If ever a street has undergone a complete change in personality, it's Caroline Street in Key West; at times housing stately mansions belonging to the island's founding aristocrats while later becoming notorious for its rough-shod reputation as a shrimpers hangout.
Named for a sister of John Whitehead, one of the island's first owners in the 1820s, Caroline Street is one of the oldest in Key West, appearing on some of the earliest maps.
But it did not always offer an eclectic mix of boutiques, home décor shops, guesthouses, art galleries, coffee shops and restaurants.
While the street now parallels the city's Historic Seaport district, with recreational sailboats, snorkeling catamarans and waterfront restaurants, it formerly was the closest street to the island's commercial fishing fleet. As such, it was home to the denizens of the docks, a rough-and-ready crowd of shrimpers, turtle fishermen and other mariners.
The historic building at 800 Caroline St. that now houses apartments up top and an upscale boutique on the ground floor was famously known as the Red Doors.
It was built in 1868 as part of a real estate speculation project by the Pinder and Curry families, and then became a cigar factory in the late 1800s before the industry moved largely to Tampa, according to the sign on the front of the building that details its history.
By 1906, the building was a ship's chandlery, servicing the working vessels that lined the nearby waterfront.
In the Depression years of the 1930s, the building was home to a grocery and hardware store, still catering to the needs of the neighborhood's fishermen.
"When shrimping became important to Key West in the 1950s, the building, under a succession of owners and names, became one of the toughest bars on the Gulf Coast," the sign boasts, adding that the building earned the nickname "Bucket of Blood" for the number of stabbings, fights and "quiet murders" alleged to have taken place on what is now one of Key West's most distinctively historic streets.
The bar at 900 Caroline St. was at times known at the Conch Gardens, Wagon Wheel Inn and the Red Doors Inn and is also said to have been used as brothel, where women paid rent for small rooms in which to welcome shrimpers back to land after a long time at sea, said former Key West City Commissioner Bill Verge.
Caroline Street also was home to Pauline Hemingway's drapery and upholstery shop after she divorced the famous author.
Pauline Hemingway stayed on in Key West and went into business on Caroline Street, according to J. Wills Burke's book "The Streets of Key West."
Caroline Street once again is on the verge of another metamorphosis. A new luxury hotel is waiting in the wings between Elizabeth and William streets, while a new, large West Marine is planned for the area near the ferry terminal at Grinnell Street.
Businessmen also have plans to create an upscale brewery in the old building that once housed the popular Waterfront Market.
A wooden Harbor Walk now connects all parts of the waterfront, where tourists can stroll with a frozen drink in hand and look at the stately schooners that dock in front of Schooner Wharf Bar.
Caroline Street looks nothing like it once did, but if history provides any clue to the future, the street will always remain an important link between the island and its waterways.