Engine Size
 

Whats the biggest engine without modifing that would fit in the 66. Looking at the 392 but would settle with a 302 with supercharger.

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66 Mustang Black W/ Black
289 Hi-Po 65'heads, MSD
Lunati High lift Cam
750CFM Carb Heddman Headers, Hurst Shifter

If it was me, I would go with that 392 crate engine. With 430 HP for $6000, that isn't bad, especially for a street driven car.

Rev

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'66 Coupe, 306, 300 HP, C-4, 13.97 e.t., 100.3 mph
1/4 mi.

will I have any clearance problems as far as headers go. I was thinking maaybe the shorty headers if any thing.

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66 Mustang Black W/ Black
289 Hi-Po 65'heads, MSD
Lunati High lift Cam
750CFM Carb Heddman Headers, Hurst Shifter

I think Hooker and Heddman both make headers specically for that swap (351W into early Mustang). I would contact them to be sure.

Rev

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'66 Coupe, 306, 300 HP, C-4, 13.97 e.t., 100.3 mph
1/4 mi.

I tried to fit a 351 into my car once and it wouldn't even come close to fitting. I was told by a very reputable classic car rebuilder that the shock towers had moved in a little and require pulling back to original position, it was undesirable for me because it was expensive and I wouldn't trust metal that has been bent twice. I installed a monte bar and export brace and they didn't push them out, they just keep them from coming in any more. You should measure you towers and make sure it is correct.

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65 fastback
347 DFI injected, TFS heads, T5, 4.11 9", tc subframe conns, torq thrust D's
A little history lesson using today's tech.

i just finished going from a 306 to a new 347 for my 65 FB. If you could use the same block, a stroker kit for about a grand, maybe use the same cam, some aftermarket TFS heads, or something similar, you could achieve some good power, and not have that fit problem. Coast has a kit that now keeps the rings out of the floating bushing, so the longevity concerns are gone. If you go supercharger you will have to build a low compression motor, that would be a dog without it, or get your hp from a higher compression motor and forget the supercharger.
Although my 65 is focused primarely on the track, and built for that application, it did make 604.6 hp at 7200 and 487 ft/lbs of torque at 5400-6200. Should give you an idea of what a stroker can do. (NO power adders BTW).

Ron