Sunset at Mallory Square is the thing everyone does in Key West, and it is better organized than it looks. There is an actual institution behind it.
Somebody leases this dock every night
“The Key West Cultural Preservation Society, Inc. was established in 1984. It is a not for profit corporation established to support the arts. The main function of the organization is to manage Sunset Celebration, Key West’s premiere nightly arts festival.”
And the mechanism, which is the fact of this page:
“The CPS leases Mallory Square Dock from the City of Key West, Florida for four hours nightly and in turn rents space to artisans.”
Four hours a night, leased from the city, every night. What looks like an organically occurring crowd is a nightly arts festival with a landlord, a management structure and paid pier managers.
Which is why the art is not junk
“Participation Committee — Volunteer entity approved by the board of directors who’s primary job is to ensure the authenticity of art exhibited at Sunset Celebration.”
There is a committee whose job is to keep imported souvenir stock off the dock. In a town with a great deal of imported souvenir stock, that is worth knowing — the work on Mallory Square at sunset has been vetted by people who care about the difference.
And one line from the organization’s stated mission that we think says more about Key West than anything else on this page:
“Provide funds for the legal defense of artists who are illegally arrested in the course of their profession.”
What it actually is
“Sunset Celebration is a nightly arts festival at Mallory Square in Key West, Florida. The participants of this Key West attraction consist of arts and crafts exhibitors and psychics, street performers, food carts, and of course the thousands of tourists from around the world who visit this Key West art show.”
When to arrive
“Each night around one hour before sunset masses of people, both locals and tourists alike, flock to the water’s edge to experience a multicultural happening and to watch the sun sink into the Gulf.”
An hour before. Earlier and nothing has started; later and you are behind three rows of people.
When sunset is. In Key West it comes earliest, at about 5:38 p.m., from late November into early December, and latest, at about 8:20 p.m., from late June to about 10 July. In mid-September it is about 7:30 p.m. and in mid-October about 7:00. Those are the U.S. Naval Observatory’s figures in local time; for your exact date, use its sunrise and sunset calculator and be on the square an hour before. The best-time page has the sunset for the middle of every month, and December, when it sets earliest, has its parades and New Year’s Eve drops on a page of their own.
Do not drive
The Mallory Square lot is at 412 Wall St, it has 100 spaces, a 10-hour maximum, and it charges $7 an hour — the only city lot at that rate, and $48 for a day.
It is also the single most obvious place to drive at sunset, which is exactly why it is the wrong one. Walk, bike, or take the $2 bus — the options are here, and the full parking rate card is here.
One thing that can change the evening
Mallory Square Dock is a working cruise berth. The city’s own calendar for the T-Pier has two event types in its legend: “Cruise Ship at Mallory T-Pier” and “Powerboat Race Day.”
Ships are typically in port until about 5 p.m., so most days they are gone before the square fills. A late departure, or a race day, changes what you walk into. How to check is here.
What you are standing on
“In 1823, Commodore David Porter established a base of operations for an anti-piracy squadron on this property. After piracy was suppressed, this area became a hub for the wrecking industry. Buildings on this property were then used for storage and auction of goods salvaged from shipwrecks.”
“In 1961, the City of Key West and the Old Island Restoration Foundation decided to restore this area.”
An anti-piracy base, then a salvage auction yard, then a restoration project, now a nightly arts festival on a four-hour lease.
And the building on the edge of it with the best story:
“In 1960, the Key West Players, a local theater group, found a home in this warehouse with the help of fellow Player, Tennessee Williams. … The building and theatre group then became known as the Waterfront Playhouse, which is considered the oldest continuously running theatre group in Florida today.”
Tennessee Williams helped find a theater company a warehouse, and it is still running.
Square or boat?
Honestly, do both, on different evenings.
The square is free, loud, crowded and full of jugglers, cats, psychics and food carts. It is the communal version, and it is the one everyone remembers.
A sunset sail is the opposite experience — off the dock, on the water, looking back at the island, with a drink and no crowd. It is also the only way to be somewhere the sun sets over open water with nobody standing in front of you.
The three sails below all carry free cancellation up to 24 hours before departure, and the comparison between them is here. One of them, Honest Eco’s dolphin-and-sunset catamaran, sails mid-October to April only; the dolphin tours page has the rest of the year. The square costs nothing and needs no booking, which is the honest reason to do it first.
