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How I’m Taking A Cruise Every Year For Free

Free Disney Cruise Strategy

Gosh, this looks stress free

Cruises are the ultimate in stress-free vacationing. Change my mind.

All I have to do is get myself to port via airline with relaxing lounges on layovers and free uber rides from the terminal. Then I check-in and locate my room aboard a floating all(ish) inclusive resort, unpack, and literally not worry about a single thing until it’s over.

My food is always in the same known locations unless I feel frisky and want to change it up. I don’t have to make cuisine decisions in a back and forth “well what do YOU want to eat?” downward spiraling argument. I don’t have to worry about transportation anywhere since the resort moves with me. Entertainment is there if I want it and bars are there if I don’t. It cannot get better from this burned-out logistician’s viewpoint.

No, I don’t want to explore new cities and take social media pictures by tourist traps and rely on public transportation and constantly have an eye out for security. I want to walk into a little slice of floating paradise, float my happy behind on over to another little slice of paradise, not worry about logistics, rinse and repeat. I’m relaxed just thinking about it.

Disney Cruises

I, for one, welcome our new mouse eared overlords

Of course, there are varying degrees of cruising experience. We can’t be blowing precious leave time on Carnival, the Best Western’s of the cruising industry. But top-tiered cruising experiences are admittedly not cheap and the king of not cheap cruising slaps two round mouse ears on everything they do.

Of course, for your pretty penny, you get a grand experience in attention to detail and a surprising amount of adult-only space for a travel company fashioned around kid’s movies. I was not a fan when my then-fiancee (now wife of five years) wanted to get married on a Disney cruise — but I have since been convinced of the merit in cruising with the mouse.

Quality wise, Disney far surpasses any other cruise line I have sailed with. The food is better, the rooms are larger and nicer, the employees are friendlier, Castaway Cay is superior to any other private island, the entertainment and activities are always a notch above, and the clientelle is frankly just more upscale (I don’t want no scrubs). Contrary to popular belief, it isn’t just a floating cartoon themed playground — everything is upper crust, and there are designated areas for kids with (almost) around-the-clock childcare, and plenty of adult-only locations as well. It’s the perfect cruise for families, singles, and DINKs alike, and I have never once questioned whether I was getting my money’s worth.

And thus, my enduring yearly stress-free vacation will be cruising the Disney seas in an everlasting pursuit of conch coolers at Castaway Cay. Why they don’t serve those on the ship, I will be forever bitter about. I also used to be bitter about having to bite the cost bullet. Our first Disney cruise (wedding) and subsequent cruise (honeymoon) cost a moderate $1723.70 and $1597.34 respectively, for two of us at five nights each in a veranda stateroom. That same 5 night, 2 person veranda room is an extravagant $3833 this year. How is that a sustainable yearly vacation?

I’ll Take The Free Option, Please

Travel credits are best credits

Of course, the answer is credit cards. No, I do not mean to say we charge it and drown in interest-bearing debt for years. I mean to say that this sweet game we call churning will pay for my cruise tickets, year after year, so long as I maintain active duty service.

The spouse and I have the following annual fee waived credit cards: Chase Sapphire Reserve (CSR) x4, US Bank Altitude Reserve (AR) x2, and the Citi Prestige (CP) x2. With the $300/year travel credit per CSR, $325/year travel credit per AR, and $250 travel credit per CP, holding these cards nets us a cool $2350 per year, every year. That’s free travel dollars that will auto reimburse my Disney cruise charges. Granted, it won’t cover another veranda 5-night itinerary, but we can slum it on the inside of the ship for $2440 on a 7-night voyage.

In the future, I plan to snag us each a Korean SkyPass Select card, netting another $200 credit per card, bringing the yearly Disney cruise fund to a respectable $2750. How do you like them apples with mouse ears carved into them?

Starting From Scratch

Would ya just look at it? She’s a real beaut.

If this is your first toe-dip into the credit card game and perpetual free Disney cruising (or perpetual free anything) has piqued your interest, here’s how to get to this point. CAUTION: while this is the fastest avenue to stacking travel credits, it is NOT the best path to building the optimal card portfolio. See our guide here for that path.

First, you’ll want to get the Chase Freedom and Freedom Unlimited card. It doesn’t matter in which order, just grab them both and meet whatever lousy sign up bonuses they have at the time. Then do the same for your spouse. Also at this time, open a joint checking account with US Bank. They often do new account bonuses so you might even be able to snag $300 for your efforts.

31 days after your first Chase card get the Chase Sapphire Reserve. Meet the sign-up bonus (probably 50k UR points after $4k spend in 3 months). Rinse and repeat for your spouse. You should now be somewhere around 6 months in and holding 6 credit cards.

Then, apply for a US Bank Altitude Reserve card. Meet the sign-up bonus (likely 50k Flexpoints for $4500 spend in 3 months). Rinse and repeat for your spouse. You should now be somewhere around 12 months in and holding 8 credit cards.

This sunset is a subtle wink that the post is ending

Finally, go ahead and apply for a Citi Prestige. Meet the sign-up bonus (likely 50k ThankYou points for $4000 spend in 3 months). Rinse and repeat for your spouse. You should now be somewhere around 18 months in and holding 10 credit cards.

Make a call to Chase, upgrade your Freedoms and Freedom Unlimiteds to Sapphire Reserves and voila, you now have 6 Sapphire Reserves, 2 Altitude Reserves, and 2 Prestiges. That’s a grand total of $2950 travel credits and about 325,000 various points worth a respectable $3250 cashback at their lowest redemption value. If you want to be a hero and get Korean Skypass Selects, add another $400 to that travel credit number. 18 months is a very conservative timeline and this can likely be done much sooner if you can meet the minimum spends faster. Just remember to wait 366 days to upgrade Chase cards.

Let me know when you finish and I’ll tweet the deets for our yearly TDWise Disney Cruise meetup!



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