A Walking Tour from the Southernmost Point

The Southernmost Point is a great place to start exploring Key West on foot. Within about two miles you can see a Victorian mansion, a butterfly garden, Hemingway’s house, a 19th-century lighthouse, the start of U.S. Highway 1, a presidential retreat and the island’s famous sunset celebration. This self-guided route runs from the buoy north to Mallory Square. Allow half a day with stops, or a full day if you tour the museums.

Distance: about 2 miles one way  |  Terrain: flat sidewalks  |  Best time: start in the morning, finish at sunset

South St & Whitehead St. Start with the photo everyone comes for. Through early 2027 the original buoy is closed for seawall and plaza construction, so take your picture with the full-size replica one block east at 1400 Duval Street, then peek at the construction at the original corner. Details on our buoy location page. Get there early to beat the line.

1400 Duval St. Right beside the replica buoy stands the Southernmost House, a grand Queen Anne-style mansion built in 1896 for Judge Vining Harris and his wife, Florida Curry, daughter of William Curry, often called Florida’s first millionaire. Across the street at the foot of Duval is a small public beach, a pleasant spot to dip your toes in the Atlantic.

938 Whitehead St. Directly across from the Hemingway Home, the Key West Lighthouse was built in 1848 to replace an earlier tower destroyed by the great hurricane of 1846. Climb the 88 steps to the top for one of the best views on the island, and visit the restored keeper’s quarters museum at its base.

Whitehead St & Fleming St. Keep heading north on Whitehead to find the sign marking the southern end of U.S. Route 1, which runs more than 2,300 miles up the East Coast to Fort Kent, Maine. The Southernmost Point is the end of the country; Mile 0 is the end of the road. Both make great photos.

111 Front St. Head west into the Truman Annex to the white clapboard house where President Truman spent 175 days of his presidency, working and relaxing in Key West’s winter sun. Guided tours show the house much as he left it.

Mallory Square, off Front St. Finish on the waterfront for Key West’s nightly Sunset Celebration, with jugglers, musicians, food vendors and a crowd that applauds as the sun drops into the Gulf. Check our sunset times by month and aim to arrive 45 minutes early. From here, Duval Street’s restaurants and bars are steps away.

If you would rather spend the afternoon on a beach, Fort Zachary Taylor Historic State Park is reached through the Truman Annex at the end of Southard Street. It has a Civil War-era brick fort, a shady picnic area and a rocky beach with good snorkeling, and it extends a little farther south than the buoy itself. Read why in Is It Really the Southernmost Point?

Tips for the walk: carry water and sunscreen, wear comfortable shoes, and check opening hours and ticket prices before you go, since they change seasonally. Want to see more “southernmost” sights? See our list of Key West’s southernmost landmarks.