
Sign up to save your podcasts
Or


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!
By Sailing Doodles4.3
66 ratings
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!

38,670 Listeners

16,581 Listeners

2,043 Listeners

530 Listeners

9,507 Listeners

2,012 Listeners

2,905 Listeners

5,488 Listeners

6,079 Listeners

11 Listeners

16,242 Listeners

9,902 Listeners

136 Listeners

10,910 Listeners

4,451 Listeners