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20 “BEST” Sailboats I’d Choose If I Were Starting Over at 55

#SailingAfter55 #OlderSailors #SmartBoatChoices #LowEffortSailing #PracticalSailing #LongTermOwnership
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If I were starting again at 55, I wouldn’t chase speed.
I wouldn’t chase size.
And I wouldn’t assume I still want the same boat I loved at 40.

In this video, I share 20 sailboats I would seriously consider if I were beginning again at 55 — with clearer priorities and a longer ownership horizon.
These are boats chosen for manageable workloads, stable motion, simpler systems, reasonable insurance profiles, and resale markets that don’t disappear after a few years.

“Best” doesn’t mean perfect.
It means realistic.
Boats that reduce friction, conserve energy, and stay cooperative when sailing solo or short-handed.

This isn’t nostalgia, and it isn’t performance ranking.
It’s a practical reset — looking at boats through the lens of longevity, effort, and how ownership feels 10–15 years down the line.

If you were starting over today, what would you value differently?

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