Quick Verdict
Pick Key West if Mallory Square sunsets, Hemingway House mornings, and reef snorkels matter most. Pick St. Louis if Gateway Arch tram rides, Forest Park free museums, and Cardinals games beat island prices.
🏆 Key West wins 74 OVR vs 65 · attribute matchup 6–1
Key West
United States
St. Louis
United States
Key West
St. Louis
How do Key West and St. Louis compare?
$170 a day in Key West gets you a hotel split, a charter sail to Marquesas, and a Mallory Square sunset margarita; the same $170 in St. Louis covers a Central West End hotel, a Cardinals lower-bowl ticket, and a Mama's toasted-ravioli dinner with leftovers. Key West is the southernmost American end-of-the-road — a 4-mile-by-1-mile coral island, Hemingway's six-toed cats at the Whitehead Street house, conch fritters at B.O.'s Fish Wagon, and a Mallory Square sunset celebration with jugglers and bagpipers nightly. St. Louis is a Mississippi river-port giant — the 630-foot Gateway Arch, free Forest Park (zoo, art museum, history museum, all genuinely free), and the toasted-ravioli plates that locals will defend.
Mid-range budgets are $350 in Key West against $160 in St. Louis — a 120% premium driven entirely by the island's hotel scarcity (only 12,000 rooms across a 4-mile island, all peak in winter). A B.O.'s Fish Wagon conch-fritter platter is $18; a Pappy's Smokehouse burnt-end plate in St. Louis is $20. Key West wins on tropical scenery, snorkel/diving access (Looe Key reef is a 35-minute boat ride), and a quirky walkable Old Town. St. Louis wins on free attractions, stadium experiences (Cardinals tickets are $25 lower-bowl on weeknights), and value top-to-bottom.
Practical tip: target Key West December through April only — May through August brings 90°F humidity and hurricane probability, and the conch-and-Hemingway crowd thins. Hotel prices peak around Fantasy Fest (late October) and the Hemingway look-alike contest (mid-July). St. Louis is best April through October. Pick Key West for Hemingway House mornings, Mallory Square sunsets, and Looe Key snorkel days. Pick St. Louis for Gateway Arch tram rides, Forest Park free museums, and Cardinals games.
💰 Budget
🛡️ Safety
Key West
Key West is generally a safe small city for tourists. Old Town is well-policed and busy; the main risks are alcohol-related incidents (Duval Street late-night), aggressive scooter rentals on busy streets, sun exposure, and the seasonal hurricane risk. Petty theft from rental scooters and unattended beach belongings does occur. The island's relaxed, party-oriented culture means common sense is your best safety tool.
St. Louis
St. Louis has high reported crime rates city-wide — but they're heavily concentrated in specific North Side neighbourhoods that visitors have no reason to enter. The tourist neighbourhoods (Downtown around the Arch, Soulard, The Hill, Central West End, Forest Park, Tower Grove, Clayton, University City) are well-policed and safe day and night. Common-sense urban precautions apply: secure valuables in cars, avoid walking alone late, use rideshare after midnight in less busy areas.
🌤️ Weather
Key West
Key West has a tropical savanna climate moderated by surrounding water — temperatures stay narrowly between 18°C (winter low) and 32°C (summer high) all year. There is a wet season (May–October, with afternoon thunderstorms and hurricane risk) and a dry season (November–April, which is also peak tourist season). Hurricane risk is real — Hurricane Irma in 2017 caused major damage to the Lower Keys.
St. Louis
St. Louis has a humid continental climate at the southern edge — hot, humid summers (heat index regularly above 38°C / 100°F in July–August), cold winters with occasional ice storms, and dramatic spring weather including tornado risk in March–May. The city sits in the lower Tornado Alley and has a functional warning siren system. Spring (April–May) and autumn (September–October) are the only months without weather extremes.
🚇 Getting Around
Key West
Key West Old Town is small (about 2 miles by 4 miles total island) and the historic centre is almost entirely walkable. Bicycles are the favourite local transport — flat terrain, dedicated bike lanes, and bike racks everywhere. The Duval Loop bus is free; Uber and Lyft operate but are more expensive than in Miami. Renting a car for the week is unnecessary unless you're visiting other Keys; parking in Old Town is scarce and expensive ($4-8/hour, $25/day in city lots).
Walkability: Old Town is one of the most walkable small-city centres in America — flat, compact, shaded by tropical canopy, and full of architectural detail. The full Duval Street walk takes 25 minutes end to end. Bicycles extend the comfortable range to the entire island.
St. Louis
St. Louis is a driving city — the metro area sprawls 60 miles end-to-end and the dominant mode of transport is the private car. The MetroLink light rail (two lines, blue and red) connects the airport, downtown, Forest Park, Clayton, and East St. Louis on a single useful axis; MetroBus covers the rest. Most visitors rent a car for at least part of their stay, particularly to reach The Hill, Soulard, and the Botanical Garden. Uber and Lyft operate everywhere and are inexpensive ($8–$25 for most trips within the city).
Walkability: Inside individual neighbourhoods (Soulard, The Hill, Central West End, Forest Park) walking is excellent. Between neighbourhoods St. Louis is a driving city — distances are real Midwest distances and surface streets are fast but built for cars, not pedestrians. The Delmar Loop in University City is the longest pure pedestrian commercial strip; the Old Courthouse-to-Arch riverfront is the most photogenic walk.
📅 Best Time to Visit
Key West
Jan–Apr, Dec
Peak travel window
St. Louis
Apr–May, Sep–Oct
Peak travel window
The Verdict
Choose Key West if...
you want a quirky, walkable, southernmost-US tropical destination with Hemingway history, the Conch Republic, the best key lime pie, and a daily sunset ritual
Choose St. Louis if...
You want a Midwestern river city with cheap baseball tickets, world-class free museums in a giant park, and the best toasted ravioli on Earth.
Key West
St. Louis
You might also compare
Key WestvsSt. Louis
Try another