Dan, Dan, Dan - A road excursion [in any scale or intensity] is simply not in the same level of learning, planning or capability as compared to large scale [or even medium large scale] boating! :D

Naturally, I would highly recommend taking a few courses ie. boat handling especially in confined spaces and navigation, basic maintenance of the engines on board. After he buys the boat, a Captained cruise.... to pick his brain.

On an experienced vessel ??

Yep, and experienced cruisers know what I mean.

Before this gets too far off track...

All I am saying is that if you follow one school of thought in prepping for ocean crossings( the path often suggested at Safety at Sea national level seminars)...prep time fills and goes by quickly and isn't just a handful of short local shakedown cruises....it can be pretty intense.

John,
Sounds like my wife and I are on the exact same schedule! Retire in three years and go - maybe not around the world but certainly the entire east coast and islands. My budget is not quite the same but close. We have looked extensively at Kady's, Nordhavn and Fleming in addition to many others. We seem to have settled on the F55 and are just back from a sea trial in Stuart last week. To be fair you should take a close look at the Krogan Express which has the same hull and twin engine as the Fleming. I'd love for us to keep tabs on each other to see how each ends up. Cheers and welcome aboard!!

Cross oceans on a Krogen Express? [emoji15]