The Complete Key West Travel Guide: Bars, Beaches, and a Fort in the Middle of the Ocean
Key West occupies a strange space in American travel. It's the southernmost point of the continental US, closer to Havana than Miami. It's a place that "seceded" from the country as a joke in 1982 and still prints its own tongue-in-cheek passports. It's a party town and a literary landmark and a coral reef snorkeling destination and a Civil War fort museum — all crammed onto an island 1 mile wide and 4 miles long.
Four days is the perfect amount of time. Here's how to do it right.
Overview
Getting there: Drive US-1 from Miami (4-5 hours, one of the world's best road trips) or fly into EYW
Best time: November-April (dry, warm, peak season). May-June for lower prices with good weather
Getting around: Walk or rent a bike ($15-25/day). No car needed on the island
Day 1: Duval Street and Mallory Square
Duval Street runs from the Atlantic Ocean to the Gulf of Mexico — about a mile of bars, restaurants, and shops. Walk the whole thing.
Start at the Southernmost Point buoy (corner of Whitehead and South). The famous photo takes 15-30 minutes with the queue. Go early morning or evening to avoid the worst lines.
Walk up Duval: Browse the boutiques, duck into Sloppy Joe's for a frozen drink (Hemingway's bar — loud, touristy, mandatory), then Captain Tony's Saloon around the corner (the original Sloppy Joe's location, covered in business cards and bras, pure Key West).
Evening: Mallory Square sunset celebration. Arrive an hour before sunset. Street performers — sword swallowers, trained cats, tightrope walkers — build the energy. The crowd grows. The sun drops into the Gulf. Everyone applauds. It's corny and genuine and you should do it at least once.
Dinner at El Siboney — Cuban restaurant on Catherine Street. Ropa vieja ($16), Cuban sandwich ($12), black beans and rice. Authentic, cheap by Key West standards, and packed with locals.
Day 2: Hemingway, History, and Snorkeling
Morning: Ernest Hemingway Home & Museum ($18, open 9AM-5PM). The 1851 colonial estate is charming — lush tropical garden, the pool he built for $20,000 (when his wife complained about the cost, he gave her a penny and said "take the last penny I have"). The six-toed cats (60+, descended from his original) roam freely. The writing studio above the carriage house is intact.
Walk to the Harry S. Truman Little White House ($23, 30-minute tour). The winter White House where Truman, Eisenhower, and JFK made presidential decisions. Surprisingly interesting.
Afternoon: Snorkeling trip. Half-day trips ($45-65, 3-4 hours) depart from the Historic Seaport. Key West sits near North America's only living barrier reef — elkhorn coral, parrotfish, sea turtles, nurse sharks. Equipment provided. Best visibility April-July.
Dinner at Santiago's Bodega — tapas-style small plates ($8-16 each). The yellowtail snapper ceviche and Cuban seared tuna are standouts. Cozy, candlelit, on Bahama Street.
Day 3: Dry Tortugas or Fort Zachary
This is the day that separates a good Key West trip from a great one.
Option A: Dry Tortugas National Park ($200 Yankee Freedom ferry, full day). A massive hexagonal Civil War-era fortress 70 miles west of Key West, accessible only by ferry or seaplane. The ferry includes breakfast, lunch, and snorkeling gear. 2.25 hours each way.
Fort Jefferson is architecturally staggering — 16 million bricks, a moat, and it was never finished. The snorkeling around the island is extraordinary — crystal-clear water, coral gardens, tropical fish. This is one of the most unique experiences in the US.
Book 2-3 weeks ahead. Totally worth the $200.
Option B: Fort Zachary Taylor Beach ($6/vehicle + $2.50/person). The best beach in Key West, inside a state park with its own Civil War-era fort. Rocky shoreline with excellent snorkeling right off the beach (bring water shoes). Shaded picnic areas. Less crowded than Smathers Beach. The fort tour is free with admission.
Day 4: Beach Day and Final Sunset
Morning: Lazy start. Coffee at Cuban Coffee Queen (small stand near the waterfront, $3-5 for cortadito and a ham croqueta). Walk to Smathers Beach (the main public beach) or rent a bike and explore the residential streets of Old Town — tropical Victorian houses painted in pastel colors.
Lunch: Garbo's Grill — a food truck in a parking lot on Caroline Street. Korean short rib tacos ($8), fish tacos ($7). Don't let the setting fool you — this is some of Key West's best food.
Afternoon: Last Duval Street walk. Pick up key lime pie from Kermit's ($6-8/slice — the real thing, tart and creamy with a graham cracker crust). Browse the galleries and shops you missed.
Final sunset: Skip Mallory Square (you did that on Day 1). Instead, watch from Fort Zachary Taylor Beach or the Hyatt Centric rooftop bar on Duval — cold drink, sunset view, less crowds.
Where to Eat
Spot
Known For
Price
El Siboney
Cuban food (ropa vieja)
$12-18
Santiago's Bodega
Tapas, ceviche
$8-16/plate
Garbo's Grill
Korean-fish tacos (food truck)
$7-10
Blue Heaven
Brunch with roosters
$15-25
Kermit's
Key lime pie
$6-8/slice
Cuban Coffee Queen
Cortadito, croquetas
$3-5
Sloppy Joe's
Atmosphere (not food)
$10-18
Budget Tips
Walk everywhere. The island is tiny.
Bike rental ($15-25/day) is cheaper than any other transport
Happy hours run 4-7PM at most Duval Street bars — half-price drinks
Skip the Conch Tour Train ($35) — you can walk the same route for free
Sunsets are the best free entertainment in Key West
Visit in May-June or November for 30-40% lower hotel rates
Grocery stores exist — cook breakfast in your rental to save $15-20/day
Safety
Reef-safe sunscreen only (non-reef-safe is banned to protect the coral)
Hurricane season: June 1 - November 30 (peak August-October). Travel insurance recommended
Duval Street late at night is loud and boozy but generally safe
Lock your bike — theft happens
The sun is intense year-round. SPF 50+, reapply every 2 hours
The Contrarian Take
Smathers Beach is overrated. It's the biggest beach in Key West, which gets it onto every list. But the water is shallow, the seagrass can be thick, and it's packed with cruise ship day-trippers.
Fort Zachary Taylor Beach is better in every way — cleaner water, better snorkeling, shaded picnic areas, a Civil War fort to explore. And it costs $6 to enter, which keeps the crowds manageable. Go there instead.
