Key West sells a dozen near-identical sunset cruises from the same harbor at the same hour. The three worth choosing between here run $79 to $117.18, and the listings are close to useless for telling them apart.
Three things actually differ.
1. Sailboat or motor catamaran
This is the biggest difference and almost no listing leads with it.
A sailboat — a schooner or a smaller yacht — is quiet, tilts, carries fewer people, and is the thing people imagine when they book. A motor catamaran is stable, loud, carries a lot more people and is closer to a floating bar.
Neither is wrong. They are completely different evenings and they appear in the same search results at similar prices.
2. What “open bar” means
Ranges from two drink tickets to genuinely unlimited, and both are written as “drinks included.”
On a sail of two hours or less, the bar can be most of the price difference between two boats. On this page it runs the other way: the $79 sail pours champagne, white wine, margaritas and craft beer, and the $117.18 schooner beer and wine. The schooner’s extra buys the 1939 boat and about half an hour more on the water, not the drinks.
3. How many people
Twenty versus a hundred and twenty. Capacity is rarely stated plainly and it determines whether you get a seat at the rail, how long the bar line is, and whether it feels like a booze cruise.
Smaller boats sell out first for exactly this reason.
What about Mallory Square?
Mallory Square is the free version and it is worth an evening. The whole town turns out, the street performers are genuinely good, and it is a ten-minute walk from most of Old Town.
It is also, on any given night in season, a few thousand people on a concrete dock with the sun going down behind a cruise ship. You are watching the sunset from the land, facing a crowd.
The boat is a different evening, not a more expensive version of the same one. You are out on the water off Mallory with the island behind you, someone hands you a drink, and there are two dozen people aboard instead of two thousand. That is why the small boats sell out first.
Do both if you have the nights. If you only have one, take the boat.
Which one to book
If you want one recommendation and no more reading: the $79 sunset sail with the bar included. It is about an hour and a half on the water, the bar is included rather than a tab, and it is capped at 24 people so you get a spot at the rail when the light goes. Free cancellation up to 24 hours out.
Want the boat to be the point rather than the drinks? The schooner When And If, $117.18. It is the 1939 vessel built for General Patton, the crew sail it properly for two hours, and they will put you on the wheel. It books about three weeks ahead.
Here between mid-October and April and want dolphins as well as the sunset? Honest Eco’s catamaran, $117.17, is a dolphin search and a sunset sail in one three-hour evening. It has no snorkeling, and it does not run from May to mid-October; in 2026–27 it sails from 15 October to 30 April. The dolphin tours page covers the year-round alternatives and the rules for watching wild dolphins.
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