What to Expect
Ships either anchor and tender or dock at Mallory Square; all passengers arrive at the same dock. Old Town Key West — the historic residential and commercial district — begins immediately at the pier. Duval Street, the main tourist strip, runs south from here to the beach. Everything of note is walkable. Key West's character is genuinely its own — a wreckers' port, a sponge-fishing capital, a Navy town, and a writers' colony. All of that leaves visible traces in the architecture and the general attitude.
Getting Around
Old Town is entirely walkable — the historic district is roughly 1 mile by 1 mile. Rental bikes are everywhere ($15–25/day) and are the best way to cover the island quickly. The Conch Train (a tram tour) runs through Old Town for $35 and is a useful orientation for first-timers who prefer to get their bearings before walking. Smathers Beach (the main beach, on the Atlantic side) is 2 miles from the pier — rideshare or bike to get there.
Tipping and Currency
USD. Tip 15–20% at restaurants. Bar service expects $1 per drink as a baseline — servers will remind you about this more assertively than in most ports. Conch Train tour operators: $2–5 per passenger is appreciated. Bike rental shops: no tip expected.
What to Eat
Conch is Key West's food identity — conch fritters, conch chowder, and raw conch salad are on menus everywhere. Better versions are away from Duval: Garbo's Grill (a truck in a parking lot, a genuine local favorite for fish tacos), Blue Heaven in Bahama Village (brunch and lunch, famous for the yard roosters), and B.O.'s Fish Wagon (a waterfront shack with excellent fish sandwiches). Sloppy Joe's is the Hemingway bar — the historical connection is contested, but one drink in the atmosphere is worth it.
Beaches
Key West's beaches are minor — thin strips of imported sand on a coral rock island. Smathers Beach on the Atlantic side is the longest and most swimmable. Fort Zachary Taylor State Park ($4 parking, $2.50 per person entry) has the island's best snorkeling, directly off a reef rock beach. The reef at Fort Taylor is live and accessible without a boat — bring a mask and fins.
Culture and History
The Hemingway Home ($17) is an excellent museum — his desk, personal library, and the six-toed cats in a well-preserved Spanish Colonial house. The Mel Fisher Maritime Heritage Museum ($18.50) has the actual treasure from the Atocha and Margarita shipwrecks — gold bars, emeralds, and silver coins you can walk around. Both are genuinely good. The southernmost point buoy is a free photo stop with a reliably long line — plan for 20 minutes if you want the photo, or skip it if you don't.
Traveling with Kids
Key West is better for older children and teenagers who can appreciate the Old Town quirks and the history. Fort Zachary Taylor has snorkeling, picnic areas, and a beach that works for families. The Key West Aquarium ($19 adults, $11 kids) on Front Street is small but has touch tanks. Younger children will find Key West a walking tour of things they cannot touch — the character of the place is in the architecture and energy, which takes time to appreciate.