SUNSET
Sunset sail — where locals actually go (it's not Mallory Square)
Mallory's a scene. It's fine. But if you actually want to sit down, hear yourself talk, and watch the sun drop, you go out the harbor and turn right.
Mallory Square is what a first-time visitor pictures when they picture Key West sunset. Street performers, cruise ship in the background, a thousand cameras all pointed at the same horizon. It's not bad. It's just crowded and it's just the beginning of the light show — you're seeing the sun set over other tourists' heads.
The sunset sail leaves the harbor at 6 or 6:30 depending on the month. You clear the channel, you turn west, and by 7 you're two miles offshore watching the sun hit the water with nothing between you and the horizon except the Marquesas.
There are basically three types of sunset sails and the price gaps between them are real.
The catamaran party sail — big cats like Fury and Sebago running 40-70 people, open bar, live music. This is a bachelorette-vibe sunset. If your group is 6+ and you want energy, this is it. About $85-$110 a head.
The mid-size schooner or classic sail — 20-40 people, quieter, wine and beer, actual sailing (they'll cut the engine). Danger Charters, Argo, the old wooden schooners. About $110-$150 a head, and you're on a boat that was built for sailing, not for booze cruising.
The private six-pack — you and up to five other people on a boat you have to yourself. About $700-$900 for the boat, not per person. Split by 6, it's cheaper than the party sail and you can bring whatever you want on board.
Whichever one you pick, the trick is the timing. Book the earlier launch. Not because the sunset is better then — it's the same sun — but because the boat is at anchor for the actual sunset instead of racing back to the dock. You want to be sitting still when it drops. Otherwise you're the group taking their sunset picture through the rigging on the way home.
