The Ernest Hemingway Home (60 Six-Toed Cats) & Key West Lighthouse

Halfway down leafy Whitehead Street (at the 900 block) sit Key West's two most famous historic sites directly across the street from each other, allowing you to visit both in two hours: the 1851 Ernest Hemingway Home & Museum and the 1848 Key West Lighthouse, three blocks north of the Southernmost Point Buoy.

1. The Ernest Hemingway Home & Museum (907 Whitehead Street)

Built in 1851 by marine architect Asa Tift out of native oolitic limestone quarried on the grounds (sitting 16 feet above sea level, so its basement stays dry in storms), this French-Colonial villa was gifted to Ernest Hemingway and his second wife Pauline Pfeiffer by her Uncle Gus in 1931. During his decade here, Hemingway wrote A Farewell to Arms, Death in the Afternoon, The Green Hills of Africa, The Snows of Kilimanjaro and To Have and Have Not.

• Cash Only at the Gate: the front ticket booth accepts cash only and includes a 30-minute guided tour; check current admission rates on the official website before visiting.
• The 60 Polydactyl (Six-Toed) Cats: in the 1930s, a ship captain gifted Hemingway a white six-toed cat named Snow White (sailors prized polydactyl cats for extra grip on pitching decks). Today, roughly 60 direct descendants of Snow White, named after famous writers and actors like Gertrude Stein, Pablo Picasso and Audrey Hepburn, rule the gardens.
• The 'Last Penny' Swimming Pool (1938): while Hemingway was covering the Spanish Civil War, Pauline spent a small fortune blasting through solid coral rock to build Key West's first in-ground swimming pool. Upon seeing the bill, Ernest joked that she had taken his last penny and pressed a 1934 coin into the wet cement patio, where it remains embedded today.

2. The 1848 Key West Lighthouse & Keeper's Quarters (938 Whitehead Street)

Cross Whitehead Street to the 1848 Key West Lighthouse, where payment cards are accepted and the free Duval Loop bus stops outside. Built after an 1846 hurricane destroyed the original tower where keeper Barbara Mabrity served for 32 years, climbing the 88 spiral iron steps to the 26-metre balcony gives you a sweeping view straight down into Hemingway's garden and across Old Town to both oceans.