Well, for my world I've already technically done it "halfway" aboard my Bristol 29.9!by around the world, I'll assume you mean Jamestown, Block Island or such...
Started at Bayshore LI, 03JUL04 ~1600 headed west to NY Harbor (Prop wrap 3 miles south of Jones inlet just after sunset, led to swimming in 90' of water at night playing the JAWS theme in my head!!
)Passed under the Verrazano-Narrows Bridge by 0100, past the United Nations at 6AM (Happy 4th, not a SOUL around in the East River!!) to enter the Long Island Sound at ~0730.
Arrived at Mt Sinai Harbor about 1600. I hated that 15 horse Yanmar on that 8900 lb boat!! 1kt SOG fighting the outgoing Hudson Tide underneath the Verrazano! Seemed to take forever!!
And THAT folks is why I FOUGHT to come back to a 
!! I love my power to sail ratio!! 
Sure beats making 125nm at an avg 5.02 SOG!!Also, ZEPHYR developed a pretty substantial stuffing box leak during the night (~4 gal/30 minutes). The previous owner did not have an electric bilge pump. Needless to say,when we moored I learned how to tighten a stuffing box. The following day after that I installed an electronic bilge pump with switch! So I prefer Outboards now for two reasons...prop wraps (raise the motor!) and stuffing box issues....it always seemed like I was worrying about it, is it too tight? too loose? is the shaft bent? how's the cutlass bearing? etc.. Anyway, I digress.
So the goal now, hopefully the others in our area will as well, is to enter the annual "Around Long Island Regatta" so I may complete the circumnavigation of "my" world!!
"Sub" Ed
(with HP of course) should have NO problem.
