A local's guide
Explore Key West
Coral reefs, cigar-scented streets, legendary sunsets and a festival for every season. Here is how we would spend your days — all within easy reach of Casa Azul.
The essentials
Best things to do in Key West
From iconic landmarks to hidden gardens — our favorite experiences on the southernmost island.
01
Sunset at Mallory Square
The nightly Sunset Celebration brings street performers, food carts and applause as the sun dips into the Gulf. Or skip the crowds and watch from Casa Azul's rooftop.
02
Duval Street & Old Town
Stroll 1.25 miles of galleries, boutiques, rooftop bars and live music, then wander the quiet lanes lined with conch cottages and bougainvillea.
03
Ernest Hemingway Home & Museum
Tour the Spanish Colonial home where Hemingway wrote in the 1930s — still home to dozens of his famous six-toed cats.
04
Fort Zachary Taylor State Park
A Civil War-era fort with a shady, rocky beach, clear water and some of the best shore snorkeling on the island.
05
Southernmost Point Buoy
The famous striped marker 90 miles from Cuba. Go early morning for the photo without the line.
06
Butterfly & Nature Conservatory
A glass-domed garden alive with hundreds of butterflies, flamingos and tropical birds.
07
Truman Little White House
President Truman's winter retreat, with guided tours through presidential history in a leafy compound.
08
Key West Lighthouse
Climb 88 steps for sweeping views over Old Town's rooftops and the sea beyond.
09
Smathers & Higgs Beaches
Palm-lined sand on the Atlantic side for swimming, paddleboarding and beach volleyball.
10
Key lime pie & Cuban coffee
A Key West rite of passage: a slice of tart, creamy key lime pie and a café con leche from a walk-up window.
11
Key West Botanical Garden
Right on Stock Island — a tranquil tropical forest with native trees, ponds and butterflies.
12
Historic Seaport & Key West Bight
Harbor-front restaurants, schooners and raw bars — the departure point for many sunset sails and reef trips.
Find tours
Tours & adventures
The Florida Keys' coral reef is the only living barrier reef in the continental U.S. Here is how to experience it — and much more.
On the water
Sunset sails
Sip champagne aboard a classic schooner or catamaran as the sky turns gold. Most depart from the Historic Seaport.
Ask us to arrangeReef
Snorkel & dive trips
Half-day trips to the reef to swim with parrotfish, rays and sea turtles in warm, clear water. Many combine snorkeling with a sunset sail.
Ask us to arrangeDay trip
Dry Tortugas National Park
About 70 miles west by ferry or seaplane: Fort Jefferson, empty beaches and extraordinary snorkeling. Book months ahead.
Official park infoFrom Stock Island
Fishing charters
Stock Island is a sport-fishing hub. Choose offshore for mahi and tuna, or the flats for tarpon, bonefish and permit with a licensed captain.
Book a charterEco
Kayak & paddleboard
Paddle quiet mangrove channels for rays, herons, baby sharks and the occasional manatee.
Rent kayaksThrills
Jet ski island tour
A guided loop around Key West with stops for views of the Southernmost Point, Fort Zach and Sunset Key.
Book jet skisLand
Trolley & Conch Train
Hop-on narrated tours of Old Town — the easiest way to get your bearings on the first day.
Plan with Visit Florida KeysTaste
Food & cocktail tours
Conch fritters, Cuban sandwiches, key lime pie and rum tastings on a guided walk through Old Town.
Get recommendationsAfter dark
Ghost & history walks
Lantern-lit tours of haunted mansions, pirate lore and Robert the Doll's legend.
Get recommendationsEvents calendar
A festival for every month
Plan your stay around Key West's legendary celebrations. Book early for major events — a 4-night minimum applies during Fantasy Fest.
January Peak season
- Key West Literary SeminarWriters and readers gather for talks and readings
- Key West Food & Wine FestivalTastings, dinners and waterfront events
February Dry & sunny
- Old Island Days Art FestivalFine art shows in Old Town
- Peak snorkeling visibilityCalm, clear winter days
March Spring
- Conch Shell Blowing ContestA quirky, beloved island tradition
- Garden & house toursPeek inside historic Old Town homes
April Spring
- Conch Republic Independence CelebrationParades, bed races and a mock naval “battle”
- Key West Woof WeekBear community week
- Key West Songwriters FestivalApr 28 – May 2, 2027
May Shoulder
- Songwriters Festival finaleIntimate shows island-wide
- Fewer crowds, warm waterGreat value for couples
June Summer
- Key West PrideEarly June · parade on Duval Street
- Hurricane season beginsJune 1 – Nov 30
July Summer
- Hemingway DaysAround July 21 · look-alike contest and more
- Lobster mini-seasonLate July · sport diving for spiny lobster
- Fourth of July fireworksOver the water
August Summer
- Tropical HeatMid-August · men's festival and pool parties
- Lobster season opensEarly August
September Quiet season
- WomenfestEarly September · celebration for queer women
- Best rates of the yearPeaceful island pace
October Festival season
- Fantasy FestOct 16 – 25, 2026 · parade Sat Oct 24
- Goombay FestivalCaribbean street fair in Bahama Village
- Key West Bear WeekendLate October
November Shoulder
- Key West Film FestivalScreenings and filmmaker talks
- Offshore powerboat racesWorld championship racing off the harbor
December Holidays
- Holiday Lighted Boat ParadeDecorated boats glide through the harbor
- New Year's Eve dropsConch shell, pirate wench and a drag queen in a giant red shoe
★ Signature events. Dates change every year — always confirm with the official organizers before you book. Looking for LGBTQ+ events? See our Gay Key West guide.
Day trips up the Keys
Beyond the island
- Boca Chica & Geiger Key15 min
- National Key Deer Refuge, Big Pine Key40 min
- Looe Key Reef snorkeling45 min
- Bahia Honda State Park50 min
- Seven Mile Bridge & Marathon1 hr
Approximate drive times from The Perry Marina along the Overseas Highway (US-1).
When to visit
Key West by season
Winter · December to March
Warm, dry and breezy with highs in the mid-70s °F. The busiest and most festive time of year — book early.
Spring · April to May
Sunny, calm seas and highs in the 80s. Ideal for snorkeling, sailing and the Songwriters Festival.
Summer · June to September
Hot and humid with short afternoon showers. Lower rates, Pride, lobster season and quieter beaches.
Fall · October to November
Festival season with Fantasy Fest, then pleasant, uncrowded weeks in November.
How far is Stock Island from Duval Street?
About 5 miles, or roughly 15 minutes by car. The Perry Hotel runs a shuttle, and rideshare and golf carts are easy options.
Casa Azul · Key West
Adventure by day, the water by night
Come home to your own rooftop deck after every Key West adventure.
Book your stay