Key West Conch & Hemingway Walk

Audubon House and Tropical Gardens

Explore a beautifully restored 1800s residence filled with period pieces and surrounded by lush gardens designed to echo the island’s natural beauty. This refined retreat offers a look at the more elegant, artistic side of early Key West.

Bahama Village

Home to bright Caribbean architecture and deep Bahamian heritage, this lively district reflects the traditions, faith, and community bonds that shaped working-class Key West. It’s one of the most culturally rich areas on the island.

Conch Tour Train

A beloved Old Town icon, the open-air Conch Train has introduced visitors to the island’s stories for generations. Its cheerful clatter represents Key West’s long-standing love of sharing history in a fun, approachable way.

Duval Street

Stretching from ocean to ocean, Duval pulses with music, bars, boutiques, and local legends. It’s the energetic thread that runs through Key West life, offering a mix of nightlife, history, and colorful personalities.

Ernest Hemingway Home and Museum

Hidden behind a coral-rock wall, this Spanish Colonial home is where Hemingway crafted some of his most enduring works. Its gardens—and the famously polydactyl cats—create a peaceful refuge with strong literary echoes.

Green Parrot Bar

Once a simple neighborhood shop, the Green Parrot grew into a laid-back bar known for live music and local camaraderie. Its relaxed vibe captures the island’s tradition of storytelling, connection, and unpretentious fun.

Harry S. Truman Little White House

This unassuming residence served as President Truman’s winter headquarters, where he worked, rested, and met with advisors. Today, it stands as a unique link between Key West’s small-town atmosphere and major national decisions.

Key West Cemetery

Built above ground, this historic burial place chronicles hurricanes, shipwrecks, and the colorful lives of island residents. Humorous epitaphs and intimate memorials reflect Key West’s distinctive mix of hardship, humor, and heart.

Key West Historic Memorial Sculpture Garden

Located near the waterfront, this garden honors the people—from artists to civic leaders—who shaped the island’s past. The statues create a contemplative space where history feels especially close.

Key West Lighthouse and Keeper’s Quarters Museum

Climb the lighthouse stairs for panoramic views of Old Town, then explore the restored home of the lightkeepers who once protected ships from danger. It’s a vivid reminder of the island’s maritime roots.

Mallory Square

Best known for its nightly sunset celebration, Mallory Square blends performers, artists, and ocean breezes into one lively gathering. By day, it remains a relaxed hub that captures the island’s playful personality.

Oldest House Museum and Gardens

This early 19th-century Conch home reveals how residents lived during Key West’s frontier era. The garden paths and breezy porches preserve the charm of a quieter, simpler island life.

Sloppy Joe’s Bar

A favorite haunt of Hemingway and a meeting place for adventurers of all kinds, Sloppy Joe’s has thrived for nearly a century. Its lively spirit and historic feel make it a Duval Street classic.

Southernmost House

Recognizable by its rosy coral exterior, this stately mansion sits near the Atlantic and reflects the prosperity of Key West’s early maritime boom. It remains one of the island’s most distinctive architectural gems.

The Armory

Once used for military drills and civic events, this solid structure speaks to Key West’s strategic role in coastal defense. It also hints at the island’s ability to repurpose old spaces for new community uses.

Tennessee Williams Museum

This intimate space celebrates the playwright’s long relationship with Key West, showcasing personal artifacts and rare recordings. It highlights how the island supported his creative freedom and artistic evolution.

The Studios of Key West

Located in the former armory, this bustling arts center hosts exhibitions, performances, and workshops. It continues the island’s legacy of nurturing bold, experimental creativity.

Casa Marina Hotel

Opened in 1920 as one of Key West’s first luxury hotels, Casa Marina signaled the island’s shift toward tropical tourism. Its sweeping lawns and oceanfront location still evoke that early era of elegance.

Angela Street

A peaceful, tree-lined road named for a woman of local lore, Angela Street showcases Key West’s quieter residential charm. Its cottages and shaded sidewalks offer a calm, authentic glimpse of daily island life.