Mallory Square Sunset Celebration
Free (tips appreciated for performers)
Festivals & Events
Key West's nightly arts festival on the harborside plaza — happening 365 days a year, weather permitting, for two hours leading up to sunset. Street performers, fire-jugglers, escape artists, psychics, craft vendors, and food carts gather around the iconic open-air space as the sun drops into the Gulf of Mexico.
Address: Mallory Square, 400 Wall Street, Key West, FL 33040
Tip: Arrive 90 minutes before sunset for a front-row spot at the seawall. Bring small bills for tips — most performers do hat-pass rounds at the end of their acts. Free public restrooms in the adjacent Mallory Square parking garage.
🌐 Official Website
Southernmost Point Buoy
Free
Quirky Landmarks
The 12-foot concrete buoy at the corner of South and Whitehead Streets, marking 90 miles to Cuba and the southernmost point of the continental United States — one of the most photographed spots in Florida since it was dedicated in 1983. Even the line to take a photo is part of the experience.
Address: Corner of South Street and Whitehead Street, Key West, FL 33040
Tip: The original buoy site is closed for seawall and street reconstruction through late 2026 — an official full-scale replica welcomes visitors at Duval Pocket Park (1400 Duval Street) in the meantime. Lines move fastest at sunrise or just before sunset.
🌐 Official Website
Duval Street
Free to walk
Strolling & Food
Key West's 14-block main thoroughfare runs from the Gulf-side Mallory Square to the Atlantic — a mile-and-a-quarter of historic Conch houses, indie shops, art galleries, open-air bars, and the famously eccentric corner of Sloppy Joe's where Hemingway drank in the 1930s. Free to walk; people-watching is the main attraction.
Address: Duval Street, Key West, FL 33040
Tip: Walk the whole length end-to-end at least once — the upper Duval end (near the cemetery) is quieter and more residential than the rowdy lower-Duval section near Mallory Square. The free Duval Loop bus runs 8am-midnight and connects most attractions.
🌐 Official Website
Smathers Beach
Free (parking $5/hour street meter)
Beaches
Key West's longest public beach — about a half-mile of palm-lined white sand running along South Roosevelt Boulevard on the Atlantic side. Beach volleyball nets, restrooms, outdoor showers, snack bars, and rentable lounges. The wide sand and shallow water make it Key West's most family-friendly free beach.
Address: S Roosevelt Boulevard, Key West, FL 33040
Tip: Open daily 7am to 11pm. Park free at the Key West Airport on weekends and walk 10 minutes to skip the $5/hr meter rates. The free Duval Loop bus stops at Smathers — no parking hassle if you're staying in Old Town.
🌐 Official Website
Higgs Beach (Clarence S. Higgs Memorial Beach Park)
Free
Beaches
A 16.5-acre Monroe County oceanfront park with imported white Caribbean sand, the only shore-accessible underwater marine park in the US, beach volleyball, pickleball, tennis courts, two dog parks, and a children's playground. Also home to the African Refugee Cemetery — the only such site in the country, listed on the National Register in 2012.
Address: Atlantic Boulevard between White and Reynolds Streets, Key West, FL 33040
Tip: Open 7:30am to sunset. Free parking lot fills early on weekends. Don't miss the African Refugee Cemetery interpretive trail at the west end of the beach — 295 Africans rescued from illegal slave ships in 1860 are buried here.
🌐 Official Website
Fort Zachary Taylor Historic State Park
$6 per vehicle (up to 8 people) / $4.50 single occupant / $2 pedestrians
Beaches & History
An 1845 brick Civil War fort on the Atlantic tip of Key West, now a Florida state park with the best swimming beach in town. Wide sandy beach with reliable shade from pine trees, clear water for snorkeling, and a guided fort tour at noon daily. The southernmost beach within a Florida state park.
Address: 601 Howard England Way, Key West, FL 33040
Tip: The $6/vehicle fee covers the whole carload — cheapest sand-and-snorkel deal in Key West when split among 4 people. Tree shade is hard to find on most Key West beaches; this is the exception. Bike or walk in for the $2 fee.
🌐 Official Website
Historic Key West City Cemetery
Free
Quirky Landmarks
A 19-acre above-ground cemetery (high ground for Key West means 16 feet above sea level) established in 1847 after the 1846 hurricane displaced the previous burial ground. Between 80,000 and 100,000 people are buried here — many in stacked above-ground vaults with famously irreverent epitaphs ('I told you I was sick'). Still an active cemetery with about 100 burials a year.
Address: 701 Passover Lane, Key West, FL 33040
Tip: Free self-guided tour maps are available at the front gate. Best walked early morning before it gets hot — there's almost no shade. The Sandra Sawyer 'I told you I was sick' headstone is one of the most-photographed; it's roughly halfway in along the main path.
🌐 Official Website
Hemingway Home & Museum
$19 adults / $7 children 6-12 / Free under 5
History & Culture
The 1851 Spanish Colonial home where Ernest Hemingway lived from 1931-1939 and wrote 'To Have and Have Not,' 'For Whom the Bell Tolls,' and 'A Farewell to Arms.' Family heirlooms, his writing studio in the converted carriage house, and 50-60 polydactyl (six-toed) cats descended from Hemingway's original cat Snow White still roam the property.
Address: 907 Whitehead Street, Key West, FL 33040
Tip: Open daily 9am-5pm with no reservations needed — tours start every 15 minutes and run 20-30 minutes guided. The cats sleep all over the property; ask the guide which is the current 'mayor.' Adjacent free attraction: walk one block to the Key West Lighthouse across the street.
🌐 Official Website
Key West Lighthouse & Keeper's Quarters Museum
$17 adults / $9 youth 7-18 / Free under 7 ($1.50-2 off booking online)
History & Culture
An 1848 working lighthouse — 88 steps up the iron spiral staircase to the lantern room with 360-degree Key West rooftop views. The restored 1887 Keeper's Quarters at the base houses Fresnel-lens history, shipwreck artifacts, and the personal stories of the 12 keepers and their families who served here over 121 years.
Address: 938 Whitehead Street, Key West, FL 33040
Tip: Buy online for the small discount ($15.50 adult / $7.50 youth). Climb is steep and narrow — not for anyone with claustrophobia or knee issues. Directly across the street from the Hemingway Home; pair the two for a half-day Old Town circuit.
🌐 Official Website
Bahama Village
Free to walk
Strolling & Food
A 16-block historic neighborhood southwest of Duval, settled by Bahamian sponge-divers and cigar workers in the 1800s — Key West's traditional Black community and one of its most architecturally intact Conch districts. Petronia Street is the spine: pastel-painted shotgun cottages, the historic Glad Tidings Tabernacle, the Curry Mansion landmark district, and a handful of Caribbean-influenced cafes.
Address: Petronia Street, Key West, FL 33040
Tip: Walk Petronia from Whitehead west to Truman — about 10 blocks of quiet Conch architecture. Stop for Bahamian conch fritters at Blue Heaven (cash discount); the open-air courtyard has cats, chickens, and live music most evenings.
🌐 Official Website