Sailing · Key West
Key West sunset sail: the schooner alternative to Mallory Square
Sunset sailings leave the harbour an hour or two before dusk.
- The activity
- An evening sail out of Key West harbour timed so that sunset happens from the water rather than from the shore.
- Location
- Departures from the Historic Seaport at Key West Bight, around Elizabeth, Greene and William Streets.
- Duration
- About two hours, timed to the sunset so the departure shifts through the year. Your confirmed time comes with the booking rather than being fixed.
- Best time to arrive
- Thirty minutes before departure, at the office on Lazy Way Lane between Conch Republic and Schooner Wharf. Early boarding is what secures a place at the rail.
- Admission cost
- From about $65 per person on a 70-foot catamaran, including champagne, wine, a full liquor bar, beer and soft drinks, along with hearty appetizers such as peel-and-eat shrimp, and live music. Rated across more than 3,800 reviews, the most of any Key West sunset sail.
- Types of boat
- Traditional two-masted schooners such as the Appledore, the square-rigged Jolly II Rover, larger catamarans with music and food, and small private charters.
- Included
- Most sailings include beer, wine, champagne, sangria and soft drinks. The better-rated boats add hors d'oeuvres and live music, and the traditional schooners let you help hoist the sails and take the wheel.
- Included
- Typically an open bar with champagne, wine, beer, sangria and soft drinks, and often hors d'oeuvres. Guest numbers on the better schooners are capped around 22 to 28.
What to expect
The sail out leaves the harbour under canvas rather than engine where conditions allow, working out past the anchored fleet and into open water west of the island.
The sunset is the point, and from the water it is a different proposition to Mallory Square: no crowd, no performers, and the sun going down over open sea with the island behind you.
The open bar and appetizers are included in the fare: champagne, wine, a full liquor bar and beer, with hors d’oeuvres passed by the crew and live music on deck. It is what makes the two hours feel like an evening rather than a boat trip.
Vessel size is the one thing to weigh. Smaller schooners carry a few dozen passengers and larger catamarans considerably more, and it changes the character of the sail entirely.
The honest takeaway
Almost uniformly well reviewed. The one thing worth weighing is vessel size, since the larger boats carry more passengers.
What visitors praise
- The best view of the sunset in Key West. Unobstructed, and away from the crowds ashore.
- Genuine sailing on the schooners. Engines off and sails up is the version most reviewers recommend.
- Good value with the bar included. Unlimited drinks and appetisers offset much of a $65 to $110 ticket.
- Calm water. The lee side of the island is sheltered in most conditions.
What visitors find difficult
- Crowded party boats. The largest catamarans can feel packed.
- Weather dependent. Cloud on the horizon can flatten the sunset entirely.
- Sells out. Peak-season evenings book several days ahead.
- Short window. Late arrival means the boat leaves without you.
Drawn from the recurring themes in public visitor reviews of the activity and the tours that reach it. We do not reproduce individual reviews or aggregate scores; for current ratings, check Viator or another booking platform directly.
Getting there
Departures are from the Historic Seaport at the north end of Old Town, walkable from most hotels and a short taxi from anywhere on the island. Parking nearby is limited and expensive.
Check in thirty minutes before the stated sailing time; boats leave on the sunset, not on the passengers.
How to make the most of the day
- 1Choose a schooner if you want the sailing. The catamarans are for the party.
- 2Book two or three days ahead in season. The good boats fill first.
- 3Arrive thirty minutes early. Boarding opens half an hour before departure and the boats leave on the sunset, not on the passengers.
- 4Bring a light layer. It is cooler on the water than ashore once the sun goes.
- 5Walk Mallory Square afterwards. The street performers continue long after sunset.
- 6Book about three weeks ahead in season. The best-rated sunset sails average around 23 days of advance booking.
A little more background
Key West's sunset celebration at Mallory Square has run nightly since the 1960s and is one of the reasons the town's harbour retains its working schooners. Several of the vessels sailing today are historic or replica ships kept in commission by the tourist trade.
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