Key West is small (4 miles by 2 miles), walkable, and impossibly easy. You don't need a complicated plan. What you need is to stop trying to do everything and pick the right three things. This is the guide we'd hand to a friend flying in tomorrow.
Day One: Land, walk, sunset.
Drop your bags. Walk to Mallory Square via Duval (yes, it's touristy — you'll do it once). Grab a key lime ice. Be at the Historic Seaport by 5:30pm for a sunset sail — Schooner America 2.0 is the locals' move. Dinner at Half Shell Raw Bar after.
Day Two: Water day.
Book a half-day reef snorkel + sandbar combo (Fury or Sebago). Pack reef-safe sunscreen. Lunch is on the boat. Back by 4pm — happy hour at Schooner Wharf, then a casual dinner. If you have energy, walk the Hemingway House at sunset.
Day Three: Old Town slow.
Cuban coffee at 5 Brothers (the locals' counter, no menu, just point). Bike or scooter the perimeter — Truman Annex, Fort Zachary, the cemetery. Lunch at Blue Heaven (yes, the rooster). Afternoon kayak the mangroves or Conch Cart cruise around Old Town.
Don't bother with...
Renting a car (you don't need one in Old Town). Most chain restaurants. Shell shops on Duval (touristy mark-ups). Booking the same activity twice — there's too much to see.
- Skip: Conch Train if you have any mobility — walking is faster.
- Skip: Jet ski tours unless you specifically want one — there's better water further up the Keys.
- Skip: Big Duval St bars on a weekend night unless you want spring break energy.
How long should I stay?+
3 nights is the minimum to feel the rhythm. 5 is the sweet spot. A week and you'll start running out of new things — that's when you take a day trip up to Bahia Honda.
What's the best time of year?+
April–May and October–early December: warm water, fewer crowds, lower prices than peak. December–March is peak season (warm, dry, expensive).
Should I rent a car?+
Only if you're staying in New Town or want to drive up the Keys. Old Town is fully walkable. A bike or golf cart (Conch Carts has 4-, 6-, and 8-seaters) is more useful than a car.
What should I pack?+
Reef-safe sunscreen (required for tours). Water shoes if you're snorkeling. A light jacket for boats at sunset. Cash for tipping captains and bartenders.