Booking Now: runDisney Castaway Cay Challenge Cruise

I once joked that the regular Castaway Cay 5K held by the Disney Cruise Line was the most expensive 5K in the world.

I was wrong.

The most expensive 5K in the world title is now held by the runDisney Castaway Cay Challenge 5K.   This isn’t a complaint, just a fact.

runDisney Castaway Cay Challenge

FACT:  You have to pay for and run at least 1 race (5K, 10K, Half or Full Marathon) at Walt Disney World during MarathonWeekend.

FACT:  You have to pay for and board the Disney Dream (one of the Disney Cruise Line vessels) immediately after you run one of those races mentioned above.

FACT:  You have to pay to enter the challenge, where the normal Castaway Cay 5K is a free offering on the ship.

FACT:  I ran this in 2015 was only on this cruise because this race was offered! Our cabin would have been empty if this special challenge was not happening. This was a sentiment many fellow Princesses shared as we waited in the corrals and chatted at the after party.

Alright, so it may not be the most expensive 5K in the world, but it’s certainly the most expensive one I’ve run at approximately $UmNoWayImSayin’ per mile when I added in all my expenses.

Dang.  Trust me- that was some coin.

This guy totally gets it.

This guy totally gets it.

I’m sure your next question is: was “worth it?”

Well- yeah.

Of course it was!  It was my Christmas, my Valentine’s Day, and my birthday present all wrapped up in one week-long gift!

I do this for you- I knew you’d want to know what this experience was like so, I, Shenanigans, took one for the team.  I’m a giver like that.

Okay, I can’t even say that with a straight face.  Bahahaha.

This is a recap of the event. The Walt Disney World Marathon weekend is the only race offering the Challenge at this time. And the ship is filling up quickly!

If you are Disney Cruising Dream(ing), let’s talk & quote you something amazing. There are still a lot of great cabins available on this race, and I promise you will not regret a week of pampering by DCL after your marathon weekend!

Oh- and since this is the month of Beauty and the Beast, it’s a perfect place to fill you in on this exciting news.

Beauty and the Beast will become brand-new stage spectacular aboard Disney Cruise Line. It will debut on the Disney Dream on November 6th of this year… so all of us heading out for the Castaway Cay challenge this January will get to see it! Who’s with us?!

Email me at for your no-obligation quote!



runDisney Castaway Cay Challenge Race Re-Cap

Our Castaway Challenge occurred after the Princess Half Marathon.

We picked up our bibs, shirts and information at the Expo at Walt Disney World.  Once I completed the 10K I looked to my running and cruising buddy, Diane, and pronounced that we were half way to the Castaway Cay Challenge medal.  We were pumped!

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When we boarded the ship we had a few days to recover from all the running at PHM weekend.  Diane and I were cruising with DisBroad Tania and all three of us were nursing some post Princess soreness.  The day at Castaway Cay was scheduled for Wednesday and it was perfectly placed for our purposes.

runDisney held a speakers panel on the ship to share information about the race.  They showed us the race course (different course from the normal “free” 5K) and explained the logistics.  There would be “surprises” on the course (code for characters!), a new route, and even water/food/typical runDisney support.

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I’ve learned from other cruisers that this was very different from the normal, ie FREE, Castaway Cay 5K.  It’s nice to see that the medal was not the only thing that was changed when they charged us an entry fee!

In case you are wondering, the weather and contingency plan?  If we couldn’t dock for some reason we would meet at the theater and they would hand us our medals.  #whompwhomp

I laughed but there were some groans of disappointment out there.  Runners: we are crazy!  We actually want to RUN to earn the medal.  Who knew?

People, do not let me attempt to salute in pictures anymore. I simply can't do it correctly! Gah! But cute picture otherwise.

People, do not let me attempt to salute in pictures anymore. I simply can’t do it correctly! Gah! But cute picture otherwise.

Our group decided to dress in costume.  I mean, would you expect anything less?  Diane was the brain child behind this one.  It turned out adorable.

There was an A and a B corral in our race.  They took off about 5 minutes apart.

This cute little tape separated A & B.

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Since we were all there post Princess Half Marathon, we had a very special guest at the start line:  Princess Minnie Mouse!

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For the first time in my runDisney career, there were no fireworks at the start.

#firstworldproblems I know.

I honestly was too excited to even notice but it was one of those little touches that you do come to expect from a Disney race.

As we waved goodbye to the staff manning the start, we took off on our intervals and headed down the air strip.  We sent Tania ahead in case there was a long line for the first character (there was not, but she waited for us) and Diane and I took it pretty slow at a 14 minute mile pace.  Her back was hurting, my feet were tender, and well, we were running ON AN ISLAND.

There was no need to rush this!

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The support and characters were fantastic! Fun Cast Members came out to cheer us on and we had 4 character stops.

I loved this course.  We ran down the air strip a bit to the first character (Daisy) and then turned right down an out and back section along the private adult beach.

Diane was familiar with the island since she’s cruised a gazillion times before and was a great running partner.  She pointed out the sights and made sure we veered off course a smidge to get that pretty picture of the ocean and beach in the right hand corner.

After the out and back we headed back down the airstrip.  This was where the only water stop was located.  We were handed small bottles of Dasani which tasted GREAT on this humid morning.

Soon we were running into “the loop.”  I understand that the normal Castaway Cay 5K runs this loop twice and that constitutes the full 5K course.

The loop was fine- ONCE, thankyouverymuch.  I’m not sure I’d bother with the normal Castaway Cay 5K since the course was so different.  I loved running out toward the beach where we could feel the breeze and see a bit of the water waiting for us!

At the finish line we were greeted with the runDisney snack box, water, and Powerade.

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The fun was not over when the medals were given out!

On the final night of the cruise, runDisney and the Disney Cruise Line hosted an exclusive runners reception.

We had food, we had drink specials (Rum RUNNERS, of course!), an ice sculpture and of course, a Princess.


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Jeff Galloway took pictures and signed my medal.  He’s such a great ambassador for the sport and for runDisney.  I love chatting with him at every race!

With the completion of this event, my Princess Half Marathon weekend—err, week!- finally came to an end.

I ran 22.4 miles and earned 5 gorgeous new medals.

I am a very happy Shenanigans.

Word on the ship indicated that another Challenge event was not currently on the books.  I’m hopeful that this situation will change but at the time of cruising we were told this was the only event currently planned.  Wine and Dine was mentioned as a possibility, but so far there has not been an announcement.

If this breaks your heart and you really need that runDisney medal with a cruise ship AND a castle on it someday down the road, be sure to let your feelings be known through email, social media, or an old fashioned phone call.  I know Disney Cruise Line and runDisney always take their guests preferences into consideration.  If you want a chance to save your pennies and run this race, shout it out!

Did you run either Castaway Cay Challenges?  Would you like the chance to run one of these special events in the future?

About Patty

Patty Holliday is a wife and mother of four. She's a travel agent specializing in Disney & Universal vacations- and loves a candid confession. Find her in Virginia (or anywhere frequent flyer miles or her trusty minivan takes her.)


  1. Cute race outfits – this looked like a blast – thanks for sharing!

  2. YAYAYAYAYAY!! Loved reading this! Sounds like a great race and should I suddenly inherit a ridiculous amount of money, this is definitely going on the list of how to spend it (should they do it again). Thanks for the great recap! Are you going to write about the cruise itself? Because I want to read all about the cruise! (yes, I am very demanding. Sorry.)

    • I’m writing about the cruise for SURE. It was something I didn’t know I needed in my life until I experienced it. I’m now #TeamDCL fo sho!

  3. OK, As expected, I am drooling. runDisney + Disney Cruising sounds like the perfect combination to me; an installment plan would help! Crossing my fingers and pennies for the Wine & Dine. Thanks so much for sharing and keeping my dream alive Patty!

  4. I’m so happy we shared this experience! I had a blast cruising and running with you and Tania. Uno, Dos, Tres…McFarland!

  5. Your costumes were awesome.
    Thank you so much for sharing this experience. I’m sidelined from PHM & Tink for a bit until the wee one is old enough to make a Disney trip, so I’m living though updates like this one.

  6. I loooooooved this race combined with Princess combined with the cruise so much. As much as I missed the family, I’m so happy I had you and Diane to share this experience with! So…next year? 🙂

  7. Erin/Hans says:

    Thanks Patty for this recap! I wonder if the extra characters are just a bonus for this event because from some of the reading I’ve done on the regular Castaway Cay 5K, there are characters at the beginning and end but not much during the race? But honestly I don’t know, I’ll let you know how it goes next month!

  8. You guys got a reception? Glad for you but UGH for those of us who did the actual inaugural. Nothing like that in January!

  9. Love this article and your recap of the challenge! Thanks for sharing! While I’m an “old” Disney fan, I’m rather new to the races and cruises. Our first cruise is booked for July, celebrating my 40th birthday!, and I was finally able to register for the Wine & Dine. Any suggestions as to how to plan better next time if I wanted to do the challenge? Thanks!

    • It looks like the only Castaway Challenge will be after Marathon weekend. I just saw it shared on the 2017 Marathon website. So sign up for that one next!

  10. I always enjoy reading your stories, they are so interesting. I see that you got a medal. Glad for you!

  11. Hey Patty!

    Were your striped shirts tech fabric or did upu all just suck it up and wear cotton? I’m looking for stripes for Wine & Dine.

    • They were costumes from Amazon or Ebay. Where’s Waldo? lol So nope- not tech fabric. But for a 5K it wasn’t too bad. I can’t say I’d want to run a half in them though.

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