SeaPeople Live S2 ep. 6 | The Boat You Actually Need with Conor Dugan

Podcasts

Aug 21, 2026

Conor Dugan sails a small sailboat heeled over on the water beneath full sails as the sun breaks through the clouds.

Stop Building the Perfect Boat. Go Sailing.

Most people shopping for a cruising boat eventually end up asking the same questions:
Catamaran or monohull?
How much boat do I really need?
What upgrades are actually worth paying for?
And how much money am I about to dump into a boat that I’ll never get back?

Conor Dugan has seen that decision from almost every angle. He’s cruised the East Coast and Bahamas on his own 35-foot monohull, worked as a professional captain, run large charter cats, and now sells both sailing and power catamarans.

Watch the full conversation here:

Cat vs. Monohull, Refits, Resale Mistakes & a Wild Jimmy Cornell Story

In this episode of SeaPeople Live, we get into the mistakes buyers make when outfitting a boat, why expensive refits rarely pay you back, what the used-boat market actually looks like right now, and why sometimes the smartest move is to buy something simple and “grip it and rip it.”
We also get into one of Conor’s stranger sailing experiences: joining Jimmy Cornell aboard an experimental all-electric Outremer for an ambitious voyage that did not go according to plan.
There are failed passages, dead batteries, hand-steering through the night, some very candid thoughts about weather routing, and possibly an NDA or two.

But the best advice comes at the end:
Buy the boat that works for the life you’re actually going to live and then sail the hell out of it.