Key West

Key Facts
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
Top Highlights

Mallory Square Sunset Celebration
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.

Ernest Hemingway Home & Museum
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.

Duval Street
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.

Dry Tortugas National Park
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.

Snorkeling at the Coral Reef
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.

Southernmost Point Buoy
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.

Fort Zachary Taylor Beach
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.
Planned Itinerary
7-Day Key West Itinerary
Arrival & Mallory Square Sunset
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
Hemingway, Duval Street & Key Lime Pie
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
Snorkeling the Coral Reef
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
Rest Day — Kayaking & Island Vibes
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
Dry Tortugas National Park Day Trip
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
Conch Republic Culture & Water Sports
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
Departure Day — Conch Fritters & Farewell
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
14-Day Key West Itinerary
Arrival & Mallory Square Sunset
Arrive EYW or drive Overseas Highway from Miami (3.5-4 hrs). Old Town walkable.
Arrival and check-in(1 hour)
If driving, stop at Bahia Honda SP (MM 37). EYW taxi $15-20
Rent a bicycle(30 minutes)
$15-25/day. Best way around 1x4 mile island
Mallory Square Sunset Celebration(2 hours)
Free. Performers, food vendors. Applause at sunset. Nightly ritual
Dinner at Santiago's Bodega(1.5 hours)
Tapas. Tuna nachos ($16), key lime brie ($14)
Hemingway, Duval & Key Lime Pie
Literary history, bar crawl, and essential food.
Hemingway Home(1.5 hours)
$18. Six-toed cats, writing studio. Tours every 15 min
Southernmost Point Buoy(30 minutes)
Free. Photo line 15-30 min. 90 miles from Cuba
Lunch at Blue Heaven(1 hour)
Banana bread French toast ($16). Chickens roaming. Cash only
Duval Street walk(2 hours)
Sloppy Joe's, Captain Tony's, Green Parrot. No cover
Key lime pie at Kermit's(30 minutes)
Pie on stick dipped in chocolate ($6)
Snorkeling the Reef
North America's only living barrier reef.
Reef snorkeling trip(3.5 hours)
$45-65. Equipment included. Turtles, parrotfish, nurse sharks
Lunch at Eaton Street Seafood(45 minutes)
Fish sandwich ($12), conch ceviche ($14). Cash. Local
Fort Zachary Taylor Beach(2.5 hours)
$6/vehicle + $2.50. Best beach. Snorkeling off shore. Fort tour free
Sunset at Sunset Pier(1.5 hours)
Ocean Key Resort. Rum runners ($14), live music
Rest Day — Kayaking & Island Vibes
Slower pace with eco-tours.
Mangrove kayak tour(2 hours)
$50-65. Eco-tour through backcountry. Sharks, rays, birds
Brunch at Cafe Sole(1 hour)
Hogfish ($28), lobster Benedict ($22). BYOB
Butterfly Conservatory(1 hour)
$15. Glass dome with 50+ species
Free afternoon(2 hours)
Shops, Shipwreck Museum ($15), or hammock time
Dinner at Latitudes(2 hours)
Sunset Key private island. Free boat. Fresh catch ($38). Reserve
Dry Tortugas Day Trip
70 miles west. Fort Jefferson, pristine snorkeling.
Yankee Freedom ferry(2.25 hours)
$200 RT. Breakfast, lunch, snorkel gear included. Departs 8AM
Fort Jefferson(2 hours)
16 million bricks. Moat walk, Dr. Mudd cell
Snorkeling Garden Key(1.5 hours)
Crystal clear. Turtles, coral. Equipment provided
Beach time(1 hour)
Pristine white sand, turquoise water
Return ferry(2.25 hours)
Light dinner at Garbo's Grill — fish tacos ($8)
Conch Culture & Water Sports
Eccentric Key West history and more water time.
Key West Cemetery(1.5 hours)
Free. Above-ground. 'I Told You I Was Sick.' Morning best
Truman Little White House(1 hour)
$20. Winter White House. Guided tours only
Lunch at El Siboney(45 minutes)
Cuban. Ropa vieja ($14), Cuban sandwich ($10). Cash only
Jet ski or parasailing(1.5 hours)
Jet ski $80-100/hr. Parasailing $65-85
Rest Day — Beach & Slow Exploration
Free day to explore at your own pace.
Morning at Smathers Beach(2 hours)
Free. Key West's longest beach (2 miles). Calm, shallow water. Rent a beach chair ($15/day)
Lunch at Pepe's Cafe(1 hour)
Oldest restaurant in Key West (1909). Steak and eggs ($16). Local vibe on Caroline Street
Free afternoon(3 hours)
Audubon House and Gardens ($14), Mel Fisher Maritime Museum ($15, treasure from 1622 Atocha shipwreck), or take a glass-bottom boat ($45, 2 hours)
Dinner at Cafe Marquesa(1.5 hours)
Fine dining on Fleming Street. Pan-seared grouper ($36), key lime crème brûlée ($14). Intimate, excellent. Reservations essential
Lower Keys Day Trip — Bahia Honda & Big Pine
Drive north on the Overseas Highway to the most beautiful beaches in the Keys.
Drive to Bahia Honda State Park(45 minutes)
$4.50/person + $2/vehicle. MM 37. Two of the best beaches in the Florida Keys — Calusa Beach and Sandspur Beach. Warm, clear water, palm trees
Snorkeling at Looe Key(3 hours)
Boat tour from Bahia Honda ($45-60). One of the most pristine reef sections in the Keys. Outstanding coral and fish diversity. Equipment provided
Lunch at No Name Pub on Big Pine Key(1 hour)
MM 31. Hidden dive bar covered in dollar bills. Pizza ($14-18), cold beer. Follow the signs down a dirt road. Cash preferred. Truly off the beaten path
National Key Deer Refuge(1 hour)
Free. Big Pine Key. The endangered Key deer (smallest deer in North America, 2-3 feet tall) roam freely. Drive slowly on Key Deer Boulevard. Best at dawn and dusk
Return to Key West(45 minutes)
Dinner at Hot Tin Roof — rooftop at Ocean Key Resort. Caribbean fusion ($28-42), harbor sunset views
Fishing & Foodie Day
Deep-sea fishing or flats fishing followed by eating your catch.
Half-day fishing charter(4 hours)
$700-1200 for the boat (split with group of 4-6). Target: mahi-mahi, yellowtail, grouper, kingfish. Flats fishing (tarpon, bonefish, permit) is $500-700 for 2 people. Book through the Historic Seaport charter boats
Cook your catch at a local restaurant(1.5 hours)
Several restaurants will cook your catch for $15-20/person. Half Shell Raw Bar on the Seaport is the most popular. They'll fry, grill, or blacken your fish
Afternoon rest(2 hours)
Pool time or nap after early morning on the water
Dinner at Nine One Five(1.5 hours)
Tapas and wine on Duval. Lobster ceviche ($18), duck confit ($22). Second-floor balcony with people-watching. Reservations recommended
Arts, History & Sunset Sail
Deeper cultural exploration and a sunset under sail.
Key West Museum of Art & History(1 hour)
$10. Inside the old Customs House (1891). Rotating exhibits on Keys art and history. Small but well curated. Near Mallory Square
Key West Tropical Forest & Botanical Garden(1 hour)
$10. Only frost-free botanical garden in the US. Two freshwater ponds, endangered species, and native butterflies. Peaceful and uncrowded. On Stock Island
Lunch at Date & Thyme(45 minutes)
Plant-based organic cafe. Smoothie bowls ($14), grain bowls ($16). Healthy alternative to the seafood-and-bar routine
Sunset sailing cruise(2 hours)
Danger Charters or Sebago ($65-85). Catamaran cruise with champagne, beer, and wine included. Sail through the harbor with the sunset behind you. A more intimate sunset experience than Mallory Square
Dinner at Seven Fish(1.5 hours)
Tiny local favorite. Fresh fish prepared simply — grilled mahi ($28), banana chicken ($24). Reservations essential — only seats 15. Worth the effort
Rest & Free Day
Fully open day.
Sleep in and late brunch(2 hours)
Banana Cafe on Duval — French crepes ($12-16). Or Old Town Bakery for pastries ($4-6)
Free afternoon(4 hours)
Revisit favorite beaches, Fort Zachary for more snorkeling, or take a ghost tour (Old Town Trolley Ghost Tour, $30, evening). Or just sit at the Green Parrot with a cold beer and live music
Dinner at Louie's Backyard(2 hours)
Atlantic-front fine dining. The deck over the ocean is magical at sunset. Grilled hogfish ($38), lobster ($42). Reservations essential. One of Key West's most special dinners
Scuba Diving or SUP Yoga
Choose your water adventure — go deep or find your balance.
Option A: Scuba diving(4 hours)
Two-tank dive trip ($100-150). Key West has shallow reef (15-30 ft) with excellent visibility. PADI certification required. Try the Vandenberg wreck dive (artificial reef, 100 ft) for advanced divers
Option B: Stand-up paddleboard yoga(1.5 hours)
$45-55. SUP yoga on calm backcountry waters. No experience needed — surprisingly fun even for beginners. Several operators offer classes at sunrise
Lunch at Hogfish Bar & Grill(1 hour)
Stock Island (5 min drive). Hogfish sandwich ($18) — the local fish you can't get anywhere else. Waterfront, casual, real fishermen eating here. Not touristy
Free afternoon(2 hours)
Last chance to visit Hemingway House, buy key lime products, or just bike the residential streets
Dinner at A&B Lobster House(1.5 hours)
Upstairs fine dining overlooking the Historic Seaport. Lobster thermidor ($45), key lime baked Alaska ($14). Classic, reliable, waterfront
Marathon & Middle Keys Day Trip
Drive 1 hour north for the best bridge views, a turtle hospital, and more reef.
Drive the Seven Mile Bridge(30 minutes)
The most spectacular section of the Overseas Highway. The old bridge alongside provides a photo perspective. Stop at the bridge viewing area on the Marathon side
Turtle Hospital tour(1.5 hours)
$27 adults. Guided tour of the rehabilitation facility for sea turtles. See permanent residents and learn about rescue efforts. Reservations required — book online. Educational and touching
Sombrero Reef snorkeling(3 hours)
Boat from Marathon ($45-55). One of the best snorkeling reefs in the Florida Keys — large brain corals, sea fans, and abundant fish. Equipment included
Lunch at Keys Fisheries(1 hour)
Marathon. Lobster reuben ($18), stone crab claws ($24/lb, October-May). Waterfront picnic tables overlooking the marina. Cash or card
Return to Key West(1 hour)
Final dinner at your favorite restaurant — revisit Blue Heaven, Seven Fish, or Santiago's
Departure Day — Conch Fritters & Farewell
Final Key West morning.
Bike ride through residential Old Town(1 hour)
Quiet streets, Victorian houses, tropical gardens
Breakfast at Harpoon Harry's(45 minutes)
Conch fritters ($12), shrimp omelet ($14). Opens 6:30AM
Last Duval shopping(45 minutes)
Key lime products at Kermit's, rum from Key West Distillery ($10 tasting)
Departure(30 minutes)
EYW taxi $15. If driving: 4 hours to Miami with stops
21-Day Key West Itinerary
Arrival & Mallory Square Sunset
Arrive EYW or drive Overseas Highway (3.5-4 hrs from Miami).
Arrival(1 hour)
Stop Bahia Honda if driving. EYW taxi $15-20
Rent bicycle(30 minutes)
$15-25/day
Mallory Square sunset(2 hours)
Free. Performers, food vendors. Nightly ritual
Dinner at Santiago's Bodega(1.5 hours)
Tapas. Tuna nachos ($16)
Hemingway, Duval & Key Lime
Literary history, bars, and essential eats.
Hemingway Home(1.5 hours)
$18. Six-toed cats, writing studio
Southernmost Point(30 minutes)
Free. Photo line. 90 mi from Cuba
Lunch at Blue Heaven(1 hour)
French toast ($16). Chickens. Cash only
Duval Street walk(2 hours)
Sloppy Joe's, Green Parrot. No cover
Key lime at Kermit's(30 minutes)
Pie on stick ($6)
Snorkeling the Reef
North America's only barrier reef.
Reef trip(3.5 hours)
$45-65. Turtles, sharks, coral
Lunch at Eaton St Seafood(45 minutes)
Fish sandwich ($12). Cash
Fort Zachary Beach(2.5 hours)
$6+$2.50. Best beach. Snorkeling. Fort tour
Sunset Pier cocktails(1.5 hours)
Rum runners ($14), live music
Rest — Kayaking & Island Vibes
Eco-tours and laid-back culture.
Mangrove kayak(2 hours)
$50-65. Sharks, rays, birds
Brunch at Cafe Sole(1 hour)
Hogfish ($28). BYOB
Butterfly Conservatory(1 hour)
$15. 50+ species
Dinner at Latitudes(2 hours)
Sunset Key. Free boat. Reserve
Dry Tortugas Day Trip
Fort Jefferson, pristine snorkeling.
Ferry(2.25 hours)
$200 RT. Meals and gear included
Fort Jefferson(2 hours)
16 million bricks. Civil War fort
Snorkeling(1.5 hours)
Crystal clear. Turtles, coral
Beach(1 hour)
Pristine, no development
Return(2.25 hours)
Garbo's Grill fish tacos ($8)
Cemetery, White House & Sports
History and water sports.
Cemetery walk(1.5 hours)
Free. Famous tombstones
Truman White House(1 hour)
$20. Guided tours
Lunch at El Siboney(45 minutes)
Cuban. Ropa vieja ($14). Cash
Jet ski/parasailing(1.5 hours)
$80-100 or $65-85
Rest Day
Free day.
Smathers Beach(2 hours)
Free. 2 miles, calm water
Lunch at Pepe's(1 hour)
Oldest restaurant (1909). Steak & eggs ($16)
Free afternoon(3 hours)
Museums, glass-bottom boat, or rest
Dinner at Cafe Marquesa(1.5 hours)
Grouper ($36), crème brûlée ($14). Reserve
Lower Keys — Bahia Honda & Big Pine
Best beaches and Key deer.
Bahia Honda State Park(2 hours)
$4.50+$2. Two stunning beaches
Looe Key snorkeling(3 hours)
$45-60. Pristine reef
Lunch at No Name Pub(1 hour)
Pizza ($14-18). Dollar-bill-covered walls. Cash
Key Deer Refuge(1 hour)
Free. Smallest deer in N. America
Return for dinner(1.5 hours)
Hot Tin Roof rooftop ($28-42)
Fishing & Cook Your Catch
Deep-sea or flats fishing.
Half-day charter(4 hours)
$700-1200/boat. Mahi, grouper, yellowtail
Cook at Half Shell Raw Bar(1.5 hours)
$15-20 to cook your catch. Fried, grilled, blackened
Dinner at Nine One Five(1.5 hours)
Lobster ceviche ($18). Duval balcony
Arts & Sunset Sail
Museums and sailing.
Museum of Art & History(1 hour)
$10. 1891 Customs House
Botanical Garden(1 hour)
$10. Only frost-free garden in US
Lunch at Date & Thyme(45 minutes)
Plant-based. Bowls ($14-16)
Sunset sail(2 hours)
$65-85. Champagne, wine included
Dinner at Seven Fish(1.5 hours)
15 seats. Mahi ($28). Reserve
Rest & Free Day
Open day.
Late brunch at Banana Cafe(1.5 hours)
French crepes ($12-16)
Free afternoon(4 hours)
Ghost tour ($30), beach, Green Parrot
Dinner at Louie's Backyard(2 hours)
Atlantic-front. Hogfish ($38). Reserve
Diving or SUP Yoga
Water adventures.
Scuba diving(4 hours)
$100-150. Two-tank reef dive. Vandenberg wreck for advanced
Lunch at Hogfish Bar(1 hour)
Stock Island. Hogfish sandwich ($18). Real fishermen
Dinner at A&B Lobster House(1.5 hours)
Lobster thermidor ($45). Seaport views
Marathon & Middle Keys
Seven Mile Bridge, turtles, reef.
Seven Mile Bridge drive(30 minutes)
Most spectacular highway section
Turtle Hospital(1.5 hours)
$27. Sea turtle rehab. Reserve
Sombrero Reef snorkeling(3 hours)
$45-55. Brain corals, abundant fish
Lunch at Keys Fisheries(1 hour)
Lobster reuben ($18), stone crab
Islamorada Day Trip
Drive 1.5 hours to the 'Sport Fishing Capital of the World.'
Drive to Islamorada(1.5 hours)
MM 80. Beautiful bridge views along the way
Robbie's Marina tarpon feeding(1 hour)
MM 77.5. $4 for a bucket of fish. Hand-feed massive tarpon from the dock. Tourist trap in the best way
Theater of the Sea(2 hours)
$33. Swim with dolphins ($200), sea lion shows, nature trails. Intimate marine park (since 1946)
Lunch at Morada Bay Beach Cafe(1 hour)
Beachfront dining on white sand. Toes in the water, cocktail in hand. Fish tacos ($18), mojitos ($14). Monthly full moon parties
Return to Key West(1.5 hours)
Casual dinner
Rest & Free Day
Another open day.
Free exploration(5 hours)
Revisit Fort Zachary, try a new restaurant, take a walking food tour ($65, 3 hours), or rent a scooter ($40-70/day) and explore Stock Island
Dinner at Cafe Sole(1.5 hours)
Return for hogfish. BYOB
Backcountry Eco-Tour
Explore the mangrove backcountry most visitors never see.
Full-day backcountry tour(6 hours)
$175-250. Kayak or boat through the Great White Heron National Wildlife Refuge. See nurse sharks, rays, dolphins, sea turtles, and hundreds of bird species. Lunch on a remote sandbar. Honest Eco or Lazy Dog Adventures
Afternoon rest(2 hours)
Recovery after full day on the water
Dinner at Michael's Restaurant(1.5 hours)
Upscale on Margaret Street. Steak and seafood ($30-45). Live piano. Reservations recommended
Art & Architecture Walk
Key West's vibrant art scene and unique architecture.
Key West art galleries walk(2 hours)
Free. Walk through galleries on Duval, Whitehead, and Greene Streets. The Studios of Key West has rotating exhibits and artist talks. Wyland Gallery for marine art
Architecture walking tour(2 hours)
Self-guided or Historic Florida Keys Foundation tour ($20). See Conch houses (shotgun-style with wraparound porches), Victorian mansions, and the unique 'eyebrow house' design (slanting rooflines that shade upper windows)
Lunch at Sandy's Cafe(45 minutes)
Cuban coffee window on White Street. Cuban mix sandwich ($8), cafe con leche ($3). Locals' pick. Counter service
Harry Truman pool swim(1.5 hours)
The former presidential pool at the Truman Waterfront Park is now a public pool ($10/day). Or free beach access at nearby Dog Beach (dogs welcome)
Dinner at The Stoned Crab(1.5 hours)
Stone crab claws (seasonal, market price), whole fried snapper ($32). Casual waterfront at the Hurricane Hole Marina
Cooking Class & Food Tour
Learn to cook Key West cuisine.
Key West cooking class(3 hours)
$85-120. Learn to make key lime pie, conch fritters, and Caribbean seafood. Several companies offer classes — Key West Food Tours has kitchen sessions. Book online
Key West Food Tour walking(3 hours)
$65. Guided walking tour of 5-6 restaurants and food shops. Taste Cuban coffee, conch, key lime, and local craft beer. 1.5-mile walk through Old Town. Good alternative if cooking class is full
Free afternoon(2 hours)
Hammock time, pool, or beach
Dinner at Thirsty Mermaid(1.5 hours)
Raw bar and seafood on Simonton. Oysters ($3 each), cioppino ($28). Walk-in bar seating
Rest & Final Beach Day
Second-to-last full day — all about relaxation.
Morning at Fort Zachary(3 hours)
One last snorkel at the best beach. Bring a packed lunch
Ghost and legends tour(1.5 hours)
$25-30. Evening walking tour through haunted spots. Robert the Doll, the Artist House, and the cemetery. Creepy and entertaining. Multiple companies operate nightly
Farewell dinner at Blue Heaven(1.5 hours)
Return one last time. Lobster Benedict ($24) for dinner. Chickens, cats, and live music. The quintessential Key West experience
Final Full Day — Greatest Hits
Revisit your favorites.
Sunrise at Smathers Beach(1 hour)
Free. The eastern-facing beach catches sunrise. Peaceful with few people
Final bike ride through Old Town(1.5 hours)
Hit your favorite streets, quiet corners, and photo spots one last time
Lunch at Garbo's Grill(45 minutes)
Best fish tacos ($8). Tiny truck. Korean BBQ tacos too
Final sunset at Mallory Square(2 hours)
One last applause for the sun. Find the performers you loved
Farewell dinner at Latitudes or Seven Fish(2 hours)
Return to your favorite. Make it memorable
Departure Day
Final Key West morning.
Breakfast at Harpoon Harry's(45 minutes)
Conch fritters ($12). Opens 6:30AM
Last Kermit's key lime run(30 minutes)
Grab pie, cookies, and hot sauce to take home
Departure(30 minutes)
EYW taxi $15. Or 4 hours to Miami
Travel Tips
Visa & Entry
US Entry Requirements
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.
transport
You Don't Need a Car in Key West
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.
The Overseas Highway Drive Is Spectacular
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.
Local Customs
Conch Republic Culture
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.
Budget
Key West Is Expensive — Budget Accordingly
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).
Safety
Sun Protection Is Critical
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 Awareness
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.
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