The Southernmost Point Buoy, Truman Little White House & Bahama Village

Walking south and west from the Ernest Hemingway Home takes you through three distinct chapters of Key West history: the island's famous photo monument on the Atlantic shore, the Afro-Bahamian neighbourhood of Bahama Village, and the shaded compound of the Harry S. Truman Little White House.

1. The Southernmost Point Buoy (Corner of South & Whitehead Streets)

Originally marked by a wooden sign that tourists frequently stole as souvenirs, in 1983 the City of Key West erected a 4-tonne, 3.6-metre-tall (12-foot) concrete buoy painted like a marine navigation marker reading: 'The Conch Republic, 90 Miles to Cuba, Southernmost Point Continental U.S.A.'

• Two Insider Tips: 1) From mid-morning through the afternoon, the single-file photo queue down South Street takes 30 to 45 minutes, so walk or cycle here soon after sunrise (grabbing a Cuban café con leche on the way) to take photos with nobody in line, or wave to family on the live Southernmost Point Webcam mounted across the street; 2) Geographical trivia: the actual southernmost land tip sits 200 metres west inside the U.S. Navy's Truman Annex fence, making this buoy the southernmost publicly accessible point.

2. The Harry S. Truman Little White House (111 Front Street, Truman Annex)

Tucked inside the tree-shaded lanes of the gated Truman Annex neighbourhood (free to walk or cycle through during the day), the 1890 Harry S. Truman Little White House is Florida's only presidential museum. In November 1946, ordered by his doctor to seek warm sunshine, President Harry S. Truman fell in love with these breezy naval quarters, returning for 11 working holidays totalling 175 days and holding cabinet meetings in Hawaiian shirts. Join the 45-minute guided tour to see his 1949 desk, walnut poker table and rooms where Eisenhower, Kennedy, Carter and Clinton also stayed. Next door sits the complimentary Florida Keys Eco-Discovery Center.

3. Walking Bahama Village (Petronia Street)

Settled in the 1830s by Black Bahamian mariners, sponge divers and wreckers, the colourful wooden cottages along Petronia Street in Bahama Village house Key West's famous backyard restaurant (Blue Heaven, where Hemingway refereed Friday boxing matches in the 1930s), La Crêperie French Cafe and Santiago's Bodega.