Boca Grande has always been known as a
unique island, but there are some nuances
that even a seasoned visitor may not know
about. For instance, have you heard about the
“Dam” streets? Home to some of the most
interesting architecture on Gasparilla Island,
featuring a pleasant mishmash of old fishing
cottages and modern, roomy homes on large
lots, the three streets off Railroad Avenue (across
from the back of Boca Bay) wind through the
canal systems and end in cul-de-sacs. Their names
are “Damfiwill,” “Damficare” and “Damfino.”
According to the Boca Grande Historical
Society, the streets were originally recorded by
Lee County as 2nd, 3rd and 4th Streets many
years ago, but this was at a time when directions
were given more like “turn at the corner where
that crooked tree is” instead of “turn north at
3rd Street.” One day a resident of one of the
streets needed to have some lumber delivered.
When asked what his address was he defered to
his fishing captain, who was with him at the time.
“Damn if I know,” he replied.
Written By Marcy Shortuse
Photos by Dusty Hopkins & the Boca Beacon archives
Once the lumber was delivered the driver, thinking
he was being clever, stopped and put up a handmade
sign at the corner of E. Railroad Avenue and 3rd
Street which read, “Damfino.” And that is what it has
been known as ever since.
Not long after that a cocktail party was held, and
many of those who attended lived on those streets.
When it was suggested they come up with something
more imaginative than their numbered street
names someone from the crowd called out, “Who
cares?” That led to a discussion of a new name for
4th Street, Damficare. Finally, 2nd Street was named
by a woman who lived on that road, who one day
placed a sign by E. Railroad that said, “Damfiwill.”
There is really no way to describe any set style of
architecture on any of the three streets, which makes
it a very interesting drive on a leisurely golf cart ride.
You will find anything from Richmond homes to
Spanish and Mediterranean style, with a mix of
traditional current Florida, old Florida and
contemporary architecture mixed in. It’s truly a
neighborhood that speaks of the way Boca Grande
used to be.
March/April 2019 GASPARILLA ISLAND 73