Walk on Whitehead Street

A one-mile hike along beautiful Whitehead Street is a delightful exploratory adventure on a scenic street that’s shaded and leafy, lined with giant sprawling Banyan trees and an exotic Kapok tree. You’ll pass by authentic residential cottages, quirky shops and an occasional hop-on, hop-off Conch Trolley. 

Here, you can conveniently experience a few of the island city’s most fascinating cultural and maritime attractions.

Wear comfortable supportive sandals or shoes, and be on the lookout for colorful, boisterous roosters.

Start at the Southernmost Point at 1400 Whitehead St. and South Street. This concrete, larger-than-life landmark buoy overlooking the turquoise Atlantic Ocean is closer to Havana, at just 90 miles away, than it is to Miami. Visitors line up here for photos, so come prepared to wait a bit if you’re not an early riser.

The historic, restored Key West Lighthouse & Keeper’s Quarters was erected in 1847, guiding mariners until it was decommissioned in 1969. Get a tour, and climb the 88 winding steps to the top for the island city’s best sweeping views. The lighthouse is across the street from famed author Ernest Hemingway’s home, where he lived and wrote in the 1930s.

The Ernest Hemingway Home & Museum, 907 Whitehead St., is the island city’s most popular attraction. The late author’s home and second-story writing studio offers a glimpse into American literary history. Here, Hemingway wrote “To Have and Have Not,” set in Depression-era Key West, and other notable works. Some visitors come just to hang around with more than 60 polydactyl (six-toed) cats — descendants of Hemingway’s first six-toed cat Snow White — living on the property. 

The ramshackle Green Parrot Bar, 601 Whitehead St. at the corner of Southard Street, dates back to 1890 and is a popular local’s hang-out. Known for its musical acts, locals’ gatherings and lively happy hours, it’s billed as a “sunny place for shady people.”

With a trunk circumference of more than 30 feet, the landmark The Kapok Tree, at 502 Whitehead St., is one of the country’s most famous Kapok trees, estimated to be more than 100 years old. It sprouts blooming pink and white flowers in spring and summer. A white-framed sign with descriptive details marks the spot.

Just steps away is a photo stop at the Mile Marker Zero sign, marking the end (or the beginning, depending on your perspective) of highway U.S. 1 at 409 Whitehead St. and the corner of Fleming Street.

At 301 Whitehead St., stop and look up to see the sign marking the birthplace of Pan American World Airways on Oct. 28, 1927, with the first scheduled U.S. international air service from Key West to Havana. 

The Audubon House & Tropical Gardens, 205 Whitehead St., is a restored historic home showcasing original engravings by artist and ornithologist John James Audubon, who commemorated his Key West visit with sketches of 18 new species for his famed “Birds of America” folio. An onsite gallery store sells high-quality prints.

The Mel Fisher Maritime Museum, less than 45 feet away at 200 Greene St., showcases the richest single collection of the Western Hemisphere’s 17th-century maritime and shipwreck antiquities, including the treasure of the Spanish galleon Nuestra Señora de Atocha. The facility, the Keys’ only fully accredited museum, is also a shipwrecks research institution. Behind-the-scenes lab tours are offered.

Allow a half day to eight hours, with lunch, to explore shops and attractions for a leisurely and memorable Whitehead Street day trip. From here, you can take a 5-minute stroll over to Mallory Square, famed for its nightly sunset celebrations.

Difficulty level: Easy
Best for: Sightseers, history lovers
Admission: From $15.50 for general admission to Key West Lighthouse & Keeper’s Quarters, open daily 10 a.m. to 5 p.m.; $19, adult general admission at Ernest Hemingway Home & Museum, open daily 9 a.m. to 5 p.m.; $16 for adults at Audubon House & Gardens, open daily 9:30 a.m. to 4:15 p.m.; $17.50 for adults at Mel Fisher Museum, open daily at 10 a.m., with last visitors admitted at 4 p.m.
Address: Southernmost Point, Whitehead and South streets
Nearby lodging: The Banyan Resort, Lighthouse Inn, Coco Plum Inn, Wicker Guesthouse
Nearby dining: Moondog Café & Bakery, First Flight Island Restaurant & Brewery, Café Marquesa, Blue Heaven