who want to duplicate what I am doing (assuming you are comfortable with signing up for credit cards): first, only one of you needs to apply for the Starwood American Express, though you can both apply and combine your points and reach the 40,000 point goal faster if you don't have the time to put the extra spend on one card. The other person, or both of you, can apply for the Sapphire Preferred, assuming you can meet the combined minimum spends on all of the cards. If you can't meet the spend on these cards simultaneously, then get the Starwood card first since room availability will get tougher as time goes on. Then move on to the Sapphire card. Southwest will always let you use points for their flight if a seat is available, and that is one of the reasons I love them. One last note: if Southwest is not a great option where you live, you can also transfer your Chase points to your United account (if that airline works better for you) or simply use the Chase points through Chase's travel portal for slightly less value, but unlimited flexibility.
If you want to stay on Disney property at a non-Disney hotel, then the Swan and Dolphin are just about the best you can get. With regard to the flights portion of your trip, I am merely using the Chase Sapphire Preferred as an example of how to get there. There are lots of other cards that can help you get there as well, but the point of the article is: you can have this vacation, too!