He crossed the finish line of a 100-mile ultramarathon in the Florida Keys, showered on the beach, and drove straight to Fort Lauderdale to board the brand-new Disney Destiny the next morning. Nine-time DCL sailor Josh joins us to break down how he pairs grueling endurance races with Disney cruises — and what boarding a ship on legs that just ran four marathons back to back actually feels like.

In this episode:

• How Josh turned Disney cruising from post-race recovery into a full-blown tradition across nine sailings
• The wild 24 hours between crossing the finish line at Keys 100 and boarding at Port Everglades
• Why trip insurance won't cover an ultramarathon-plus-cruise combo, and what that risk actually looks like
• His honest take on the Destiny's dining, entertainment, and Wish-class layout, including one hot take about Lookout Cay vs. Castaway Cay
• The one piece of advice he gives every Disney cruiser: be fluid, not over-scheduled
• What's next for his race-and-sail tradition

"There is no moment like when they finally check your last passport, your last little thing, and you're like, OK, we're here."

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The views expressed in this podcast are our own and do not reflect the views of the Walt Disney Company, Disney Cruise Line or any other travel provider discussed or mentioned.