City brief Key West Mallory menus are a tax. Cuban breakfast, one named dinner, and sunset from the sidewalk. Loading the printable brief… VacationMath orientation — not live rates When to go Early May and late September–October after the heaviest summer, before winter northbound rates. Top money-saving tips Cuban Coffee Queen or a ventanita breakfast. Mallory Square menus are a tax.Sunset from the sidewalk. Skip a paid pier ticket on Lean — the sun does the same work.El Siboney or Garbo’s for Lean dinner. Blue Heaven early if leftover covers the wait.Stay Old Town. A cheap Stock Island room plus a nightly cab is not Lean.Fort Zach beach + fort is the cheap outdoor ticket. Parasail is leftover.Dry Tortugas is a full ferry day — only if leftover covers it. Do not stack Tortugas, a sunset sail, and a seaplane in three nights.EYW air is a premium. Midweek, or drive from Miami as a priced day, not a surprise.Key lime pie once. Happy-hour conch fritters are a snack, not dinner. Build a hard-budget plan