• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Home
  • About/Hire Me
    • About Me
    • Hire Me
    • Contact
    • Family
    • Faith
    • FAQ
    • My Running Story
    • Recipes
  • Disney
  • Fitness
    • runDisney Information Page
    • Fitness
    • Races
  • Parenting
  • Travel

Through Heather's Looking Glass

  • Disney
  • Fitness
  • Travel
  • family
  • About Me

Inaugural Castaway Cay Challenge 5k

January 15, 2015 | Disney, runDisney, running, Travel

The Inaugural Castaway Cay Challenge 5k took place yesterday morning on Disney’s beautiful private island. Over 700 runners took to the beautiful course surrounded by lush tropical landscape, rolling waves, and an island breeze (well, some days!)

Any cruise that sails to the island has had a 5k in recent years, but this is the first time you could run a runDisney race in Walt Disney World, the follow immediately with a Disney Cruise Line cruise. If you completed a race at WDW and the Castaway 5k, you would also get the challenge medal, which is absolutely beautiful! (Please note you have to register for this challenge!)

Inaugural Castaway Cay Challenge 5K Event on Disney Cruise Line Private Island

The cruise is on the beautiful Disney Dream, for four nights as it sails to the Bahamas. The ship left from Port Canaveral, FL on Monday. Runners also have access to special speakers, merchandise, and activities all surrounding the Castaway Challenge.

Inaugural Castaway Cay Challenge 5K Event on Disney Cruise Line Private Island

There will be another Castaway Cay Challenge 5k following on the heels of the runDisney Princess half marathon weekend next month. Space is still available for this challenge, check out runDisney.com for details on registration.

I do hope runDisney and Disney Cruise Line continue this partnership with more races, as I would love to be able to participate! Who doesn’t want to relax on a Bahamian cruise after running hard at a runDisney event?

QOTD: What are your thoughts on this challenge? Is this something you would like to participate in?

Like this:

Like Loading...

Sign up for my newsletter

Reader Interactions

Comments

  1. Jen says

    January 15, 2015 at 5:14 am

    I hope they do it for Wine and Dine!

  2. Mindy @ Road Runner Girl says

    January 15, 2015 at 8:11 am

    Oh I would LOVE to do the Castaway Challenge one day!!!

  3. Lesley says

    January 15, 2015 at 8:23 am

    With 4 race weekends at Disneyland, maybe Disney Cruise needs a Castaway Cay island on the west coast too.

  4. Ashley says

    January 15, 2015 at 10:29 am

    I would love to participate, but Disney cruises are so expensive!

    • Heather says

      January 15, 2015 at 10:51 am

      They are but totally worth it! You def. get what you pay for. They are amazing.

  5. Karen :0) says

    January 16, 2015 at 7:16 am

    Can’t wait! This event looks like SO much fun!!

  6. Joy Hargraves says

    January 16, 2015 at 3:55 pm

    I JUST GOT BACK!!!!!! It was a lot of fun, and rD was on board all week. They also had a QnA session. At this time, there are NO PLANS to do any more of the CC5K Challenges after Princess. They may re-evaluate after feedback from us and the Princess crew. So if you want in on this Challenge, DO IT NOW for Princess, or your magical moment may have passed!!! They redid the regular 5K medallions, and you will continue to be able to get those for the normal CC5K. Find me on Facebook for more pictures, and I do plan on blogging about my time there!!!! I am glad I did this!!! Disney Cruise Line is far, far, far superiour to any other cruise line out there!! You absolutely get what you pay for!!

    • Heather says

      January 18, 2015 at 8:22 am

      I”m so excited they are finally changing the medals. I have 5 of the plastic ones at least! A lot of people who got the marathon weekend survey after that race said one of the questions was about interest in doing this after Wine and Dine, so I hope the keep it up!
      I always tell my clients that about DCL when they get sticker shock, you DO get what you pay for!

  7. Amanda says

    January 18, 2015 at 8:55 am

    Sure hope they continue this challenge series!! Everything I’ve read, so far, states nothing is in the works for future CC challenge runs after Princess wknd! Hubby and I did 2013 WDW race and cruise. Also, 2014 TOT race and cruise. So, technically, I’ve completed this twice. 😉
    Sure would enjoy the “official” bling….. ** fingers crossed **

Trackbacks

  1. runningwithsass says:
    January 15, 2015 at 2:31 am

    Inaugural Castaway Cay Challenge 5k

    The Inaugural Castaway Cay Challenge 5k took place yesterday morning on Disney’s beautiful private island

  2. Never Say Never...to runDisney - Through Heather's Looking Glass says:
    April 29, 2015 at 1:48 am

    […] for the runDisney marathon weekend! I found out yesterday morning that they are offering the castaway challenge after the race, which I ssoooo badly want to do. I have talked to and begged runDisney to partner […]

Primary Sidebar

I am Heather Montgomery, a 30 something southern girl living in Knoxville, Tennessee with my husband Bobby, 10-year-old daughter Emma Kate, and our goldendoodles Dolly and Luna. I’m just a regular girl who likes to workout, travel, hang with my family, text, and eat chips and queso. Be sure to check out my “about me” page for more info!
Thank you for visiting, and feel free to contact me with questions, (or for PR inquiries or press trip invites) at Support@HeathersLookingGlass.com.

Please, no guest post requests. 🙂

More about me

Privacy Policy

You can also find me here:

  • Facebook
  • Instagram
  • Pinterest
  • RSS
  • Twitter
  • YouTube

Recent Posts

  • Family Fun in Tuscaloosa: Your Ultimate Getaway Beyond Game Day
  • 5 Reasons to Try a New Way of Travel
  • Experience Superhero-Sized Fun at Gaylord Opryland DC Summer
  • Digital Nomads: Safely Working Remotely While You Roam
  • Tips for Surviving (and Thriving) as a Travel Ball Mom

 

Search

How to Start a Blog

How to start a blog
We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites.
  • Disney
  • Fitness
  • Travel
  • Family
🌴 GIVEAWAY ALERT!🌴 Ready to escape to para 🌴 GIVEAWAY ALERT!🌴 

Ready to escape to paradise? I spent a few dreamy days at Margaritaville Beach Resort Fort Myers, and I’m giving YOU the chance to win 2 FREE nights at this beachfront oasis! 😍☀️ #margaritavillepartner

Here are 5 things I didn’t expect to love so much (but totally did):
1️⃣ Fins Up Beach Club — live music, great drinks, and cabana vibes for days!
2️⃣ The Rooms — bright, coastal decor and ocean views that make you feel like you’re living inside a vacation postcard.
3️⃣ The Spa — a total hidden gem. My massage was next-level relaxation.
4️⃣ The Restaurants — from casual beachfront bites to more elevated dining, the food alone is worth the trip.
5️⃣ The Vibe — laid-back luxury with the perfect mix of fun and relaxation. It’s always 5 o’clock here! 🍹

✨ Whether you’re staying overnight or popping in with a day pass, Margaritaville Beach Resort Fort Myers Beach is pure island bliss.

🎉 Now YOU could win a 2-night stay!

🏖️ Prize: Complimentary Two-Night Stay at Margaritaville Beach Resort Fort Myers Beach
⚠️ Blackout dates apply.

How to Enter:
✅ Like this post & follow both @HeathersLG and @margaritavillefortmyers
✅ Tag at least 2 friends in the comments (extra comments = extra entries!)
✅ Comment: Are you a pool or beach person?

🌟 BONUS (not mandatory) for 5 extra entries: SHARE this post on your stories and TAG me so I can see it!

Good luck — and remember, it’s always island time somewhere! 🌊🍹

Redemption Details:
Winner must book by August 31, 2025
Valid for travel between August 1, 2025 – June 30, 2026

Must be 18+ to enter
Giveaway closes midnight July 25, 3025. Not sponsored by Instagram. 

#MargaritavilleResort #FortMyersBeach #BeachClubVibes #CabanaLife #SpaDay #BeachGetaway #ResortGiveaway #FinsUp
I’ve had an interesting first few days of being I’ve had an interesting first few days of being in my 40’s. A bit of a nerve wracking medical week I guess you could say. 

Have you ever had an MRI? Do you suffer from hearing loss? 👂 

#thisis40 #hearingloss #mri #inmy40s #40andfabulous
✨ This is what radiance looks like ✨ #ad Sin ✨ This is what radiance looks like ✨ #ad 

Since turning forty, I’ve been all about simple changes that help me feel strong, healthy, and confident — inside and out. 

Adding Organixx Collagen to my coffee each morning has been one of the easiest ways to support my skin, hair, and joints while juggling busy mom life. It blends right in and makes me feel like I’m doing something good for myself every single day. 

Because for me, it’s not just about looking good — it’s about feeling my best, staying active, and showing up for the people and moments that matter most. 
Radiance starts from within, and @organixxco helps make it part of my everyday routine.

🤩Use code HMONTGOMERY to save 10%! Link is in my bio.

 #organixx #organixxcollagen #CollagenRoutine #GlowFromWithin #BusyMomLife #ThisIsWhatRadianceLooksLike
I LOVE @disneyphotopass photographers! We have met I LOVE @disneyphotopass photographers! We have met some of the kindest most fun cast members while getting our pictures taken. 

If you don’t get pics taken with them often you probably won’t get this reel, and that’s ok. IYKYK. It’s all in good fun! 💚

What did I miss/forget?😆

#disneyphotopass #photopassphotographer #disneypics #disneyfunny #disneymeme
Follow me for more parenting hacks. 💁🏻‍♀ Follow me for more parenting hacks. 💁🏻‍♀️

#backtoschool #parentinghack #backtoschooltips #backtoschoolshopping
I turned 40 today. 🎉 Hitting a milestone like t I turned 40 today. 🎉 Hitting a milestone like this has me reflecting—not just on what I’ve accomplished, but on who I’m becoming.

I’ve always been driven to achieve, to push, to prove. But lately, I’ve been learning to celebrate presence over performance, connection over perfection.

Today wasn’t about checking a box or hitting a goal—it was about pausing, feeling grateful, and eating a ridiculous amount of cake with people I love. And honestly? That feels like growth.

Here’s to 40: more aligned, more grounded, and still a little extra. 😉

#thisis40 #40andfabulous #thankyoujesusfor40years #birthdaygirl❤️ #40andoverclub
Turning 40 tomorrow. 🎂 Big milestones always Turning 40 tomorrow. 🎂 

Big milestones always make me pause and ask:
What am I proud of?
What needs to shift?
Am I becoming the woman I want to be?

💡 As an Enneagram 3, I’ve always been wired to achieve — and for a long time, that meant shaping myself into whatever version I thought people would like best.

There are tables where it’s clear I’m not welcome — and that used to wreck me.
But at 40? I don’t do cliques. I don’t do shrinking or contorting to be accepted. 👀

I’ll always be kind. I’ll always be respectful. But I’m done dragging a chair to tables that were never built for me.

I’m moving over. Making space.
Creating my own table.

✨Who’s in?

#ThisIs40
#OwnYourStory
#ReelTalk
#Over30Club
#ChristianWomen
#PersonalGrowthJourney
#enneagram3

Copyright © 2025 · Through Heather's Looking Glass · Theme by Bella Creative Studio

%d