TRIP OVERVIEW
Day 1 – Ernest Hemingway Home and Museum · Key West Butterfly and Nature Conservatory · Duval Street · Mallory Square · Mallory Square – Sunset Celebration
Day 2 – Fort Zachary Taylor Historic State Park · Key West Aquarium · Harry S Truman Little White House · Key West Cemetery · Higgs Beach
Day 1
From Hotel: 🚕 8 min → Ernest Hemingway Home and Museum
1. Ernest Hemingway Home and Museum
The Spanish Colonial house where Hemingway lived 1931–1940 and wrote A Farewell to Arms and To Have and Have Not. A National Historic Landmark; 40 to 50 polydactyl cats — descendants of his six-toed cat — live on the grounds. The first private swimming pool in Key West was built here in 1938.
🚶 8 min · 🚕 3 min → Key West Butterfly and Nature Conservatory
2. Key West Butterfly and Nature Conservatory
A glass-domed habitat housing 50 to 60 butterfly species alongside tropical birds, two flamingos, and cascading waterfalls. The conservatory maintains a controlled tropical climate year-round; butterflies emerge from pupae in a hatching window visible to visitors.
🏛️ Daily 9:00am - 5:00pm
⏰ ~1 hr
🚶 3 min · 🚕 2 min → Duval Street
3. Duval Street
Key West's main thoroughfare — a one-mile corridor from the Gulf of Mexico to the Atlantic. Lined with Conch-style Victorian houses, galleries, and the island's most storied establishments. The street has been at the heart of Key West's bohemian literary identity since the late 19th century.
🚶 20 min · 🚕 9 min → Mallory Square
4. Mallory Square
A historic waterfront plaza at the island's northwest tip. Street performers and artisans have gathered here since the 19th century; the nightly Sunset Celebration draws hundreds to watch the sun drop into the Gulf. The site was once Key West's cigar-rolling and sponge-market waterfront.
🚶 1 min · 🚕 2 min → Mallory Square – Sunset Celebration
5. Mallory Square – Sunset Celebration
Key West's nightly ritual — the waterfront plaza fills with street performers, acrobats, jugglers, and artisans as the sun drops into the Gulf. The Sunset Celebration began in the 1960s counterculture era and has continued every evening since. The view from the wharf is unobstructed.
No pictures found.
🚕 12 min → hotel
Day 2
From Hotel: 🚕 14 min → Fort Zachary Taylor Historic State Park
1. Fort Zachary Taylor Historic State Park
A Third System brick fort completed in 1866 on Key West's southwestern tip. The fort controlled the Florida Straits during the Civil War and never fell to Confederate forces. Its moat filled with sand in the 1890s, preserving thousands of Civil War cannons. The park also has the island's best natural sand beach.
🏛️ Daily 8:00am - 5:00pm
⏰ ~1 hr 30 min
🚶 24 min · 🚕 8 min → Key West Aquarium
2. Key West Aquarium
One of the oldest open-air aquariums in the United States, opened in 1934. The waterfront facility on Mallory Square holds nurse sharks, tarpon, loggerhead sea turtles, and stingrays. Daily guided shark feedings and interactive touch tanks showcase the Florida Keys marine ecosystem.
🚶 7 min · 🚕 6 min → Harry S Truman Little White House
3. Harry S Truman Little White House
The Key West Naval Station's 19th-century Commanding Officer's Quarters, used by President Truman as his Winter White House during 11 vacations between 1946 and 1952. Restored to its 1949 appearance; guided tours cover the rooms where Truman conducted Cold War business. Eisenhower and Kennedy also used the property.
🚶 20 min · 🚕 9 min → Key West Cemetery
4. Key West Cemetery
A 19-acre walled cemetery established in 1847 after a hurricane destroyed the island's original burial ground. Key West's coral-limestone substrate forces above-ground burial — whitewashed tombs stacked several feet high line the paths. Notable for darkly humorous epitaphs; the cemetery holds roughly 100,000 burials.
🚶 21 min · 🚕 6 min → Higgs Beach
5. Higgs Beach
Key West's most popular public Atlantic-side beach — a calm strip of sand with a pier, volleyball courts, and picnic pavilions. A memorial marks the African Cemetery, the burial ground of Africans who died aboard slave ships intercepted by the US Navy between 1858 and 1860.
🚕 9 min → hotel
📅 Tours
Viator
A 90-minute guided walk through Key West's historic Old Town district — Victorian architecture, hidden courtyards, the island's most storied blocks, and the stories behind the Conch Republic's founding moments. Small groups of no more than 15.
⏳ 1 hr 30 min · 👥 Small group
🚶 4 min · 🚕 2 min
The Conch Tour Train has circled Key West's historic sites since 1958 — a 90-minute narrated loop covering 14 miles and 100 points of interest including the Hemingway Home, Truman Little White House, and the Southernmost Point buoy. Hop-on/hop-off available at two depots.
⏳ 1 hr 30 min · 👥 Group
🚶 5 min · 🚕 2 min
A 2-hour catamaran sail departing just before sunset — open bar, live music, and unobstructed views of the sun dropping below the Gulf horizon from the water. Covers the western reef areas where spinner dolphins are frequently spotted.
⏳ 2 hr · 👥 Max 49
🚶 10 min · 🚕 3 min
A guided snorkeling trip to the only living coral reef in the continental United States — the Florida Reef, 6 miles offshore. Snorkeling gear and wetsuit provided; marine naturalist narrates the reef ecosystem. The reef runs the length of the Florida Keys and is the third largest in the world.
⏳ 3 hr · 👥 Small group
🚶 10 min · 🚕 3 min
Tandem or solo parasailing 400 to 800 feet above the Gulf of Mexico — on clear days you can see the Atlantic on the opposite side of the island from altitude. Flight time is 8 minutes in the air.
⏳ 1 hr · 👥 Small group
🚶 10 min · 🚕 3 min
A 30 or 60-minute seaplane flight over the reef, the backcountry flats, the uninhabited Lower Keys, and the sandbars. The only way to see the full length of the Florida Keys from the air without a charter jet.
⏳ 30 min · 👥 Max 8
🚕 8 min
A guided 2-hour kayak through the mangrove tunnels and backcountry flats of the Great White Heron National Wildlife Refuge north of Key West — spotted eagle rays, manatees, and bottlenose dolphins in the clear shallow water above seagrass beds.
⏳ 2 hr · 👥 Small group
🚶 10 min · 🚕 3 min
GetYourGuide
A 2-hour catamaran sunset cruise from the Historic Seaport — open bar included, live music, and the full Gulf sunset view from the water. Departs 90 minutes before sunset each evening.
⏳ 2 hr · 👥 Group
🚶 10 min · 🚕 3 min
A catamaran reef snorkel to the living Florida coral reef — the only barrier reef in North America. Snorkel gear, fins, and flotation included. Morning, afternoon, and sunset departure options with complimentary drinks on the return.
⏳ 3 hr · 👥 Small group
🚶 10 min · 🚕 3 min
A 2-hour walking tour of Old Town focused on the island's architectural history — the Conch-style Victorian houses, the sponge-trading warehouses, the cigar-rolling heritage, and the Cuban and Bahamian immigrant communities that built the neighborhood.
⏳ 2 hr · 👥 Small group
🚶 4 min · 🚕 2 min
A guided 2-hour kayak through the mangrove tunnels and backcountry flats north of Key West — spotted eagle rays, manatees, and bottlenose dolphins in the clear shallow water above seagrass beds.
⏳ 2 hr · 👥 Small group
🚶 10 min · 🚕 3 min
A 2-hour guided walk through the Key West literary world — the Hemingway Home, the bars where he drank, the harbor where he fished, and the island's broader connection to Tennessee Williams, John Dos Passos, and the writers who followed them here.
⏳ 2 hr · 👥 Small group
🚶 6 min · 🚕 3 min
TripAdvisor
A sunset sail aboard a classic gaff-rigged schooner — the most traditional way to watch the Key West sunset from the water. Open bar included; departs 90 minutes before sunset from the Historic Seaport.
⏳ 2 hr · 👥 Group
🚶 10 min · 🚕 3 min
A 2-hour small-group walk of Key West's historic Old Town covering the island's naval, literary, cigar, and Conch Republic history with a local guide. Groups capped at 12 for a personalised experience.
⏳ 2 hr · 👥 Max 12
🚶 4 min · 🚕 2 min
A guided 3-hour snorkel trip to the Florida living reef — the only barrier coral reef in the continental United States. All gear provided; marine naturalist explains the reef ecology throughout.
⏳ 3 hr · 👥 Small group
🚶 10 min · 🚕 3 min
☕ Cappuccino
Bad Boy Burrito · 4.3⭐ · 890+ reviews
Sippin' · 4.4⭐ · 480+ reviews
Glazed Donuts · 4.6⭐ · 620+ reviews
Cuban Coffee Queen · 4.5⭐ · 2800+ reviews
Key West Coffee Roasters · 4.4⭐ · 310+ reviews
🫕 Restaurants Near Hotel
El Siboney · 4.3⭐ · 2400+ reviews
Cash-only Cuban spot since 1984. Ropa vieja and pork in big portions.
🏛️ Daily 11:00am - 9:30pm
💵 Cash Only
🚶 3 min · 🚕 2 min
Nine One Five · 4.4⭐ · 1200+ reviews
New American tapas in a Victorian on Duval — small plates and a candlelit porch.
🏛️ Daily 5:00pm - 10:00pm
🚶 4 min · 🚕 2 min
Santiago's Bodega · 4.4⭐ · 1600+ reviews
Tapas wine bar in Bahama Village — Spanish small dishes by candlelight.
🏛️ Daily 5:30pm - 11:00pm
🚶 5 min · 🚕 2 min
Antonia's Restaurant · 4.3⭐ · 680+ reviews
Refined Italian on Duval — handmade pasta and ossobuco.
🏛️ Daily 6:00pm - 10:00pm
🚶 5 min · 🚕 2 min
Café Sole · 4.5⭐ · 820+ reviews
French-Provençal cooking in a street garden — bouillabaisse and duck confit.
🏛️ Tuesday - Sunday 5:30pm - 10:00pm
🚫 Closed Monday
🚶 8 min · 🚕 3 min
🍽️ Downtown Restaurants
Pepe's Café · 4.2⭐ · 2100+ reviews
Key West's oldest restaurant, open since 1909. Eggs, grits, Cuban toast.
🏛️ Daily 6:30am - 10:00pm
Blue Heaven · 4.3⭐ · 5200+ reviews
Open-air brunch in Bahama Village — banana Foster French toast and pancakes.
🏛️ Daily 8:00am - 3:00pm · 6:00pm - 10:30pm
Bagatelle · 4.2⭐ · 1400+ reviews
Tropical American in a Victorian on Duval — jerk chicken and mango pork.
🏛️ Daily 11:00am - 10:00pm
Mo's Restaurant · 4.4⭐ · 1100+ reviews
Cuban-American on White Street — roast pork, plantains, and yellow rice.
🏛️ Monday - Saturday 11:00am - 10:00pm
🚫 Closed Sunday
El Meson de Pepe · 4.1⭐ · 1800+ reviews
Cuban on Mallory Square — picadillo, ropa vieja, and pressed Cubano.
🏛️ Daily 11:00am - 11:00pm
🍮 Local Tastes
Key Lime Pie
The Florida Keys' defining dessert — a tart pale yellow custard made from Key lime juice in a graham cracker crust. The original used sweetened condensed milk. Key West claims the invention; Florida designates it the official state pie.
Cuban Coffee
A ritual brought by Cuban cigar workers in the 1870s. Cuban espresso is brewed sweetened; a colada is a shared cup divided into smaller cups. The cortadito adds steamed milk. Served at walk-up windows across Old Town.
Conch Fritters
Deep-fried fritters from conch — the sea snail that names Key West natives. The meat is diced with onion, pepper, and spices, battered and fried to a crisp shell. Found at virtually every casual restaurant on the island.
Cuban Bread
A long white loaf with a crisp crust and tender interior, baked with lard and scored with a palm frond — a tradition from Cuban cigar workers who settled Key West in the 1870s. Served toasted with butter or pressed into a Cuban sandwich.
🏓 Pickleball
Higgs Beach Courts · Outdoor
10 free outdoor courts at the beach; group play starts daily at 8:30am
🏛️ Daily 6:00am - 11:00pm
🚕 5 min
🐾 The Six-Toed Cats and the City That Led Florida
Ernest Hemingway lived in Key West from 1931 to 1939, and the cats that roam his house today are descendants of a polydactyl cat — a cat with six toes on each front paw — given to him by a ship's captain. The Hemingway Home keeps around 40 to 50 of these cats, roughly half of which carry the polydactyl trait. They're named after famous figures, they have the run of the property, and they are technically in violation of Monroe County's three-cat household limit. The city has repeatedly tried to regulate them; the federal government has also weighed in. The cats remain.
Less well known: Key West was the largest city in Florida by population through much of the 1880s and 1890s — larger than Jacksonville, larger than Tampa, larger than Miami, which barely existed. The city's wealth came from two industries: wrecking — salvaging cargo from ships that ran aground on the reef — and cigar manufacturing. Cuban cigar makers relocated to Key West during and after the Ten Years' War against Spanish rule, and by the 1880s the city had over 100 cigar factories producing millions of cigars annually. A labor dispute eventually pushed most of the industry north to Tampa's Ybor City, and Key West never recovered its Florida-leading population. It had a population of roughly 18,000 in 1890; Tampa surpassed it shortly after.