So playing around with those pesky “sound alike but have different meaning” words, I came up with the following:
Chilly chilies from Chile are in the chilli at Chilis.
Translation: " Refrigerated hot peppers from a South American country are in the spicy meat and bean stew at a national restuarant chain."
Five (semi) homonyms in a ten word sentence!
Does anyone have any others? Or, to throw down the gauntlet, can anyone beat five homonyms in a single sentence?
The Tartars ate Steak Tartare with tartar sauce and got tartar on their teeth.
He Sheared Shere Khan with Shears and sheer audacity.
An Ode to the Spelling Chequer
Prays the Lord for the spelling chequer
That came with our pea sea!
Mecca mistake and it puts you rite
Its so easy to ewes, you sea.
I never used to no, was it e before eye?
(Four sometimes its eye before e.)
But now I’ve discovered the quay to success
It’s as simple as won, too, free!
Sew watt if you lose a letter or two,
The whirled won’t come two an end!
Can’t you sea? It’s as plane as the knows on yore face
S. Chequer’s my very best friend
I’ve always had trubble with letters that double
“Is it one or to S’s?” I’d wine
But now, as I’ve tolled you this chequer is grate
And its hi thyme you got won, like mine.
—Janet E. Byford
And of course those master’s of frozen confections Ben and Jerry - Whirled Peas flavor.
Phlosphr: Well dang. I mean, my goodness! Wow.
errrrm… there are at least eight discrete meanings for “cant”; but I’m not equal to the task of getting them all into a sentence.
I note with amusement that a search of Vancouver craigslist housing ads for the keyword “specious” turns up 15 specious ads in the last month.
(Not a homonym, but I’ve been itching to point that out and it’s not worth its own thread.)
The classic:
Buffalo buffalo Buffalo buffalo buffalo buffalo Buffalo buffalo.
Yeah, but if the locals weren’t insane with how they pronounce the name of the town Chili, NY (scroll down) I could have done you one better:
Chilly chilies from Chile are in the chili at the Chili Chilis. 
Tonight drank two tequilas too many to walk.
Watching his skydiving son, a man may well wonder, “Will my heir in the air err 'ere he opens his parachute?!”