Best Time to Visit
November to April (dry season, 22-28°C, peak tourist season)
Language
English (some Spanish)
Currency
US Dollar (USD)
Time Zone
EST (UTC-5), EDT (UTC-4) in summer
Airport
Key West International (EYW)
Population
25,500 (city proper)
Climate
Tropical, warm year-round (24-33°C), hurricane season June-November, humid summers
Safety Rating
Very Safe (Level 1) — low crime, main concern is sunburn and overhydration at bars
Getting There
Fly to EYW or drive the Overseas Highway (US-1) from Miami — 160 miles, 3.5-4 hours, across 42 bridges
Every evening, two hours before sunset, street performers, artists, and food vendors gather at Mallory Square for a nightly festival culminating in applause as the sun drops into the Gulf of Mexico. Free to attend. Arrive 1 hour early for a good spot. Buskers include sword swallowers, tightrope walkers, and trained cats. A quintessential Key West ritual.
The 1851 colonial estate where Hemingway wrote some of his greatest works (1931-1939), now home to 60+ polydactyl (six-toed) cats descended from his original cat. Entry: $18 adults. Open 9AM-5PM daily. Guided tours every 15 minutes (30 minutes long). See his writing studio above the carriage house. One of the most charming literary sites in America. Allow 1-1.5 hours.
Key West's mile-long main strip running from the Atlantic to the Gulf with bars, restaurants, and shops on every block. Start with a frozen drink at Sloppy Joe's (Hemingway's favorite bar), browse boutiques, and end at the Southernmost Point buoy. No cover at most bars. Happy hours run 4-7PM at many spots. Best experienced on foot. Allow an evening.
A remote island fortress 70 miles west of Key West, accessible only by ferry or seaplane. The Yankee Freedom ferry: $200 adults round trip, includes breakfast, lunch, and snorkeling gear (2.25 hours each way). Fort Jefferson is a massive unfinished Civil War-era hexagonal fort. World-class snorkeling in crystal-clear water. Seaplane: $365 round trip (40 minutes). Book weeks ahead.
Key West sits near North America's only living barrier reef. Half-day snorkeling trips: $45-65 per person (3-4 hours), departing from the Historic Seaport. See elkhorn coral, parrotfish, sea turtles, and nurse sharks. Operators provide equipment. Best visibility: April-July. Full-day trips to the Marquesas or backcountry flats ($150+) are available for serious snorkelers.
The iconic red, yellow, and black concrete buoy marking the southernmost point of the continental US — just 90 miles from Cuba. Free to visit. Expect a 15-30 minute line for photos (longer in peak season). Best at sunrise or evening to avoid crowds and harsh midday light. Located at the corner of Whitehead and South Streets. Allow 30 minutes including the wait.
A hidden gem — the best beach in Key West, inside a state park with a Civil War-era fort. Entry: $6/vehicle + $2.50/person. Open 8AM-sunset. Rocky shoreline with excellent snorkeling right off the beach (bring water shoes). Shaded picnic areas and a snack bar. Less crowded than Smathers Beach. The fort tour is free with admission. Allow half a day.
Fly into Key West International (EYW) or drive the Overseas Highway from Miami (3.5-4 hours, 42 bridges over turquoise water). Old Town is walkable — no car needed.
Arrival and hotel check-in(1 hour)
If driving from Miami, stop at Bahia Honda State Park (MM 37, $4.50/person) for swimming and the old bridge photo. If flying, taxi from EYW is $15-20 (10 minutes)
Rent a bicycle(30 minutes)
$15-25/day from Eaton Bikes or any of dozens of rental shops. Old Town Key West is only 1x4 miles — bikes are the best way to get around
Mallory Square Sunset Celebration(2 hours)
Arrive 1 hour before sunset. Street performers (sword swallowers, trained cats, tightrope walkers), artists, and food vendors. Free. The crowd applauds when the sun drops into the Gulf. A nightly Key West ritual
Dinner at Santiago's Bodega(1.5 hours)
Tapas bar in Old Town. Tuna wonton nachos ($16), key lime brie ($14). Extensive wine list. Walk-in at the bar or reserve a table. Lively atmosphere
Explore Key West's literary history, Duval Street culture, and essential food.
Ernest Hemingway Home & Museum(1.5 hours)
$18. Colonial estate where he wrote For Whom the Bell Tolls and A Farewell to Arms. 60+ six-toed cats roam the gardens. Guided tours every 15 minutes. The writing studio above the carriage house is fascinating
Southernmost Point Buoy(30 minutes)
Free. Iconic red/yellow/black buoy — 90 miles from Cuba. Expect a 15-30 minute photo line. Go early morning or evening for shorter waits
Lunch at Blue Heaven(1 hour)
Key West institution in an old boxing ring where Hemingway refereed. Banana bread French toast ($16), key lime pancakes ($14). Chickens roam the outdoor dining area. Cash only. Expect a wait
Duval Street afternoon walk(2 hours)
Mile-long main strip from Atlantic to Gulf. Frozen drinks at Sloppy Joe's (Hemingway's bar), Captain Tony's (the original Sloppy Joe's location), and the Green Parrot (local favorite since 1890). Most bars have no cover
Key lime pie tasting(30 minutes)
Kermit's Key West Key Lime Shoppe — pie on a stick dipped in chocolate ($6). Or Blonde Giraffe for traditional ($8/slice). A key lime pie must be yellow (not green) and on a graham cracker crust
Key West sits near North America's only living barrier reef. Half-day on the water.
Morning reef snorkeling trip(3.5 hours)
$45-65 per person. Depart from Historic Seaport 9AM. Operators provide equipment. See elkhorn coral, parrotfish, sea turtles, and nurse sharks. Best visibility April-July. Companies: Fury Water Adventures or Honest Eco
Lunch at Eaton Street Seafood Market(45 minutes)
No-frills fish market with picnic tables. Fish sandwich ($12), lobster bisque ($10), conch ceviche ($14). Freshest seafood in Key West. Cash preferred. Local, not touristy
Fort Zachary Taylor Beach(2.5 hours)
$6/vehicle + $2.50/person. Key West's best beach inside a state park. Rocky shoreline with excellent snorkeling right off the beach (bring water shoes). Shaded areas, snack bar, and a Civil War fort to explore (free with admission)
Sunset cocktail at Sunset Pier(1.5 hours)
Ocean Key Resort's outdoor bar right on the water. Rum runners ($14), live music. One of the best sunset spots outside Mallory Square
A slower pace with water activities and laid-back Key West culture.
Kayak tour of the mangroves(2 hours)
$50-65/person. Guided eco-tour through the backcountry mangrove channels. See juvenile sharks, rays, sea stars, and wading birds. SUP tours also available. Lazy Dog Adventures or Key West Eco-Tours
Brunch at Cafe Sole(1 hour)
French-Caribbean cuisine. Hogfish ($28), lobster eggs Benedict ($22). A local favorite away from Duval Street. Reservations recommended. BYOB (no corkage)
Key West Butterfly & Nature Conservatory(1 hour)
$15. Walk through a climate-controlled glass dome with 50+ butterfly species, exotic birds, and tropical plants. Surprisingly calming. Adjacent to Southernmost Point area
Free afternoon(2 hours)
Browse the shops on Duval, visit the Key West Shipwreck Museum ($15), or just hammock at your guesthouse. This is Key West — doing nothing is encouraged
Dinner at Latitudes on Sunset Key(2 hours)
Take the free hotel launch from Westin Marina. Private island dining with sunset views. Fresh catch ($38), key lime soufflé ($16). Reservations required. The boat ride alone is special
70 miles west to the most remote national park in the continental US. Fort Jefferson, pristine snorkeling, and untouched beaches.
Yankee Freedom ferry to Dry Tortugas(2.25 hours)
$200 adults round trip. Includes breakfast, lunch, and snorkeling gear. Departs 8AM from Historic Seaport, returns 5:15PM. Book weeks ahead at drytortugas.com. Alternatively: seaplane ($365, 40 minutes each way) for a shorter but spectacular trip
Fort Jefferson exploration(2 hours)
Free with ferry ticket. Massive unfinished hexagonal Civil War fort with 16 million bricks — the largest masonry structure in the Americas. Moat walk, cannon rooms, and the Dr. Samuel Mudd cell (Lincoln assassination conspirator)
Snorkeling at Garden Key(1.5 hours)
Crystal-clear water right off the beach. Nurse sharks, sea turtles, and spectacular coral. The moat wall of the fort creates a unique reef habitat. Equipment provided with ferry
Beach time on Garden Key(1 hour)
Pristine white sand beach with turquoise water. No development, no vendors — just you and the birds. One of the most remote beaches you can easily access in the US
Return ferry to Key West(2.25 hours)
Arrive back around 5:15PM. Light dinner at Garbo's Grill — tiny food truck with the best fish tacos in Key West ($8). Corner of Southard and Thomas
Deep dive into Key West's eccentric culture and one last day on the water.
Key West Cemetery walking tour(1.5 hours)
Free self-guided (map at visitor center) or guided ($15). 19-acre above-ground cemetery with famously witty tombstones ('I Told You I Was Sick'). Historic Creole and Cuban sections. Morning is best for light and temperature
Truman Little White House(1 hour)
$20. The former winter White House where Truman, Eisenhower, and JFK worked. Guided tours only. The restored 1890 house and grounds are charming. Truman spent 175 days here as president
Lunch at El Siboney(45 minutes)
Authentic Cuban restaurant off the tourist trail. Ropa vieja ($14), Cuban sandwich ($10), black beans and rice ($6). Cash only. Massive portions. Open 11AM-9PM
Jet ski or parasailing(1.5 hours)
Jet ski: $80-100/hour from Fury Water Adventures. Parasailing: $65-85 for 10 minutes at 500 feet — views of the entire island and the reef below. Or glass-bottom boat tour ($45, 2 hours) if you prefer staying dry
Last Mallory Square sunset(1.5 hours)
Return for one final sunset celebration. Try a different viewing spot — the rooftop bar at Ocean Key Resort, or the Westin's sunset deck
Final Key West morning before departure.
Morning bike ride through residential Old Town(1 hour)
Free (with rental). Ride through the quiet residential streets away from Duval — wooden Victorian houses with tin roofs, tropical gardens, and cats everywhere. The architecture is unique to the Keys
Breakfast at Harpoon Harry's(45 minutes)
Old-school diner. Conch fritters ($12), Key West shrimp omelet ($14). One of the few places that opens early (6:30AM). Cash preferred. Local crowd
Last shopping on Duval(45 minutes)
Key lime everything (cookies, soap, hot sauce) at Kermit's. Conch shells and nautical gifts. Pick up a bottle of local rum from the Key West Distillery tasting room ($10 tasting)
Airport transfer or Overseas Highway departure(30 minutes)
EYW is 4 miles from Old Town ($15 taxi). If driving: fill up gas before leaving Key West — it's expensive on the Keys. Allow 4 hours to Miami with stops
ESTA visa waiver for 40 eligible countries ($21, valid 2 years). All other nationalities need a B1/B2 tourist visa — apply at the US embassy 2-3 months ahead. Canadian citizens do not need a visa. Passport must be valid for 6 months beyond your stay.
Old Town Key West is only 1 mile by 4 miles — everything is walkable or bikeable. Rent a bicycle ($15-25/day) from one of dozens of shops. Scooter rentals: $40-70/day. Parking is extremely limited and expensive ($3-5/hour, $25-40/day). If you drove down the Keys, park at your hotel and walk. The free Duval Loop bus circulates the main drag every 15 minutes.
If driving from Miami, US-1 (Overseas Highway) is one of the world's most scenic drives — 113 miles across 42 bridges over turquoise water. Allow 4-5 hours with stops. Must-stop: Bahia Honda State Park (mile marker 37) for swimming, the old Bahia Honda Bridge for photos, and Robbie's Marina (mile marker 77.5) to hand-feed tarpon ($4). Fill up on gas in Homestead — Keys gas is 20-30% more expensive.
Key West famously 'seceded' from the US in 1982 as the Conch Republic — a tongue-in-cheek protest that became part of local identity. Must-try local foods: conch fritters ($12-15 for a basket), key lime pie (Joe's Stone Crab or Kermit's, $6-8/slice), and a Cuban mix sandwich. Sloppy Joe's, Captain Tony's, and the Green Parrot are the essential bars.
Hotels average $250-500/night in peak season (December-April). Budget hotels start at $150. Restaurant meals: $20-50 per person. The biggest mistake: not booking accommodation early — prices spike and rooms sell out months ahead for Fantasy Fest (October) and Christmas/New Year. Save by visiting in May, June, or November (shoulder season, 30-40% cheaper, still warm).
Key West is at the same latitude as the Sahara Desert — UV radiation is intense year-round. Apply reef-safe SPF 50+ every 2 hours (Key West bans non-reef-safe sunscreen to protect the coral reef). Wear a hat and polarized sunglasses. Sunburn can happen in 20 minutes. Stay hydrated — the heat and alcohol combination causes rapid dehydration.
Hurricane season runs June 1 to November 30, peaking August-October. Key West is a small, low-lying island — evacuation orders should always be followed (there's only one road out). Check NOAA forecasts before booking. Travel insurance with hurricane coverage is strongly recommended for summer/fall visits. The upside: hurricane season has the lowest hotel rates.
Travel GuidesHow long is the drive? Do I need a car once I'm there? Is hurricane season actually dangerous? 14 questions, answered without the tourism brochure spin.
Travel GuidesBoth promise turquoise water and sunsets. One has Hemingway's cats and $200 ferry rides to a Civil War fort. The other has swimming pigs and private island resorts.
Travel GuidesFour days is all you need for Hemingway's cats, Mallory Square sunsets, North America's only coral reef, and a Civil War fort accessible only by ferry.
