DiscoverSailing Doodles PodcastRetire & Sail Away? Here’s the Truth
Retire & Sail Away? Here’s the Truth

Retire & Sail Away? Here’s the Truth

Update: 2025-09-25
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Ever dreamed of selling it all and retiring to sail the world? In this episode of The Sailing Doodles Podcast, Bobby breaks down what it really takes to make that dream happen. From health and fitness (because sailing isn’t a spectator sport), to money and income streams, to choosing the right boat and lifestyle — we cover it all.


Whether you’re 55 and planning ahead or 67 and wondering if it’s too late, this episode gives you the honest truth about the realities of retiring at sea.


Topics include:


Why your health matters more than your bank account


How much money you really need to cruise full-time


Passive vs. non-passive income while sailing


Why your boat should be paid off before you cast off


The mental and lifestyle adjustments that make or break retirement cruising


Subscribe for more stories, tips, and real talk about life on the water!

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Retire & Sail Away? Here’s the Truth

Retire & Sail Away? Here’s the Truth

Bobby White