Situated within the historic "Old Town" district, Caroline Street was part of the original infrastructural layout of the island at the time of its 1829 mapping by William Whitehead.

Caroline Street was named for a sibling of Whitehead; his brother, John, became interested in the island after a shipwreck left him stranded in 1819.

Between Whitehead and Telegraph Lane just a few hundred feet to the northeast, Caroline is a quiet, shaded street, before its left (northern) side opens up to a strip of businesses and shops.

Although many of these houses were constructed quickly and cheaply, their builders employed the same techniques that were used at the time to craft boats, lending them resistance to extreme weather.

As Caroline continues toward the northeast, it crosses William Street and offers an obscured view of the Gulf of Mexico side of the island and vessels at port.

[1][5] Caroline Street is situated along the northwestern side of the island, in a historic district known as Old Town Key West.

[8] The original map from William Whitehead's survey shows the northwestern corner of the island, bounded by present-day Angela Street, designated as "town plot".

[9] Eventually, the street was excluded from the lot of the Truman Annex, and disconnected from the water at its northeastern terminus by the construction of the former City Electric Power Plant on new land.

[10] The dynamics of the project changed throughout its course; in early 2011, the city approved spending for specific updates to infrastructure along the corridor, including improved lighting and signs, a more extensive sidewalk system, and versatility with regard to bicycle and pedestrian traffic.

[12] Early in his career, Jimmy Buffett co-wrote "Woman Goin' Crazy on Caroline Street" with Steve Goodman.