A schooner under full sail silhouetted against the setting sun off Key West, the sky burnt orange above open water

Mile 0 · Key West, Florida

Sunset sails, reef days and a fort 70 miles out to sea

Pastel conch houses, roosters in the road and boats heading out at golden hour. We'll help you pick the sail, get a Dry Tortugas ferry seat in time and find a bed near the dock, with real, dated prices.

We'll help you pick the sail, get a Dry Tortugas ferry seat in time and find a bed near the dock.

Joe Parks · CC BY 2.0

Sails, tours & charters

Golden hour on the water is the main event, and the reef, the fish and the fort fill the days.

Every trip, with its price → grouped by what you want from the day.

First time in Key West?

  1. Get here

    One road, one airport, one boat: 159 miles from Miami on the only road in, or about 3.5 hours by ferry from Fort Myers Beach.

    The drive, by mile marker

  2. Pick where to stay

    Old Town puts you in walking distance of almost everything; here's how to check a rental is licensed.

  3. Book the Dry Tortugas first

    One ferry, 175 people a day, and it sells out weeks ahead. Book it before the rest of the trip, for day one or two.

  4. Sunset on the water

    The three sails worth choosing between, from $79, and what each one includes.

Beaches

Key West's beaches are small. These are the good ones, plus the big one 37 miles up the road.

Compare all 4 beaches → by parking, snorkeling, crowds and whether you can walk in.

Plan the trip

All 24 planning guides → from the Dry Tortugas to the cemetery.

Get a heads-up when Key West changes

Every page here carries the date we last checked it. This is that same checking, sent to you instead of waited for — a ferry price moving, a boat changing hands, a beach closed for works.

Leave an address and we'll write when something in Key West actually changes. That is the whole list — no schedule, no filler, and some months nothing at all.

No schedule and no filler — we email when there is something worth saying, which some months is nothing. Unsubscribe any time. How we handle your address.

Or skip the form entirely — everything we send is also posted on the changelog, free and dated.

Photo credits