Visiting Key West? 10 Things You Shouldn’t Miss

You’ll want to visit the Southernmost Point Buoy early to beat crowds, meet Hemingway’s famous six-toed cats at his historic home, and explore Fort Zachary Taylor’s Civil War cannons plus beautiful beach. Don’t miss Mallory Square‘s nightly sunset celebration with street performers, the remote Dry Tortugas National Park day trip, and Duval Street’s lively bars. The Shipwreck Museum showcases authentic maritime treasures, while the aquarium offers hands-on marine encounters. Continue below for insider tips and detailed planning advice.

Stand at the Southernmost Point Buoy (But Go Early or Late)

While Key West’s famous Southernmost Point Buoy draws thousands of visitors daily, you’ll save time and sweat by timing your visit strategically. Skip the midday madness when lines stretch 30-60+ minutes and blazing heat makes waiting unbearable. Instead, arrive at sunrise or late evening for the shortest queues and most comfortable photo conditions.

Currently, you’ll find the full-scale replica at Duval Pocket Park (1400 Duval Street) while the original corner undergoes seawall reconstruction until late 2026.

The 12-foot concrete marker maintains its iconic “90 Miles to Cuba” message and colorful bands, preserving the photo tradition that’s captivated visitors since 1983. The buoy also celebrates Key West’s unique Conch Republic heritage from the island’s famous 1982 secession. Early or late visits also offer softer lighting that’ll make your Instagram shots pop without harsh shadows.

Meet Hemingway’s Six-Toed Cats at His Historic Home

Though Ernest Hemingway left Key West in 1940, his most enduring residents never did—dozens of polydactyl cats still roam his former home at 907 Whitehead Street, drawing visitors who often come specifically for the felines rather than the Nobel Prize writer’s memorabilia.

You’ll find about 50-60 cats freely wandering the house and gardens. Roughly half of these cats display extra toes that give their paws a distinctive “mitten” appearance. The cats have weathered major storms at the property, including surviving Hurricanes Irma and Ian without harm.

These descendants trace back to Snow White, a six-toed cat gifted to Hemingway in the 1930s. The museum staff maintains each cat’s health and continues Hemingway’s tradition of naming them after celebrities—you might meet cats named Joan Crawford or Ezra Pound lounging on the author’s furniture.

Explore Fort Zachary Taylor’s Civil War History and Beach

Since you’re already exploring Key West’s historic attractions, Fort Zachary Taylor offers a compelling blend of Civil War history and one of the island’s best beaches. This National Historic Landmark houses the largest collection of Civil War-era seacoast cannons in the U.S., discovered during 1960s excavations.

You’ll learn how the fort remained in Union hands throughout the Civil War, serving as headquarters for naval blockade operations that captured 299 Confederate ships.

The fort is part of Fort Zachary Taylor Historic State Park, where you can take self-guided tours through casemates and see artillery displays. Construction of this impressive fortress began in 1845 following the War of 1812 to defend the southeastern U.S. coast.

After exploring the history, you’ll have access to one of Key West’s finest beaches. It’s an excellent value since one admission gets you both historical education and beach time at this “Gibraltar of the Gulf.”

Experience the Sunset Celebration at Mallory Square

As the day winds down in Key West, you’ll want to join the legendary Sunset Celebration at Mallory Square—a nightly ritual that’s evolved from informal hippie gatherings in the late 1960s into one of the island’s most iconic (and free) attractions.

Located at Old Town‘s northwest edge, the square offers unobstructed western views over the Gulf of Mexico, creating perfect sunset viewing conditions.

Arrive at least an hour before sunset to secure a good spot and explore the nightly arts festival. You’ll find street performers including magicians, jugglers, and musicians creating an open-air theater atmosphere.

Local artisans sell handmade crafts, jewelry, and Key West-themed artwork. The square’s transformation from a maritime hub in the 19th century to today’s cultural center reflects Key West’s evolution from working port to tourist destination.

When the sun finally disappears into vivid pinks and oranges, join the crowd’s traditional applause—a custom credited to playwright Tennessee Williams.

Take a Day Trip to Remote Dry Tortugas National Park

When you’re ready to escape Key West’s crowds for something truly extraordinary, book passage to Dry Tortugas National Park—a collection of seven remote islands floating 70 miles west in the Gulf of Mexico’s crystal-clear waters.

You’ll need to take the Yankee Freedom III ferry (about $200) for a 2.25-hour journey, departing around 7 a.m. and returning by 5:30 p.m.

Once there, you’ll explore massive Fort Jefferson, built with 16 million bricks and steeped in Civil War history. Don’t miss the free guided tour led by knowledgeable park rangers who bring the fort’s fascinating history to life during a comprehensive 90-minute experience.

The real draw is snorkeling in pristine waters where 99% of the park lies underwater. You’ll spot tropical fish, sea turtles, and nurse sharks around the fort’s ruins.

Book well ahead—this popular day trip fills up fast.

Climb the Key West Lighthouse for Island Views

While exploring Key West’s flat streets gives you one perspective of this tiny island, climbing the 88 iron steps of the historic Key West Lighthouse rewards you with sweeping 360-degree views that reveal just how small and sea-surrounded this famous outpost really is.

Built in 1848 after the original was destroyed by a hurricane, this 65-foot tower houses a Third Order Fresnel lens and offers unmatched panoramic views of Old Town’s treetops and surrounding waters.

The moderately challenging climb takes about 30-45 minutes total, including time at the museum in the restored Keeper’s Quarters.

You’ll pay an admission fee covering both the tower climb and exhibits featuring maritime artifacts and lighthouse history.

Wear supportive, non-slip shoes for the narrow spiral staircase. The lighthouse operated continuously until 1969 when declared obsolete and deactivated by the U.S. Coast Guard.

Stroll Duval Street for Bars, Music, and Local Character

Where else can you find 200 bars and restaurants packed into a single mile-long stretch that connects two oceans? Duval Street delivers Key West’s legendary nightlife experience without breaking the bank.

You’ll discover everything from dive bars to rooftop lounges, most with relaxed dress codes.

Hit iconic spots like Sloppy Joe’s for Hemingway history and live music, or Irish Kevin’s for high-energy crowd interaction. The street was named after William Pope Duval, Florida’s first territorial governor, and has been central to Key West’s development since the early 1800s.

The famous Duval Pub Crawl lets you bar-hop until dawn, mixing with cruise passengers, artists, and locals in the same venues.

Don’t miss the local flavors—conch fritters, fish tacos, and Key lime pie are available at casual eateries throughout your stroll.

The street transforms from laid-back shopping during the day to neon-lit Caribbean party atmosphere after dark.

Discover Maritime History at the Shipwreck Museum

After soaking up Duval Street’s party atmosphere, you’ll find a fascinating contrast at the Shipwreck Museum, where 400 years of maritime disasters and fortune-hunting come alive through authentic artifacts and interactive displays.

You’ll learn how Key West’s position on dangerous Gulf Stream trade routes made it America’s wrecking capital, turning locals into some of the country’s wealthiest citizens during the 1800s. Wrecker captains built lookout towers to spot shipwrecks first and claim salvage rights before competitors arrived.

The centerpiece Isaac Allerton exhibit showcases treasures from 1856’s most valuable wreck, while Spanish galleon artifacts span centuries of salvage history. Don’t miss trying to lift the 64-pound silver bar from Nuestra Señora de las Maravillas.

Interactive displays reveal how wreckers operated under federal maritime law, combining rescue missions with profitable salvage operations that shaped Key West’s economy.

Get up Close With Marine Life at Key West Aquarium

Once you’ve explored Key West’s shipwreck treasures, you’ll discover an equally mesmerizing underwater world at the Key West Aquarium, where hands-on encounters bring you face-to-face with over 250 marine species native to Florida’s waters.

You’ll love the interactive touch tank, where you can handle conchs, sea stars, and hermit crabs under supervision. Don’t miss the guided sessions where you’ll touch rays and small sharks safely.

The aquarium’s low tanks let kids see marine life at eye level, making it perfect for families. As Key West’s first attraction, this historic venue has been welcoming visitors since 1934 and continues to provide educational experiences for all ages.

Plan around the daily tours—Sea Turtle Conservation Tours feature rescued residents Rocky, Lola, Spike, and Hector, while the Atlantic Shores tours showcase nurse sharks and grouper in a massive 50,000-gallon tank. Each experience includes expert commentary about conservation and Florida’s marine ecosystems.

Wander Among Butterflies at the Nature Conservatory

Why settle for glimpsing butterflies through glass when you can walk among hundreds of free-flying tropical species at Key West’s Nature Conservatory? This glass-domed rainforest habitat houses up to 1,800 butterflies from 50–60 species worldwide, plus 20+ exotic birds and two resident flamingos named Rhett and Scarlett.

You’ll spend about 30–60 minutes exploring the warm, humid environment filled with cascading waterfalls and flowering plants. Start with the 15-minute educational film, then wander the conservatory where butterflies land freely around you. The Learning Center displays live caterpillars and features a world map showing species origins.

Located at 1316 Duval Street, it’s open daily 9 a.m.–5 p.m. (last admission 4:30 p.m.). The attraction has earned recognition as the #1 Attraction in Key West by The Peoples Choice Awards for four consecutive years. Bring your camera for incredible close-up shots.

The Sum Up

You’ve got plenty to explore in Key West without breaking the bank. Many attractions like the Southernmost Point and Mallory Square won’t cost you anything, while others offer reasonable admission fees. Plan your days around free activities and splurge selectively on experiences like Dry Tortugas or the aquarium. Don’t forget to budget for food and drinks—especially if you’re planning to sample Duval Street’s famous bar scene.