Sunset in Key West: Sailboat, Schooner or Mallory Square

Key West sells the sunset harder than anything else it has, and for once the marketing is not lying: the island faces west into open water, the horizon is unbroken, and there is a nightly public ritual built around it. There are 23 sunset offers in our inventory with 3,085 reviews between them, starting at €43.39.

The decision is not really which boat. It is whether you want to be on the water or on the square.

First, the time – it moves a long way

This trips people up more than anything else, because they book a 7 pm table in February.

Sunset in Key West falls around 5:39 pm on 1 December and around 5:51 pm on 31 December. In midsummer it is around 8:13 pm on 1 June and 8:21 pm on 21 June. Early September is around 7:47 pm, end of September around 7:16 pm.

That is a swing of roughly two hours and forty minutes across the year. A “sunset sail” in January leaves in what feels like late afternoon and has you back before seven. The same boat in June leaves after most restaurants have seated their first round. Check the departure time on the booking page rather than assuming an evening; in winter, a sunset cruise and dinner afterwards is comfortable, and in June it is late.

Mallory Square, honestly

The Sunset Celebration at Mallory Square is run by the Key West Cultural Preservation Society, a non-profit arts organisation. Their own visitor information says the festival begins around two hours before sunset and ends approximately soon after sunset, that it takes place every night, seven days a week, 365 days a year, weather permitting, and that it is totally free to attend.

Two practical things from the same source. They recommend arriving about an hour after the start, when the crowd has grown and the performers are working – turning up right at the beginning gets you an empty square. And the Mallory Square car park is, in their own words, expensive: $4.00 per hour.

What you get is street performers, arts and crafts stalls, psychics and food carts, on a stone quay, with a lot of other people. What you do not get is quiet, a seat, or an unobstructed view unless you are early. If the words “cruise ship crowd” make you tense, this is not your evening – but it costs nothing to look, and it is two minutes from the Key West Aquarium at 1 Whitehead Street.

The boats, by what kind of evening you want

Loud, included, sociable. The Signature Sunset Cruise is the most booked trip here that is nothing but a sunset cruise – 509 reviews, 4.6 stars, €70.19 for 2 hours on a catamaran the operator calls the Sandie Cat. Unlimited open bar including rum runners, Champagne, margaritas and draft beer, a spread of finger food, live music. The sunset sail with a live band is the same idea at €64.27 and rates 4.8 stars from 199 people. A two-hour sunset sail with live music and unlimited drinks sits at €70.19.

Quiet, wooden, slower. The schooner sunset sail aboard the America 2.0 is the best-rated sunset trip here with more than a hundred reviews behind it: 4.9 stars from 335 people. The operator describes a 105-foot schooner with teak decks, mahogany trim and 3,600 square feet of canvas, 2 hours, €107.62, with drinks and an hors d’oeuvres plate, leaving from 202 William Street. It costs half again as much as the party catamarans, and the reason people pay it is the absence of a DJ.

Other wooden options: the Appledore Star champagne sail at €96.53, a wind-and-wine schooner sail at €117.54, and a two-masted windjammer with champagne at €78.97.

Dinner on board. The sunset dinner cruise with buffet, open bar and live music is €81.60 for 2 hours, 288 reviews. This is the one to pick in December, when the boat is back at the dock by seven and you would otherwise be looking for dinner at an awkward hour.

Something other than sunset. The schooner full moon night sail runs 1 hour 30 minutes at €73.61 – a different thing entirely, and only on the nights it is offered. A tiki boat sunset cruise is €69.36 for 90 minutes.

What nobody mentions

Sunset is when everything happens at once. The reef snorkel boats with a sunset option and the dolphin sunset trips are out on the same water at the same hour. If your trip already ends at sunset, you have already bought the sunset – do not book a second one for the same evening.

Open bar is the price, not a gift. The gap between the €43 snorkel-with-sunset-option boats and the €107 schooner is largely drinks and crowd size. If you are not drinking, the cheap party boat is poor value and the schooner is worse.

Weather cancels this. A cloudy evening is not a refund. The celebration runs weather permitting; the boats sail and you get the sky you get.

Clouds are not the enemy people think. The photograph people come back with is almost never a clear sky – it is a sky with something in it to catch the light.

If you only have one evening

Do both, in this order: board a two-hour boat that leaves around sunset, and walk to Mallory Square afterwards if there is still noise coming off it. In winter that works easily. In June the square will have emptied by the time you are back on land, so reverse it – celebration first, late sail after – or accept that you are choosing one.

Prices here are shown in euros because GetYourGuide converts them; the operators bill in US dollars.