Key West, Florida
Key West self-guided walking tour: Old Town.
A free, original loop through Old Town Key West: Mallory Square, the Custom House, Audubon House, the Truman Little White House, the Ernest Hemingway Home, the Key West Lighthouse, the Southernmost Point buoy, the San Carlos Institute and St. Paul’s Episcopal Church on Duval Street. Read the stops here, then open the mapped route on your iPhone.
Start at Mallory Square
Begin on Wall Street at Mallory Square, on the harbor. The loop heads south along Whitehead Street past the Custom House, Audubon House, Truman Annex, the Hemingway Home and the lighthouse to the Southernmost Point, then returns north along Duval Street. Key West is hot and sunny for much of the year and shade along the streets is patchy, so carry plenty of water, wear a hat and walk early or late in the day. The City of Key West has roadwork near the Southernmost Point in fall 2026, so follow posted detours. The route follows mapped pedestrian paths, but it has not been walked on site by Daily Wander.
- On iPhone, get Daily Wander if you do not have it.
- Return to this page and tap Open the tour in Daily Wander. Check the preview, then choose Open in Daily Wander.
- In the app, review the route and choose Start this route or Save route. Keep this guide handy for the stop notes.
Museum visits, tickets and meals are separate and are not included in the walking time. Follow local signs, closures and diversions.
Nine stops, in walking order
The route uses public viewpoints. Check the linked sources for current access before planning a visit inside.
Stop 1
Mallory Square
Begin on Wall Street at the edge of Mallory Square, on the harbor at the northwest corner of Old Town. The square has been the center of Key West’s social and trading life since the town began in the early 1820s. Ships belonging to master wrecker Asa Tift unloaded goods salvaged from shipwrecks at these docks, and the cargo went into his warehouses on the waterfront. Townspeople came here for news and shopping. Walk to the water’s edge, where the Sunset Celebration gathers two hours before sunset, and look west across the harbor.
Stop 2
Key West Custom House
Walk south to Front Street and the large red brick building on its corner. The Custom House opened to the public in 1891 in the Richardsonian Romanesque style and held the Collector of Customs, the post office, a federal courthouse and the Lighthouse 7th District office. The Navy took it over for communications and offices in 1932. After decades boarded up, it was bought by the State of Florida in 1992 and leased to the Key West Art & Historical Society, which restored it as a museum over nine years. Look for the engraved bricks on the southeast walkway.
Stop 3
Audubon House and Tropical Gardens
Walk around the Custom House to Whitehead Street and south to Greene Street. Captain John Huling Geiger, a harbor pilot and master wrecker, built this house for his family between 1846 and 1849, after an October 1846 hurricane damaged or destroyed nearly every home in Key West. In 1958 it was due to be torn down for a gas station until Mitchell and Frances Wolfson bought it. After two years of restoration it opened in 1960 as a museum recalling John James Audubon’s 1832 visit to Key West. Look past the fence into the garden.
Stop 4
Truman Little White House
Continue south on Whitehead Street and turn right into Truman Annex, following the walkway west to the Little White House. It was built in 1890 as Quarters A and B, a two-family home for the Navy commandant and paymaster, and became a single-family house in 1911. Thomas Edison lived here for six months in 1918 while working on new weapons for the war effort. Harry S. Truman first came in 1946 and made 11 working vacations to Key West as president, then returned five more times. If the Truman Annex gate is closed, view the area from the Whitehead Street entrance.
Truman Little White House: A Brief History of the Little White House
Stop 5
Ernest Hemingway Home and Museum
Walk back out of Truman Annex to Whitehead Street and follow it south about half a mile to the corner of Olivia Street. Ernest Hemingway first reached Key West in April 1928, by way of Havana, and finished A Farewell to Arms in town while waiting three weeks for a car. In 1931 his wife Pauline’s Uncle Gus bought this house on Whitehead Street for them. It was built in 1851 in the Spanish Colonial style, from native rock quarried on the grounds. Ernest and Pauline divorced in 1940. Look at the stone walls of the house from the sidewalk.
Stop 6
Key West Lighthouse
Cross Whitehead Street to the white tower on the opposite side. The Navy set up a base in Key West in 1823, and the shallow, reef-filled waters soon made the need for a lighthouse clear. The present lighthouse opened in 1848 with a woman as its keeper, something almost unheard of at the time. It later gained a third-order Fresnel lens, a taller tower to send its light farther, and electric power. The Coast Guard decommissioned it in 1969. The Key West Art & Historical Society website lists 88 steps to the top. Look up at the lantern.
Key West Art & Historical Society: Key West Lighthouse & Keeper’s Quarters
Stop 7
Southernmost Point buoy
Walk south on Whitehead Street and then east to the southern end of Duval Street, following any posted detours around the roadway work. The City of Key West put up its anchored concrete buoy in 1983 to mark the corner of South and Whitehead Streets as the southernmost point in the continental United States, a mere 90 miles from Cuba. Since September 4, 2025, while the seawall and roadway are repaired, a temporary buoy has stood at 1499 Duval Street, at the southern end of Duval. Look south across the water toward Cuba.
Stop 8
San Carlos Institute
Walk north on Duval Street for about two-thirds of a mile to number 516. Cuban exiles founded the San Carlos Institute in 1871 while planning Cuba’s independence from Spain, and it was rebuilt on this Duval Street lot in 1890 after the 1886 fire. José Martí called it “La Casa Cuba” and addressed a large gathering here on January 3, 1892. After a 1919 hurricane damaged it beyond repair, Cuban architect Francisco Centurión designed the present building, which opened on October 10, 1924. Look up at its arches.
Stop 9
St. Paul’s Episcopal Church
Continue north on Duval Street to Eaton Street. The congregation signed its Act of Association on Christmas Day 1832, after the city council authorized the parish. A hurricane destroyed the first church, of coral rock, on October 11, 1846; the second burned in the Great Fire of March 1886; and a hurricane took the third on October 11, 1909. The present concrete church, the fourth on the site, held its first service on June 8, 1919, and its stained glass went in from 1920. To finish, walk north on Duval Street and left on Front Street to Mallory Square.
Keep the route with you
The tour link opens a route preview with an iPhone handoff. You can also download the GPX and open it from Files → Share → Daily Wander. The app shows the route; this page supplies the stop descriptions.
Key West walking-tour questions
How long is this Key West walking tour?
The mapped loop is about 2.8 miles (4.5 km). That is roughly 55 minutes of moving time at 3 mph; allow 2–3 hours with stops.
Where is the Southernmost Point buoy right now?
The City of Key West put up its concrete buoy in 1983 to mark the corner of South and Whitehead Streets, but since September 4, 2025 the city lists a temporary buoy at 1499 Duval Street, at the southern end of Duval, while the seawall and roadway are repaired. In September 2026 the city announced about 180 days of road closures and detours around South, Duval, United and Whitehead Streets for the Southernmost Point roadway project, so follow posted signs.
Is the Mallory Square Sunset Celebration free?
Yes. The Key West Cultural Preservation Society, the nonprofit arts group that manages the Sunset Celebration, says it is free to attend. It takes place every night of the year, weather permitting, beginning about two hours before sunset and ending soon after. The street performers are not paid by the event and rely on tips from the crowd.
Can I follow the route on my iPhone?
Yes. Tap Open the tour in Daily Wander, check the route preview and choose Open in Daily Wander. If you need the app, install it first and return to this page. The page supplies the stop notes; the app shows the walking route.
Does the walk return to the start?
Yes. The loop starts and finishes at Mallory Square.
Can I download the GPX instead?
Yes. Download the GPX from this page, save it in Files on iPhone and share it to Daily Wander. The route geometry is available under the Open Database License.
Make another walk from your hotel
For a different distance or a loop from another starting point, use the US walking-route planner. Daily Wander can suggest a separate loop from the location you choose.
More self-guided tours: Charleston, Savannah, New Orleans French Quarter, New Orleans Garden District, Nashville, Washington DC, New York, Philadelphia, San Francisco, Boston Freedom Trail, St. Augustine, San Diego, Seattle and Amsterdam.
Original itinerary by VANTH Studio. Reviewed October 20, 2026. Route geometry from OpenStreetMap via the FOSSGIS pedestrian router; distance measured along the track. Actual time depends on your pace, stops and diversions. Access to venues is controlled by their operators.