What to do once you land inKey WestFind your bearings
Key West is the end of the road — literally, Mile Marker 0 — and it feels like it. This tiny island runs on its own time: flip-flops are formal wear, happy hour starts at noon, and roosters own the streets. It's tropical, quirky, historic, and defiantly itself. Think Caribbean vibes without a passport.
Neighborhoods
Old Town — Historic heart with Victorian gingerbread houses, Duval Street bars, and most of the island's restaurants and shops
Duval Street — The main drag from Gulf to Atlantic. Bars, galleries, and tourist shops on top, better spots on the side streets
Bahama Village — Historic Bahamian neighborhood with local restaurants, art galleries, and Blue Heaven's legendary brunch
New Town — Where locals live: grocery stores, strip malls, and Smathers Beach — the longest public beach on the island
Best time to visit
November through April for dry season and perfect 75 to 85°F weather. Summer is hot, humid, and hurricane-possible but cheaper. Avoid Fantasy Fest (late October) unless that's your scene.
Getting around
Rent a bike or scooter. The island is only 4 miles long and 1 mile wide — you can bike anywhere in 15 minutes
Street parking is brutal. If you drove down, park it at your hotel and forget about it
The free Duval Loop bus runs a circuit through Old Town and New Town every 15 minutes
The drive down from Miami is 3.5 hours on the Overseas Highway. Stop at Bahia Honda State Park along the way
Key areas
Old TownDuval StreetMallory SquareBahama VillageSmathers Beach
Zero-dollar wins
1
Mallory Square sunset celebrationNightly sunset festival with street performers, jugglers, psychics, and the whole island watching the sun drop into the Gulf
2
Southernmost Point buoyThe iconic red, yellow, and black buoy marking the southernmost point in the continental US. Free photo op, early morning avoids lines
3
Fort Zachary Taylor beachBest snorkeling beach on the island with a historic Civil War fort. $6 for cars but free if you bike or walk in
4
Key West CemeteryQuirky, historic graveyard with funny tombstones ('I told you I was sick'). Self-guided walking tour through 19 acres of history
5
Rooster spottingWild roosters and chickens roam freely everywhere. They're protected by law and strut around like they own the place (they do)
6
Smathers BeachLongest public beach on the island with calm, shallow water. Free parking, bring your own chair and snorkel gear
Treat yourself
(we think it's worth it)
Latitudes on Sunset Key$80 to $140
Take a free boat to a private island for beachfront fine dining. Sunset views are unreal and the catch of the day is always freshSantiago's Bodega$50 to $90
Tapas and cocktails in a candlelit space. The lobster empanadas and date-wrapped bacon are worth every pennyCafe Sole$60 to $100
French-Caribbean fine dining on a quiet side street. Hogfish meunire is the signature and it's impossibly goodPrivate sunset sail$75 to $150
Charter a catamaran for sunset with champagne and snacks. 2-hour trips run from the Historic SeaportThe legendary bites
The dishes this city perfected
Blue Heaven$15 to $30
Outdoor brunch under tropical trees where Hemingway refereed boxing matches. Roosters wander between tablesLobster Benedict with key lime hollandaiseKermit's Key West Key Lime Shoppe$5 to $8
The definitive key lime pie on the island. Frozen on a stick, dipped in chocolate, is the moveFrozen key lime pie on a stick dipped in dark chocolateEl Siboney$12 to $20
No-frills Cuban restaurant beloved by locals since 1984. Massive portions of ropa vieja and fried plantainsRopa vieja with black beans, rice, and madurosGarbo's Grill$10 to $18
Tiny food trailer in a parking lot serving some of the best tacos on the island. Korean short rib is legendaryKorean short rib taco with kimchi slawPepe's Cafe$12 to $22
The oldest eating house in Key West (1909). Breakfast is the move: pancakes, eggs, and strong coffee in a wooden shackKey West shrimp and gritsWhere locals eat
Where residents actually go
Sandy's Cafe$1 to $4
Walk-up window Cuban coffee for $1. The colada (sweet espresso to share) is how locals start every morningGarbo's Grill$8 to $14
Tiny food truck in a parking lot off Greene Street. Fish tacos and Korean BBQ that locals queue for dailyEl Siboney$10 to $18
Cash-only Cuban spot on Catherine Street where locals go for massive plates of roast pork and yellow riceBien$12 to $20
Modern Vietnamese-inspired spot on Petronia Street. Locals love the pho and lemongrass chicken banh miDate & Thyme$12 to $20
Organic cafe with smoothie bowls, grain bowls, and cold-pressed juices. Health food in a land of fried everythingHogfish Bar & Grill$14 to $25
On Stock Island (one bridge over), this dockside spot is where commercial fishermen eat. Hogfish sandwich is the callGo off-script
1
Snorkeling the reefNorth America's only living barrier reef is 6 miles offshore. Half-day trips hit the best spots for $50 to $70 including gear
2
Hemingway Home & six-toed catsTour the Nobel laureate's 1930s home where 60+ polydactyl cats (descended from his original) roam free. $18 admission
3
Kayak through mangrovesPaddle through the mangrove channels of the Key West Wildlife Refuge. Spot herons, rays, and juvenile sharks in crystal-clear water
4
Duval crawl (the right way)Skip the tourist bars on upper Duval. Start at The Porch, hit Green Parrot (oldest bar, 1890), and end at Better Than Sex dessert bar
Insider intel + tourist traps
Tips
- ✓Happy hour is religion here. Half-price oysters at Alonzo's, $5 margaritas at El Meson, and $1 oysters at Half Shell Raw Bar between 4 and 6pm
- ✓Bring reef-safe sunscreen. Regular sunscreen is banned in the Florida Keys to protect the coral reef
- ✓Rent a bike, not a car. The island is tiny, parking is $30/day, and you'll see more on two wheels anyway
- ✓Go to Mallory Square 30 minutes before sunset to get a good spot and see all the performers set up
“Biked everywhere, ate key lime pie three times a day, watched sunset at Mallory Square every single night. Five days wasn't enough. Simplest, happiest vacation I've taken.”
Skip
- ✗Sloppy Joe's on Duval: the 'Hemingway bar' is mostly frozen drinks and cover bands. He actually drank at Captain Tony's around the corner
- ✗Conch Tour Train for $35: you'll see the whole island in 90 minutes from a goofy train, or you could rent a bike for $15/day and explore at your own pace
- ✗Sunset cruise for $90+: Mallory Square sunset is free and the boat ones are often crowded party boats with bad music