Key West looks simple on the map — it's the last island at the bottom of Florida. But the logistics of getting there, getting around, and not going broke deserve some honest answers.
A: Drive. The Overseas Highway (US-1) from Miami to Key West is 113 miles across 42 bridges over turquoise water and it's one of the most spectacular drives in the world. Allow 4-5 hours with stops.
Must-stops: Bahia Honda State Park (mile marker 37) for swimming and the old bridge photo, and Robbie's Marina (mile marker 77.5) to hand-feed giant tarpon ($4 for a bucket of fish).
Fill up on gas in Homestead — Keys gas is 20-30% more expensive.
A: Key West's airport (EYW) is tiny. Limited direct flights, mostly from Miami, Fort Lauderdale, and Atlanta. Tickets are often $300-500+ round trip. If flying, go through Miami (MIA) and either rent a car for the drive or take the Keys Shuttle ($35-45 one way, 4 hours).
A: No. And you actively don't want one. Old Town Key West is 1 mile by 4 miles — everything is walkable or bikeable. Parking is extremely limited and expensive ($3-5/hour, $25-40/day). If you drove the Keys, park at your hotel and forget the car exists.
Rent a bicycle ($15-25/day) — it's the local way to get around. Scooter rentals run $40-70/day. The free Duval Loop bus circles the main drag every 15 minutes.
A: Uber and Lyft work in Key West but availability is limited, especially late at night. Taxis are more reliable. But honestly, the island is so small that you'll rarely need either.
A: Key West is expensive. Hotels average $250-500/night in peak season (December-April). Budget options start around $150/night. Fantasy Fest (October) and Christmas/New Year week are the most expensive — book months ahead.
The shoulder seasons (May-June, November) drop 30-40% and the weather is still warm. Hurricane season (August-October) has the lowest rates but comes with obvious risks.
A: Old Town (near Duval Street and Mallory Square) puts you in walking distance of everything. The Bahama Village area is slightly cheaper and has more local character. The New Town side is less charming but more affordable with parking.
A: Every evening, two hours before sunset, street performers, artists, and vendors gather at Mallory Square for a nightly celebration. Sword swallowers, tightrope walkers, trained cats, fire eaters. The crowd builds, the sun drops into the Gulf of Mexico, everyone applauds. It's free, genuinely fun, and a quintessential Key West ritual.
Arrive an hour early for a good spot along the waterfront wall.
A: If you have any interest in literature, absolutely. The 1851 colonial estate where Hemingway wrote some of his greatest works (1931-1939) is charming, and the 60+ six-toed cats descended from his original cat are everywhere. Guided tours every 15 minutes, 30 minutes long. His writing studio above the carriage house is intact.
Even if you're not a Hemingway fan, the cats alone are worth the visit.
A: The Dry Tortugas is a remote national park 70 miles west of Key West — a massive hexagonal Civil War-era fortress (Fort Jefferson) on a tiny island surrounded by crystal-clear water. It's accessible only by ferry or seaplane.
Yankee Freedom ferry: $200 round trip (includes breakfast, lunch, and snorkeling gear). 2.25 hours each way. Full day trip.
Seaplane: $365 round trip, 40 minutes each way. More time at the fort.
The snorkeling is world-class — crystal water, coral gardens, tropical fish. The fort itself is architecturally fascinating. Book 2-3 weeks ahead in peak season.
Is it worth $200? Yes. One of the most unique day trips in the US.
A: The iconic red, yellow, and black concrete buoy marks the southernmost point of the continental US — 90 miles from Cuba. Free to visit. Expect a 15-30 minute line for photos. Best at sunrise or evening to avoid crowds and harsh midday light.
It's a quick stop, not a destination. 10 minutes for the photo, then move on.
A: Three things are non-negotiable:
For bars: Sloppy Joe's (Hemingway's favorite, loud and touristy but mandatory), Captain Tony's (the original Sloppy Joe's location, divey and authentic), and the Green Parrot (local's bar since 1890, live music, no food).
A: Yes. Restaurant meals run $20-50 per person. Grocery shopping and cooking in a rental is the budget move. For cheaper eats, get Cuban food from Cuban Coffee Queen ($8-12 sandwiches) or tacos from Garbo's Grill ($5-8 each) — a food truck in a parking lot that's better than most sit-down restaurants.
A: Hurricane season runs June 1 to November 30, peaking August-October. Key West is a small, low-lying island with only one road out (US-1). Evacuation orders should always be followed.
The risk is real but not constant. Most hurricane seasons pass without a direct hit. 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.
A: 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). Sunburn can happen in 20 minutes. Wear a hat and polarized sunglasses.
| Item | Cost |
|---|---|
| Miami to Key West drive | 4-5 hours, gas ~$30 |
| Hotel (peak season) | $250-500/night |
| Bike rental | $15-25/day |
| Hemingway Home | $18 |
| Dry Tortugas ferry | $200 round trip |
| Snorkeling trip | $45-65 |
| Key lime pie slice | $6-8 |
| Conch fritters | $12-15 |
Travel Guides
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